Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 15, 2011, Pages 4404-4408

  Singh, Nimisha ^a   Pandey, Sarvesh Kumar ^a   Anand, Namrata ^a   Dwivedi, Richa ^a   Singh, Shyam ^a   Sinha, Sudhir Kumar ^a   Chaturvedi, Vinita ^a   Jaiswal, Natasa ^a   Srivastava, Arvind Kumar ^a   Shah, Priyanka ^a   Siddiqui, M Imran ^a   Tripathi, Rama Pati ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Glucosidase inhibitor; Antitubercular agents; bis Benzylidenecycloalkanones; Cycloalkyl fused 2 aminopyrimidines; DHFR inhibitor; Glycogen phosphorylase inhibitor

Indexed keywords

8 (ARYLIDENE) 4 (ARYL) 5,6,7,8 TETRAHYDROQUINAZOLIN 2 YLAMINE DERIVATIVE; 9 (ARYLIDENE) 4 (ARYL) 6,7,8,9 TETRAHYDRO 5H CYCLOHEPTAPYRIMIDIN 2 YLAMINE DERIVATIVE; ALPHA GLUCOSIDASE; ANTIDIABETIC AGENT; BENZYLIDENE DERIVATIVE; CYCLOALKANONE; GLYCOGEN PHOSPHORYLASE; GUANIDINE; PYRIMIDINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BACTERIAL STRAIN; CHEMICAL REACTION; DIABETES MELLITUS; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; EX VIVO STUDY; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MOLECULAR MODEL; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

ALPHA-GLUCOSIDASES; ANTITUBERCULAR AGENTS; BINDING SITES; COMPUTER SIMULATION; ENZYME INHIBITORS; GLYCOGEN PHOSPHORYLASE; HYPOGLYCEMIC AGENTS; MODELS, MOLECULAR; MYCOBACTERIUM TUBERCULOSIS; PYRIMIDINES; QUINAZOLINES;

MYCOBACTERIUM TUBERCULOSIS;

EID: 79960363633     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.06.040     Document Type: Article

References (39)

