1044
J.N. Sangshetti, D.B. Shinde / European Journal of Medicinal Chemistry 46 (2011) 1040e1044
6.1.12. 3-(1-(1-Benzylpiperidin-4-yl)-1H-1,2,3-triazol-4-yl)-5-
phenyl-1,2,4-oxadiazole (4l)
13C NMR (CDCl3)
d
¼ 27.2, 44.2, 61.4, 124.8, 128.1, 129.3, 130.2,
131.0, 132.1, 134.1,135.0, 164.4, 172.4, 175.2
Yellowish white solid. Melting Point-221e222 ꢀC.
MS: m/z ¼ 435 [M þ H]þ.
1H NMR (400 MHz, CDCl3):
d
¼ 7.9e7.4 (m, 10H), 7.32 (s, 1H),
4.80e4.70(m, 1H), 4.09e4.02 (m, 2H), 3.22 (s, 2H), 2.90e2.85 (m,
2H), 2.07e2.04 (m, 2H), 1.85e1.82 (m, 2H)
6.1.18. 5-(4-Chlorophenyl)-3-(1-(1-(methylsulfonyl)piperidin-4-yl)-
1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole (4r)
13C NMR (CDCl3)
d
¼ 27.2, 50.1, 61.6, 66.2, 124.5, 127.6, 128.1,
Off white solid. Melting Point-201e203 ꢀC
128.9, 129.6, 130.5, 131.0, 138.3, 147.0, 164.5, 174.7.
1H NMR (400 MHz, CDCl3):
d
¼ 7. 77e7. 45 (m, 4H), 7.32 (s, 1H),
MS: 387 [M þ H]þ.
4.79e4.68 (m, 1H), 4.34e4.29(m, 2H), 3.24 (s, 3H), 2.90e2.86 (m,
2H), 2.64e2.32 (m, 2H), 2.09e1.84 (m, 2H)
13C NMR (CDCl3) 27.0, 41.5, 49.0, 61.0, 125.5, 128.2, 129.1, 130.0,
130.8, 135.1, 164.1, 176.0.
6.1.13. 5-(4-Chlorophenyl)-3-(1-(1-methylpiperidin-4-yl)-1H-1,2,3-
triazol-4-yl)-1,2,4-oxadiazole (4m)
MS: m/z ¼ 410 [M þ H]þ.
Yellowish solid. Melting Point-224e226 ꢀC.
1H NMR (400 MHz, CDCl3):
d
¼ 7.86e7.44 (m, 4H), 7.21 (s, 1H),
Acknowledgment
4.86e4.80 (m, 1H), 3.84e3.63 (m, 2H), 3.37e3.22 (m, 2H), 3.02 (s,
3H), 2.00e1.89 (m, 2H) 1.84e1.78 (m, 2H).
13C NMR (CDCl3)
d
¼ 27.0, 47.4, 56.2, 61.5, 124.1, 128.1, 129.0,
The authors are thankful to Council for Scientific and Industrial
Research (CSIR), New Delhi for financial assistance. The authors are
thankful to Principal, Maharashtra Institute of Pharmacy Pune for
providing the facility for in vitro antifungal activity. The authors are
also thankful to the Head, Department of Chemical Technology,
Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-
431004 (MS), India for providing the laboratory facility.
130.4, 131.2, 135.0, 164.1, 175.3
MS: m/z ¼ 345 [M þ H]þ.
6.1.14. 5-(4-Chlorophenyl)-3-(1-(1-ethylpiperidin-4-yl)-1H-1,2,3-
triazol-4-yl)-1,2,4-oxadiazole(4n)
White solid. Melting Point-267e269 ꢀC.
1H NMR (400 MHz, CDCl3):
d
¼ 7.75e7.42 (m, 4H), 7.35 (s, 1H),
References
4.89e4.80 (m, 1H), 4.45e4. 38 (q, 2H), 4.28e4.24 (m, 2H),
3.00e2.92 (m, 2H), 2.22e2.18 (m, 2H), 2.12e1.90 (m, 2H), 1.43e1.40
(t, 3H).
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Farmaco 5 (2004) 397e404.
