Hayun Hayun
University of Indonesia, Pharmacy, Faculty Member
- As a lecturer in the Universitas Indonesia since 1988edit
Asam salisilat memiliki aktivitas anti-inflamasi dan antioksidan, namun dapat menimbulkan efek samping pada saluran cerna. Modifikasi gugus karboksilat senyawa tersebut menjadi turunan amida dapat menjadi solusi untuk mengatasi... more
Asam salisilat memiliki aktivitas anti-inflamasi dan antioksidan, namun dapat menimbulkan efek samping pada saluran cerna. Modifikasi gugus karboksilat senyawa tersebut menjadi turunan amida dapat menjadi solusi untuk mengatasi kekurangannya. Pada penelitian ini dilakukan sintesis senyawa analog salisilamida,2‐hidroksi‐N‐(piridin‐2‐il)benzamida (1) dan turunan basa Mannich-nya (2a-b). Berdasarkan uji aktivitas penghambatan denaturasi protein senyawa sintesis menunjukkan aktivitas antiinflamasi, dengan rentang nilai IC50 = 0.121-0.145 mM. Aktivitas tersebut lebih rendah dibandingkan piroksikam yang digunakan sebagai senyawa standar (IC50 = 0,0073 mM). Hasil penambatan molekuler menunjukkan bahwa rasio afinitas ikatan COX-2/COX-1 dan interaksi ligan semua senyawa hasil sintesis tidak selektif terhadap COX-2.
Research Interests:
Tyrosinase is an enzyme that catalyzes melanin biosynthesis. Recently, it has become a popular target for developing cosmetics as a skin lightening or skin whitening agent, an anti-aging agent, an anti-wrinkle agent, and other... more
Tyrosinase is an enzyme that catalyzes melanin biosynthesis. Recently, it has become a popular target for developing cosmetics as a skin lightening or skin whitening agent, an anti-aging agent, an anti-wrinkle agent, and other therapeutics for skin disorders. Based on the previous reports, many compounds have been developed and designed to be tyrosinase inhibitors, including ferulic acid and cinnamic acid derivatives. However, until now, the use of these compounds in commercial cosmetic products has been limited. It may be due to chemical instability, lipophilicity, and poor efficacy. In this review, we assessed research studies to discuss the structure-activity of ferulic acid and its derivatives, which can contribute to their better efficacy as anti-tyrosinases. Either ferulic acid as a single compound or its hybridization with other cinnamic acid derivatives proved beneficial in designing tyrosinase inhibitors as active functional groups. The structure-activity of the phenyl ring's substituent improved inhibitory effects on monophenolase activity, especially the halogen substituent. In addition, the alkyl chain length and other functional groups linked, such as amide and acetyl groups, could alter the inhibitory properties, including hydrophobicity, to produce a more stable complex ligand-receptor.
Research Interests:
We prepared six novel curcumin indazole analogs and confirmed their structures by Fourier transform infrared, nuclear magnetic resonance, and mass spectra. Subsequently, their cytotoxicity was tested using the Michigan Cancer Foundation... more
We prepared six novel curcumin indazole analogs and confirmed their structures by Fourier transform infrared, nuclear magnetic resonance, and mass spectra. Subsequently, their cytotoxicity was tested using the Michigan Cancer Foundation (MCF-7) proliferation assay against the Michigan Cancer Foundation (MCF-7), HeLa, WiDr, and vero cell lines. This study found that the compounds we prepared were more active against WiDr than HeLa and MCF-7. The activity of 3b, 3c, 3d, and 5a against WiDr (colorectal carcinoma) cells was higher than curcumin and tamoxifen. Their selectivity index (SI) indicated that several synthesized compounds showed more selectivity (SI value > 2) than positive controls tamoxifen and doxorubicin (SI value < 2.00). Three compounds (3a, 3b, and 3c) showed high SI against WiDr cells (3.74, 5.27, and 4.39, respectively). Compound 3b produced the highest cytotoxic activity, especially against WiDr cells (IC 50 = 27.20 µM) with excellent selectivity (SI = 5.27). Therefore, the compound should be further developed as an anticancer agent for colorectal carcinoma.
