Browse > Article
http://dx.doi.org/10.5012/jkcs.2011.55.5.760

Synthesis of Novel Series of Various Substituted1-(5-(2-p-tolyloxyquinolin-3-yl)-2-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)ethanone and its Antibacterial Activity  

Joshi, Ratnadeep S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Mandhane, Priyanka G. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Chate, Asha V. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Gill, Charansingh H. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Publication Information
Journal of the Korean Chemical Society / v.55, no.5, 2011 , pp. 760-764 More about this Journal
Abstract
A new series of 1-(5-(2-tolyloxyquinoline-3-yl)-2-(pyridine-4-yl)-1,3,4-oxidiazol-3(2H)-yl)ethanones were synthesized from cyclisation of N'-((2-(p-tolyloxy)quinoline-3-yl)methylene) isonitonohydrazide in acetic unhydride at reflux condition for 3-4 hr. The structures of the new compounds were confirmed by elemental analyses as well as IR, 1H NMR and mass spectral data. All the synthesized compounds were screened for their antibacterial activities against various bacterial strains. Several of these compounds showed potential antibacterial activity.
Keywords
1,3,4 oxadiazole; Quinoline; Isoniazide; Cyclisation; Antibacterial activity;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 Joshi, R. S.; Mandhane, P. G.; Khan, W.; Gill, C. H. J. Het. Chem. DOI 10.1002/jhet.653.   DOI
2 Christine, H. F.; Michael, H. C. Antimicrob. Agents Chemother. 1986, 29, 386.   DOI   ScienceOn
3 Hodogaya, Chemical Co. Ltd., Jap. Pat. 1980, 80, 27024
4 Hodogaya, Chem. Abstr. 1980, 93, 232719q.
5 Hakko Chem. Ind. Co. Ltd., Brit. Pat. 1,266,542/1972
6 Hakko Chem. Abstr. 1972, 77, 5474g.
7 Singh, H.; Yadav, L. D. S. Agric. Biol. Chem. 1976, 40, 759.   DOI
8 Misato, T.; Ko, K.; Honma, Y.; Konno, K.; Taniyama, E. Inst. Phys. Chem. Res. Jap. Pat. 1977, 772508
9 Misato, T.; Ko, K.; Honma, Y.; Konno, K.; Taniyama, E. Chem. Abstr. 1977, 87, 147054.
10 Imramovsky; S. Polanc; J. Vinsova; M. Kocevar; J. Jampylek; Z. Reckova; J. Kaustova; Bioorg. Med. Chem. 2007, 15, 2551.   DOI
11 H. Marrakchi; G. Laneelle; A. Quemard, Microbiology 2000, 146, 296.
12 Joshi, R. S.; Mandhane, P. G.; Dabhade S. K.; Gill, C. H. J. Chin. Chem. Soc. 2010, 57, 1227
13 Joshi, R. S.; Mandhane, P. G.; Diwakar, S. D.; Gill, C. H., Ultrason. Sonochem. 2010, 17, 298   DOI
14 Joshi, R. S., Mandhane, P. G., Badadhe, P. V., Gill, C. H.; Ultrason. Sonochem. 2011, 18, 735   DOI
15 Mandhane, P. G.; Joshi, R. S.; Nagargoje, D. R.; Gill, C. H.; Tett. Letts. 2010, 51, 1490   DOI
16 Joshi, R. S.; Mandhane, P. G.; Shaikh, M. U.; Kale, R. P.; Gill, C. H. Chin. Chem. Lett. 2010, 21, 432.
17 Joshi, R. S.; Mandhane, P. G.; Diwakar, S. D.; Dabhade, S. K. Gill, C. H., Bioorg. Med. Chem. Letts. 2010, 20, 3721   DOI
