Design, Synthesis and Biological Evaluation of   Some Novel 2,5-Disubstituted-1,3,4-Oxadiazole Derivatives

Yogesh Murti; Vaibhav Mehrotra; Devender Pathak

Articles

Vol. 2 No. 4 (2011): October-December 2011

Design, Synthesis and Biological Evaluation of Some Novel 2,5-Disubstituted-1,3,4-Oxadiazole Derivatives

Yogesh Murti^▸^▾
Vaibhav Mehrotra^▸^▾
Devender Pathak^▸^▾

Requires Subscription or Fee pdf (INR 2000)

Submitted: December 20, 2024
Published: 2011-11-15

Abstract

In the present work, some novel 2,5-disubstituted-1,3,4-oxadiazole derivatives were synthesized by reacting different substituted phenyl semicarbazides with substituted benzaldehydes to yield aryl semicarbazones which finally underwent in situ cyclisation using chloramine-T. The newly synthesized compounds (1-10) were analyzed for elemental analysis and the structures were confirmed by FTIR, 1H NMR and Mass spectral data. The results of biological activities revealed that all the synthesized 2,5-disubstituted-1,3,4-oxadiazoles are potential lead compounds in search of new chemical entities viz. antimicrobial and analgesic agents.

References

[1] Loknatha, K.M.; Manoj, K.C.; Shekharshetty, H.; Rajasekhara, K.; Ranjana, N.N. Indian J. Heterocycl. Chem., 1999, 8, 335.
[2] Kocabalkanli, A.; Ates, O.; Otuk, G. IL Farmaco, 2001, 56(12), 975.
[3] Kucukguzel, S.G.; Oruc, E.E.; Rollas, S.; Sahin, F.; Ozbek, A. Eur. J. Med. Chem., 2002, 37(3), 197.
[4] Mogilaiah, K.; Vidya, K. Ind. J. Med. Chem., 2006, 45B, 1905.
[5] Mulwad, V.V.; Bhaskar, A.C. Ind. J. Chem., 2006, 45B, 1710.
[6] Somani, R.R.; Shirodkar, P.Y.; Toraskar, M.P.; Kadam,V. J. Indian J. Pharm. Educ. Res., 2008, 42, 53.
[7] Singh, C.R.; Singh, R.P.; Tripathi, S.P. Indian J. Heterocycl. Chem. 2006, 15, 345.
[8] Li, Y.; Lin, J.; Zhang, H.; Yang, X.; Liu, Z. Bioorg. Med. Chem. Lett., 2006, 16(8), 2278.
[9] Dwivedi, S.; Siddiqui, I.R.; Shukla, P.K.; Singh, P.K. J. Ind. Chem. Soc., 2006, 83, 89.
[10] Song, B.A.; Chen, C.J.; Yang, S.; Bhadury, P.S.; Liu, F.; Lu, P. Bioorg. Med. Chem., 2007, 15(12), 3981.
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[14] Vagdevi, M.H.; Ravindra, K.C.; Vaidya, V.P.; Chandrashekhar, C. Indian J. Heterocycl. Chem., 2006, 15, 283.
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[16] Reddy, V.M.; Jayamma, Y.; Sarangapani, M. Indian J. Heterocycl. Chem., 1996, 6, 111.
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[18] Emam, A.A.E.; Kadi, A.A.; Brollosy, N.R.E.; Deeb, O.A.A.; Habib, E.E.; Ibrahim, T.M. Eur. J. Med. Chem., 2007, 42(2), 235.
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[20] Medebielle, M.; Mohand, S.A.; Burkhloder, C.; Dolbier,W. R.; Laumond, G.; Aubertin, A.M. J. Fluor. Chem., 2005, 126, 535.
[21] Tan, T.M.C.; Chen, Y.; Kong, K.H.; Bai, J.; Li, Y.; Lim,S. G.; Ang, T.H.; Lan, Y. Antiviral Research, 2006, 71, 7.
[22] Elmagd, W.S.I.A.; Hashem, A.I.; Youssef; A.S.A.; Kandeel, K.A. Eur. J. Med. Chem., 2007, 42(7), 934.
[23] Hazarika, J.; Kataky, J.C. Indian J. Heterocycl. Chem., 1998, 8, 83.
[24] Swain, A.P. U.S. Patent 2, 883, 391, 1959.
[25] Va’zquez, N.G.; Salinas, G.M.M.; Fajardo, Z.V.D. Bio. Med. Chem., 2007, 15(16), 5502.
[26] Liszkieicz, H.; Kowalska, M.W.; Wietrzyk, J.; Opolski A. Indian J. Chem., 2003, 42B, 2846.
[27] Song, B.; Jin, L.; Chen, J.; Chen, Z.; Yang, S.; Li, Q.; Ho, D.; Xu, R. Bioorg. Med. Chem. Lett., 2006, 16(19), 5036.
[28] Husain, A.; Ahmabd, A,; Alam, M.; Ajmal, M.; Ahuja, P. Eur. J. Med. Chem., 2009, 44, 3798.
[29] Jayashankar, B.; Lokanath Rai, K.M.; Baskaran, N.; Sathish, H.S. Eur. J. Med. Chem., 2009, 44, 3898.
[30] Amir, M.; Shikha, K. Eur. J. Med. Chem., 2004, 39, 535.
[31] Sawant, R.L.; Lanke, P.D. Int. J. Drug Des. & Discov., 2010, 4(1), 336.
[32] Bhardwaj, S.; Parashar, B.; Parashar, N.; Sharma, V.K. Arch. Appl. Sci. Res., 2011, 3(2), 558.
[33] Jain, K.; Bhardwaj, S.; Parashar, N.; Sharma, V.K. Int. J. Biopharm., 2011, 2(1), 14.
[34] Bauer, A.W.; Kirby, W.M.; Sherris, J.C.; Turck, M. Am.J. Clin. Path., 1966, 45, 493.
[35] Vogel, G.H.; Vogel, W.H. Drug discovery and evaluation; Springer Verlag, Berlin, 1998, p. 413.
[36] Turner, R.A. Screening methods in pharmacology; Academic Press: New York, 1971, pp. 100–113.

