Synthesis and biological studies of novel 2-(4-substitutedbenzylthio)-5-amino-6-(benzo[d]thiazol-2-yl)-7-(4-chlorophenyl)pyrido-[2,3-d]-pyrimidin-4(3H)-one derivatives

Organic Communications

Volumn 4, Issue 2, 2011, Pages 33-41

  Suresh, M ^a   Lavanya, P ^b   Naga Raju, K ^b   Jonnalagadda, Sreekanth B ^a   Venkata Rao, C ^b  

^a UNIVERSITY OF KWAZULU NATAL   (South Africa)

^b SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

2 (4 substitutedbenzylthio) 5 amino 6 (benzo d thiazol 2 yl) 7 (4 chlorophenyl)pyrido 2,3 d pyrimidin 4(3H) one; antibacterial; Antifungal

Indexed keywords

EID: 84859356477     PISSN: None     EISSN: 13076175     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. Quiroga, J.; Insuasty, H.; Insuasty, B.; Abonia, R.; Cobo, J.; Sanchez, A..; Nogueras, M. New aspects on the selective synthesis of 7-arylpyrido[2,3-d]pyrimidines. Tetrahedron 2002, 58, 4873-4877.
2. Wamhoff, H.; Lichtenthaeler, L. Heterocyclic Beta-Enamino Esters .22. Pyrido[2,3-D]Pyrimidines from 2-Amino-3-Ethoxycarbonyl-1,4,5,6-Tetrahydropyridine And Isocyanates, Isothiocyanates, Imidates, Formamide, And Lactim Ethers. Chem. Ber. 1978, 111, 2297-2306.
3. Borrell, J. I.; Teixido, J.; Martinez-Teipel, B.; Matallana, J. L.; Copete, M. T.; Llimargas, A.; Garcia, E. Synthesis and Biological Activity of 4-Amino-7-oxo-Substituted Analogues of 5-Deaza-5,6,7,8-tetrahydrofolic Acid and 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid. J. Med. Chem. 1998, 41, 3539-3545.
4. Bratz. M.; Kober. R.; Seele. R.; Saupe. T.; Meyer. N.; Walker. N.; Landes. A.; Walter. H.; Canadian. Patent. Appl. A novel one-pot three-components reaction: synthesis of indeno[2',1':5,6]pyrido[2,3:4",5"]pyrimido[2",1"-c]triazole-5,7-dione. A new ring system. US Patent 2,078,4767, (1993); Chem Abstr., 120, 77293b, (1994).
5. Parish, H. A.; Gilliom, R. D.; Purcell, W. P.; Browne, R. K.; Spirk, R. F.; White, H. D. Synthesis and diuretic activity of 1,2-dihydro-2-(3-pyridyl)-3H-pyrido-[2,3-d]pyrimidin-4-one and related compounds. J. Med. Chem. 1982, 25, 98-102.
6. Deyanov, A. B.; Niyazov, R. K.; Nazmetdinov, F. Y.; Syropyatov, B. Y.; Kolla, V. E.; Konshin, M. E. Amides, Nitriles of 2-Arylamino-5-Carboxy(Carbethoxy)-6-Methylnicotinic Acids And 1-Aryl-6-Carbethoxy-7-Methyl-4-Oxo-1,4-Dihydropyrido[2,3-D]Pyrimidines - Synthesis And Biological-Activity. Khim Farm Zh. 1991, 25, 26-28.
7. Heckler, R. E.; Jourdan, G. P. Eur. Patent 414 386, 1991.
8. Heckler, R. E.; Jourdan, G. P. Chem. Abstr. 1991, 115, 71630.
9. Heidelberger, C.; Ansfield, F. Experimental and Clinical Use of Fluorinated Pyrimidines In Cancer Chemotherapy. J. Cancer Res., 1963, 23, 1226-1243.
10. Baba, M.; Pauwels, R.; Herdewijn, P.; De Clercq, E.; Desmyster, J.; Vandepulfe, M. Both 2',3'-dideoxythymidine and its 2',3'-unsaturated derivative (2',3'-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro. Biochem Biophys Res Commun. 1987, 142, 128-134.
11. De Clercq, E. Chemotherapeutic approaches to the treatment of the acquired immune deficiency syndrome (AIDS). J Med Chem. 1986, 29, 1561-1569.
12. De Clercq, E. Potential of bromovinyldeoxyuridine in anticancer chemotherapy. Anticancer Res. 1986, 6, 549-556.
13. Jones, A. S.; Verhelst, G.; Walker, R. T. The synthesis of the potent anti-herpes virus agent, -5(2-bromovinyl)-2'-deoxyuridine and related compounds. Tetrahedron Lett. 1979, 20, 4415-4418.