Allantoin is a compound contained in comfrey leaves. This research aims to obtain optimal condition parameters of ionic liquid-ultrasound-assisted extraction (IL-UAE) comfrey leaves to attract allantoin compounds. Comfrey leaves are... more
Allantoin is a compound contained in comfrey leaves. This research aims to obtain optimal condition parameters of ionic liquid-ultrasound-assisted extraction (IL-UAE) comfrey leaves to attract allantoin compounds. Comfrey leaves are extracted with eight ionic liquids by ultrasound-assisted extraction (UAE) and screened for allantoin levels. The best ionic liquid from the screening results is optimized response surface methodology (RSM) with Box-Behnken design with three factors and three levels to determine the optimum extraction conditions for allantoin levels. Determination of levels is carried out with TLC densitometry. The results of the IL screening obtained [HMIM]Cl as the best IL in the evaluation of optimization of extraction parameters. The results of optimization of extraction condition parameters [HMIM]Cl obtained the highest allantoin levels on the sixth run of 306.396 μg / g of powder at the ratio of solvents to powders of 10 mL / g, concentrations [HMIM] Cl 1 mol / L ...
Research Interests:
Comfrey (Symphytum officinale L.) contains rosmarinic acid which has different pharmacological activities, such as antioxidant and anti-inflammatory activities. However, the medicinal use of comfrey is limited by the hepatotoxic effect of... more
Comfrey (Symphytum officinale L.) contains rosmarinic acid which has different pharmacological activities, such as antioxidant and anti-inflammatory activities. However, the medicinal use of comfrey is limited by the hepatotoxic effect of lycopsamine in comfrey, which overshadows the health benefits of rosmarinic acid. Natural deep eutectic solvents (NADES) have a wide range of extraction properties, that provides a new approach to the detoxification of comfrey. In the present study, betaine-based and choline chloride-based NADES were screened for selective extraction of rosmarinic acid over lycopsamine. Ultrasonication was used in conjunction with NADES extraction. The chemical profile of the NADES extracts on antioxidant, anti-inflammatory and hepatotoxic activities were investigated using some chemical reagents. Betaine-urea (1:2 molar ratio, 50% water) obtained the highest content of rosmarinic acid and a low level of lycopsamine (1.934 and 0.018 mg/g, respectively). Betaine-ure...
Research Interests:
Research Interests:
Research Interests:
New decahydroacridine-1,8-dione derivatives have been synthesized from 3-aminocyclohex-2-en-1-one. The compounds were characterized based on spectroscopic data and assessed their antioxidant and anti-inflammatory properties both in-vitro... more
New decahydroacridine-1,8-dione derivatives have been synthesized from 3-aminocyclohex-2-en-1-one. The compounds were characterized based on spectroscopic data and assessed their antioxidant and anti-inflammatory properties both in-vitro and in-silico. All the compounds exhibited poor in-vitro antioxidant activity but high in-vitro anti-inflammatory activity. An in-silico study using Autodock v 4.2 integrated LigandScout software 4.4.3. against the COX-1 (PBD ID: 1CQE) and COX-2 (PBD ID: 6COX) enzymes indicated that all the compounds could interact with both enzymes. Except for 3c against COX-1, the compounds’ interaction with both enzymes exhibited binding energy lower than diclofenac and curcumin. The results confirm that the compounds have a high potential to be antiinflammatory agents and deserve further development.
Research Interests:
Spectral data of the title compound.
Objective: This present study was intended to design sustained release tablet containing diclofenac sodium using a matrix of excipient co-processed xanthan gum-crosslinked amylose. Methods: In the previous study, xanthan gum and amylose... more
Objective: This present study was intended to design sustained release tablet containing diclofenac sodium using a matrix of excipient co-processed xanthan gum-crosslinked amylose. Methods: In the previous study, xanthan gum and amylose have been physically and chemically modified by the co-processed and crosslinking method, resulting co-processed excipient xanthan gum-crosslinked amylose are Co-CLA6-XG and Co-CLA12-XG (method A); CL6-Co-A-XG and CL12-Co-A-XG (method B) with each ratio 1:1, 1:2 and 2:1. All excipients had a good swelling index, high viscosity and good gel strength, good characteristics to be used as a matrix for sustained release tablet dosage form. In this study, a tablet with excipient Co-CLA6-XG, Co-CLA12-XG, CL6-Co-A-XG and CL12-Co-A-XG were formulated by direct compression method. The prepared formulations were evaluated for weight variation, thickness, and diameter, hardness, friability, drug content estimation, swelling index, in vitro drug release are within...
