Browse > Article
http://dx.doi.org/10.5012/bkcs.2011.32.7.2171

Synthetic Route for New (Z)-5-[4-(2-Chloroquinolin-3-yl) Methoxy]benzylidinethiazolidine-2,4-diones  

Jawale, Dhanaji V. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Pratap, Umesh R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Mane, Ramrao A. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.7, 2011 , pp. 2171-2177 More about this Journal
Abstract
Synthetic route has been developed for the synthesis of new (Z)-5-[4-(2-chloroquinolin-3-yl) methoxy]benzyl-idinethiazolidine-2,4-diones (6a-h) starting from 2-chloro-3-hydroxymethyl quinolines (2a-h). The hydroxy methyl quinolines on tosylation yielded (3a-h). Condensation of the tosyl intermediates with 4-hydroxy benzaldehydes has been carried in DMF in presence of $K_2CO_3$ and obtained 4-quinolinyl methoxy benzaldehydes (4a-h). Conveniently Knoevenagel condensation of quinolinyl methoxy benzaldehydes (4a-h) and 2, 4-thiazolidinedione (5) has been carried in PEG-400 in presence of L-proline and obtained better yields of the titled compounds (6a-h).
Keywords
2,4-Thiazolidinedione; Quinoline; L-Proline; PEG-400; Etheral linkage;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 Meth-Cohn, O.; Narine, B.; Tarnowski, B. J. Chem. Soc. Perkin Trans. 1 1981, 1520.
2 Bekhit, A. A.; El-Sayed, O. A.; Aboulmagd, E.; Park, J. Y. Eur. J. Med. Chem. 2004, 39, 249.   DOI   ScienceOn
3 Gadekar, L. S.; Arbad, B. R.; Lande, M. K. Org. Chem.: An Ind. J. 2008, 4, 458.
4 Shelke, K. F.; Sapkal, S. B.; Kakade, G. K.; Sadaphal, S. A.; Shingate, B. B.; Shingare, M. S. Green Chem. Lett. Rev. 2010, 3, 17.   DOI
5 Bhattarai, B. R.; Kafle, B.; Hwang, J. S.; Khadka, D.; Lee, S. M.; Kang, J. S.; Hamd, S. W.; Han, I. O.; Park, H.; Cho, H. Bioorg. Med. Chem. Lett. 2009, 19, 6161.   DOI   ScienceOn
6 Madhavan, G. R.; Chakrabarti, R. K.; Reddy, A.; Rajesh, B. M.; Balraju, V.; Rao, R. B.; Iqbal, J. Bioor & Med. Chem. 2006, 14, 584.   DOI   ScienceOn
7 Madhavan, G. R.; Chakrabarti, R.; Kumar, S. K. B.; Misra, P.; Rao, N. V. S.; Balraju, M. V.; Kasiram, K.; Babu, R. K.; Suresh, J.; Lohray, B. B.; Lohray, V. B.; Iqbal, J.; Rajagopalan, R. Euro. J. Med. Chem. 2001, 36, 627.   DOI   ScienceOn
8 Yoshitata, O.; Teruo, M.; Mishiko, N.; Motoyuki, J.; Norio, K. Chem. Pharm. Bull. 1992, 40, 907.   DOI   ScienceOn
9 Liu, Z.; Huang, Y.; Zhang, W.; Ma, L.; Li, J.; Wang, X.; Li, J.; Shen, J. J. Comb. Chem. 2008, 10, 632.   DOI   ScienceOn
10 Pokalwar, R. U.; Hangarge, R. V.; Kategaonkar, A. H.; Shingare, M. S. Russian J. Org. Chem. 2009, 45, 430.   DOI
11 Brag, B. L.; Vidya, B.; Bheema, P. R.; Gurram, R. M.; Nagahelli, M.; Kovvidi, N. R.; Pmaulapati, G. R.; Chakraborthy, R.; Reeba, K. V.; Ramanujam, R.; Rao, N. V.; Hemant, K. J.; Swaminathan, S. http://pubs.acs.org/doi/abs/10.1021/jm970444e J. Med. Chem. 1998, 41, 1619.   DOI   ScienceOn
