A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthes... more A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but-3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for their antioxidant and antimicrobial activities. Compared to the test reference (Ascorbic acid, 88.0%), the antipyrinyl thienyl ketones 13a and 13b substituted with methyl and/or hydroxyl groups at the thiophene ring system displayed excellent antioxidant properties, 87.8% and 87.2%, respectively. Additionally, antipyrinyl thienyl ketones 13a and 13b showed high antibacterial activities, and their relative activity index (which ranges from 68% to 91.7%) was close to that of a reference compound, Ampicillin.
A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of... more A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of the precursor N-(4-substituted-phenyl)-5-(2-chloroacetamido)-4-cyano-3-methylthiophene-2-carboxamides 4a and 4b with different sulfur and/or nitrogen nucleophilic reagents (namely; mercaptoacetic acid, 2mercaptobenzothiazole, 5-(phenylamino)-1,3,4-thiadiazole-2-thiol, 2-mercapto-4,6-dimethylnicotinonitrile, 3arylazo-4-mercapto-4-(phenylamino)-but-3-en-one derivatives, ammonium thiocyanate, piperidine and/or morpholine). The structures of the prepared thiophene compounds were characterized by spectral analysis. Their cytotoxicity was evaluated against two human cancer cell lines (HepG2 and MCF-7) and indicated promising results. Pretreatment of HepG2 cells with the tested compound 4b sensitized the cells to the cytotoxicity of sorafenib, leading to a significant decrease in the IC50 from 3.9 to 0.5 µM.
ABSTRACT. A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemical... more ABSTRACT. A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but-3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4-yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for ...
A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of... more A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of the precursor N-(4-substituted-phenyl)-5-(2-chloroacetamido)-4-cyano-3-methylthiophene-2-carboxamides 4a and 4b with different sulfur and/or nitrogen nucleophilic reagents (namely; mercaptoacetic acid, 2mercaptobenzothiazole, 5-(phenylamino)-1,3,4-thiadiazole-2-thiol, 2-mercapto-4,6-dimethylnicotinonitrile, 3arylazo-4-mercapto-4-(phenylamino)-but-3-en-one derivatives, ammonium thiocyanate, piperidine and/or morpholine). The structures of the prepared thiophene compounds were characterized by spectral analysis. Their cytotoxicity was evaluated against two human cancer cell lines (HepG2 and MCF-7) and indicated promising results. Pretreatment of HepG2 cells with the tested compound 4b sensitized the cells to the cytotoxicity of sorafenib, leading to a significant decrease in the IC50 from 3.9 to 0.5 µM.
A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthes... more A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but-3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for their antioxidant and antimicrobial activities. Compared to the test reference (Ascorbic acid, 88.0%), the antipyrinyl thienyl ketones 13a and 13b substituted with methyl and/or hydroxyl groups at the thiophene ring system displayed excellent antioxidant properties, 87.8% and 87.2%, respectively. Additionally, antipyrinyl thienyl ketones 13a and 13b showed high antibacterial activities, and their relative activity index (which ranges from 68% to 91.7%) was close to that of a reference compound, Ampicillin.
Herein, the building block synthon cyano-(furan-2-ylmethylene)-acetohydrazide (3) was synthesized... more Herein, the building block synthon cyano-(furan-2-ylmethylene)-acetohydrazide (3) was synthesized and utilized for constructing a wide variety of nitrogen heterocyclic compounds. Cyclization of acetohydrazide 3 in boiling EtOH and 0.5 ml piperidine afforded 2-cyano-(furan-2-ylmethylene)-3-phenylacrylohydrazide (5). Also, a new series of a new chromen-2-imine derivatives 8a-d have been synthesized via stirring starting moiety 3 with 2-hydroxy-5-(phenyldiazenyl)benzaldehyde derivatives 6a-d under heating at 50 °C in the presence of piperidine as a catalyst. Moreover, coupling of active methylene 3 with arylamine diazonium salts 10 a-h formed the corresponding 2-(2-furan-2-ylmethylene)hydrazineyl)-N-(4-substitutedphenyl)-2-oxoaceto-hydrazonoyl cyanide derivatives 11a-h in overall good yields. Furthermore, creating molecules with pyrazole rings was prepared by coupling acetohydrazide 3 with heterocyclic amine diazonium salts 14-16. The structural elucidation was achieved for the target molecules by different spectral parameters such as FTIR, 1 H NMR, and 13 C NMR spectra. Molecular modeling studies displayed the geometrical structures for the investigated compounds by using the geometrical studies (DFT) of the synthesized molecules that were investigated by the initio/3021 G quantum mechanical method. The in vitro cytotoxic activity of new furan-hydrazide derivatives against the HepG-2 cell line was evaluated using the reference doxorubicin. Compounds 8a and 8b exhibited high reactivity against the HepG-2 cell line, with IC-50 values of 9, and 8.1 μM, respectively. Cell cycle studies indicate that the most potent furan derivatives 8a and 8b arrested cells at the G2/M phase and induced apoptosis.
