Antibacterial and antifungal screening of newly synthesized benzimidazole-clubbed chalcone derivatives

Medicinal Chemistry Research

Volumn 22, Issue 8, 2013, Pages 3688-3697

  Parikh, Kalpesh ^a   Joshi, Deepkumar ^a  

^a Sheth MN Science College   (India)

Author keywords

Antimicrobial activity; Benzimidazole; Chalcones; MIC

Indexed keywords

2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N (4 CINNAMOYLPHENYL)ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (2 HYDROXYNAPHTHALEN 1 YL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (2 HYDROXYPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (2 NITROPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (2,5 DIMETHOXYPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (3 BROMOPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (3 CHLOROPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (3,4 DIMETHOXYPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (4 BROMOPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (4 CHLOROPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (4 HYDROXYPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (4 METHOXYPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 (4 NITROPHENYL)ACRYLOYL]PHENYL]ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) N [4 [3 [4 (DIMETHYLAMINO)PHENYL]ACRYLOYL]PHENYL]ACETAMIDE; 2 BENZIMIDAZOLETHIOL DERIVATIVE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; BENZIMIDAZOLE DERIVATIVE; CHALCONE DERIVATIVE; CIPROFLOXACIN; FLUCONAZOLE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CANDIDA ALBICANS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; INFRARED SPECTROSCOPY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 84879503805     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0369-3     Document Type: Article

References (31)

