Design, synthesis and antimicrobial properties of novel 3,3a,4,5,6,7-hexahydroindazole and arylthiazolylpyrazoline derivatives

Medicinal Chemistry

Volumn 9, Issue 1, 2013, Pages 45-52

  Bishnoi, Abha ^a   Singh, Suruchi ^a   Tiwari, Anil K ^a   Sethi, Arun ^a   Tripathi, Chandrakant Mani ^b  

^a UNIVERSITY OF LUCKNOW   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Antibacterial activity; Antifungal activity; Arylthiazolylpyrazoline; Cyclization; Diastereoselectivity; Heterocycles

Indexed keywords

3,3A,4,5,6,7 HEXAHYDROINDAZOLE DERIVATIVE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84874057129     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340613804488422     Document Type: Article

References (41)

1. Cragg, G. M.; Newman, D. J.; Snader, K. M. Natural products in drug discovery and development. J. Nat. Prod., 1997, 60, 52-60.
2. Afolayan, A. J. Extracts from the shoots of Arctotis arctotoides inhibit the growth of bacteria and fungi. Pharmaceut. Biol., 2003, 41, 22-25.
3. Graham, J. G.; Zhang, H.; Pendland, S. L.; Santarsiero, B. D.; Mesecar, A. D.; Cabieses, F.; Farnsworth, N. R. Antimycobacterial Naphthopyrones from Senna oblique. J. Nat. Prod., 2004, 67, 225-227.
4. de Oliveira, M. F.; de Oliveira, J. H.; Galetti, F. C.; de Souza, A. O.; Silva, C. L.; Hajdu, E.; Peixinho, S.; Berlinck, R. G. Antimycobacterial brominated metabolites from two species of marine sponges. Planta Med., 2006, 72, 437-441.
5. Silverman, R.B. Organic Chemistry of Drug Design and Drug Action, Academic Press: San Diego, CA, USA, 1992.
6. Thompson, L.A.; Ellman, J. A. Synthesis and Applications of Small Molecule libraries. Chem. Rev., 1996, 96, 555-600.
7. Chande, M. S.; Barve P. A.; Suryanarayan, V. Synthesis and antimicrobial ctivity of novel spirocompounds with pyrazolone and pyrazolthione moiety. J. Heterocyclic Chem., 2007, 44, 49-53.
8. de Leon, C.Y.; Ganem, B. A new approach to porphobilinogen and its analogs. Tetrahedron, 1997, 53, 7731-7752.
9. Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Synthesis of 2,3,5-substituted pyrrole derivatives. Tetrahedron Lett., 2002, 43, 4491-4493.
10. Daidone, G.; Maggio, B.; Schillari, D. Salicylanilide and its heterocyclic analogs. A comparative study of their antimicrobial activity. Pharmazie, 1990, 45, 441-442.
11. Almerico,A. M.; Diana, P.; Barraja, P.; Dattolo, G.; Mingoia, F.; Loi, A. G.; Scintu, F.; Milia, C.; Puddu, I.; La Colla, P. Glycosidopyrroles Part 1. Acyclic derivatives: 1-(2-hydroxyethoxy) methylpyrroles as potential anti-viral agents. Il Farmaco, 1998, 53, 33-40.
12. Kaiser, D. G.; Glenn, E. M. Correlation of plasma 4,5-bis (pmethoxyphenyl)-2-phenylpyrrole-3-acetonitrile levels with biological activity. J. Pharm. Sci., 1972, 61, 1908-1911.
13. Gazit, A.; App, H.; McMohan, G.; Chen, J.; Levitzki, A.; Bohmer, F. D. Tyrphostins. 5. Potent Inhibitors of Platelet-Derived Growth Factor Receptor Tyrosine Kinase: Structure-Activity Relationships in Quinoxalines, Quinolines, and Indole Tyrphostins. J. Med. Chem., 1996, 39, 2170-2177.
14. Hudak, W. J.; Tilford, C. H.; Lewis, R. Antihypertensive agents. Substituted 3-pyrrolemethylamines. J. Med. Chem., 1971, 14, 328-331.
15. Jungheim, L. N.; Holmes, R. E.; Ott, J. L.; Ternansky, R. J.; Draheim, S. E.; Neel, D. A.; Stepherd, T. A.; Sigmund, S. K. Antimicrobial Agents and Chemotherapy. In: Abstracts of 26th Interscience Conference, New Orleans, LA, USA, September 28-October 1, 1988, Paper 601.
16. Jungheim, L.N.; Holmes, R.E.; Ternansky, R.J.; Stepherd, T.A.; Neel, D.A.; Draheim S.E.; Pike, A.J.; Wu, C.Y.E. Abstracts of 28th Interscience Conference on Antimicrobial Agents and Chemotherapy, Los Angels, CA, USA, October 23-26, 1988, Paper 240.
17. Ternansky, R. J.; Draheim, S. E. [3.3.0] Pyrazolodinones: An efficient synthesis of a new class of synthetic antibacterial agents. Tetrahedron Lett., 1990, 31, 2805-2808.
18. Palaskar, E.; Aytemir, M.; Uzbay, I. T.; Erol, D. Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines. Eur J Med Chem., 2001, 36, 539-543.
19. Akihiko, T.; Yoshihiro, O.; Keiko, O.; Hideo, T.; Motoji, K.; Masaaki, W.; Jun-ichi, Y. Synthesis and antibacterial activity of a novel series of DNA gyrase inhibitors: 5-[(E)-2-arylvinyl]pyrazoles. Bioorg. Med. Chem. Lett., 2005, 15, 4299-4303.
