in Wiley Online Library (wileyonlinelibrary.com), 2019
Considering oxatriazino[a]isoindole as a wealthy structure for developing molecules of impressiv... more Considering oxatriazino[a]isoindole as a wealthy structure for developing molecules of impressive therapeutic potentials, some new oxatriazino[3,2-a]isoindoles analogs were synthesized. Thus, 3-mercapto-6H-[1,2,4,5]oxatriazino[3,2-a]isoindol-6-one (5), was prepared as one-pot three-components product and subjected to a series of manipulations including cycloaddition reactions to annulate a series of pharmacophoric motif conjugates. The structures of the newly synthesized compounds were elucidated based on their correct elemental and spectroscopic data.
Considering pteridine as a privileged structure for developing probes of impressive therapeutic p... more Considering pteridine as a privileged structure for developing probes of impressive therapeutic potentials, some new pteridine conjugates were synthesized by aminomethylation of benzopteridinethione with a variety of primary aromatic amines and formaldehyde solution (37%) through Mannich reaction. Proposed mechanism of formation of the synthesized compounds was discussed, and the structure of the newly synthesized compounds was elucidated based on their IR, 1H NMR, 13C NMR , mass spectral and elemental analysis. Furthermore, some selected compounds were evaluated in vitro for their anti-microbial activities; the preliminary data stated that, the majority of the tested compounds exhibited significant anti-microbial activity. Analogues 22, 23, 20, 19, 24 and 15 were found to be the most potent against the all tested microorganisms.
Herein, we reported the efficient synthesis of new azoles as bio-functional analogs, employing th... more Herein, we reported the efficient synthesis of new azoles as bio-functional analogs, employing the easily obtainable N-acetyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (1), as a versatile precursor. The structures of the newly synthesized compounds were elucidated based on their IR, 1H NMR, 13C NMR mass spectral and elemental analysis. Furthermore, some selected compounds were evaluated in vitro for their anti-microbial activities; The preliminary bioassay results indicate that, the majority of the tested compounds exhibited significant anti-microbial activity. Compounds 12, 11, 18, 30, 22, 3 and 2 were found to be the most potent against the tested microorganisms with minimum inhibitory concentration ≤ (12.25 µg/ mL), indicating that conjugates bearing thiazole moiety, as well as those with N-substituted electron-withdrawing groups, exhibited higher potency than the rest of other compounds
in Wiley Online Library (wileyonlinelibrary.com). In our approach to synthesize bioactive molecul... more in Wiley Online Library (wileyonlinelibrary.com). In our approach to synthesize bioactive molecules, a series of novel N-heterocycles were synthesized and evaluated for their in vitro antitumor activity against a panel of three human cancer cell lines, namely, human breast cancer cell line (MCF-7), human cervical cancer cell line (HeLa), and human prostate cancer PC-3. The majority of the tested compounds exhibited significant cytotoxic activity toward the tested tumor cell lines. Analogues 33, 34, 31, 38, 21, 23, 22, and 20 exhibited considerable cytotoxic activities comparable with standard drug 5-fuorouracil. Compound 33 displayed superior cytotoxicity with IC 50 value of 4.12 ± 1.21 μg/mL against HeLa tumor cell line.
Considering quinoxaline as a privileged structure for developing probes of impressive therapeutic... more Considering quinoxaline as a privileged structure for developing probes of impressive therapeutic potentials, some new azole and azine conjugates of quinoxaline were synthesized. Thus, ethyl 3-amino-1,4- dihydroquinoxaline-2-carboxylate (2) was prepared as one-pot three-component product and incorporated in a series of manipulations including cyclocondensation reactions to afford a series of pharmacophoric motif conjugates 8–12, 14, 15–17, 20–23, 24–29, 30–37, and 38–43 in fair yields. The newly synthesized were characterized by IR, 1H NMR, 13C NMR, and mass spectral data.
Herein, we report the one-pot cyclization of Biginelli Adduct, ethyl 4-(2-hydroxyphenyl)-6-methyl... more Herein, we report the one-pot cyclization of Biginelli Adduct, ethyl 4-(2-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (I) to the oxygen-bridged adduct, ethyl 2-methyl-4-thioxo-3,4,5,6-tetrahydro-2H-2,6-methanobenzo[g] [1,3,5]oxadiazocine-11-carboxylate (II) in a high yield and purity under mild reaction condition using zinc(II) perchlorate hexahydrate as a highly efficient catalyst. The cyclic product (II) was characterized both in the solid state and in solution using FTeIR, 1 H NMR, and UVevisible spectroscopy. Theoretical calculations using density functional theory with B3LYP/ 6-311þþG(d,p) level were used to further investigate the structure properties. DFT calculations (gas phase) revealed the stability of cyclic compound II (3.45 kcal/mol) than compound I. In addition, the anticancer activity of II was investigated using MCF-7 human breast cell line. The results revealed a moderate activity with 223.55 mg/ml IC 50 value.
