Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents

Bioorganic and Medicinal Chemistry Letters

Volumn 26, Issue 7, 2016, Pages 1704-1708

  Subhedar, Dnyaneshwar D ^a   Shaikh, Mubarak H ^a   Arkile, Manisha A ^b   Yeware, Amar ^b   Sarkar, Dhiman ^b   Shingate, Bapurao B ^a  

^a DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Antitubercular; Cytotoxicity; Green protocol; Multicomponent reaction

Indexed keywords

1,3 THIAZOLIDIN 4 ONE DERIVATIVE; CYTOTOXIC AGENT; ISONIAZID; RIFAMPICIN; THIAZOLIDINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

A549 CELL LINE; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; CATALYSIS; CHEMICAL REACTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLOCONDENSATION; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HCT116 CELL LINE; IN VITRO STUDY; MCF 7 CELL LINE; MYCOBACTERIUM BOVIS BCG; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; ONE POT SYNTHESIS; REACTION TIME; ANIMAL; CELL LINE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG EFFECTS; ECONOMICS; GREEN CHEMISTRY; HUMAN; MICROBIAL SENSITIVITY TEST; MYCOBACTERIUM BOVIS; PROCEDURES; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUBERCULOSIS; VETERINARY;

ANIMALS; ANTITUBERCULAR AGENTS; CELL LINE; COMBINATORIAL CHEMISTRY TECHNIQUES; GREEN CHEMISTRY TECHNOLOGY; HUMANS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM BOVIS; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINES; TUBERCULOSIS;

EID: 84962721119     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2016.02.056     Document Type: Article

References (59)