18 Joshi, R. S., Mandhane, P. G., Khan, W., Gill, C. H. Bull. Korean Chem. Soc. 2010, 31, 2341.   DOI
19 Joshi, R. S., Mandhane, P. G., Dabhade, S. K., Gill, C. H.; Green Chem. Lett. Rev. 2010, 3(3), 191   DOI
20 Joseph, J. P.; Harry, L. Y. Chem. Abstr. 1964, 61, 8317b.
21 Hokfelt, B.; Jonsson, A. J. Med. Chem. 1962, 5, 247.   DOI
22 Ansel, P. S. U.S.Patent 2,883,391, 1959.
23 Ansel, P. S. Chem. Abstr. 1959, 53, 16157g.
24 Hiroshi, K.; Isaq, H.; Shigeki, O.; Zassokenkyn 1969, 8, 46
25 Hiroshi, K.; Isaq, H.; Shigeki, O.; Chem. Abstr. 1970, 73, 108544b.
26 Derappe, C.; Rips, R.; Albert, O. Aurousseau, M. Chim. Ther. 1968, 3, 181
27 Derappe, C.; Rips, R.; Albert, O. Aurousseau, M. Chem. Abstr. 1968, 69, 106626y.
28 Chiyomaru, I.; Takita, K.; Ito, H.; Kumiai Chem. Ind. Co. Ltd. Jap. Pat. 1972, 72 07, 549
29 Deshmukh, A. A.; Sattur, P. B.; Sheth, U. K. Indian. J. Exp. Biol. 1976, 4, 166.
30 SenGupta, A. K.; Garg, M.; Chandra, U. J. Indian Chem. Soc. 1979, 56, 1230.
31 Chiyomaru, I.; Takita, K.; Ito, H.; Chem. Abstr. 1972, 77, 549.
32 O Neal, J. B.; Rosen, H.; Russel, P. B.; Adams, A. C.; Blumenthal, A. J. Med. Pharm. Chem. 1962, 5, 617   DOI
33 O Neal, J. B.; Rosen, H.; Russel, P. B.; Adams, A. C.; Blumenthal, A. Chem. Abstr. 1962, 57, 9168c.
34 Kurzer, F. Org. Compd. Sulphur, Selenium, Tellurium, 1974, 4, 417.
35 Thomas, J. Ger. Pat. 2,403, 357/1974
36 Thomas, J. Chem. Abstr. 1974, 81, 136153g.
37 Yale, H. L.; Losee, K. J. Med. Chem. 1966, 9, 478.   DOI
38 Turner, S. R. Colman Products Ltd. Ger. Pat. 1978, 2, 727, 146
39 Turner, S. R. Chem. Abstr. 1978, 88, 105357s.
40 MethCohn, O.; Narine, B.; Tarnowski, B.; Hayes, R.; Keyzad, A.; Rhouti, S.; Robinson, A. J. Chem. Soc. Perkin Trans. 1981, 1, 2509
41 Bhaduri, A. P. Synlett. 1990, 557.
42 Craig, J. C.; Person, P. E. J. Med. Chem. 1971, 14, 1221.   DOI
43 Mccormick, J. L.; Mckee, T. C.; Cardellina, J. H.; Boyd, M. R. J. Nat. Prod. 1996, 59, 469   DOI
44 Chen, I. S.; Chen, H. F.; Cheng, M. J.; Chang, Y. L.; Teng, C. M.; Tsutomu, I.; Chen, J. J.; Tsai, I. L. J. Nat. Prod. 2001, 64, 1143   DOI
45 Nadaraj, V.; Selvi, S. T.; Sasi, R. Arkivoc. 2006, x, 82.   DOI
46 Dillard, R. D.; Pavey, D. E.; Benslay, D. N. J. Med Chem. 1973, 16, 251.   DOI
47 Sukhova, N. M.; Lidak, M.; Zidermane, A.; Pelevina, I. S.; Voronia, S. S. Khim. Farm. Zh. 1989, 23, 1226.
48 Atwell, G. J.; Bangaley, B. C.; Denny, W. A. J. Med. Chem. 1989, 32, 396.   DOI
49 Patel, H. V.; Vyas, K. V.; Fernandes, P. S. Ind. J. Chem. 1990, 29(B), 836.
50 Saito, I.; Sando, S.; Nakatani, K. Bioorg. Med. Chem. 2001, 9, 2381.   DOI
51 Andries, K.; Verhasselt, P.; Guillemont, J.; Goehlmann, H. W. H.; Neefs, J. M.; Winkler, H.; Van Gestel, J.; Timmerman, P.; Zhu, M.; Lee, E.; Williams, P.; De Chaffoy, D.; Huitric, E.; Hoffner, S.; Cambau, E.; Truffot-Pernot, C.; Lounis, N.; Jarlier, V. A. Science, 2005, 307, 223.   DOI   ScienceOn
52 Joseph, J. P.; Harry, L. Y. U.S.Patent 3,141,022, 1961