– 2-(5,10-Dioxo-1,4-diphenyl-3,4-dihydrobenzo[g]quinoxalin-2(1H,5H, 10H)-ylidene)hydrazinecarboth... more – 2-(5,10-Dioxo-1,4-diphenyl-3,4-dihydrobenzo[g]quinoxalin-2(1H,5H, 10H)-ylidene)hydrazinecarbothioamide (4) and 2-((4-oxothiazolidin-2-ylidene)-hydrazono)-1,4-diphenyl-1,2,3,4-tetrahydrobenzo[g]quinoxaline-5,10-dione (5), were prepared and utilized as versatile building blocks, via incorporating in series of conversions including cyclocondensation reactions to afford a series of four and fivepharmacophoricmotif conjugates 10, 13, 18, 20, 21, 25, 30, 31, 32, 33 and 34 in fair yields. In continuation of our research work 112 aiming at merging of chemical architectures of significant pharmacophoric activities for developing verifications of impressive therapeutic potentials, in particular against profound diseases; we initiated a program aiming at merging of p-quinone, azole and thiazole moieties in single architectures. Conjugates with the quinoid structure establish one of the most delightful classes of compounds in organic chemistry. Their syntheses as well as their assorted chemical and physical properties have been collected in the two volumes of Patai's series the chemistry of functional groups. 13 The chemistry of
in Wiley Online Library (wileyonlinelibrary.com), 2019
Considering oxatriazino[a]isoindole as a wealthy structure for developing molecules of impressiv... more Considering oxatriazino[a]isoindole as a wealthy structure for developing molecules of impressive therapeutic potentials, some new oxatriazino[3,2-a]isoindoles analogs were synthesized. Thus, 3-mercapto-6H-[1,2,4,5]oxatriazino[3,2-a]isoindol-6-one (5), was prepared as one-pot three-components product and subjected to a series of manipulations including cycloaddition reactions to annulate a series of pharmacophoric motif conjugates. The structures of the newly synthesized compounds were elucidated based on their correct elemental and spectroscopic data.
Considering pteridine as a privileged structure for developing probes of impressive therapeutic p... more Considering pteridine as a privileged structure for developing probes of impressive therapeutic potentials, some new pteridine conjugates were synthesized by aminomethylation of benzopteridinethione with a variety of primary aromatic amines and formaldehyde solution (37%) through Mannich reaction. Proposed mechanism of formation of the synthesized compounds was discussed, and the structure of the newly synthesized compounds was elucidated based on their IR, 1H NMR, 13C NMR , mass spectral and elemental analysis. Furthermore, some selected compounds were evaluated in vitro for their anti-microbial activities; the preliminary data stated that, the majority of the tested compounds exhibited significant anti-microbial activity. Analogues 22, 23, 20, 19, 24 and 15 were found to be the most potent against the all tested microorganisms.
Herein, we reported the efficient synthesis of new azoles as bio-functional analogs, employing th... more Herein, we reported the efficient synthesis of new azoles as bio-functional analogs, employing the easily obtainable N-acetyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (1), as a versatile precursor. The structures of the newly synthesized compounds were elucidated based on their IR, 1H NMR, 13C NMR mass spectral and elemental analysis. Furthermore, some selected compounds were evaluated in vitro for their anti-microbial activities; The preliminary bioassay results indicate that, the majority of the tested compounds exhibited significant anti-microbial activity. Compounds 12, 11, 18, 30, 22, 3 and 2 were found to be the most potent against the tested microorganisms with minimum inhibitory concentration ≤ (12.25 µg/ mL), indicating that conjugates bearing thiazole moiety, as well as those with N-substituted electron-withdrawing groups, exhibited higher potency than the rest of other compounds
in Wiley Online Library (wileyonlinelibrary.com). In our approach to synthesize bioactive molecul... more in Wiley Online Library (wileyonlinelibrary.com). In our approach to synthesize bioactive molecules, a series of novel N-heterocycles were synthesized and evaluated for their in vitro antitumor activity against a panel of three human cancer cell lines, namely, human breast cancer cell line (MCF-7), human cervical cancer cell line (HeLa), and human prostate cancer PC-3. The majority of the tested compounds exhibited significant cytotoxic activity toward the tested tumor cell lines. Analogues 33, 34, 31, 38, 21, 23, 22, and 20 exhibited considerable cytotoxic activities comparable with standard drug 5-fuorouracil. Compound 33 displayed superior cytotoxicity with IC 50 value of 4.12 ± 1.21 μg/mL against HeLa tumor cell line.