1. 1 Isambert, N., Duque, M.M.S., Plaquevent, J.C., Genisson, Y., Rodriguez, J., Constantieux, T., Chem. Soc. Rev., 40, 2011, 1347.
2. 2 Pansare, D.N., Mulla, N.A., Pawar, C.D., Shende, V.R., Shinde, D.B., Bioorg. Med. Chem. Lett., 24, 2014, 3569.
3. 3(a) Patel, N.B., Patel, H.R., Shaikh, F.M., Rajani, D., Med. Chem. Res., 23, 2014, 1360.
4. 3(b) Tripathi, A.C., Gupta, S.J., Fatima, G.N., Sonar, P.K., Verma, A., Saraf, S.K., Eur. J. Med. Chem., 72, 2014, 52 and references cited therein.
5. 4 Suthar, S.K., Jaiswal, V., Lohan, S., Bansal, S., Chaudhary, A., Tiwari, A., Alex, A.T., Joesph, A., Eur. J. Med. Chem., 63, 2013, 589.
6. 5 Murugesan, V., Tiwari, V.S., Saxena, R., Tripathi, R., Paranjape, R., Kulkarni, S., Makwana, N., Suryawanshi, R., Katti, S.B., Bioorg. Med. Chem., 19, 2011, 6919.
7. 6 Bhalgat, C.M., Darda, P.V., Bothara, K.G., Bhandari, S.V., Gandhi, J., Ramesh, B., Eur. J. Med. Chem., 76, 2014, 580.
8. 7 Nikalje, A.P.G., Shaikh, A.N., Shaikh, S.I., Khan, F.A.K., Sangshetti, J.N., Shinde, D.B., Bioorg. Med. Chem. Lett., 24, 2014, 5558.
9. 8 Cakir, G., Kucukguzel, I., Guhamazumder, R., Tatar, E., Manvar, D., Basu, A., Patel, B.A., Zia, J., Talele, T.T., Kaushik-Basu, N., Arch. Pharm. Chem. Life Sci., 348, 2015, 10.
10. 9 Raza, S., Srivastava, S.P., Srivastava, D.S., Srivastava, A.K., Haq, W., Katti, S.B., Eur. J. Med. Chem., 63, 2013, 611.
11. 10 Isloor, A.M., Sunil, D., Shetty, P., Malladi, S., Pai, K.S.R., Maliyakkl, N., Med. Chem. Res., 22, 2013, 758.
12. 11 Jain, A.K., Vaidya, A., Ravichandran, V., Kashaw, S.K., Agrawal, R.K., Bioorg. Med. Chem., 20, 2012, 3378 and references cited therein.
13. 12 Kumar, K.S.S., Hanumappa, A., Vetrivel, M., Hegde, M., Girish, Y.R., Byregowda, T.R., Rao, S., Raghavan, S.C., Rangappa, K.S., Bioorg. Med. Chem. Lett., 25, 2015, 3616.
14. 13(a) Pansare, D. N.; Shinde, D. B. J. Saudi Chem. Soc., http://dx.doi.org/10.1016/j.jscs.2015.10.005.
15. 13(b) Lill, A.P., Rodl, C.B., Steinhilber, D., Stark, H., Hofmann, B., Eur. J. Med. Chem., 89, 2015, 503.
16. 13(c) Chauhan, K., Sharma, M., Trivedi, P., Chaturvedi, V., Chauhan, P.M.S., Bioorg. Med. Chem. Lett., 24, 2014, 4166.
17. 13(d) Pansare, D.N., Shinde, D.B., Tetrahedron Lett., 55, 2014, 1107.
18. 13(e) Pansare, D.N., Shinde, D.B., Open Chem. J., 2, 2015, 40.
19. 14(a) Srivastava, S.K., Srivastava, S.L., Srivastava, S.D., J. Indian Chem. Soc., 77, 2000, 104.
20. 14(b) Srivastava, T., Haq, W., Katti, S.B., Tetrahedron, 58, 2002, 7619.
21. 14(c) Rawal, R.K., Srivastava, T., Haq, W., Katti, S.B., J. Chem. Res., 5, 2004, 368.
22. 14(d) Yadav, A.K., Kumar, M., Yadav, T., Jain, R., Tetrahedron Lett., 50, 2009, 5031.
23. 14(e) Thakare, M.P., Kumar, P., Kumar, N., Pandey, S.K., Tetrahedron Lett., 55, 2014, 2463.
24. 14(f) Pang, H.X., Hui, Y.H., Fan, K., Xing, X.J., Wu, Y., Yang, J.H., Shi, W., Xie, Z.F., Chin. Chem. Lett., 2012, 10.1016/j.cclet.2015.10.029.
25. 14(g) Gudurudu, V., Nguyen, V., Dalton, J.T., Miller, D.D., Synlett, 2004, 2357.
26. 14(h) Sadashiva, C.T., Narendr, J.N., Chandra, S., Kavitha, C.V., Thimmegowda, A., Subhash, M.N., Rangappa, K.S., Eur. J. Med. Chem., 44, 2009, 4848.
27. 14(i) Kumar, R.C., Kumar, D., J. Indian Chem. Soc., 77, 2002, 492.
28. 14(j) Holmes, C.P., Chinn, J.P., Look, G.C., Gorden, E.M., Gallop, M.A., J. Org. Chem., 60, 1995, 7328.
29. 14(k) Azgomi, N., Mokhtary, M., J. Mol. Catal. A: Chem., 398, 2015, 58.
30. 14(l) Sharma, R., Veera, G., Devi, B., Reddy, K.S., Reddy, M.V., Kondapi, A.K., Bhaskar, C., Heterocycl. Commun., 21, 2015, 187.
