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Microwave Assisted Synthesis, Characterization, Molecular Docking and Antiinflammatory Activity of p-Methoxy Cinnamic Acid Derivatives
Asian Journal of Chemistry,
Vol. 30 No. 8 (2018): Vol 30 Issue 8
Abstract
All the title compounds benzamido-(4-methoxy)-N2-(arylidene)cinnamic acid hydrazide (1-13) were synthesized by the microwave irradiation of a-benzamido-(4-methoxy)cinnamalhydrazide (II) with different aromatic/hetero aromatic aldehydes and characterized by IR, 1H and 13C NMR, Mass spectral and elemental analysis. Furthermore, all the new derivatives were screened for antiinflammatory activity by Carrageenan induced rat paw edema method. Compound 3, 6 and 12 exhibited highest activities, which are further supported by molecular docking studies showed -9.7, -8.1 and -8.6 as dock scores respectively. All the title compounds obey the Lipinski rule of five and devoid from toxicity assessed by Molinspiration and Osiris online predictors respectively.
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- M. Soujanya, M. Lakshmi narayana, T.Sarala devi, S. Anusha and G. Rajitha, Int. J. Pharmacy Technol., 6, 6193 (2014).
- C.A. Winter, E.A. Risley and G.W. Nuss, Proc. Soc. Exp. Biol. Med., 111, 544 (1962); https://doi.org/10.3181/00379727-111-27849.
- Molinspiration cheminformatics [homepage on the internet], Available from: http://www.molinspiration.com. [Cited 2013 March 3]. http://www.Molinspiration.Com/cgi-bin/properties.
- P. Ertl, B. Rohde and P. Selzer, J. Med. Chem., 43, 3714 (2000); https://doi.org/10.1021/jm000942e.;
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- A. Verma, Asian Pacific J. Trop. Biomed., 3, S1735 (2012).
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References
P. McGettigan and D. Henry, JAMA, 296, 1633 (2006); https://doi.org/10.1001/jama.296.13.jrv60011.
E. Pontiki, D. Hadjipavlou-Litina, G. Geromichalos and A. Papageorgiou, Chem. Biol. Drug Des., 74, 266 (2009); https://doi.org/10.1111/j.1747-0285.2009.00864.x.
E. Pontiki and D. Hadjipavlou-Litina, Bioorg. Med. Chem., 15, 5819 (2007); https://doi.org/10.1016/j.bmc.2007.06.001.
S. Naz, S. Ahmad, S. Ajaz Rasool, S. Asad Sayeed and R. Siddiqi, Microbiol. Res., 161, 43 (2006); https://doi.org/10.1016/j.micres.2005.05.001.
M. Sova, Mini Rev. Med. Chem., 12, 749 (2012); https://doi.org/10.2174/138955712801264792.
E. Pontiki, D. Hadjipavlou-Litina, K. Litinas and G. Geromichalos, Molecules, 19, 9655 (2014); https://doi.org/10.3390/molecules19079655.
P. De, M. Baltas and F. Bedos-Belval, Curr. Med. Chem., 18, 1672 (2011); https://doi.org/10.2174/092986711795471347.
L.Y. Zang, G. Cosma, H. Gardner, X. Shi, V. Castranova and A. Vallyathan, J. Physiol. Cell Physiol., 279, C954 (2000); https://doi.org/10.1152/ajpcell.2000.279.4.C954.
K. Mnafgui, A. Derbali, S. Sayadi, N. Gharsallah, A.S. Elfeki and N. Allouche, J. Food Sci. Technol., 52, 4369 (2015); https://doi.org/10.1007/s13197-014-1488-2.
M. Soujanya and G. Rajitha, Asian J. Chem., 29, 2479 (2017); https://doi.org/10.14233/ajchem.2017.20785.
G. Rajitha, K.V.S.R.G. Prasad, A. Umamaheswari, D. Pradhan and K. Bharathi, Med. Chem. Res., 23, 5204 (2014); https://doi.org/10.1007/s00044-014-1091-0.