Keywords

1,3,4-Oxadiazole
chloramine-T
antimicrobial
analgesic activity

How to Cite

Murti, Y., Mehrotra, V., & Pathak, D. (2011). Design, Synthesis and Biological Evaluation of Some Novel 2,5-Disubstituted-1,3,4-Oxadiazole Derivatives . International Journal of Drug Design and Discovery, 2(4), 659–665. Retrieved from https://ijddd.com/index.php/ijddd/article/view/89

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[1] [1] Loknatha, K.M.; Manoj, K.C.; Shekharshetty, H.; Rajasekhara, K.; Ranjana, N.N. Indian J. Heterocycl. Chem., 1999, 8, 335.

[2] [2] Kocabalkanli, A.; Ates, O.; Otuk, G. IL Farmaco, 2001, 56(12), 975.

[3] [3] Kucukguzel, S.G.; Oruc, E.E.; Rollas, S.; Sahin, F.; Ozbek, A. Eur. J. Med. Chem., 2002, 37(3), 197.

[4] [4] Mogilaiah, K.; Vidya, K. Ind. J. Med. Chem., 2006, 45B, 1905.

[5] [5] Mulwad, V.V.; Bhaskar, A.C. Ind. J. Chem., 2006, 45B, 1710.

[6] [6] Somani, R.R.; Shirodkar, P.Y.; Toraskar, M.P.; Kadam,V. J. Indian J. Pharm. Educ. Res., 2008, 42, 53.

[7] [7] Singh, C.R.; Singh, R.P.; Tripathi, S.P. Indian J. Heterocycl. Chem. 2006, 15, 345.

[8] [8] Li, Y.; Lin, J.; Zhang, H.; Yang, X.; Liu, Z. Bioorg. Med. Chem. Lett., 2006, 16(8), 2278.

[9] [9] Dwivedi, S.; Siddiqui, I.R.; Shukla, P.K.; Singh, P.K. J. Ind. Chem. Soc., 2006, 83, 89.

[10] [10] Song, B.A.; Chen, C.J.; Yang, S.; Bhadury, P.S.; Liu, F.; Lu, P. Bioorg. Med. Chem., 2007, 15(12), 3981.

[11] [11] Karthikeyan, M.S.; Prasad, D.J.; Mahalinga, M.; Holla,B. S.; Kumari, N.S. Eur. J. Med. Chem., 2007, 1.