p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-subst... more p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-substituted thiophene derivatives. The basic-catalyzed reaction of 1 with various thiocarbamoyl compounds such as 2-acetyl-2substituted-thioacetanilides 2a,b, 3-arylazo-4-mercapto-4-phenylaminobuten-2-ones 5a-c, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylates 8a-c, N-aryl-2-cyano-3-mercapto-3-phenylamino-acrylamides 11a-c, N-aryl-2-(mercapto(phenylamino)methylene)-3-oxo-butanamides 14a-c, and 2mercapto-4,6-dimethylnicotinonitrile 17 led to the production of their corresponding substituted thiophene compounds 4a-b, 7a-c, 10a-c, 13a-c, 16a-c, and 19 in moderate yields. The newly synthesized thiophene compounds were deduced according to FTIR, 1 H NMR, 13 C NMR, 19 F NMR, and mass analyses along with micro-analytical data. The synthesized thiophene compounds were tested to evaluate their antibacterial and antioxidant activities. The majority of the synthesized thiophenes showed good to moderate anti-bacterial and antioxidant activities. The hydroxythiophene compound 4a showed extremely high antibacterial activity with inhibition zones 15-21 mm (from 60 to 87.5% activity indices). It inhibits bacterial growth and approaches the activity of Ampicillin, which inhibits bacteria with areas of inhibition from 23 to 25 mm. The hydroxythiophene compound 4a showed excellent antioxidant properties (85.9%) relative to the reference, Ascorbic acid (88.0%).
p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-subst... more p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-substituted thiophene derivatives. The basic-catalyzed reaction of 1 with various thiocarbamoyl compounds such as 2-acetyl-2substituted-thioacetanilides 2a,b, 3-arylazo-4-mercapto-4-phenylaminobuten-2-ones 5a-c, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylates 8a-c, N-aryl-2-cyano-3-mercapto-3-phenylamino-acrylamides 11a-c, N-aryl-2-(mercapto(phenylamino)methylene)-3-oxo-butanamides 14a-c, and 2mercapto-4,6-dimethylnicotinonitrile 17 led to the production of their corresponding substituted thiophene compounds 4a-b, 7a-c, 10a-c, 13a-c, 16a-c, and 19 in moderate yields. The newly synthesized thiophene compounds were deduced according to FTIR, 1 H NMR, 13 C NMR, 19 F NMR, and mass analyses along with micro-analytical data. The synthesized thiophene compounds were tested to evaluate their antibacterial and antioxidant activities. The majority of the synthesized thiophenes showed good to moderate anti-bacterial and antioxidant activities. The hydroxythiophene compound 4a showed extremely high antibacterial activity with inhibition zones 15-21 mm (from 60 to 87.5% activity indices). It inhibits bacterial growth and approaches the activity of Ampicillin, which inhibits bacteria with areas of inhibition from 23 to 25 mm. The hydroxythiophene compound 4a showed excellent antioxidant properties (85.9%) relative to the reference, Ascorbic acid (88.0%).
A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dion... more A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4hydroxy-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)naphthalene-1,4-dione (7) and naphtho[2,3-b]furan-3,4,9(2H)-trione (6) based on lawsone 'that plays as important precursor' was synthesized by reaction with 1,3diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2chloroacetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds. Supplemental data for this article is available online at here.