13C NMR (CDCl3)
d
¼ 14.0, 28.0, 50.2, 53.5, 61.0, 124.8, 127.7,
128.9, 130.0, 131.1,134.5, 163.0, 174.5
MS : m/z ¼ 359 [M þ H]þ.
6.1.15. 1-(4-(4-(5-(4-Chlorophenyl)-1,2,4-oxadiazol-3-yl)-1H-1,2,3-
triazol-1-yl)piperidin-1-yl)ethanone (4o)
Yellow solid. Melting Point-233e234 ꢀC.
1H NMR (400 MHz, CDCl3):
d
¼ 7.79e7.30 (m, 4H), 7.28 (s, 1H),
4.90e4.81 (m, 1H), 4.30e4.26 (m, 2H), 3.30(s, 3H), 2.90e2.87 (m,
2H), 2.65e2.35 (m, 2H), 2.10e1.86 (m, 2H)
13C NMR (CDCl3)
d
¼ 20.8, 27.5, 43.0, 60.8, 123.5, 127.5, 128.4,
129.5, 130.6, 133.2, 165.1, 174.3, 177.0
MS: m/z ¼ 373 [M þ H]þ.
[12] D.R. Hou, S. Alam, T.C. Kuan, M. Ramanathan, T.P. Lin, M.S. Hung, Bioorg. Med.
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Bioorg. Med. Chem. Lett. 18 (2008) 6244e6247.
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6.1.16. 1-(4-(4-(5-(4-Chlorophenyl)-1,2,4-oxadiazol-3-yl)-1H-1,2,3-
triazol-1-yl)piperidin-1-yl)propan-1-one (4p)
Yellowish solid. Melting Point-198e200 ꢀC.
1H NMR (400 MHz, CDCl3):
d
¼ 7.74e7.42 (m, 5H), 7.30 (s, 1H),
b) L.B. Clapp, in: A.R. Katritzky, C.W. Rees (Eds.), Comprehensive Heterocyclic
Chemistry, vol. 6, Pergamon, Oxford, 1984, pp. 365e391;
c) S.J. De Melo, A.D. Sobral, H.L. Lopes, R.M. Srivastava, J. Braz. Chem. Soc.
9 (1998) 465e468.
4.90e4.81 (m,1H), 4.40e4.44 (q, 2H), 4.24e4.29 (m, 2H), 2.98e2.84
(m, 2H), 2.23e2.18 (m, 2H), 1.88e2.12 (m, 2H), 1.48e1.44(t, 3H).
13C NMR (CDCl3)
d
¼ 11.2, 26.0, 27.2, 44.3, 60.6, 123.7, 128.6,
[15] M. Ono, M. Haratake, H. Saji, M. Nakayama, Bioorg. Med. Chem. 16 (2008)
6867e6872.
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[17] a) R.R. Nagawade, V.V. Khanna, S.S. Bhagwat, D.B. Shinde, Eur. J. Med.Chem.
40 (2005) 1325e1330;
129.2, 130.2, 130.9,134.1, 164.0, 173.9, 176.1
MS: m/z 387 [M þ H]þ.
6.1.17. (4-(4-(5-(4-Chlorophenyl)-1,2,4-oxadiazol-3-yl)-1H-1,2,3-
triazol-1-yl)piperidin-1-yl)(phenyl)methanone (4q)
Yellow solid. Melting Point-223e224 ꢀC.
b) N.D. Kokare, J.N. Sangshetti, D.B. Shinde, Synthesis 18 (2007) 2829e2834;
c) J.N. Sangshetti, N.D. Kokare, D.B. Shinde, J. Heterocycl. Chem. 45 (2008)
1191e1194;
d) J.N. Sangshetti, R.R. Nagawade, D.B. Shinde, Bioorg. & Med. Chem. Lett. 19
(2009) 3564e3567.
1H NMR (400 MHz, CDCl3):
4.82e4.70(m, 1H), 4.10e4.02 (m, 2H), 2.93e2.85 (m, 2H), 2.15e2.10
(m, 2H), 1.84e1.81 (m, 2H)
d
¼ 7.90e7.38 (m, 9H), 7.35 (s, 1H),
[18] a) D. Greenwood, R.C.B. Slack, J.F. Peutherer, Medical Microbiology, fourteenth
ed. ELBS, London, 1992, 1.