Concise and facile synthesis of novel pyrano[2, 3-d]pyrimidine-7-one/thione derivatives as in vitro antimicrobial and antitubercular agents

Letters in Drug Design and Discovery

Volumn 8, Issue 9, 2011, Pages 750-757

  Mistry, Prashant T ^a   Kamdar, Nimesh R ^a   Haveliwala, Dhaval D ^a   Patel, Saurabh K ^a  

^a VEER NARMAD SOUTH GUJARAT UNIVERSITY   (India)

Author keywords

Antimicrobial activity; Antitubercular activity; Pyranopyrimidine; Pyrimidine thione; Pyrimidone

Indexed keywords

5 AMINO 3 METHYL 1,4 DIPHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 3 METHYL 1,4 DIPHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; 5 AMINO 4 (2 CHLOROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (2 CHLOROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; 5 AMINO 4 (3 BROMOPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (3 BROMOPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; 5 AMINO 4 (3 CHLOROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (3 CHLOROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; 5 AMINO 4 (3 NITROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (3 NITROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; 5 AMINO 4 (4 CHLOROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (4 CHLOROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; 5 AMINO 4 (4 FLUOROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (4 FLUOROPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THONE; 5 AMINO 4 (4 HYDROXYPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (4 HYDROXYPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; 5 AMINO 4 (4 METHOXYPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (4 METHOXYPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; 5 AMINO 4 (4 METHYLPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) ONE; 5 AMINO 4 (4 METHYLPHENYL) 3 METHYL 1 PHENYL 4,8 DIHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 D]PYRIMIDINE 7(1H) THIONE; AMPICILLIN; ANTIINFECTIVE AGENT; CHLORAMPHENICOL; CIPROFLOXACIN; GRISEOFULVIN; NYSTATIN; PYRANO[2,3 D]PYRIMIDINE 7 ONE DERIVATIVE; PYRANO[2,3 D]PYRIMIDINE 7 THIONE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 80052991584     PISSN: 15701808     EISSN: 1875628X     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Sheng, C. K.; Li, J.; Hideo, N. Studies on heterocyclic compounds: synthesis and analgesic and anti-inflammatory activities of 3, 4-dimethylpyrano[2, 3-c]pyrazol-6-one derivatives. J. Med. Chem., 1984, 27, 539-544.
2. William, L. P.; Francis, J. The structure determination of antibiotic compounds from hypericum uliginosum. J. Amer. Chem. Soc., 1968, 90(17), 4716-4723.
3. Soizic, P.; Valerie, T.; Brigitte, S. J.; Michel, K.; Stewart, T. C.; Francois T.; Yves, L. J. Antimycobacterial benzofuro[3, 2-f]chromenes from a 5-bromochromen-6-ol. Synthesis, 2007, 10, 1566-1570.
4. Dhanabal, T.; Suresh T.; Mohan, P. S. Synthesis of new 1, 10-diethoxy-1H-pyrano[4, 3-b]quinolines and their antibacterial studies. Ind. J. Chem., 2006, 45-B, 523-525. (Pubitemid 43533583)
5. Hartmut, S.; Wilhelm, B. Fungicidally active pyrano-pyrazole derivatives. U. S. Patent 4, 515, 801, May 7, 1985.
6. Samantha, J. A.; William, F. H.; Jai, P. S.; Colin, W. S.; Lawrence, E. S. Pharmaceutical compounds. U. S. Patent 5,514,706, May 7, 1996.
7. Paronikyan, E. G.; Noravyan, A. S.; Dzhagatspanyan, I. A.; Nazaryan, I. M.; Paronikyan, R. G. Synthesis and neurotropic activity of pyrrolo[2, 3-c]pyran (thiopyran, pyridine) and pyrano (thiopyrano, pyrido) [4', 3':4, 5]pyrrolo-[1, 2-b]asym-triazine derivatives. Pharmaceutical Chemistry Journal, 2001, 35(2), 63-65.
8. Lee, Y. R.; Xia, L. Concise total synthesis of biologically interesting pyranochalcone natural products: citrunobin, boesenbergin-A, boesenbergin-B, xanthohumol-C and glabrachromene. Synthesis, 2007, 20, 3240-3246. (Pubitemid 350013372)
9. Seref, D.; Faten, D. A.; Baland, S. O.; Yagmur, T. Some 6-substituted 3-aryl-7-oxothiazolo[4, 5-d]pyrimidin-2 (3H)-thione derivatives and their antimicrobial activities. Phosphorus, Sulfur, and Silicon and the Related Elements, 2007, 182(8), 1793-1803.
10. Corre, L. L.; Girard, A. L.; Aubertin, J.; Radvanyi, F.; Benoist-Lasselin, C.; Jonquoy, A.; Mugniery, E.; Legeai-Mallet, L.; Busca, P.; Merrer, Y. L. Synthesis and biological evaluation of a triazolebased library of pyrido[2, 3-d]pyrimidines as FGFR3 tyrosine kinase inhibitors. Org. Biomol. Chem., 2010, 8, 2164-2173.