20. Nauduri, D.; Reddy, G. B. Antibacterials and Antimycotics : Part 1 : Synthesis and Activity of 2-Pyrazoline Derivatives. Chem. Pharm. Bull., 1998, 46, 1254-1260.
21. Goda, F. E.; Maarouf, A. R.; Bendary, E. R. Synthesis and Antimicrobial Evaluation of New Isoxazole and Pyrazole Derivaties. S. Pharm. J., 2003, 11, 111-117.
22. Turan-Zitouni, G.; Özdemir, A.; Güven, K. Synthesis of Some 1-[(N, N-Disubstituted thiocar bamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2- pyrazoline Derivatives and Investigation of Their Antibacterial and Antifungal Activities. Arch. Pharm. Pharm. Med. Chem., 2005, 338, 96-104.
23. Turan-Zitouni, G.; Özdemir, A.; Kaplancikli, Z. A.; Chevallet, P.; Tunali, Y. Synthesis and Antimicrobial Activities of Some 1-[(N, N-Disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines. Phosphorus Sulfur Silicon Relat. Elem., 2005, 180, 2717-2724.
24. Burguete, A.; Pontiki, E.; Hadjipavlou-Litina, D.; Villar, R.; Vicente, E.; Solano, B.; Ancizu, S.; Pérez-Silanes, S.; Aldanaa, I.; Monge, A. Synthesis and anti-inflammatory/ antioxidant activities of some new ring 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues. Bioorg. Med. Chem Lett., 2007, 17, 6439-6443.
25. Turan-Zitouni, G.; Chevallet, P.; Kiliç, F.S.; Erol, K. Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity. Eur. J. Med. Chem., 2000, 35, 635-641.
26. Altintas, H.; Ates, O.; Kocabalkanli, A.; Birteksoz, S.; Otuk, G. Synthesis, characterization and evaluation of antimicrobial activity of Mannich bases of some 2-[(4-carbethoxymethylthiazol-2-yl)imino]-4-thiazolidinones. Indian J. Chem., 2005, 44B, 585-590.
27. Bhambi, D.; Sharma, C.; Sharma, S.; Salvi, V. K.; Talesara, G. L. Synthesis and pharmacological studies of some phthalimidoxy substituted spiro-thiazolidinone derivatives of isatin. Indian J. Chem., 2009, 48B, 1006-1012.
28. Reddy, C. S.; Srinivas, A.; Nagaraj, A. Synthesis, Nematicidal and Antimicrobial Properties of Bis-[4-methoxy-3-[3-(4-fluorophenyl)-6-(4- methylphenyl)-2(aryl)-tetrahydro-2H-pyrazolo[3,4-d]thiazol-5-yl]phenyl]methanes. Chem. Pharm. Bull., 2009, 57(7), 685-693.
29. Siddiqui, N.; Arshad, M. F.; Ahsan, W.; Alam, M. S. Thiazoles: A Valuable Insight Into The Recent Advances and Biological Activities. Int. J. Pharm. Sci. Drug Res., 2009, 1, 136-143.
30. Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. R.; Westwell, A. D.; Stevens, M. F. G. Antitumor Benzothiazoles. 16. Synthesis and Pharmaceutical Properties of Antitumor 2-(4-Aminophenyl)benzothiazole Amino Acid Prodrugs. J. Med. Chem., 2002, 45, 744-747.
31. Kalaf, A. A.; El-Shafei, A. K.; El-Sayed, A. M. Synthesis of some new bicyclic pyrazoline derivatives. J. Heterocycl. Chem., 1982, 19, 609-612.
32. Lorand, T.; Szako, D.; Foldesi, A.; Parkanyi, L.; Kalman, A.; Neszmelyi, A. Synthesis and stereochemistry of substituted bi- and tri-cyclic 4,5-dihydropyrazoles. J. Chem. Soc. Perkin Trans. I 1985, 481-486.
33. Sohar, P. Nuclear Magnetic Reasonance Spectroscopy, Vol. II, CRC Press: Boca Raton, Florida, 1983.
34. Nasar, M.N.A.; Said, S.A. Novel 3, 3a, 4, 5, 6, 7-Hexahydroindazole and Arylthiazolylpyrazoline derivatives as Anti-inflammatory Agents. Arch. Pharm. Pharm. Med. Chem. 2003, 336, 551-559.
35. Vorländer, D.; Hobohm, K. Ueber die Condensation von Ketopentamethylen mit Aldehyden. Ber., 1896, 29, 1836-1841.
36. Vorländer, D.; Kunze, K. Über Verbindungen des Cyclohexanons mit Benzaldehyd. Ber., 1926, 59, 2078-2085.
37. Garland, C.E.; Reid, E. E. Some new derivatives of Cyclohexanone. J. Am. Chem. Soc., 1925, 47, 2333-2340.
38. Vorländer, D. Säure, Salz, Ester und Addukt. Ber., 1925, 58, 118-143.
39. Huitric, A. C.; Kumler, W. D. The Dipole Moments, Spectra and Structure of Some New 2-Phenyl-, 2-Benzyl-, 2-(p-Halobenzylidene)- and 2,6-Bis-(p-halobenzylidene)-cyclohexanones. J. Am. Chem. Soc., 1956, 78, 614-622.
40. Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Susceptibility Testing. Approved standard M2-A6. CLSI, Wayne, PA USA, 1997.
41. Sahm, D. F.; Washington, J. A. In: Manual of Clinical Microbiology, Ballows A., Hausler Jr. W. J., Herrmann K. L., Isenberg H. D., Shadomy H. J., Eds.; ASM: Washington DC, 1991; 5th ed., pp. 1105.