Research Interests:
Research Interests:
Research Interests:
Using heat-induced protein denaturation technique, a series of novel synthesized 1,5-diarylpyrazole compounds, namely 2-methoxy-4-(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol (1) and its aminomethyl derivatives (2a-e) were evaluated for... more
Using heat-induced protein denaturation technique, a series of novel synthesized 1,5-diarylpyrazole compounds, namely 2-methoxy-4-(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol (1) and its aminomethyl derivatives (2a-e) were evaluated for their anti-inflammatory potentiality. The structures of the synthesized compounds were elucidated using FTIR, NMR (1H & 13C) and mass spectral data. The study found that the activity of aminomethyl derivatives (2a-e) was higher than that of parent compound 1. In this series, aminomethyl derivatives bearing dimethylamino-methyl, diethylaminomethyl and pyrrolidinomethyl moieties (2a, 2c and 2e, respectively) were more active than diclofenac sodium, which was used as a standard. A study on the structure-activity relationship (SAR) suggested that the activity of aminomethyl moiety of the compound was influenced by its pKa value. Thus, novel compounds act as potential anti-inflammatory agents.
Research Interests:
Research Interests:
We synthesized a novel compound, 5-(6-hydroxy-6-methyl-5-oxoheptan-2-yl)-2-methylphenyl acetate, in a good yield by oxidation of 1-O-acetyl-xanthorrizol using potassium permanganate in acidic condition. The structure was elucidated by... more
We synthesized a novel compound, 5-(6-hydroxy-6-methyl-5-oxoheptan-2-yl)-2-methylphenyl acetate, in a good yield by oxidation of 1-O-acetyl-xanthorrizol using potassium permanganate in acidic condition. The structure was elucidated by Fourier Transform Infrared (FTIR), 1H-Nuclear Magnetic Resonance (NMR) and 13C-NMR, two-dimensional (2D)-HSQC, Distortionless Enhancement by Polarization Transfer (DEPT), 2D-Heteronuclear Multiple Bond Correlation (HMBC), and High-Resolution Mass Spectra (HRMS) spectral data.
Research Interests:
Research Interests:
Research Interests:
Research Interests:
Research Interests:
Research Interests:
Research Interests:
Research Interests:
Research Interests:
A series of novel asymmetrical mono-carbonyl analogs of curcumin (AMACs) were 12 synthesized and evaluated for cytotoxic activity using the brine shrimp lethality test (BSLT) and the 13 methyl thiazolyl tetrazolium assay against Vero,... more
A series of novel asymmetrical mono-carbonyl analogs of curcumin (AMACs) were 12 synthesized and evaluated for cytotoxic activity using the brine shrimp lethality test (BSLT) and the 13 methyl thiazolyl tetrazolium assay against Vero, HeLa, and MCF7 cell lines. The structures of the 14 synthesized compounds were confirmed by Fourier transform infrared spectrophotometry (FTIR), 15 1H-nuclear magnetic resonance (NMR), 13C-NMR, and mass spectral data. The results of the 16 cytotoxicity evaluation showed that the synthesized compounds exhibited moderate to very high 17 toxic activity in BSLT, requiring a concentration of 13.06–714.49 μg/mL to kill half the population. 18 Most of the compound exhibited cytotoxic activity against HeLa cell lines, comparable to the 19 activity of cisplatin with a concentration of the synthesized compounds required to inhibit 50% of 20 the growth of the cell lines (IC50) value of 40.65–95.55 μM, and most of the compounds tested 21 against MCF7 cell lines ex...