12 Lesyk, R. B.; Zimenkovsky, B. S.; Troc'ko, N. Ukrainica Bioorganica Acta. 2004, 1, 29.
13 Lesyk, R. B.; Zimenkovsky, B. S. Curr. Org. Chem. 2004, 8, 1547.   DOI   ScienceOn
14 Mohareb, R. M.; Fleita, D. H. Heteroatom Chem. 2002, 13, 258.   DOI   ScienceOn
15 Herrding, D. A.; Christmann, L. T.; Clark, T. J.; Holmes, D. J.; Rittenhouse, S. F.; Takata, D. T.; Venslavsky, J. W. Bioorg. Med. Chem. Lett. 2003, 13, 3771.   DOI   ScienceOn
16 Bruno, G.; Costantino, L.;Curinga, C.; Maccari, R.; Monforte, F.; Nicolo, F.; Ottana, R.; Vigoritac, M. G. Bioorg. & Med. Chem. 2002, 10, 1077.   DOI   ScienceOn
17 Gubert, S.; Braojos, C.; Anglada, L.; Bolos, J.; Pllacin, C. J. Heterocycl. Chem. 1992, 29, 55.   DOI
18 Ali, A. M.; Saber, G. E.; Mahfouz, N. M.; El-Gendy, M. A.; Radwan, A. A.; Hamid, M. A. Arch Pharm. Res. 2007, 30, 1186.   과학기술학회마을   DOI   ScienceOn
19 Maccari, R.; Ottanà, R.; Ciurleo, R.; Rakowitz, D.; Matuszczak, B.; Laggner, C.; Langer, T. Bioorg. & Med. Chem. 2008, 16, 5840.   DOI   ScienceOn
20 Luo, Y.; Ma, L.; Zheng, H.; Chen, L.; Li, R.; He, C.; Yang, S.; Ye, X.; Chen, Z.; Li, Z.; Gao, Y.; Han, J.; He, G.; Yang, L.; Wei, Y. J. Med. Chem. 2010, 53, 273.   DOI   ScienceOn
21 Alhaider, A. A.; Adbekader, M. A.; Lien, E. J. J. Med. Chem. 1985, 28, 1394.   DOI
22 Cai, W.; Xu, D.; Yiyao, G. 1987, 18, 62. Chem Abstr 107, 1987, 236651v.
23 Edmont, D.; Rocher, R.; Plisson, C.; Chenault, J. Bioorg. Med. Chem. Lett. 2000, 10, 1831.   DOI   ScienceOn
24 Oguchi, M.; Wada, K.; Honma, H.; Tanaka, A.; Taneko, T.; Sakakibara, S.; Ohsumi, J.; Serizawa, N.; Fujiwara, T.; Horikoshi, H.; Fujita, T. J. Med. Chem. 2000, 43, 3052.   DOI   ScienceOn
25 Malamas, M. S.; Sredy, J.; Gunawan, I.; Mihan, B.; Sawicki, D. R.; Seestaller, L.; Sullivan, D.; Flam, B. R. J. Med. Chem. 2000, 43, 995.   DOI   ScienceOn
26 Saltiel, A. R.; Olefsky, J. M. Diabetes 1996, 45, 1661.   DOI   ScienceOn
27 Fujita, T.; Sugiyama, Y.; Taketomi, S.; Sohda, T.; Kawamatsu, Y.; Iwatsuka, H.; Suzuoka, Z. Diabetes 1983, 32, 804.   DOI   ScienceOn
28 Klirwer, S. A.; Lenhard, J. M.; Wilson, T. M. Cell 1995, 83, 813.   DOI   ScienceOn
29 Chang, A. Y.; Wyse, B. M.; Gilchrist, B. J.; Peterson, T.; Diani, A. R. Diabetes 1983, 32, 830.   DOI   ScienceOn
30 Lehman, J. M.; Moore, L. B.; Smith Oliver, T. A.; William, O. W.; Willson, T. M.; Kliewer, S. A. J. Biol. Chem. 1995, 270, 12953.   DOI   ScienceOn
31 Momose, Y.; Meguro, K.; Ikeda, H.; Hatanka, C.; Oi, S.; Sohda, T. Chem. Pharm. Bull. 1991, 39, 1440.   DOI   ScienceOn
32 Cantello, B. C. C.; Cawthorne, M. A.; Haigh, D.; Hindley, R. M.; Smith, S. A.; Thurlby, P. L. Bioorg. Med. Chem. Lett. 1994, 4, 1181.   DOI   ScienceOn
33 Momura, M.; Kinoshita, S.; Satoh, H.; Maeda, T.; Murakami, K.; Tsunodam, M.; Miyachi, H.; Awano, K. Bioorg. Med. Chem. Lett. 1999, 9, 533.   DOI   ScienceOn
34 Hong, W. L.; Joong, B. A.; Sung, K. K.; Soon, K. A.; Deok, C. H. Org. Proc. Res. & Dev. 2007, 11, 190.   DOI   ScienceOn