Design and synthesis of positional isomers of 1-alkyl-2-trifluoromethyl-5 or 6-substituted benzimidazoles and their antimicrobial activity

Medicinal Chemistry Research

Volumn 22, Issue 3, 2013, Pages 1229-1237

  Sathaiah, G ^a   Ravi Kumar, A ^a   Chandra Shekhar, A ^a   Raju, K ^a   Shanthan Rao, P ^a   Narsaiah, B ^a   Raghuram Reddy, A ^b   Lakshmi, D ^b   Sridhar, B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b KAKATIYA UNIVERSITY   (India)

Author keywords

Antibacterial; Antifungal; Benzimidazole; Rhizhopus oryzae; Trifluoromethyl

Indexed keywords

1 (3 CHLOROPROPYL) 5 NITRO 2 TRIFLUOROMETHYL 1H BENZIMIDAZOLE; 1 (3 CHLOROPROPYL) 6 NITRO 2 TRIFLUOROMETHYL 1H BENZIMIDAZOLE; 1 (4 CHLOROBUTYL) 6 NITRO 2 (PERFLUOROETHYL) 1H BENZIMIDAZOLE; 1 (4 CHLOROBUTYL) 6 NITRO 2 TRIFLUOROMETHYL 1H BENZIMIDAZOLE; 1 (4 CHLROBUTYL) 5 NITRO 2 (PERFLUOROETHYL) 1H BENZIMIDAZOLE; 1 ALKYL 2 TRIFLUOROMETHYL BENZIMIDAZOLE; 1 ETHYL 5 NITRO 2 TRIFLUOROMETHYL 1H BENZIMIDAZOLE; 1 ETHYL 6 NITRO 2 TRIFLUOROMETHYL 1H BENZIMIDAZOLE; 2 (6 NITRO 2 TRIFLUOROMETHYL 1H BENZIMIDAZOL 1 YL)ACETONITRILE; 5 NITRO 1 (PROP 2 YNYL) 2 TRIFLUOROMETHYL 1H BENZIMIDAZOLE; 6 NITRO 1 (PROP 2YNYL) 2 TRIFLUOROMETHYL) 1H BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; ETHYL 2 (5 NITRO 2 TRIFLUOROMETHYL 1H BENZIMIDAZOLE 1 YL)ACETATE; ETHYL 2 [5 NITRO 2 (PERFLUOROETHYL) 1H BENZIMIDAZOLE 1 YL]ACETATE; ETHYL 2 [6 BENZOYL 2 (TRIFLUOROMETHYL) 1H BENZO[D]IMIDAZOLE 1 YL]ACETATE; ETHYL 2 [6 NITRO 2 (PERFLUOROETHYL) 1H BENZIMIDAZOLE 1 YL]ACETATE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACILLUS SUBTILIS; CANDIDA ALBICANS; DRUG DESIGN; DRUG SYNTHESIS; ESCHERICHIA COLI; ISOMER; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PSEUDOMONAS AERUGINOSA; RHIZOPUS ORYZAE; SACCHAROMYCES CEREVISIAE; STAPHYLOCOCCUS AUREUS; X RAY CRYSTALLOGRAPHY;

EID: 84874105729     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0131-x     Document Type: Article

References (15)

1. Banks RE (1979) Organofluorine chemicals and their industrial applications. Ellis Horwood, Chichester
2. Banks RE (1982) Preparation, properties and industrial applications of organofluorine compounds. Ellis Horwood, Chichister
3. Bruker (2001) SAINT (Version 6.28a) & SMART (Version 5.625). Bruker AXS Inc., Madison
4. Denny WA, Rewcastle GW, Bagulaey BC (1990) Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, anew class of minimal-interacting agents which may not act via topoisomerase-II. J Med Chem 33:814-819
5. Farukh A, Bhawana M, Shamin (2005) Synthesis, antibacterial, antifungal activity & interaction of CT-DNA with a new benzimidazole derived Cu(II) complex. Eur J Med Chem 40:1103
6. Fransisco HL, Alicia HC, Rafeal C, Gabriel NV, Olivia SA, Manuel H, Libian GM (2010) Synthesis and biological activity of 2-(trifluoromethyl)-1H- benzimidazole derivatives against some protozoa and Trichinella spiralis. Eur J Med Chem 45:3135
7. Gabriel NV, Roberto C, Aliica HC, Cilian G, Fransisco KL, Suan V, Raual M, Rafeal C, Manuel H, Rafel C (2001) Synthesis and antiparasitic activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives. Bioorg Med Chem Lett 11:1879
8. Gabriel NV, de Maria MRV, Cilian G, Victor M, Lucia G, Alicia H, Rafeal C, Fransisco HL (2006) Synthesis and antiprotozoal activity of some 2-(trifluoromethyl)-1H-benzimidazole bioisosteres. Eur J Med Chem 41:135
9. Juan V, Roberto C, Alicia HC, Lilian G, Fransisco HL, Gabriel NV, Amparo T, Rafel C, Manuel H, Rafel C (2002) Synthesis and antiparasitic activity of 1H-benzimidazole derivatives. Bioorg Med Chem Lett 12:2221
10. Keith WAM, Allen CB, Sharon H, Richard EJ, Thomas RM (1978) 1-[4-(4-Chloro phenyl)-2-(2,6-di chloro phenyl thio)-n-butyl]-1H-imidazole nitrate a new point antifungal agent. J Med Chem 21:840
11. Kurumurthy C, Sambasiva Rao P, Veeraswamy B, Santosh Kumar G, ShanthanRao P, Narsaiah B, Velatooru LR, Pamanji R, Venkateswara Rao J (2011) Synthesis of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives and their anticancer activity. Eur J Med Chem 46:3462-3468
12. Maxwell WA, Brody G (1971) Antifungal activity of selected benzimidazole compounds. Appl Microbiol 21:944
13. Nakamura Shoshiro (2005) Structure of azomycin, a new antibiotic. Chem Pharm Bull 3:379
14. Sheldrick GM (2008) Acta Crystallogr A64:112-122
15. Venkat Reddy G, Ravikanth S, Maitraie D, Narsaiah B, Shanthan Rao P, Harakrishna K, Murthy USN, Ravi B, Ashok Kumar B, Parthasarathy T (2009) Design, synthesis, structure-activity relationship and antibacterial activity series of novel imidazo fused quinolone carboxamides. Eur J Med Chem 44:1570-1578