A series of diethylamine Mannich base of asymmetrical mono-carbonyl analogs of 10 curcumin (AMACs) were synthesized and evaluated for cytotoxic activity against Hela Cell lines. 11 The structures of the synthesized compounds were... more
A series of diethylamine Mannich base of asymmetrical mono-carbonyl analogs of 10 curcumin (AMACs) were synthesized and evaluated for cytotoxic activity against Hela Cell lines. 11 The structures of the synthesized compounds were confirmed on the basis of FTIR, 1H-NMR, 12 13C-NMR and mass spectral data. Preliminary cytotoxic test using BSLT showed that all the 13 synthesized compounds exhibited more potent cytotoxic activity than that of curcumin. While 14 results of MTT assay showed that all the synthesized compounds exhibited more potent 15 antiproliferative activity against HeLa cell lines than that of cisplatin. Compound 2b exhibited as 16 the most potent compound of the series. Compound 2a, 2b, 2c, and 2f had IC50 (μM) less than that 17 of compound 1a, 1b, 1c and 1f indicating that the addition of diethylamine Mannich base improves 18 the antiproliferative activity of the parent compound. 19
The study of synthesis and antibacterial activity test of N,N'-divanilidene-ethylendiamine was performed. N,N'-divanilidene-ethylendiamine was synthesized by reacting vaniline with ethylendiamine in ethanol pH 1, and the structure... more
The study of synthesis and antibacterial activity test of N,N'-divanilidene-ethylendiamine was performed. N,N'-divanilidene-ethylendiamine was synthesized by reacting vaniline with ethylendiamine in ethanol pH 1, and the structure was elucidated based on IR and 1H-NMR spectra data. Antibacterial activity test was performed using minimum inhibition concentration method (MIC) against Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, and Escherichia coli ATCC 25922. The results showed that N,N'-divanilidene-ethylendiamine has antibacterial activity with MIC of 2 mg/mL against the the bacteria.
Research Interests:
Nitrosodimethylamine is a carcinogenic compound which can be formed from the reaction of nitrite and dimethylamine that is found in food. Nitrosodimethylamineis activated in liver and alkylates the DNA base and producing a DNA adductssuch... more
Nitrosodimethylamine is a carcinogenic compound which can be formed from the reaction of nitrite and dimethylamine that is found in food. Nitrosodimethylamineis activated in liver and alkylates the DNA base and producing a DNA adductssuch as O6-methylguanine and N7-methylguanine that have a role incarcinogenesis. In this research, DNA was isolated from ratrs blood which waspreviously given nitrosodimethylaminers precursor, sodium nitrite anddimethylamine. DNA adducts can be obtained from hydrolysis in hydrochloricacid 0.1 N for 30 minutes at 7000C. Then the adducts were analyzed using High Performance Liquid Chromatography (HPLC), with a strong cation exchangecolumn (Supelcosil LC-SCX, 5 mm, 250 x 4.6 mm), mobile phase consisting ofammonium phosphate with a final concentration of 40 mM, pH 3.00, flow rate 1.5mL/minute, column temperature 30oC and detected at exitation wavelength 286 nm and emission wavelength 366 nm. This method gave an acceptable validation result according to accu...
Research Interests:
The determination of triprolidine hydrochloride and pseudoephedrine hydrochloride in anti influenza tablet has been performed using derivative spectrophotometry method. Triprolidine hydrochloride and pseudoephedrine hydrochloride were... more
The determination of triprolidine hydrochloride and pseudoephedrine hydrochloride in anti influenza tablet has been performed using derivative spectrophotometry method. Triprolidine hydrochloride and pseudoephedrine hydrochloride were determined by measuring the first derivative ratio amplitudes, at 227,6 nm (zero crossing for pseudoephedrine hydrochloride) and at 230,0 nm (zero crossing for triprolidine hydrochloride) respectively. The linear calibration graphs were obtained for 5-50 ppm of triprolidine hydrochloride and for 100-800 ppm of pseudoephedrine hydrochloride. The results showed that the method is rapid, simple and can be applied successfully to assay simultaneously of two components in tablet preparation. Keywords : triprolidine hydrochloride, pseudoephedrine hydrochloride, derivative spectrophotometry, zero crossing.
Research Interests:
Research Interests:
Indazole derivatives are well known to have various pharmacological activities. We synthesized a novel derivative of indazole, namely (7E)-3-(4-methoxyphenyl)-7-[(4-methoxyphenyl)methylidene]-4,5,6,7-tetrahydro-3aH-indazole by... more
Indazole derivatives are well known to have various pharmacological activities. We synthesized a novel derivative of indazole, namely (7E)-3-(4-methoxyphenyl)-7-[(4-methoxyphenyl)methylidene]-4,5,6,7-tetrahydro-3aH-indazole by condensation reaction between 3-(4-methoxyphenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole and 4-methoxy-benzaldehyde in good yield (61%).