31. 14(m) Pratap, U.R., Jawale, D.V., Bhosle, M.R., Mane, R.A., Tetrahedron Lett., 52, 2011, 1689.
32. 14(n) Prasad, D., Preetam, A., Nath, M., RSC Adv., 2, 2012, 3133.
33. 15(a) Malla, A.M., Parveen, M., Ahmad, F., Azaz, S., Alam, M., RSC Adv., 5, 2015, 19552.
34. 15(b) Zhou, Z., Deng, X., J. Mol. Catal. A: Chem., 367, 2013, 99.
35. 15(c) Khabazzadeh, H., Kermani, E.T., Jazinizadeh, T., Arab. J. Chem., 5, 2012, 485.
36. 15(d) Suryawanshi, N.S., Jain, P., Singhal, M., Khan, I., J. Appl. Chem., 1, 2012, 18.
37. 15(e) Kermani, E.T., Khabazzadeh, H., Jazinizadeh, T., J. Heterocycl. Chem., 48, 2011, 1192.
38. 15(f) Rajendran, A., Raghupathy, D., Priyadarshini, M., Int. J. Chem. Technol. Res., 3, 2011, 298.
39. 15(g) Wang, C., Zhao, W., Li, H., Guo, L., Green Chem., 11, 2009, 843.
40. 15(h) Ganeshpure, P.A., George, G., Das, J., J. Mol. Catal. A: Chem., 279, 2008, 182.
41. 15(i) Jiang, H., Wang, C., Li, H., Wang, Y., Green Chem., 8, 2006, 1076.
42. 15(j) Wang, C., Guo, L., Li, H., Wang, Y., Weng, J., Wu, L., Green Chem., 8, 2006, 603.
43. 15(k) Weng, J., Wang, C., Li, H., Wang, Y., Green Chem., 8, 2006, 96.
44. 16 Shaikh, M. H.; Subhedar, D. D.; Khan, F. A. K.; Sangshetti, J. N.; Shingate, B. B. Res. Chem. Inter., http://dx.doi.org/10.1007/s11164-015-2348-z.
45. 17(a) Shaikh M. H.; Subhedar, D. D.; Khan, F. A. K.; Sangshetti, J. N.; Nawale, L.; Arkile, M.; Sarkar, D.; Shingate, B. B. J. Heterocycl. Chem., http://dx.doi.org/10.1002/jhet.2598.
46. 17(b) Subhedar, D. D.; Shaikh, M. H.; Khan, F. A. K.; Sangshetti, J. N.; Khedkar, V. M.; Shingate, B. B. New J. Chem., http://dx.doi.org/10.1039/c6nj00021e.
47. 17(c) Shaikh, M.H., Subhedar, D.D., Arkile, M., Khedkar, V.M., Jadhav, N., Sarkar, D., Shingate, B.B., Bioorg. Med. Chem. Lett., 26, 2016, 561.
48. 17(d) Shaikh, M.H., Subhedar, D.D., Khan, F.A.K., Sangshetti, J.N., Shingate, B.B., Chin. Chem. Lett., 27, 2016, 295.
49. 17(e) Shaikh, M.H., Subhedar, D.D., Nawale, L., Sarkar, D., Khan, F.A.K., Sangshetti, J.N., Shingate, B.B., Med. Chem. Commun., 6, 2015, 1104.
50. 17(f) Shinde, P.V., Labade, V.B., Gujar, J.B., Shingate, B.B., Shingare, M.S., Tetrahedron Lett., 53, 2012, 1523.
51. 17(g) Shinde, P.V., Labade, V.B., Shingate, B.B., Shingare, M.S., J. Mol. Catal. A: Chem., 336, 2011, 100.
52. 17(h) Shinde, P.V., Kategaonkar, A.H., Shingate, B.B., Shingare, M.S., Beilstein J. Org. Chem., 7, 2011, 53.
53. 17(i) Shinde, P.V., Kategaonkar, A.H., Shingate, B.B., Shingare, M.S., Tetrahedron Lett., 52, 2011, 2889.
54. 18(a) Kumar, D., Sonawane, M., Pujala, B., Jain, V.K., Bhagat, S., Chakraborti, A.K., Green Chem., 15, 2013, 2872.
55. 18(b) Foroughifar, N., Ebrahimi, S., Chin. Chem. Lett., 24, 2013, 389.
56. 4] 20 mol % was magnetically stirred at 80 °C. The progress of the reaction was monitored by TLC using ethyl acetate/hexane as a solvent system. The reaction mixture was quenched with crushed ice and extracted with ethyl acetate (2 × 25 mL). The organic extracts were washed with brine (2 × 25 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford the corresponding crude compounds. The obtained crude compounds were recrystallized using ethanol.
57. 20(a) Khan, A., Sarkar, S., Sarkar, D., Int. J. Antimicrob. Agents, 32, 2008, 40.
58. 20(b) Sarkar, S., Sarkar, D., J. Biomol. Screening, 17, 2012, 966.
59. 21 Doyen, C.M., Moshkin, Y.M., Chalkley, G.E., Bezstarosti, K., Demmers, J.A., Rathke, C., Renkawitz-Pohl, R., Verrijzer, C.P., Cell Rep., 4, 2003, 59.