Synthesis and biological activity of peptide derivatives of iodoquinazolinones/nitroimidazoles

Molecules

Volumn 13, Issue 4, 2008, Pages 958-976

  Dahiya, Rajiv ^a   Kumar, Anil ^a   Yadav, Rakesh ^a  

^a Rajiv Academy for Pharmacy   (India)

Author keywords

5 aminosalicylic acid; Anthelmintic activity; Antimicrobial activity; Imidazole; Peptides; Quinazolinone

Indexed keywords

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTIPARASITIC AGENT; NITROIMIDAZOLE DERIVATIVE; PEPTIDE; QUINAZOLINONE DERIVATIVE;

ANIMAL; ARTICLE; BACTERIUM; CHEMISTRY; DRUG EFFECT; FUNGUS; HELMINTH; MICROBIOLOGICAL EXAMINATION; SYNTHESIS;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTIPARASITIC AGENTS; BACTERIA; FUNGI; HELMINTHS; MICROBIAL SENSITIVITY TESTS; NITROIMIDAZOLES; PEPTIDES; QUINAZOLINONES;

EID: 43049127153     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13040958     Document Type: Article

References (41)

1. Desai, N. C.; Shihora, P. N.; Moradia D. L. Synthesis and characterization of new quinazolines as potential antimicrobial agents. Indian J. Chem. 2007, 46B, 550-553.
2. Aridoss, G.; Balasubramanian, S.; Parthiban, P.; Kabilan, S. Synthesis and in vitro microbiological evaluation of imidazo(4,5-b) pyridinylethoxypiperidones. Eur. J. Med. Chem. 2006, 41, 268-275.
3. Sengupta, A. K.; Bhattacharya, T. Synthesis and antimicrobial activity of some substituted 2-phenyl-3-arylquinazol-4-ones. J. Indian Chem. Soc. 1983, 60, 373-376.
4. Yesilada, A.; Koyunoglu, S.; Saygili, N.; Kupeli, E.; Yesilada, E.; Bedir, E.; Khan, I. Synthesis, anti-inflammatory and analgesic activity screening of some new 4(3H)-quinazolinone derivatives. Arch. Pharm. Pharm. Med. Chem. 2004, 337, 96-104.
5. Navidpour, L.; Shadnia, H.; Shafaroodi, H.; Amini, M.; Dehpour, A. R.; Shafiee, A. Design, synthesis and biological evaluation of substituted 2-alkylthio-1,5-diarylimidazoles as selective COX-2 inhibitors. Bioorg. Med. Chem. 2007, 15, 1976-1982.
6. Ucucu, U.; Karaburun, N. G.; Isikdag, I. Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives. Farmaco 2001, 56, 285-290.
7. Pattan, S. R.; Reddy, V. V. K.; Manvi, F. V.; Desai, B. G.; Bhat, A. R. Synthesis of N-3-(4-(4-chlorophenyl-thiazol-2-yl)-(2-(amino)methyl)- quinazoline-4(3H)-one and their derivatives for antitubercular activity. Indian J. Chem. 2006, 45B, 1778-1781.
8. Gupta, P.; Hameed, S.; Jain, R. Ring-substituted imidazoles as a new class of anti-tuberculosis agents. Eur. J. Med. Chem. 2004, 39, 805-814.
9. Raffa, D.; Elder, M. C.; Daidone, G.; Maggio, B.; Merickech, M.; Plescia, S., Schillaci, D.; Bai, R.; Hamel, E. Synthesis, cytotoxity and inhibitory effects on tubulin polymerization of a new 3-heterocyclo substituted 2-styrylquinazolinones. Eur. J. Med. Chem. 2004, 39, 299-304.
10. Arrowsmith, J.; Jennings, S. A.; Clark, A. S.; Stevens, M. F. G. Antitumour imidazotetrazines. 41. Conjugation of the antitumour agents mitozoloamide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs. J. Med. Chem. 2002, 45, 5458-5470.
11. Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K.; Adelstein, S. J.; Kassis, A. I. Synthesis and biologic evaluation of a radioiodinated quinazolinone derivative for enzyme-mediated insolubilization therapy. Bioconjug. Chem. 2002, 13, 357-364.
12. Alagarsamy, V.; Giridhar, R.; Yadav, M. R.; Revathi, R.; Ruckmani, K.; De Clercq E. Anti HIV, antibacterial, and antifungal activities of some novel 1,4-disubstituted-1,2,4-triazolo [4,3-a]quinazolin-5(4H)-ones. Indian J. Pharm. Sci. 2006, 68, 532-535.
13. Wang, Y.; Inguaggiato, G.; Jasamai, M.; Shah, M.; Hughes, D.; Slater, M.; Simons, C. Synthesis and biological evaluation of novel 2′-deoxy- 4′-thio-imidazole nucleoside. Bioorg. Med. Chem. 1999, 7, 481-487.
14. Usifoh, C. O.; Scriba, K. E. Synthesis and anticonvulsant activity of acetylenic quinazolinone derivatives. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 261-266.
15. Miyachi, H.; Kiyota, H.; Segawa, M. Novel imidazole derivatives with subtype-selective antimuscarinic activity. Bioorg. Med. Chem. Lett. 1998, 8, 2163-2168.
16. Singh, T.; Sharma, S.; Srivastava, V. K.; Kumar, A. Synthesis, insecticidal and antimicrobial activities of some heterocyclic derivatives of quinazolinone. Indian J. Chem. 2006, 45B, 2558-2565.
17. Angibaud, P.; Bourdrez, X.; Devine, A.; End, D. W.; Freyne, E.; Ligny, Y.; Muller, P.; Mannens, G.; Pilatte, I.; Poncelet, V.; Skrzat, S.; Smets, G.; Dun, J. V.; Remoortere, P. V.; Venet, M.; Wouters, W. 5-Imidazolyl- quinazolinones, -quinazolinones and -benzo-azepinones as farnesyl transferase inhibitors. Bioorg. Med. Chem. Lett. 2003, 13, 1543-1547.
18. +-ATPase inhibitors. J. Med. Chem. 1996, 39, 596-604.
19. Dobler, M. R. Design and novel synthesis of aryl-heteroaryl-imidazole MAP kinase inhibitors. Tetrahedron Lett. 2003, 44, 7115-7117.
20. da Silva, M.; Menezes, C. M.; Ferreira, E. I.; Leite, C. Q.; Sato, D. N.; Correia, C. C.; Pimenta, C. P.; Botelho, K. C. Topliss method in the optimization of salicylic acid derivatives as potential antimycobacterial agents. Chem. Biol. Drug Des. 2008, 71, 167-172.
21. Yang, Z. C.; Yang, X. S.; Wang, B. C.; Sun, Q. Y. Structure-activity relationships of salicylic acid and its analogs in the inhibitory action on beta-lactamase. Yao Xue Xue Bao 2006, 41, 230-232.
22. Ruegg, T.; Calderon, A. I.; Queiroz, E. F.; Solis, P. N.; Marston, A.; Rivas, F.; Ortega-Barria, E.; Hostettmann, K.; Gupta, M. P. 3-Farnesyl-2- hydroxybenzoic acid is a new anti-helicobacter pylori compound from Piper multiplinervium. J. Ethnopharmacol. 2006, 103, 461-467.
23. Poojary, B.; Belagali, S. L.; Harish Kumar, K.; Holla, B. S. Synthetic and antibacterial studies on some new furanopeptides. Farmaco 2003, 58, 569-572.
24. Levit, G. L.; Anikina, L. V.; Vikharev, Y. B.; Demin, A. M.; Safin, V. A.; Matveeva, T. V.; Krasnov, V. P. Synthesis and antiinflammatory and analgesic activity of naproxen amides with amino acid derivatives. Pharm. Chem. J. 2002, 36, 232-236.