The estrogen receptor alpha (ERα) plays an important role in breast development and pro-proliferation signal activation in the normal and cancerous breast. The ERα inhibitors were potentially active as cytotoxic agents against breast... more
The estrogen receptor alpha (ERα) plays an important role in breast development and pro-proliferation signal activation in the normal and cancerous breast. The ERα inhibitors were potentially active as cytotoxic agents against breast cancer. This study was conducted in order to find Asymmetrical Hexahydro-2H-Indazole Analogs of Curcumin (AIACs) as hits of ERα inhibitor. A training set of 17 selected ERα inhibitors was used to create 10 pharmacophore models using LigandScout 4.2. The pharmacophore models were validated using 383 active compounds as positive data and 20674 decoys as negative data obtained from DUD.E. Model 2 was found as the best pharmacophore model and consisted of three types of pharmacophore features, viz. one hydrophobic, one hydrogen bond acceptor, and aromatic interactions. Model 2 was utilized for ligand-based virtual screening 186 of AIACs, AMACs, intermediates, and Mannich base derivative compounds. The hits obtained were further screened using molecular dock...
Objective: Xanthorrhizol is known to have anti-inflammatory activity. However, new xanthorrhizol derivatives with improved anti-inflammatoryactivity and reduced toxicity are needed.Methods: In this study, the derivatives of xanthorrhizol... more
Objective: Xanthorrhizol is known to have anti-inflammatory activity. However, new xanthorrhizol derivatives with improved anti-inflammatoryactivity and reduced toxicity are needed.Methods: In this study, the derivatives of xanthorrhizol were synthesized and spectroscopically characterized, and their inhibitory activities againstnitric oxide (NO) production were evaluated in RAW 264.7 macrophage cells.Results: The first stage of synthesis produced compounds 2a and 2b in 58.49% and 63.26% yields, respectively. Compounds 2a and 2b were oxidizedusing potassium permanganate, giving compounds 3a and 3b in yields of 51.92% and 43.78%, respectively. Compounds 1, 2a, 3a, and 3b alongwith diclofenac sodium (the positive control) exhibited IC50 values for NO production of 31.82, 73.85, 354.05, 97.19, and 78.43 μM, respectively. Incontrast, compound 2b did not show any inhibitory activity. Based on cytotoxicity assay, compounds 1, 2a, 2b, 3a, 3b, and diclofenac sodium had LD50values of 30.97, ...
Objective: Osteoarthritis can be treated by taking oral supplements containing compounds that can nourish bones and joints such as hyaluronic acid,methylsulfonylmethane (MSM), chondroitin, glucosamine, and collagen. This study aimed to... more
Objective: Osteoarthritis can be treated by taking oral supplements containing compounds that can nourish bones and joints such as hyaluronic acid,methylsulfonylmethane (MSM), chondroitin, glucosamine, and collagen. This study aimed to develop and validate tests for analyzing two compounds,namely, hyaluronic acid and MSM, simultaneously and to determine both their levels in a mixed sample.Methods: Hyaluronic acid derivatization was carried out using fluorenylmethyloxycarbonyl chloride and then analyzed by liquid chromatographywith fluorescence detection, while MSM was analyzed using gas chromatography. After the development of optimal conditions for each separation,system suitability tests were developed and calibration curves used for tests of accuracy and precision as well as for level determination. Hyaluronicwas detected at an excitation wavelength of 255 nm and emission wavelength of 330 nm. The mobile phase used was acetonitrile-acetate pH 4.2 (1: 4)with a flow rate of 1.0 mL/...
Jamu merupakan obat tradisional yang banyak digunakan oleh masyarakat Indonesia untuk pencegahan, pemeliharan dan pengobatan penyakit. Obat tradisional mengandung bahan tumbuhan atau hasil sarian atau campurannya. Praktek penambahan bahan... more
Jamu merupakan obat tradisional yang banyak digunakan oleh masyarakat Indonesia untuk pencegahan, pemeliharan dan pengobatan penyakit. Obat tradisional mengandung bahan tumbuhan atau hasil sarian atau campurannya. Praktek penambahan bahan kimia obat (BKO) adalah perbuatan melawan hukum. Namun masih banyak ditemukan BKO dalam produk jamu, antara lain obat analgetika dan anti inflamasi. Penelitian ini bertujuan memperoleh metode KLT-densitometri yang tervalidasi, lebih sederhana dan lebih rendah biaya pelaksanaannya untuk menganalisis parasetamol, asam mefenamat dan ibuprofen dalam jamu “pegel linu”. Sampel diekstraksi dengan etanol, kemudian dipisahkan di atas lempeng KLT silika gel GF254 dengan fase gerak campuran kloroform-etanol (8:1) dan dianalisis dengan menggunakan KLT-densitometri. Metode mempunyai spesifisitas, dan linieritas yang memuaskan, dan memenuhi kriteria presisi dan akurasi pada konsentrasi 1500 ng/bercak untuk parasetamol, 1250 ng/bercak untuk asam mefenamat, dan ...