14. Kretzschmar, E. Derivatives of 4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine. Pharmazie. 1980, 35, 253-256.
15. Shih, C.; Grindley, G. B.; Gossett, L. S.; Moran, R. G. Chem. Abstr. 1991, 115, 92863.
16. Agarwal, A.; Ashutosh, R.; Goyal, N.; Chauhan, P. M. S.; Gupta, S. Dihydropyrido[2,3-d]pyrimidines as a new class of antileishmanial agents. Bioorg Med. Chem. 2005, 13, 6678-6684.
17. Bold, R. J.; Termuhlen, P. M.; McConkey, D.J. Apoptosis, cancer and cancer therapy. Surg. Oncol., 1997, 6, 133-142.
18. Reed, J. C. Mechanisms of apoptosis avoidance in cancer. Curr. Opin. Oncol. 1999, 11, 68-75.
19. Taylor, E. C.; Palmer, D. C.; George, T. J.; Fletcher, S. R.; Tseng, C. P.; Harrington, P. J.; Beardsley, G. P.; Dumas, D.J.; Rosowsky, A.; Wick, A.; Synthesis and biological activity of L-5-deazafolic acid and Ldeazaaminopterin: synthetic strategies to 5-deazapteridines. J. Org. Chem. 1983, 48, 4852-4860.
20. Degraw, J. I.; Christie, P. H.; Colwell, W. T.; Sirotnak, F. M. Synthesis and antifolate properties of 5,10-ethano-5,10-dideazaaminopterin J. Med. Chem. 1992, 35, 320-324.
21. Broom, A. D.; Shim, J. L.; Anderson, G. L. Pyrido[2,3-d]pyrimidines. IV. Synthetic studies leading to various oxopyrido[2,3-d]pyrimidines. J. Org. Chem. 1976, 41, 1095-1099.
22. Grivsky, E. M.; Lee, S.; Sigel, C. W.; Duch, D. S.; Nichol, C. A. Synthesis and antitumor activity of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido-[2,3-d]pyrimidine. J Med. Chem. 1980, 23, 327-329.
23. Hitchings, G. H.; Baccanari, D. P.; in Folate Antagonists as Therapeutic Agents, Vol. 1, Sirotnak, F. M.; Burchall, J. J.; Ensminger, W. B.; Montgomery, J. A. Academic Press Inc., Orlando, FL, 1984, p 151.
24. Matsumoto, J.; Minami, S. Pyrido[2,3-d]pyrimidine antibacterial agents. 3. 8-alkyl- and 8-vinyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acids and their derivatives. J. Med. Chem. 1975, 18, 74-79.
25. Suzuki, N. Synthesis of Antimicrobial Agents. V. Synthesis and Antimicrobial Activities of Some Heterocyclic Condensed 1, 8-Naphthyridine Derivatives. Chem. Pharm. Bull. 1980, 28, 761-768.
26. Sharma, S. A. K.; Prakash, L. Synthesis of some pyrido[2,3-d]pyrimidine derivatives and their antimicrobial activity. Heterocyclic Commun. 1994, 1, 89-94.
27. Girreser, U; Heber, D.; Schutt, M. Synthesis of 6-substituted 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones using the Vilsmeier reaction. Tetrahedron. 2004, 60, 11511-11517.
28. Hurlbert. B. S.; Ferone. R.; Herrmann. T. A.; Hitchings. G. H.; Barnett. M.; Bushby. S. R. Studies on Condensed Pyrimidine Systems. XXV. 2,4-Diamino pyrido[2,3-d]pyrimidines. Biological Data. J. Med. Chem. 1968, 11, 711-717.
29. Cruickshank, R.; Duguid, J. P.; Marion, B. P. et al. Med. Microbiology, 12th ed., vol. 2, Churchil Livingstone, London, 1975, 196.
30. Collins, A. H., Lyne, P. M. Microbiological Methods, 4th ed.. Butterworth, London, 1976, 235-237.
31. Khan, Z. K. In vitro and vivo screening techniques for bioactivity screening and evaluation, in: Proceeding Int. workshop UNIDO-CDRI., 1997, 210-211.
32. Varma, R. S.; Khan, Z. K.; Singh, A. P. Antifungal Agents: Past, Present & Future Prospects. National Academy of Chemistry & Biology, India, Lucknow, 1998, 55-128.