[12] [12] Rai, K.M.L.; Gaonkar, S.C.; Prabhuswamy, B. Eur. J. Med. Chem., 2006, 41(7), 841.

[13] [13] Badami, V.; Prashant, R.C. J. Indian Chem. Soc., 2006, 83, 1049.

[14] [14] Vagdevi, M.H.; Ravindra, K.C.; Vaidya, V.P.; Chandrashekhar, C. Indian J. Heterocycl. Chem., 2006, 15, 283.

[15] [15] Ates, O.; Kocabalkanli, A.; Cesur, N.; Otuk, G. IL Farmaco, 1998, 53(8-9), 541.

[16] [16] Reddy, V.M.; Jayamma, Y.; Sarangapani, M. Indian J. Heterocycl. Chem., 1996, 6, 111.

[17] [17] Shingare, M.S.; Bhawsar, S.B.; Mane, D.V.; Shinde, D.B. Indian J. Heterocycl. Chem., 1995, 5, 29.

[18] [18] Emam, A.A.E.; Kadi, A.A.; Brollosy, N.R.E.; Deeb, O.A.A.; Habib, E.E.; Ibrahim, T.M. Eur. J. Med. Chem., 2007, 42(2), 235.

[19] [19] Yadav, L.D.S.; Singh, S. Indian J. Chem., 2001, 40B,440.

[20] [20] Medebielle, M.; Mohand, S.A.; Burkhloder, C.; Dolbier,W. R.; Laumond, G.; Aubertin, A.M. J. Fluor. Chem., 2005, 126, 535.

[21] [21] Tan, T.M.C.; Chen, Y.; Kong, K.H.; Bai, J.; Li, Y.; Lim,S. G.; Ang, T.H.; Lan, Y. Antiviral Research, 2006, 71, 7.

[22] [22] Elmagd, W.S.I.A.; Hashem, A.I.; Youssef; A.S.A.; Kandeel, K.A. Eur. J. Med. Chem., 2007, 42(7), 934.

[23] [23] Hazarika, J.; Kataky, J.C. Indian J. Heterocycl. Chem., 1998, 8, 83.

[24] [24] Swain, A.P. U.S. Patent 2, 883, 391, 1959.

[25] [25] Va’zquez, N.G.; Salinas, G.M.M.; Fajardo, Z.V.D. Bio. Med. Chem., 2007, 15(16), 5502.

[26] [26] Liszkieicz, H.; Kowalska, M.W.; Wietrzyk, J.; Opolski A. Indian J. Chem., 2003, 42B, 2846.

[27] [27] Song, B.; Jin, L.; Chen, J.; Chen, Z.; Yang, S.; Li, Q.; Ho, D.; Xu, R. Bioorg. Med. Chem. Lett., 2006, 16(19), 5036.

[28] [28] Husain, A.; Ahmabd, A,; Alam, M.; Ajmal, M.; Ahuja, P. Eur. J. Med. Chem., 2009, 44, 3798.

[29] [29] Jayashankar, B.; Lokanath Rai, K.M.; Baskaran, N.; Sathish, H.S. Eur. J. Med. Chem., 2009, 44, 3898.

[30] [30] Amir, M.; Shikha, K. Eur. J. Med. Chem., 2004, 39, 535.

[31] [31] Sawant, R.L.; Lanke, P.D. Int. J. Drug Des. & Discov., 2010, 4(1), 336.

[32] [32] Bhardwaj, S.; Parashar, B.; Parashar, N.; Sharma, V.K. Arch. Appl. Sci. Res., 2011, 3(2), 558.

[33] [33] Jain, K.; Bhardwaj, S.; Parashar, N.; Sharma, V.K. Int. J. Biopharm., 2011, 2(1), 14.

[34] [34] Bauer, A.W.; Kirby, W.M.; Sherris, J.C.; Turck, M. Am.J. Clin. Path., 1966, 45, 493.

[35] [35] Vogel, G.H.; Vogel, W.H. Drug discovery and evaluation; Springer Verlag, Berlin, 1998, p. 413.

[36] [36] Turner, R.A. Screening methods in pharmacology; Academic Press: New York, 1971, pp. 100–113.