P. Hernández, M. Cabrera, M.L. Lavaggi, L. Celano, I. Tiscornia, T. Rodrigues da Costa, L. Thomson, M. Bollati-Fogolín, A.L.P. Miranda, L.M. Lima, E.J. Barreiro, M. González and H. Cerecetto, Bioorg. Med. Chem., 20, 2158 (2012); https://doi.org/10.1016/j.bmc.2012.01.034.
G. Rajitha, N.Saideepa and Praneetha, Indian J. Chem., 50B, 729 (2011).
M.Soujanya and G.Rajitha, Int. J. Pharmaceut. Sci. Res., 8, 3786 (2017).
M.Soujanya and G.Rajitha, Derpharma chemica, 9, 10 (2017).
A.T. Mavrova, D. Wesselinova, N. Vassilev and J.A. Tsenov, Eur. J. Med. Chem., 63, 696 (2013); https://doi.org/10.1016/j.ejmech.2013.03.010.
E. Vavrikova, S. Polanc, M. Kocevar, K. Horvati, S. Bosze, J. Stolarikova, K. Vavrova and J. Vinsova, Eur. J. Med. Chem., 46, 4937 (2011); https://doi.org/10.1016/j.ejmech.2011.07.052.
J.D. Bhatt, C.J. Chudasama and K.D. Patel, Bioorg. Med. Chem., 23, 7711 (2015); https://doi.org/10.1016/j.bmc.2015.11.018.
J. Yinxue, T. Zhiwu and H. Meizi, Bioorg. Med. Chem., 12, 2135 (2010).
S.M. Siddiqui, A. Salahuddin and A. Azam, Eur. J. Med. Chem., 49, 411 (2012); https://doi.org/10.1016/j.ejmech.2012.01.030.
N. Karaman, E.E. Oruc-Emre, Y. Sicak, B. Çatikka, A. KaraküçükIyidogan and M. Öztürk, Med. Chem. Res., 25, 1590 (2016); https://doi.org/10.1007/s00044-016-1592-0).
G. Fareed, N. Afza, A. Versiani, N. Fareed, R. Mughal, A. Kalhoro, L. Iqbal and M. Lateef, J. Serb. Chem. Soc., 78, 1127 (2013); https://doi.org/10.2298/JSC120917126F.
M. Soujanya, M. Lakshmi narayana, T.Sarala devi, S. Anusha and G. Rajitha, Int. J. Pharmacy Technol., 6, 6193 (2014).
C.A. Winter, E.A. Risley and G.W. Nuss, Proc. Soc. Exp. Biol. Med., 111, 544 (1962); https://doi.org/10.3181/00379727-111-27849.
Molinspiration cheminformatics [homepage on the internet], Available from: http://www.molinspiration.com. [Cited 2013 March 3]. http://www.Molinspiration.Com/cgi-bin/properties.
P. Ertl, B. Rohde and P. Selzer, J. Med. Chem., 43, 3714 (2000); https://doi.org/10.1021/jm000942e.;
M. Soujanya and G. Rajitha, Letts. Drug Design Discov., 14, (2017)(In press).
S.M. Sondhi, M. Dinodia and A. Kumar, Bioorg. Med. Chem., 14, 4657 (2006); https://doi.org/10.1016/j.bmc.2006.02.014.
B. Vishwanathan, B.M. Gurupadayya and K.V. Sairam, Bangladesh J. Pharmacol., 11, 67 (2015); https://doi.org/10.3329/bjp.v11i1.23981.
A. Verma, Asian Pacific J. Trop. Biomed., 3, S1735 (2012).
A.R. Mullaicharam, N. Halligudi and H.S. Al-bahri, Int. J. Nutr. Pharmacol. Neur. Diseases, 2, 156 (2012); https://doi.org/10.4103/2231-0738.95991.