A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction o... more A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction of 4-amino-2-oxo-2H-chromene-3-carboxaldehyde (1) with activated methylene compounds as (3-acetyl-2H-chromen-2-one, 1-(10H-phenothiazin-2-yl)ethan-1-one 2-(1H-benzo[d]imidazol-2-yl)acetonitrile, quincilidin-3-one hydrochloride, 2-oxo-3-phenylpropanoic acid, thiazolidine-2,4-dione, 1,2-iminothiazolidin-4-one, 1,3-diphenylimidazolidine-2,4dione,2-methyl-2-phenyl-1,3-oxothiazolan-5-one).These compounds were screened for computational ADME and Lipinski's analysis followed by molecular docking and binding energy. The anticancer activities of the synthesized compounds were studied in breast (MCF-7). The molecular docking studies were found the oxolone moiety is a required common feature for good interaction and we found that compounds 2a, 2b, and 3 showed the highest activity toward breast cancer cell line. The structures of the new synthesized compounds were confirmed by 1 H-NMR, 13 C-NMR, IR, and MS spectroscopic methods.
in Wiley Online Library (wileyonlinelibrary.com). N-2-amino-4-(furan-2-yl)-5,6-dimethylnicotinoni... more in Wiley Online Library (wileyonlinelibrary.com). N-2-amino-4-(furan-2-yl)-5,6-dimethylnicotinonitrile (4) was utilized as key intermediate for the synthesis of some new, pyridopyrimidine, benzo[1,5][g]oxazocine, naphthoquinone, and isoindole derivatives. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1 H-NMR, and mass spectral data.
A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction o... more A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction of 4-amino-2-oxo-2H-chromene-3-carboxaldehyde (1) with activated methylene compounds as (3-acetyl-2H-chromen-2-one, 1-(10H-phenothiazin-2-yl)ethan-1-one 2-(1H-benzo[d]imidazol-2-yl)acetonitrile, quincilidin-3-one hydrochloride, 2-oxo-3-phenylpropanoic acid, thiazolidine-2,4-dione, 1,2-iminothiazolidin-4-one, 1,3-diphenylimidazolidine-2,4dione,2-methyl-2-phenyl-1,3-oxothiazolan-5-one).These compounds were screened for computational ADME and Lipinski's analysis followed by molecular docking and binding energy. The anticancer activities of the synthesized compounds were studied in breast (MCF-7). The molecular docking studies were found the oxolone moiety is a required common feature for good interaction and we found that compounds 2a, 2b, and 3 showed the highest activity toward breast cancer cell line. The structures of the new synthesized compounds were confirmed by 1 H-NMR, 13 C-NMR, IR, and MS spectroscopic methods.
A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction o... more A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction of 4-amino-2-oxo-2H-chromene-3-carboxaldehyde (1) with activated methylene compounds as (3-acetyl-2H-chromen-2-one, 1-(10H-phenothiazin-2-yl)ethan-1-one 2-(1H-benzo[d]imidazol-2-yl)acetonitrile, quincilidin-3-one hydrochloride, 2-oxo-3-phenylpropanoic acid, thiazolidine-2,4-dione, 1,2-iminothiazolidin-4-one, 1,3-diphenylimidazolidine-2,4dione,2-methyl-2-phenyl-1,3-oxothiazolan-5-one).These compounds were screened for computational ADME and Lipinski's analysis followed by molecular docking and binding energy. The anticancer activities of the synthesized compounds were studied in breast (MCF-7). The molecular docking studies were found the oxolone moiety is a required common feature for good interaction and we found that compounds 2a, 2b, and 3 showed the highest activity toward breast cancer cell line. The structures of the new synthesized compounds were confirmed by 1 H-NMR, 13 C-NMR, IR, and MS spectroscopic methods.
A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dion... more A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4hydroxy-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)naphthalene-1,4-dione (7) and naphtho[2,3-b]furan-3,4,9(2H)-trione (6) based on lawsone 'that plays as important precursor' was synthesized by reaction with 1,3diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2chloroacetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds. Supplemental data for this article is available online at here.
in Wiley Online Library (wileyonlinelibrary.com). N-2-amino-4-(furan-2-yl)-5,6-dimethylnicotinoni... more in Wiley Online Library (wileyonlinelibrary.com). N-2-amino-4-(furan-2-yl)-5,6-dimethylnicotinonitrile (4) was utilized as key intermediate for the synthesis of some new, pyridopyrimidine, benzo[1,5][g]oxazocine, naphthoquinone, and isoindole derivatives. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1 H-NMR, and mass spectral data.