1. Azam A, Hayat F, Mosely E, Attar S, Vanzyl R (2011) Antiprotozoal activity of chloroquinoline based chalcones. Eur J Med Chem 46:1897-1905. doi: 10.1016/j.ejmech.2011.02.004
2. Bandgar BP, Patil SA, Korbad BL, Nile S, Khobragade CN (2010) Synthesis and biological evaluation of β-chloro vinyl chalcones as inhibitors of TNF-α and IL-6 with antimicrobial activity. Eur J Med Chem 45:2629-2633. doi: 10.1016/j.ejmech.2010.01.050
3. Barnard DL, Smee DF, Huffman JF, Meyerson LR, Sidwell RW (1993) Anti-herpesvirus activity and mode of action of SP-303, a novel plant flavonoid. Chemotherapy 39:203-211. doi: 10.1159/000239127
4. Baviskar BA, Baviskar B, Shiradkar MR, Deokate UA, Khadabadie SS (2009) Synthesis and antimicrobial activity of some novel benzimidazolyl chalcones. E-J Chem 6(1):196-200
5. Boumendjel A, Bois F, Mariotte A-M, Conseil G, Petro AD (1999) Synthesis and biological activity of 4-alkoxy chalcones: potential hydrophobic modulators of P-Glycoprotein-mediated multidrug resistance. Bioorg Med Chem 7:2691-2695. doi: 10.1016/S0968-0896(99)00218-7
6. Castilloa R et al (2002) Synthesis and antiparasitic activity of 1H-benzimidazole derivatives. Bioorg Med Chem Lett 12:2221-2224. doi: 10.1016/S0960-894X(02)00346-3
7. De Meyer N, Haemers A, Mishra L, Pandey HK, Peters LA, Vanden Berghe DA, Vlietinck AJ (1991) 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity. J Med Chem 34:736-746. doi: 10.1021/jm00106a039
8. Dixit S, Sharma PK, Kaushik N (2012) Synthesis of novel benzimidazole derivatives: as potent analgesic agent. Med Chem Res. doi: 10.1007/s00044-012- 0083-1
9. Ducki S, Forrest R, Hadfield J, Kendall A, Lawerence NJ, McGrown AT, Rennison D (1998) Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem Lett 8:1051-1056. doi: 10.1016/S0960-894X(98)00162-0
10. Furman C, Lebeau J, Fruchart J-C, Bernier J-L, Duiez P, Cotelle N, Teissier E (2001) Di-tert-butylhydroxylated flavonoids protect endothelial cells against oxidized LDL-induced cytotoxicity. J Biochem Mol Toxicol 15:270-278. doi: 10.1002/jbt.10003
11. Gatta L, Perna F, Figura N, Ricci C, Holton J, D'Anna L, Miglioli M, Vaira D (2003) Antimicrobial activity of esomeprazole versus omperazole against Helicobacter pylori. J Antimicrob Chemother 51:439-442. doi: 10.1093/jac/dkg085
12. Go Mei-Lin, Liu Mei, Wilairat P, Rosenthal PJ, Saliba KJ, Kirk K (2004) Antiplasmodial chalcones inhibit sorbitol-induced hemolysis of plasmodium falciparum-infected erythrocytes. Antimicrob Agents Chemother 48:3241-3245. doi: 10.1128/AAC.48.9.3241-3245.2004
13. Goodman, AL (1975) 2-Mercaptobenzimidazole by reacting o-phenylene diamine and carbon disulphide. U.S. Patent 3895025. http://www. freepatentsonline.com/3895025.html
14. Hosamani KS, Shingalapur RV, Rangappa S, Hugar MH (2010) Derivatives of benzimidazole pharmacophore: synthesis, anticonvulsant, antidiabetic and DNA cleavage studies. Eur J Med Chem 45:1753-1759. doi: 10.1016/j.ejmech.2010.01.007
15. 1-dimethoxychalcone and 4-hydroxychalcone in mice. J Biol Sci 8:131-136. doi: 10.3923/jbs.2008.131.136
16. 2/EtOH. Intern J Current Pharma Res 2(4):60-62
17. Linn L-M, Zhou Y, Flavin MT, Zhou LM, Nie W, Chen F-C (2002) Chalcones and flavonoids as anti-Tuberculosis agents. Bioorg Med Chem 10:2795-2802. doi: 10.1016/S0968-0896(02)00094-9
18. Narender T, Reddy KP (2007) A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate. Tetrahedron Lett 48:3177-3180. doi: 10.1016/j.tetlet.2007.03.054
19. Patil SL, Bhalgat C, Burli S, Chithale S (2010) Synthesis, antibacterial and antioxidant properties of newer 3-(1-benzofuran-2-yl)-5-substituted aryl-1,2-oxazole. Intern J Chem Sci Applic 1(1):42-49
20. 2/EtOH: catalytic system for synthesis of chalcones. Catal Commun 9:315-316. doi: 10.1016/j.catcom.2007.06.013
21. Reffat HM (2011) Synthesis of potential anticancer derivatives of pyrido[1,2-a]benzimidazoles. Med Chem Res 21:1253-1260. doi: 10.1007/s00044-011-9636-y
22. Sarma BK, Mishra PK, Singhai PK, Singh UP (2007) Antifungal activity of 2-hydroxy 4,4′,6′trimethoxy chalcone. Mycobiology 35:72-75. doi: 10.4489/MYCO.2007.35.2.072
23. Satyanarayana M, Tiwari P, Tripathi BK, Srivastava AK, Pratap R (2004) Synthesis and anti hyperglycemic activity of chalcone based aryloxypropanolamines. Bioorg Med Chem 12:883-889. doi: 10.1016/j.bmc.2003.12. 026
24. Saxena DB, Khajuria RK, Suri OP (1982) Synthesis and spectral studies of 2-mercaptobenzimidazole derivatives. J Hetero Chem 19:681-683. doi: 10.1002/jhet.5570190350
25. Scherhag B, Kopplemann E, Wolz H (1974) Production of 2-mercaptobenzimidazole by reacting o-phenylene diamine and carbon disulphide. U.S. Patent 3842098. http://www.freepatentsonline.com/3842098.html
26. Sebti S, Solhy A, Tahir R, latif A, Boulaajaj S, Mayoral JA, García JI, Fraile JM, Kossir A, Oumimoun H (2003) Application of natural phosphate modified with sodium nitrate in the synthesis of chalcones: a soft and clean method. J Catal 213:1-6. doi: 10.1016/S0021-9517(02)00017-9
27. 2 catalyst in water. Tetrahedron Lett 52:4008-4013. doi: 10.1016/j.tetlet.2011.05.118
28. Solankee A, Kapadia K, Iric′ A, Sokovic M, Doytchinova I, Geronikaki A (2010) Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents. Eur J Med Chem 45:510-518. doi: 10.1016/j.ejmech.2009.10.037
29. Tebbe MJ, Spiyzer WA (1997) Antirhino/enteroviral vinylacetylene benzimidazoles: a study of their activity oral plasma levels in mice. J Med Chem 40:3937-3940. doi: 10.1021/jm970423k
30. Wang M-L and Liu B-L (2007) Synthesis of 2-mercaptobenzimidazole from the reaction of o-phenylenediamine and carbon disulfide in presence of potassium hydroxide. J Chin Inst Chem Eng 38:161-167. doi: 10.1016/j.jcice.2007.01.003
31. Youssef AM, Masoud GN, Khalek A, Wahab AE, Labouta IM, Hazaa AA (2012) Design, synthesis, and biological evaluation of new 4-thiazolidinone derivatives substituted with benzimidazole ring as potential chemotherapeutic agents. Med Chem Res. doi: 10.1007/s00044-012-0057-3