Synthesis and antimicrobial activity of some novel thienopyrimidines and triazolothienopyrimidines

Nitinkumar S. Shetty1, Ravi S. Lamani1, Imtiyaz Ahmed M. Khazi1
1Department of Chemistry, Karnatak University, Dharwad, India

Tóm tắt

Novel tricyclic thienopyrimidines (3, 5, 6, 9, 11, 12) and triazole fused tetracyclic thienopyrimidines (4a-c, 10a-c) were synthesized from precursors 2-amino-6-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile 1 and 2-amino-7-oxo-4,5,6,7-tetrahydro-1-benzothio-phene-3-carbonitrile 7 respectively. The corresponding precursors were prepared by employing the Gewald reaction. The structures of newly synthesized compounds were characterized by spectral and analytical data. All the compounds were screened for their biological activities. Some of the compounds displayed promising antibacterial and antifungal activities.

Tài liệu tham khảo

Gold H S and Moellering R C 1996 Engl. N. J. Med. 335 1445 Bossche V H, Marichal P and Odds F C 1994 Trends Microbial. 2 393 Cohen M L 1992 Science 257 1050 El-Kerdawy M M, Yousif M Y, El-Emam A A, Moustafa M A and El-Sherbeny M A 1996 Boll. Chim. Farmaceutico. 135 301 Modica M, Santagati M, Santagati A, Cutuli V, Mangano N and Caruso A 2000 Pharmazie 55 500 Chambhare R V, Khadse B G, Bobde A S and Bahekar R H 2003 Eur. J. Med. Chem. 38 89 Santagati N A, Caruso A, Cutuli V M and Caccamo F 1995 Il farmaco 50 689 Jennings L D, Kincaid S L, Wang Y D, Krishnamurthy G, Beyer C F, Mginnis J P, Miranda M, Discafani C M and Rabindran S K 2005 Bioorg. Med. Chem. Lett. 15 4731 Meyer M D, Altenbach R J, Basha F Z, Carroll W A, Condon S, Elmore S W, Kerwin J F, Sippy K B, Tietje K, Wendt M D, Hancock A A, Brune M E, Buckner S A and Drizin I 2000 J. Med. Chem. 43 1586 Panico A, Cardile V, Santagati A and Gentile B 2001 Il farmaco 56 959 Vorobev E V, Kletskii M E, Krasnikov V V, Mezheritskii V V and Steglenko D V 2006 Russ. Chem. Bull. 55 2247 Shishoo C J, Devani M B, Ullas G V, Ananthan S and Bhadthi V S 1981 J. Het. Chem. 18 43 Kolavi G, Hegde V and Khazi I 2006 Tetrahedron Lett. 47 2811 Kolavi G, Hegde V, Khazi I and Gadad P 2006 Bioorg. Med. Chem. 14 3069 Hegde V S, Kolavi G D and Khazi I M 2006 J. Sulfur Chem. 27 307 Rosowsky A, Chaykovsky M, Chen K K N, Lin M and Modest E J 1973 J. Med. Chem. 16 185 Dave C G and Shah R D 1998 J. Het. Chem. 35 1295 Review: Sebnis R W, Ragnekar D W and Sonawane N D 1999 J. Het. Chem. 36 333 Gewald K, Schinke E and Boettcher H 1966 Chem. Ber. 99 94 National Committee for Clinical Laboratory Standards 1996 Method for broth dilution antifungal susceptibility testing yeast. Approved standard, M27-A, 15, 10, NCCLS, VA Medical Center, Tuscon National Committee for Clinical Laboratory Standards 2002 Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Third edn, Approved standard. NCCLS document M100-S12, NCCLS, Wayne, PA, USA