A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthes... more A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but-3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for their antioxidant and antimicrobial activities. Compared to the test reference (Ascorbic acid, 88.0%), the antipyrinyl thienyl ketones 13a and 13b substituted with methyl and/or hydroxyl groups at the thiophene ring system displayed excellent antioxidant properties, 87.8% and 87.2%, respectively. Additionally, antipyrinyl thienyl ketones 13a and 13b showed high antibacterial activities, and their relative activity index (which ranges from 68% to 91.7%) was close to that of a reference compound, Ampicillin.
A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of... more A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of the precursor N-(4-substituted-phenyl)-5-(2-chloroacetamido)-4-cyano-3-methylthiophene-2-carboxamides 4a and 4b with different sulfur and/or nitrogen nucleophilic reagents (namely; mercaptoacetic acid, 2mercaptobenzothiazole, 5-(phenylamino)-1,3,4-thiadiazole-2-thiol, 2-mercapto-4,6-dimethylnicotinonitrile, 3arylazo-4-mercapto-4-(phenylamino)-but-3-en-one derivatives, ammonium thiocyanate, piperidine and/or morpholine). The structures of the prepared thiophene compounds were characterized by spectral analysis. Their cytotoxicity was evaluated against two human cancer cell lines (HepG2 and MCF-7) and indicated promising results. Pretreatment of HepG2 cells with the tested compound 4b sensitized the cells to the cytotoxicity of sorafenib, leading to a significant decrease in the IC50 from 3.9 to 0.5 µM.
ABSTRACT. A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemical... more ABSTRACT. A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but-3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4-yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for ...
A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of... more A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of the precursor N-(4-substituted-phenyl)-5-(2-chloroacetamido)-4-cyano-3-methylthiophene-2-carboxamides 4a and 4b with different sulfur and/or nitrogen nucleophilic reagents (namely; mercaptoacetic acid, 2mercaptobenzothiazole, 5-(phenylamino)-1,3,4-thiadiazole-2-thiol, 2-mercapto-4,6-dimethylnicotinonitrile, 3arylazo-4-mercapto-4-(phenylamino)-but-3-en-one derivatives, ammonium thiocyanate, piperidine and/or morpholine). The structures of the prepared thiophene compounds were characterized by spectral analysis. Their cytotoxicity was evaluated against two human cancer cell lines (HepG2 and MCF-7) and indicated promising results. Pretreatment of HepG2 cells with the tested compound 4b sensitized the cells to the cytotoxicity of sorafenib, leading to a significant decrease in the IC50 from 3.9 to 0.5 µM.
A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthes... more A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but-3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for their antioxidant and antimicrobial activities. Compared to the test reference (Ascorbic acid, 88.0%), the antipyrinyl thienyl ketones 13a and 13b substituted with methyl and/or hydroxyl groups at the thiophene ring system displayed excellent antioxidant properties, 87.8% and 87.2%, respectively. Additionally, antipyrinyl thienyl ketones 13a and 13b showed high antibacterial activities, and their relative activity index (which ranges from 68% to 91.7%) was close to that of a reference compound, Ampicillin.
Herein, the building block synthon cyano-(furan-2-ylmethylene)-acetohydrazide (3) was synthesized... more Herein, the building block synthon cyano-(furan-2-ylmethylene)-acetohydrazide (3) was synthesized and utilized for constructing a wide variety of nitrogen heterocyclic compounds. Cyclization of acetohydrazide 3 in boiling EtOH and 0.5 ml piperidine afforded 2-cyano-(furan-2-ylmethylene)-3-phenylacrylohydrazide (5). Also, a new series of a new chromen-2-imine derivatives 8a-d have been synthesized via stirring starting moiety 3 with 2-hydroxy-5-(phenyldiazenyl)benzaldehyde derivatives 6a-d under heating at 50 °C in the presence of piperidine as a catalyst. Moreover, coupling of active methylene 3 with arylamine diazonium salts 10 a-h formed the corresponding 2-(2-furan-2-ylmethylene)hydrazineyl)-N-(4-substitutedphenyl)-2-oxoaceto-hydrazonoyl cyanide derivatives 11a-h in overall good yields. Furthermore, creating molecules with pyrazole rings was prepared by coupling acetohydrazide 3 with heterocyclic amine diazonium salts 14-16. The structural elucidation was achieved for the target molecules by different spectral parameters such as FTIR, 1 H NMR, and 13 C NMR spectra. Molecular modeling studies displayed the geometrical structures for the investigated compounds by using the geometrical studies (DFT) of the synthesized molecules that were investigated by the initio/3021 G quantum mechanical method. The in vitro cytotoxic activity of new furan-hydrazide derivatives against the HepG-2 cell line was evaluated using the reference doxorubicin. Compounds 8a and 8b exhibited high reactivity against the HepG-2 cell line, with IC-50 values of 9, and 8.1 μM, respectively. Cell cycle studies indicate that the most potent furan derivatives 8a and 8b arrested cells at the G2/M phase and induced apoptosis.
