Mohammad Sayed Alam
Jagannath University
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Featured researches published by Mohammad Sayed Alam.
Bioorganic & Medicinal Chemistry | 2012
Mohammad Sayed Alam; Jung-Hyun Choi; Dong-Ung Lee
4-Aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole-3-one) and its analogues have been found to be compounds of interest for their anti-inflammatory, analgesic, antiviral, antipyretic, antirheumatic and antimicrobial activities. In the present study, Schiff base analogues of 4-aminoantipyrine were synthesized by the condensation reaction with substituted benzaldehydes and then evaluated for their antioxidant and anti-inflammatory activities. From among the synthesized compounds (3a-m, 4 and 5), 3 k and 3f exhibited the highest antioxidant activity followed by 3g, 3l, 3c, 3i, 5, 3m and 3h. The IC(50) values for compounds 3 k and 3f were found to be 0.44 and 0.93 μM, respectively, comparable to that of ascorbic acid (IC(50) 0.41 μM), a standard antioxidant agent. From the comparisons between the hydroxylated and methoxylated compounds, the rank order of antioxidant activity for the products resulting from benzylidene phenyl ring substitution was 2,4,6-OH>3,4-OH>3-OMe-4-OH>3,5-OMe-4-OH>2,4-OH>3-Me-4-OMe>3,4-OMe>4-OMe>4-OH. The structure-activity relationship study revealed that the position and nature of the substituted group on the benzylidene phenyl ring of the Schiff base analogues of 4-aminoantipyrine play an important role in their antioxidant activity. The anti-inflammatory activity of 3f, which also exhibited excellent antioxidant activity, was evaluated in terms of its inhibition of NO production, an inflammatory modulator, in LPS pretreated RAW 264.7 cells using the Griess method. We also examined whether or not this compound had effect on iNOS and COX-2 mRNA expression in RAW 264.7 cells. It was observed that compound 3f significantly reduced NO production and inhibited LPS-stimulated iNOS and COX-2 mRNA levels in a dose-dependent manner. Overall, 3f showed promising antioxidant and anti-inflammatory activities and may be used as the lead compound in a future study.
European Journal of Medicinal Chemistry | 2013
Mohammad Sayed Alam; Young-Joo Nam; Dong-Ung Lee
In the present study, a series of (Z)-2,3-diphenylacrylonitrile analogs were synthesized and then evaluated in terms of their cytotoxic activities against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15), as well as anti-microbial activities against three microbes, e.g. Staphylococcus aureus, Salmonella typhi, and Aspergillus niger. The title compounds were synthesized by Knoevenagel condensation reaction of benzyl cyanide or p-nitrobenzyl cyanide with substituted benzaldehydes in good yields. Most of the compounds exhibited significant suppressive activities against the growth of all cancer cell lines. Compound 3c was most active in inhibiting the growth of A549, SK-OV-3, SK-MEL-2, and HCT15 cells lines with IC50 values of 0.57, 0.14, 0.65, and 0.34 mg/mL, respectively, followed by compounds 3f, 3i, and 3h. Compound 3c exhibited 2.4 times greater cytotoxic activity against HCT15 cells, whereas it showed similar potency against SK-OV-3 cells to that of the standard anti-cancer agent doxorubicin. Structure-activity relationship study revealed that electron-donating groups at the para-position of phenyl ring B were more favorable for improved cytotoxic activity, whereas the presence of electron-withdrawing groups was unfavorable compare to unsubstituted acrylonitrile. An optimal electron density on phenyl ring A of (Z)-2,3-diphenylacrylonitrile analogs was crucial for their cytotoxic activities against human cancer cell lines used in the present study. Qualitative structure-cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between calculated polar surface area (PSA), a lipophobic parameter, and cytotoxic activity was found. Moreover, all compounds showed significant anti-bacterial activities against S. typhi, whereas compound 3k showed potent inhibition against both S. aureus and S. typhi bacterial strains.
Bioorganic & Medicinal Chemistry | 2017
Mohammad Sayed Alam; Sang-Un Choi; Dong-Ung Lee
A series of novel salicyl-hydrazone analogues were synthesized and evaluated for their in vitro cytotoxic activities in five human cancer cell lines, namely, lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), colon cancer (HCT15) and pancreatic cancer (MIA-PaCa-2) cells, and for their in vitro tropomyosin receptor kinase A (TrkA) inhibitory activities. Each of the compounds showed significant cytotoxicity against all cancer cells. Compound 3i was found to be most potent against all cancer cell lines with IC50 values of 2.46 (A549), 0.87 (SK-OV-3), 1.43 (SK-MEL-2), 0.89 (HCT15), and 0.48μM (MIA-PaCa-2), followed by compound 3l. Cytotoxicity of 3i was similar to that of doxorubicin (0.87μM) against HCT15 cells. Compounds 3i and 3l also showed highest TrkA inhibitory activities with IC50 values of 0.231 and 0.380μM, respectively. A SAR study of the series revealed that compounds with hydroxyl groups showed better cytotoxicity and TrkA inhibitory potency (in the following order 2,4-OH>2,3,4-OH>3,4-OH>4-OH) than compounds possessing electron donating or withdrawing groups on the benzylidenephenyl ring. Docking studies of compounds 3i and 3l conducted on the crystal structure of TrkA receptor (a promising target for anticancer agents) showed both had a high docking score and similar order of experimental TrkA inhibitory activities. The formation of several hydrogen bonds involving N and O containing moieties contributed most significantly to ligand binding and stabilization at the active site of the receptor. In addition, ligand-receptor complexes were further stabilized by π-cation, π-anion, amide-π stacked, and van der Waals interactions. Conformational analyses showed ligand molecules adopted similar conformations at the receptor active site during interactions, but that the low energy optimized conformations of compounds 3i and 3l differed.
Journal of The Korean Society for Applied Biological Chemistry | 2014
Mohammad Sayed Alam; Sanjit Saha; Dong-Ung Lee
Antimicrobial and cytotoxic activities of the leaves of Leucas aspera, a medicinal plant found in Bangladesh, were evaluated. In vitro bactericidal activity was screened against ten pathogenic or food poisoning bacteria using the disc diffusion method. In vivo cytotoxicity was examined against Artemia salina (brine shrimp nauplii). The dichloromethane fraction of the methanol extract of the leaves of Leucas aspera had strong antibacterial and cytotoxic effects, whereas the ethyl acetate fraction exhibited significant bactericidal activity against only Gram-positive bacterial strains. The active constituents, α-amyrin and α-tocopherol, were isolated for the first time from the dichloromethane fraction and their cytotoxic effects against A. salina were significant with LC50 values of 241 and 195 ppm, respectively.
Chemical & Pharmaceutical Bulletin | 2011
Mohammad Sayed Alam; Lijun Liu; Yong-Eok Lee; Dong-Ung Lee
Journal of Chemical Crystallography | 2012
Mohammad Sayed Alam; Dong-Ung Lee
Bulletin of The Korean Chemical Society | 2012
Lijun Liu; Mohammad Sayed Alam; Dong-Ung Lee
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy | 2015
Mohammad Sayed Alam; Dong-Ung Lee
Journal of Molecular Structure | 2017
Mohammad Sayed Alam; Dong-Ung Lee
Archives of Pharmacal Research | 2016
Mohammad Sayed Alam; Dong-Ung Lee