11. Venkatesan, J.; Pandeya, S. N.; Selvakumar, D. Synthesis and biological evaluation of-4, 5-dihydro-2-amino pyrimidines. Ind. J. Pharm. Sci., 2007, 69(4), 586-589. (Pubitemid 350099034)
12. Amir, M. S.; Javed, A.; Kumar, H. Pyrimidine as antiinflammatory agent: A review. Ind. J. Pharm. Sci., 2007, 69(3), 337-343. (Pubitemid 47379259)
13. Kumarswamy, M.; Prathima, N. D.; Mathias, A.; Chandrashekhar, C.; Vaidhya, V. P. Synthesis and pharmacological evaluation of 2-mercapto-4- substituted-naptho[2, 1-b]furo[3, 2-d]pyrimidines. Ind. J. Pharm. Sci., 2006, 68(6), 731-736. (Pubitemid 46457268)
14. Gupta, A. K.; Kayath, H. P.; Singh, A.; Sharma, G.; Mishra, K. C. Anticonvulsant activity of pyrimidine thiols. Ind. J. Pharmacol., 1994, 26, 227-228. (Pubitemid 24293983)
15. Paola, P.; Francesco, M. E.; Gardelli, C.; Harper, S.; Muraglia, E.; Emanuela, N.; Federica, O.; Petrocchi, A.; Poma, M.; Rowley, M.; Scarpelli, R.; Laufer, R.; Gonzalez, O. P.; Monteagudo, E.; Bonelli, F.; Hazuda, D.; Stillmock, K. A.; Summa, V. Dihydroxypyrimidine-4-carboxamides as novel potent and selective HIV integrase inhibitors. J. Med. Chem., 2007, 50, 2225-2239. (Pubitemid 46683075)
16. Gueiffier, A.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J. C.; Kerbal, A.; Essassi, E. M.; Debouzy, J. C.; Witvrouw, M.; Blache, Y.; Balzarini, J.; Clercq, E. D.; Chapat, J. P. Synthesis of acyclo-c-nucleosides in the imidazo[1, 2-α]pyridine and pyrimidine series as antiviral agents. J. Med. Chem., 1996, 39, 2856-2859. (Pubitemid 26240354)
17. Chu, X. J.; Depinto, W.; Bartkovitz, D.; So, S. S.; Vu, B. T.; Packman, K.; Lukacs, C.; Ding, Q.; Jiang, N.; Wang, K.; Goelzer, P.; Yin, X.; Smith, M. A.; Higgins, B. X.; Chen, Y.; Xiang, Q.; Moliterni, J.; Gerald, K.; Graves, B.; Lovery, A.; Fotouhi, N. Discovery of [4-amino-2-(1-methanesulfonylpiperidin-4- ylamino) pyrimidin-5-yl] (2, 3-difluro-6-methoxyphenyl) methanone (R547), A potent and selective cyclin-dependent kinase inhibitor with significant in vivo antitumor activity. J. Med. Chem., 2006, 49, 6549-6560. (Pubitemid 44657449)
18. Baraldi, P. G.; Fruttarolo, F.; Tabrizi, M. A.; Romagnoli, R.; Preti, D.; Ongini, E.; El-Kashef, H.; Carrion, M. D.; Borea, P. A. Synthesis of a new series of pyrazolo[1, 5-a]pyrimidines structurally related to zaleplon. J. Hetero. Chem., 2009, 44, 355-361. (Pubitemid 350205234)
19. Crespo, M. I.; Pages, L.; Vega, A.; Segarra, V.; Lopez, M.; Domenech, T.; Miralpeix, M.; Beleta, J.; Ryder, H.; Palacios, J. M. Design, synthesis, and biological activities of new thieno[3, 2-d]pyrimidines as selective type 4 phosphodiesterase inhibitors. J. Med. Chem., 1998, 41(21), 4021-4035. (Pubitemid 28483480)
20. Piazza, G. A.; Pamukcu, R. Method of treating a patient having precancerous lesions with phenyl cycloamino pyrimidinone derivatives. U. S. Patent 6,060,477, May 9, 2000.
21. Abdellatif, M. S. D. Fused thiazole from 2-(4-phenyl-3 (h)-thiazol-2-ylidene) malononitrile: a novel synthesis of thiazolo[3, 2-c] pyrimidine, thiazolo[3, 2-a]pyridine, pyrazolo[3, 4-d]-1, 3-thiazolino[2, 3-f]pyrimidine and arylazo thiazolylidene derivatives. Sulfur Letters, 2003, 26, 35-41.
22. Eljazi, I. A.; Abubshait, S. A. Heterocyclic o-aminonitriles: preparation of pyrazolo[3, 4-d]-pyrimidines with modification of the substituents at the 1 position. Molecules, 2001, 6, 621-638. (Pubitemid 38990300)
23. Kamdar, N. R.; Haveliwala, D. D.; Mistry, P. T.; Patel, S. K. Synthesis and evaluation of in vitro antitubercular activity and antimicrobial activity of some novel 4H-chromeno[2, 3-d]pyrimidine via 2-amino-4-phenyl-4H-chromene-3- carbonitriles. Med. Chem. Res., Article in press, DOI 10.1007/s00044-010-9399-x.
24. Kamdar, N. R.; Haveliwala, D. D.; Mistry, P. T.; Patel, S. K. Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines. Eur. J. Med. Chem., 2010, 45, 5056-5063.
25. Jin, T. S.; Wang, A. Q.; Cheng, Z. L.; Zhang, J. S.; Li, T. S. A clean and simple synthesis of 6-amino-4-aryl-5-cycno-3-methyl-1-phenyl-1, 4-dihydropyrano[2, 3-c]pyrazole in water. Synthetic Communications, 2005, 35, 137-143.
26. Rattan, A. Antimicrobials in Laboratory Medicine, Churchill, B. I., Livingstone: New Delhi, 2000, pp. 85-108.