p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-subst... more p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-substituted thiophene derivatives. The basic-catalyzed reaction of 1 with various thiocarbamoyl compounds such as 2-acetyl-2substituted-thioacetanilides 2a,b, 3-arylazo-4-mercapto-4-phenylaminobuten-2-ones 5a-c, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylates 8a-c, N-aryl-2-cyano-3-mercapto-3-phenylamino-acrylamides 11a-c, N-aryl-2-(mercapto(phenylamino)methylene)-3-oxo-butanamides 14a-c, and 2mercapto-4,6-dimethylnicotinonitrile 17 led to the production of their corresponding substituted thiophene compounds 4a-b, 7a-c, 10a-c, 13a-c, 16a-c, and 19 in moderate yields. The newly synthesized thiophene compounds were deduced according to FTIR, 1 H NMR, 13 C NMR, 19 F NMR, and mass analyses along with micro-analytical data. The synthesized thiophene compounds were tested to evaluate their antibacterial and antioxidant activities. The majority of the synthesized thiophenes showed good to moderate anti-bacterial and antioxidant activities. The hydroxythiophene compound 4a showed extremely high antibacterial activity with inhibition zones 15-21 mm (from 60 to 87.5% activity indices). It inhibits bacterial growth and approaches the activity of Ampicillin, which inhibits bacteria with areas of inhibition from 23 to 25 mm. The hydroxythiophene compound 4a showed excellent antioxidant properties (85.9%) relative to the reference, Ascorbic acid (88.0%).
p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-subst... more p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-substituted thiophene derivatives. The basic-catalyzed reaction of 1 with various thiocarbamoyl compounds such as 2-acetyl-2substituted-thioacetanilides 2a,b, 3-arylazo-4-mercapto-4-phenylaminobuten-2-ones 5a-c, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylates 8a-c, N-aryl-2-cyano-3-mercapto-3-phenylamino-acrylamides 11a-c, N-aryl-2-(mercapto(phenylamino)methylene)-3-oxo-butanamides 14a-c, and 2mercapto-4,6-dimethylnicotinonitrile 17 led to the production of their corresponding substituted thiophene compounds 4a-b, 7a-c, 10a-c, 13a-c, 16a-c, and 19 in moderate yields. The newly synthesized thiophene compounds were deduced according to FTIR, 1 H NMR, 13 C NMR, 19 F NMR, and mass analyses along with micro-analytical data. The synthesized thiophene compounds were tested to evaluate their antibacterial and antioxidant activities. The majority of the synthesized thiophenes showed good to moderate anti-bacterial and antioxidant activities. The hydroxythiophene compound 4a showed extremely high antibacterial activity with inhibition zones 15-21 mm (from 60 to 87.5% activity indices). It inhibits bacterial growth and approaches the activity of Ampicillin, which inhibits bacteria with areas of inhibition from 23 to 25 mm. The hydroxythiophene compound 4a showed excellent antioxidant properties (85.9%) relative to the reference, Ascorbic acid (88.0%).
A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dion... more A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4hydroxy-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)naphthalene-1,4-dione (7) and naphtho[2,3-b]furan-3,4,9(2H)-trione (6) based on lawsone 'that plays as important precursor' was synthesized by reaction with 1,3diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2chloroacetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds. Supplemental data for this article is available online at here.