Objective: This study was aimed to obtain a new excipient that can be used as a polymer matrix for the formulation of controlled release dosage forms.Methods: This study used coprocessing and crosslinking methods on amylose and xanthan... more
Objective: This study was aimed to obtain a new excipient that can be used as a polymer matrix for the formulation of controlled release dosage forms.Methods: This study used coprocessing and crosslinking methods on amylose and xanthan gum (XG) to obtain a new excipient that can be usedfor controlled release matrix of pharmaceutical dosage forms. The coprocessing step was conducted by drum drying, and the crosslinking step wasprepared using 6 and 12% sodium trimetaphosphate (STMP). The produced novel excipients were characterized in terms of infrared (IR) spectrum,substitution degree, moisture content, swelling index, and gel strength.Results: Our results showed that amylose–XG excipients crosslinked using 6% STMP have greater gel strength and better swelling indexes thanexcipients crosslinked using 12% STMP. All coprocessed excipients exhibited no differences in their IR spectra, whereas the crosslinked excipientsdid, indicating a structural change due to the addition of phosphate ...
Research Interests:
The simple and rapid spectrophotometric methods were developed for analysis of hydrocortisone acetate in cream pharmaceutical formulations containing nipagin as preservative. Concentration of hydrocortisone acetate was determined by... more
The simple and rapid spectrophotometric methods were developed for analysis of hydrocortisone acetate in cream pharmaceutical formulations containing nipagin as preservative. Concentration of hydrocortisone acetate was determined by measuring the first derivative absorption (ratio amplitudes) at 257.0 nm (zero crossing for nipagin). The calibration graphs were linear over the range of 4.0-40.0 ppm of hydrocortisone acetate (r= 0.9999). The limit of detection (LOD) and the limit of quantitation (LOQ) were found to be 0.9617 ppm and 3.2050 ppm, respectively. This method had good precision (repeatability and intermediate precision) with RSD < 2.0% where as the means of the recovery data (accuracy) were 102.03±0.14% and 100.23±0.69% for hydrocortisone acetate cream 1% and 2.5%, respectively. The proposed method was applied for the determination of hydrocortisone acetate in three out of four commercial cream formulations samples and the results of label claim were 102.93±0.22%, 108.48...
Research Interests:
Research Interests:
In this study, an environmentally friendly extraction method for flavonoid compound from Ixora javanica , as a new raw material candidate for herbal medicine and cosmetics, was developed. The objectives of the present work were to provide... more
In this study, an environmentally friendly extraction method for flavonoid compound from Ixora javanica , as a new raw material candidate for herbal medicine and cosmetics, was developed. The objectives of the present work were to provide recommendations for the optimal extraction conditions and to investigate the effects of any extraction parameters on flavonoid yields from the I. javanica flower. The extraction process was performed using deep eutectic solvent (DES) (choline chloride and propylene glycol at molar ratio of 1 : 1) and the ultrasound-assisted extraction method. Both single-factor and response surface analyses using three-level and three-factor Box Behnken designs were conducted to obtain the optimum flavonoid concentrations. The results showed that the optimum extraction conditions for total flavonoids featured an extraction time of 40 min, 25% water content in DES and a solid-to-liquid ratio of 1 : 25 g ml −1 . An extract obtained under optimum extraction conditions...
