Abstract
A new class of amido-linked pyrazolyl benzoxazoles, benzothiazoles and benzimidazoles was prepared and studied for their antimicrobial activity. The chloro-substituted pyrazolyl benzothiazole is the potent antibacterial agent against Bacillus subtilis and chloro-substituted pyrazolyl benzimidazole is the potent antifungal agent against Aspergillus niger.
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References
Akbay A, Oren I, Temiz-Arpaci O, Aki-Sxener E, Yalcin I (2003) Synthesis and HIV-1 reverse transcriptase inhibitor activity of some 2, 5, 6-substituted benzoxazole, benzimidazole, benzothiazole and oxazolo (4, 5-b) pyridine derivatives. Arzneim Forsch 54:266–271
Al-Muhaimeed H (1997) A parallel-group comparison of astemizole and loratadine for the treatment of perennial allergic rhinitis. J Int Med Res 25:175–181
Azoro C (2002) Antibacterial activity of crude extract of Azadiracta indica on Salmonella typhi. World J Biotechnol 3:347–357
Carpio A (1999) Albendazole therapy for subarachnoid cysticerci: clinical and neuroimaging analysis of 17 patients. Neurol J Neurosurg Psychia 66:411–412
Chung KT, Thomasson WR, Wu-Yuan CD (1990) Growth inhibition of selected food-borne bacteria, particularly Listeria monocytogenes, by plant extracts. J Applied Bacteriol 69:498–503
Clinical and Laboratory Standards Institute, “Method for broth dilution antifungal susceptibility testing of yeasts, 2002. Approved standard NCCLS Document M27-A2,” Ways, Pennsylvania
Clinical and Laboratory Standards Institute, “Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 2006. 7th edition; approved standard, CLSI Document M7-A7,” Ways, Pennsylvania
Domenick P, Erwin S, Frank V, Erwin K (1948) β-Aroylacrylic acids. Amer Chem Soc 70:3356–3360
French GL (2006) Bactericidal agents in the treatment of MRSA infections the potential role of daptomycin. J Antimicrob Chemother 58:1107–1117
Ghose AK, Viswanadhan VN, Wendoloski JJ (1999) A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J Comb Chem 1:55–68
Janovska D, Kubikova K, Kokoska L (2003) Screening for antimicrobial activity of some medicinal plants species of traditional Chinese medicine. Czech J Food Sci 21:107–110
Joshi B, Lekhak S, Sharma A (2009) Antibacterial property of different medicinal plants: Ocimum sanctum, Cinnamomum zeylanicum, xanthoxylum, armatum and Origanum majorana. J Sci Eng Technol 5:143–150
Kumar S, Bawa S, Drabu S, Kumar R, Gupta H (2009) Biological activities of pyrazoline derivatives: a recent development. Recent Pat Anti infect Drug Discov 4:154–163
Oren I, Temiz O, Yalcin I, Sener E, Altanlar N (1998) Synthesis and antimicrobial activity of some Novel 2, 5- and/or 6-substituted benzoxazole and benzimidazole derivatives. Eur J Pharm Sci 7:153–160
Richter JE (1997) Long-term management of gastroesophageal reflux disease and its complications. Am J Gastroenterol 92:34–35
Robert W, Huigens III, Samuel R, Catherine SR, Cynthia B, Steven AR, Andrew TS, Christian M (2010) The chemical synthesis and antibiotic activity of a diverse library of 2-aminobenzimidazole small molecules against MRSA and multidrug-resistant A. baumannii. Bioorg Med Chem 18:663–674
Saritha G, Sarangapani M, Prasad G, Swathi C (2011) Design, synthesis and biological evaluation of benzoxazole derivatives as cyclooxygensase-2 inhibitors. Der Pharm.Lett 3:427–432
Taj T, Kamble RR, Gireesh TM, Hunnur RK, Margankop SB (2011) One-pot synthesis of pyrazoline derivatized carbazoles as antitubercular, anticancer agents, their DNA cleavage and antioxidant activities. Eur J Med Chem 46:4366–4373
Temiz-Arpaci O, Ozdemir A, Yalcin I, Yildiz I, Aki-Sxener E, Altanlar N (2005) Synthesis and antimicrobial activity of some 5-[2-(morpholin-4-yl) acetamido] and/or 5-[2-(4-substituted piperazin-1-yl) acetamido]-2-(p-substituted phenyl) benzoxazoles. Arch Pharm Chem Life Sci 338:105–111
Ukei M, Taniguchi M (1997) UK-1, a novel cytotoxic metabolite from streptomyces SP. 5:7–02.111. Antibacterial action of dimethyl UK-1. J Antibiot (Tokyo) 50:788–790
Valeur E, BradleyM (2009) Amide bond formation beyond the myth of coupling reagents. Chem Soc Rev 38:606–631
Varga A, Aki-Sener E, Yalcin I, Temiz-Arpaci O, Tekiner-Gulbasx B, Cherepnev G, Molnar J (2005) Induction of apoptosis and necrosis by resistance modifiers benzazoles and benzoxazines on tumour cell line mouse lymphoma L5718 mdr+ cells18. In Vivo 19:1087–1091
Vinsova J, Horak V, Buchta V, Kaustova J (2005) Highly lipophilic benzoxazoles with potential antibacterial activity. Molecules 10:783–793
Winstanley P (1998) Albendazole for mass treatment of asymptomatic trichuris infections. Lancet 352:1080–1081
Wu Y-Q, Limburg DC, Wilkinson DC, Hamilton GS (2003) Formation of nitrogen-containing heterocycles using di(imidazole-1-yl)methanimine. J Hetero Chem 40:191–193
Yoshida M, Hayakawa I, Hayashi N, Agatsuma T, Oda Y, Tanzawa F, Iwasaki S, Koyama K, Furukawa H, Kurakata S, Sugano Y (2005) Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents. Bioorg Med Chem Lett 15:3328–3332
Acknowledgments
The authors are thankful to Council of Scientific and Industrial Research (CSIR), New Delhi, India for the sanction of Major Research Project. The authors Mr. L. Mallikarjuna Reddy and Mr. T. Bhanu Prakash are thankful to CSIR and UGC-BSR, New Delhi, India for the sanction of Junior Research Fellowship.
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Reddy, L.M., Prakash, T.B., Padmaja, A. et al. Synthesis and antimicrobial activity of pyrazolyl benzoxazoles, benzothiazoles and benzimidazoles. Med Chem Res 24, 970–979 (2015). https://doi.org/10.1007/s00044-014-1180-0
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DOI: https://doi.org/10.1007/s00044-014-1180-0