1. I.M. Lagoja Chem. Biodivers. 2 2005 1
2. Ackermann, P.; Stierli, D.; Jung, P. M. J.; Maienfisch, P.; Cederbaum, F. E. M.; Wenger, J. F. Int. Pat. Appl. WO 03/047347 A1, 2003.
3. Bretschneider, T.; Es-Sayed, M.; Fischer, R.; Maurer, F.; Erdelen, C.; Lsel, P. Int. Pat. Appl. WO 02/067684 A1, 2002.
4. R. Capdeville, E. Buchdunger, J. Zimmermann, and A. Matter Nat. Rev. Drug Discov. 1 2002 493
5. Sehon, C. A.; Lee, D.; Goodman, K. B.; Wang, G. Z.; Viet, A. Q. Int. Pat. Appl. WO 2006/009889 A1, 2006.
6. Goff, D. A.; Harrison, S. D.; Nuss, J. M.; Ring, D. B.; Zhou, X. A. U.S. Pat. 6,417,185 B1, 2002.
7. Pei-Pei Kung, M.D. Casper, K.L. Cook, L. Wilson-Lingardo, L.M. Risen, T.A. Vickers, R. Ranken, L.B. Blyn, J.R. Wyatt, P.D. Cook, and D.J. Ecker J. Med. Chem. 42 1999 4705
8. D.W. Fry, and M.D. Garrett Curr. Opin. Oncol. Endocr. Met. Invest. Drugs 2 2000 40
9. M.D. Garrett, and A. Fattaey Curr. Opin. Genet. Dev. 9 1999 104
10. K.C. Agarwal, V. Sharma, N. Shakya, and S. Gupta Bioorg. Med. Chem. Lett. 19 2009 5474
11. M.J. Chen, T. Shimada, A.D. Moulton, M. Harrison, and A.W. Nienhuis Proc. Natl. Acad. Sci. U.S.A. 79 1982 7435
12. A. Argyrou, M.W. Vetting, B. Aladegbami, and J.S. Blanchard Nat. Struct. Mol. Biol. 13 2006 408
13. A. Kumar, and M.I. Siddiqui J. Mol. Graph. Model. 27 2008 476
14. S. Hawser, S. Lociuro, and K. Islam Biochem. Pharmacol. 71 2006 941
15. S. Jhone, and E. Jucker Birkauser Verlag: Basel 26 1982 259
16. D.J. Brown The Chemistry of Heterocyclic Compounds 1996 John Wiley and Sons New York
17. G.P. Nichols Am. Rev. Tuberc. 76 1957 1016
18. H. Silwer, and P.N. Oscarsson Acta Med. Scand. Suppl. 335 1958 1
19. J.C. Patel Ind. J. Med. Sci. 43 1989 177
20. J. Edsall, J. Collins, and J. Gray Am. Rev. Respir. Dis. 102 1970 725
21. N. Singh, J. Pandey, A. Yadav, V. Chaturvedi, S. Bhatnagar, A.N. Gaikwad, S.K. Sinha, A. Kumar, P.K. Shukla, and R.P. Tripathi Eur. J. Med. Chem. 44 2009 1705
22. R.P. Tripathi, J. Pandey, V. Kukshal, A. Ajay, M. Mishra, D. Dube, D. Chopra, R. Dwivedi, V. Chaturvedi, and R. Ramchandran Med. Chem. Commun. 2011 10.1039/c0md00246a
23. S.S. Bisht, N. Dwivedi, V. Chaturvedi, N. Anand, M. Misra, R. Sharma, B. Kumar, R. Dwivedi, S. Singh, S.K. Sinha, V. Gupta, P.R. Mishra, A.K. Dwivedi, and R.P. Tripathi Eur. J. Med. Chem. 46 2010 5965
24. A. Ajay, V. Singh, S. Singh, S. Pandey, S. Gunjan, D. Dubey, S.K. Sinha, B.N. Singh, V. Chaturvedi, R. Tripathi, R. Ramachandran, and R.P. Tripathi Bioorg. Med. Chem. 18 2010 8289
25. N. Tewari, V.K. Tiwari, R.C. Mishra, R.P. Tripathi, A.K. Srivastava, R. Ahmad, R. Srivastava, and B.S. Srivastava Bioorg. Med. Chem. 11 2003 2911
26. S.S. Bisht, S. Fatima, A.K. Tamrakar, N. Rahuja, N. Jaiswal, A.K. Srivastva, and R.P. Tripathi Bioorg. Med. Chem. Lett. 19 2009 2699
27. M. Yu, S.S. Pochapsky, and B.B. Snider J. Org. Chem. 73 2008 9065
28. H. Saito, H. Tomioka, K. Sato, M. Emori, T. Yamane, and K. Yamashita Antimicrob. Agents Chemother. 35 1991 542
29. J.K. McClatchy Lab. Med. 9 1978 47
30. A.H. Cory, T.C. Owen, J.A. Barltrop, and J.G. Cory Cancer Commun. 3 1991 207
31. T. Mosmann J. Immunol. Methods 65 1983 55
32. P.S. Skinner, S.K. Furney, D.A. Kleinest, and I.M.M. Orme Antimicrob. Agents Chemother. 39 1995 750
33. A. Cogoli, H. Mosimann, C. Vock, A.K.V. Balthazar, and G. Semenza Eur. J. Biochem. 30 1972 7
34. T. Matsui, S. Yoshimoto, K. Osajima, T. Oki, and Y. Osajima Biosci. Biotech. Biochem. 60 1996 2019
35. G. Hubscher, and G.R. West Nature 205 1965 799
36. T.W. Rall, E.W. Sutherland, and J. Barthet J. Biol. Chem. 224 1957 463
37. J.W. Van Teeffelen, J. Brands, E.S. Stroes, and H. Vink Trends Cardiovasc. Med. 17 2007 101
38. M. Nieuwdorp J. Appl. Physiol. 104 2008 845
39. L. Rongbao, R. Sirawaraporn, P. Chitnumsub, W. Sirawaraporn, J. Wooden, F. Athappilly, S. Turley, and W.G.J. Hol J. Mol. Biol. 295 2000 307