Using heat-induced protein denaturation technique, a series of novel synthesized 1,5-diarylpyrazole compounds, namely 2-methoxy-4(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol (1) and its aminomethyl derivatives (2a-e) were evaluated for their... more
Using heat-induced protein denaturation technique, a series of novel synthesized 1,5-diarylpyrazole compounds, namely 2-methoxy-4(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol (1) and its aminomethyl derivatives (2a-e) were evaluated for their anti-inflammatory potentiality. The structures of the synthesized compounds were elucidated using FTIR, NMR (1H & 13C) and mass spectral data. The study found that the activity of aminomethyl derivatives (2a-e) was higher than that of parent compound 1. In this series, aminomethyl derivatives bearing dimethylamino-methyl, diethylaminomethyl and pyrrolidinomethyl moieties (2a, 2c and 2e, respectively) were more active than diclofenac sodium, which was used as a standard. A study on the structure-activity relationship (SAR) suggested that the activity of aminomethyl moiety of the compound was influenced by its pKa value. Thus, novel compounds act as potential anti-inflammatory agents.
Keywords: 1,5-Diarylpyrazole, Aminomethyl derivatives, Anti-inflammatory activity, Protein denaturation.
Keywords: 1,5-Diarylpyrazole, Aminomethyl derivatives, Anti-inflammatory activity, Protein denaturation.
Research Interests:
We synthesized five new Mannich bases compounds from vanillic acid and evaluated for their antioxidant activities using a free-radical DPPH and FRAP methods. The compounds' structures were confirmed based on infrared, proton NMR, carbon... more
We synthesized five new Mannich bases compounds from vanillic acid and evaluated for their antioxidant activities using a free-radical DPPH and FRAP methods. The compounds' structures were confirmed based on infrared, proton NMR, carbon NMR, and mass spectra. In this study, the compound 5-(pyrrolidin-1-ylmethyl)vanillic acid (2e) showed the best free-radical scavenger activity, while compound 2-[(diethylamino)methyl]vanillic acid (2c) showed the best as a ferric reductant. Mannich bases enhanced the free-radical scavenger activity but decreasing the ferric reduction potential of the parent compounds. The compounds were found to be moderate antioxidant agents.
Keywords: Vanillic Acid, Mannich Bases, Synthesis, Antioxidant, DPPH, FRAP.
Keywords: Vanillic Acid, Mannich Bases, Synthesis, Antioxidant, DPPH, FRAP.
Research Interests:
Objective: To further understand this compound, we synthesized and evaluated the antioxidant and anti-inflammatory activity of a series of its Mannich base derivatives. Methods: We synthesized the compounds via the previously reported... more
Objective: To further understand this compound, we synthesized and evaluated the antioxidant and anti-inflammatory activity of a series of its Mannich base derivatives. Methods: We synthesized the compounds via the previously reported Mannich reaction method. Their structures were elucidated by Fourier-transform infrared, 1 H-NMR, 13 C-NMR, and high-resolution mass spectra. The derivatives' anti-inflammatory and antioxidant activities were tested using the inhibition of protein denaturation method and the 2,2-diphenyl-2-picrylhydrazyl free radical scavenging assay. Results: The IC 50 values for the anti-inflammatory activity of the 2,6-dimethylmorpholine, pyrrolidine, 1-methylpiperazine, and dimethylamine Mannich base derivatives 2a-d were 10.67, 10.72, 37.75, and 1.93 µM, respectively; for (2E,6E)-2-({4-hydroxy-3-methoxyphenyl}methylidene)-6-(phenylmethylidene)cyclohexan-1-one (1), diclofenac sodium, and curcumin, the IC 50 values were 56.29, 1.52, and 8.43 µM, respectively. The IC 50 values for the antioxidant activity of compounds 2a-2d were 229.62, 57.29, 280.43, and 219.22 µM, respectively; for compound 1, quercetin, and curcumin, the IC 50 values were 144.22, 27.28, and 26.45 µM, respectively. Conclusion: Substituting Mannich bases into (2E,6E)-2-[(4-hydroxy-3-methoxyphenyl) methylidene]-6-(phenylmethylidene)cyclohexan-1-one enhanced its anti-inflammatory activity, but lowered its antioxidant activity. Compound 2d, (2E,6E)-2-({3-[(dimethylamino)methyl]-4-hydroxy-5-methoxyphenyl}methylidene)-6-(phenyl methylidene)cyclohexan-1-one, exhibited potent anti-inflammatory activity comparable to diclofenac sodium and four times higher than curcumin. However, further investigation of this compound's mechanism of action and toxicity is warranted.