A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction o... more A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction of 4-amino-2-oxo-2H-chromene-3-carboxaldehyde (1) with activated methylene compounds as (3-acetyl-2H-chromen-2-one, 1-(10H-phenothiazin-2-yl)ethan-1-one 2-(1H-benzo[d]imidazol-2-yl)acetonitrile, quincilidin-3-one hydrochloride, 2-oxo-3-phenylpropanoic acid, thiazolidine-2,4-dione, 1,2-iminothiazolidin-4-one, 1,3-diphenylimidazolidine-2,4dione,2-methyl-2-phenyl-1,3-oxothiazolan-5-one).These compounds were screened for computational ADME and Lipinski's analysis followed by molecular docking and binding energy. The anticancer activities of the synthesized compounds were studied in breast (MCF-7). The molecular docking studies were found the oxolone moiety is a required common feature for good interaction and we found that compounds 2a, 2b, and 3 showed the highest activity toward breast cancer cell line. The structures of the new synthesized compounds were confirmed by 1 H-NMR, 13 C-NMR, IR, and MS spectroscopic methods.
in Wiley Online Library (wileyonlinelibrary.com). N-2-amino-4-(furan-2-yl)-5,6-dimethylnicotinoni... more in Wiley Online Library (wileyonlinelibrary.com). N-2-amino-4-(furan-2-yl)-5,6-dimethylnicotinonitrile (4) was utilized as key intermediate for the synthesis of some new, pyridopyrimidine, benzo[1,5][g]oxazocine, naphthoquinone, and isoindole derivatives. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1 H-NMR, and mass spectral data.
A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction o... more A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction of 4-amino-2-oxo-2H-chromene-3-carboxaldehyde (1) with activated methylene compounds as (3-acetyl-2H-chromen-2-one, 1-(10H-phenothiazin-2-yl)ethan-1-one 2-(1H-benzo[d]imidazol-2-yl)acetonitrile, quincilidin-3-one hydrochloride, 2-oxo-3-phenylpropanoic acid, thiazolidine-2,4-dione, 1,2-iminothiazolidin-4-one, 1,3-diphenylimidazolidine-2,4dione,2-methyl-2-phenyl-1,3-oxothiazolan-5-one).These compounds were screened for computational ADME and Lipinski's analysis followed by molecular docking and binding energy. The anticancer activities of the synthesized compounds were studied in breast (MCF-7). The molecular docking studies were found the oxolone moiety is a required common feature for good interaction and we found that compounds 2a, 2b, and 3 showed the highest activity toward breast cancer cell line. The structures of the new synthesized compounds were confirmed by 1 H-NMR, 13 C-NMR, IR, and MS spectroscopic methods.
A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction o... more A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction of 4-amino-2-oxo-2H-chromene-3-carboxaldehyde (1) with activated methylene compounds as (3-acetyl-2H-chromen-2-one, 1-(10H-phenothiazin-2-yl)ethan-1-one 2-(1H-benzo[d]imidazol-2-yl)acetonitrile, quincilidin-3-one hydrochloride, 2-oxo-3-phenylpropanoic acid, thiazolidine-2,4-dione, 1,2-iminothiazolidin-4-one, 1,3-diphenylimidazolidine-2,4dione,2-methyl-2-phenyl-1,3-oxothiazolan-5-one).These compounds were screened for computational ADME and Lipinski's analysis followed by molecular docking and binding energy. The anticancer activities of the synthesized compounds were studied in breast (MCF-7). The molecular docking studies were found the oxolone moiety is a required common feature for good interaction and we found that compounds 2a, 2b, and 3 showed the highest activity toward breast cancer cell line. The structures of the new synthesized compounds were confirmed by 1 H-NMR, 13 C-NMR, IR, and MS spectroscopic methods.
A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dion... more A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4hydroxy-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)naphthalene-1,4-dione (7) and naphtho[2,3-b]furan-3,4,9(2H)-trione (6) based on lawsone 'that plays as important precursor' was synthesized by reaction with 1,3diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2chloroacetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds. Supplemental data for this article is available online at here.
in Wiley Online Library (wileyonlinelibrary.com). N-2-amino-4-(furan-2-yl)-5,6-dimethylnicotinoni... more in Wiley Online Library (wileyonlinelibrary.com). N-2-amino-4-(furan-2-yl)-5,6-dimethylnicotinonitrile (4) was utilized as key intermediate for the synthesis of some new, pyridopyrimidine, benzo[1,5][g]oxazocine, naphthoquinone, and isoindole derivatives. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1 H-NMR, and mass spectral data.
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