25. Belagali, S. L.; Harish Kumar, K.; Holla, B. S.; Bhagwat, A. Synthesis and biological evaluation of amino acid derivatives of benzothiophenes. Indian J. Heterocycl. Chem. 2001, 10, 249-252.
26. Himaja, M.; Rajiv; Ramana, M. V.; Poojary, B.; Satyanarayana, D.; Subrahmanyam, E. V.; Bhat, K. I. Synthesis and biological activity of a novel series of 4-[2′-(6′-nitro)-benzimidazolyl]benzoyl amino acids and peptides. Boll. Chim. Farm. 2003, 142, 450-453.
27. Himaja, M.; Rajiv; Ramana, M. V. Synthesis of 6-nitrobenzimidazol-1- acetyl amino acids and peptides as potent anthelmintic agents. Indian J. Heterocycl. Chem. 2002, 12, 121-124.
28. (a) Dahiya, R. Synthesis, characterization and antimicrobial studies on some newer imidazole analogs. Sci. Pharm. 2008, 76, in press [doi:10.3797/scipharm.0803-04];
29. (b) Dahiya, R.; Kaur, R. Synthesis of some 1,2,5-trisubstituted benzimidazole analogs as possible anthelmintic and antimicrobial agents. Int. J. Biol. Chem. Sci. 2008, 2, 1-13;
30. (c) Dahiya, R.; Pathak, D. Synthetic studies on novel benzimidazolopeptides with antimicrobial, cytotoxic and anthelmintic potential. Eur. J. Med. Chem. 2007, 42, 772-798;
31. (d) Dahiya, R.; Kaur, R. Synthesis and anthelmintic potential of a novel series of 2-mercaptobenzimidazolopeptides. Biosci. Biotech. Res. Asia 2007, 4, 561-566;
32. (e) Dahiya, R.; Kaur, R. Synthesis and biological screening of a novel series of 3,4,5-trisubstituted phenoxyacetic acid analogs. Aust. J. Basic Appl. Sci. 2007, 1, 525-532;
33. (f) Dahiya, R.; Pathak, D. Synthesis of novel heterocyclic analogs of 5-(4-methylcarboxamidophenyl)-2-furoic acid as potent antimicrobial agents. Indian J. Heterocycl. Chem. 2006, 16, 53-56;
34. (g) Dahiya, R.; Pathak, D.; Bhatt, S. Synthesis and biological evaluation of a novel series of 2-(4-chloro-3-methylphenoxy)acetyl amino acids and peptides. J. Saudi Chem. Soc. 2006, 10, 165-176;
35. (h) Dahiya, R.; Pathak, D. Synthesis and biological screening of a novel series of 6-nitro-2-(4-toluoyl)benzoyl amino acids and peptides. J. Nepal Pharm. Assoc. 2006, XXIV, 17-26;
36. (i) Dahiya, R.; Pathak, D.; Bhatt, S. Synthesis and biological evaluation of a novel series of 2-(2′-isopropyl-5′-methylphenoxy)acetyl amino acids and dipeptides. Bull. Chem. Soc. Ethiop. 2006, 20, 235-245;
37. (j) Dahiya, R.; Pathak, D. Synthesis and antimicrobial activity of novel series of 2-aroyl-6-nitrobenzoyl amino acids and peptides. Orient. J. Chem. 2006, 22, 123-128.
38. Mann, F. G.; Saunders, B. C. Practical Organic Chemistry; Orient Longman: New Delhi, 2001.
39. Bodanzsky, M.; Bodanzsky, A. The Practice of Peptide Synthesis; Springer: New York, 1984.
40. Bauer, A. W.; Kirby, W. M.; Sherris, J. C.; Turck, M. Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clin. Path. 1966, 45, 493-496.
41. Garg, L. C.; Atal, C. K. Anthelmintic activity of Myrsine Africana. Indian J. Pharm. Sci. 1963, 59, 240-245.