Synthesis and biological profile of substituted benzimidazoles
Tóm tắt
A series of benzimidazole derivatives was developed and its chemical scaffolds were authenticated by NMR, IR, elemental analyses and physicochemical properties. The synthesized compounds were screened for their antimicrobial and antiproliferative activities. The synthesized benzimidazole compounds were evaluated for their antimicrobial activity using the tube dilution method and were found to exhibit good antimicrobial potential against selected Gram negative and positive bacterial and fungal species. The compounds were also assessed for their anticancer activity exhibited using the SRB assay and were found to elicit antiproliferative activity against MCF7 breast cancer cell line, which was comparable to the standard drug. Antimicrobial screening results indicated that compounds 1, 2 and 19 to be promising antimicrobial agents against selected microbial species and comparable to standard drugs which included norfloxacin and fluconazole. The anticancer screening results revealed that compounds, 12, 21, 22 and 29 to show the highest activity against MCF7 and their IC50 values were more potent than 5-fluorouracil.
Tài liệu tham khảo
Grossman TH, Bartels DJ, Mullin S, Gross CH, Parsons JD, Liao Y, Grillot AL, Stamos D, Olson ER, Charifson PS, Mani N (2007) Dual targeting of GyrBand ParE by a novel aminobenzimidazole class of antibacterial compounds. Antimicrob Agents Chemother 51:657–666
Hassan GS, Kadry HH, Abou-Seri SM, Ali MM, Mahmoud AEE (2011) Synthesis and in vitro cytotoxic activity of novel pyrazolo[3,4-d]pyrim.idines and related pyrazole hydrazones toward breast adenocarcinoma MCF-7 cell line. Bioorg Med Chem 19:6808–6817
Ozkay Y, Tunali Y, Karaca H, Isikdag I (2010) Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety. Eur J Med Chem 45:3293–3298
Arora RK, Kaur N, Bansaln Y, Bansal G (2014) Novel coumarin–benzimidazole derivatives as antioxidants and safer anti-inflammatory agents. Acta Pharm Sin B 4:368–375
Alasmary FA, Snelling AM, Alafeefy ME, Awaad S, Karodia N (2015) Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents. Antimicrob Agents Mol 20:15206–15223
Oh S, Kim S, Kong S, Yang G, Lee N, Han D, Goo J, Siqueira-Neto JL, Freitas-Junior LH, Song R (2014) Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2- a]benzimidazole derivatives against Leishmaniadonovani and Trypanosomacruzi. Eur J Med Chem 84:395–403
El-Gohary NS, Shaaban MI (2017) Synthesis and biological evaluation of a new series of benzimidazole derivatives as antimicrobial, antiquorum-sensing and antitumor agents. Eur J Med Chem 131:255–262
Luo Y, Yao JP, Yang L, Feng CL, Tang W, Wang GF, Zuo JP, Lu W (2011) Synthesis and anti-Hepatitis B virus activity of a novel class of thiazolylbenzimidazole derivatives. Arch Pharm Chem Life Sci 2:78–83
Lee-Dutra A, Arienti KL, Buzard DJ, Hack MD, Khatuya H, Desai PJ, Nguyen S, Thurmond RL, Karlsson L, Edwards JP, Breitenbucher JG (2006) Identification of 2-arylbenzimidazoles as potent human histamine H4 receptor ligands. Bioorg Med Chem Lett 16:6043–6048
Sogame S, Suenaga Y, Atobe M, Kawanishi M, Tanaka E, Miyoshi S (2014) Discovery of a benzimidazole series of ADAMTS-5 (aggrecanase-2) inhibitors by scaffold hopping. Eur J Med Chem 71:250–258
Shingalapur RV, Hosamani KM, Keri RS (2009) Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. Eur J Med Chem 44:4244–4248
Cinarli A, Gurbuz D, Tavman A, Birteksoz AS (2011) Synthesis, spectral characterizations and antimicrobial activity of some Schiff bases of 4-chloro-2-aminophenol. Bull Chem Soc Ethiop 25:407–417
Kumar P, Narasimhan B, Yogeswari P, Sriram D (2010) Synthesis and antitubercular activities of substituted benzoic acid N’-(substituted benzylidene/furan-2-ylmethylene)-N-(pyridine-3-carbonyl)-hydrazides. Eur J Med Chem 45:6085–6089
Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82:1107–1112
Cappucino JG, Sherman N (1999) Microbiology—a laboratory manual. Addison Wesley California 263
Pharmacopoeia of India, vol.-Ӏ (2007) Controller of publication, ministry of health department, Govt. of India, New Delhi, 37