Considering quinoxaline as a privileged structure for developing probes of impressive therapeutic... more Considering quinoxaline as a privileged structure for developing probes of impressive therapeutic potentials, some new azole and azine conjugates of quinoxaline were synthesized. Thus, ethyl 3-amino-1,4- dihydroquinoxaline-2-carboxylate (2) was prepared as one-pot three-component product and incorporated in a series of manipulations including cyclocondensation reactions to afford a series of pharmacophoric motif conjugates 8–12, 14, 15–17, 20–23, 24–29, 30–37, and 38–43 in fair yields. The newly synthesized were characterized by IR, 1H NMR, 13C NMR, and mass spectral data.
Herein, we report the one-pot cyclization of Biginelli Adduct, ethyl 4-(2-hydroxyphenyl)-6-methyl... more Herein, we report the one-pot cyclization of Biginelli Adduct, ethyl 4-(2-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (I) to the oxygen-bridged adduct, ethyl 2-methyl-4-thioxo-3,4,5,6-tetrahydro-2H-2,6-methanobenzo[g] [1,3,5]oxadiazocine-11-carboxylate (II) in a high yield and purity under mild reaction condition using zinc(II) perchlorate hexahydrate as a highly efficient catalyst. The cyclic product (II) was characterized both in the solid state and in solution using FTeIR, 1 H NMR, and UVevisible spectroscopy. Theoretical calculations using density functional theory with B3LYP/ 6-311þþG(d,p) level were used to further investigate the structure properties. DFT calculations (gas phase) revealed the stability of cyclic compound II (3.45 kcal/mol) than compound I. In addition, the anticancer activity of II was investigated using MCF-7 human breast cell line. The results revealed a moderate activity with 223.55 mg/ml IC 50 value.
– 2-(5,10-Dioxo-1,4-diphenyl-3,4-dihydrobenzo[g]quinoxalin-2(1H,5H, 10H)-ylidene)hydrazinecarboth... more – 2-(5,10-Dioxo-1,4-diphenyl-3,4-dihydrobenzo[g]quinoxalin-2(1H,5H, 10H)-ylidene)hydrazinecarbothioamide (4) and 2-((4-oxothiazolidin-2-ylidene)-hydrazono)-1,4-diphenyl-1,2,3,4-tetrahydrobenzo[g]quinoxaline-5,10-dione (5), were prepared and utilized as versatile building blocks, via incorporating in series of conversions including cyclocondensation reactions to afford a series of four and fivepharmacophoricmotif conjugates 10, 13, 18, 20, 21, 25, 30, 31, 32, 33 and 34 in fair yields. In continuation of our research work 112 aiming at merging of chemical architectures of significant pharmacophoric activities for developing verifications of impressive therapeutic potentials, in particular against profound diseases; we initiated a program aiming at merging of p-quinone, azole and thiazole moieties in single architectures. Conjugates with the quinoid structure establish one of the most delightful classes of compounds in organic chemistry. Their syntheses as well as their assorted chemical and physical properties have been collected in the two volumes of Patai's series the chemistry of functional groups. 13 The chemistry of
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Papers by Islam H El-Azab
dihydroquinoxaline-2-carboxylate (2) was prepared as one-pot three-component product and incorporated in a series of manipulations including cyclocondensation reactions to afford a series of pharmacophoric motif conjugates 8–12, 14, 15–17, 20–23, 24–29, 30–37, and 38–43 in fair yields. The newly synthesized were characterized by IR, 1H NMR, 13C NMR, and mass spectral data.
dihydroquinoxaline-2-carboxylate (2) was prepared as one-pot three-component product and incorporated in a series of manipulations including cyclocondensation reactions to afford a series of pharmacophoric motif conjugates 8–12, 14, 15–17, 20–23, 24–29, 30–37, and 38–43 in fair yields. The newly synthesized were characterized by IR, 1H NMR, 13C NMR, and mass spectral data.