Microwave-Assisted Synthesis, in silico ADME Prediction and Antibacterial Study of 2-(Substituted acetamido)-5-Nitrobenzophenone Derivatives

Tiangang Li; Sandeep Singh; Xing Zhai; Xiangqi Meng; Rajesh K. Singh

doi:10.14233/ajchem.2015.17914

Issue

Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015

Issue Published : March 29, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Microwave-Assisted Synthesis, in silico ADME Prediction and Antibacterial Study of 2-(Substituted acetamido)-5-Nitrobenzophenone Derivatives

https://doi.org/10.14233/ajchem.2015.17914

Tiangang Li

Beijing University of Chinese Medicine, 11 Bei San Huan Dong Lu, ChaoYang District, Beijing 100029, P.R. China

Sandeep Singh

Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy, Rupnagar-140126, India

Xing Zhai

Beijing University of Chinese Medicine, 11 Bei San Huan Dong Lu, ChaoYang District, Beijing 100029, P.R. China

Xiangqi Meng

Beijing University of Chinese Medicine, Dongzhimen Hospital, Dongcheng District, Beijing 100700, P.R. China

Rajesh K. Singh

Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy, Rupnagar-140126, India

Corresponding Author(s) : Xiangqi Meng

xiangqimengbucm@126.com

Asian Journal of Chemistry, Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Article Published : March 29, 2015

Abstract

A series of novel 2-amino-5-nitrobenzophenone derivatives (3-10) were synthesized and characterized by IR, ¹H NMR and CHN elemental studies. All the synthesized compounds were subjected to in silico ADME predictions for determination for drug like properties. The values of physico-chemical parameters like molecular weight, nON value, nOHNH value, n-violations and the number of rotatable bonds of all the synthesized compounds also lies between the ranges that are required for good bioavailability. The synthesized compounds were tested for their in vitro antibacterial activity against the Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Among all the compounds synthesized compounds 4, 9, 10 have shown the maximum antibacterial activity in their group whereas compounds 3, 6, 8 have shown the minimum antibacterial activity.

Keywords

2-Aminobenzophenone Physicochemical parameters ADME Lipinski's rule of five Anti-bacterial activity

Li, T., Singh, S., Zhai, X., Meng, X., & K. Singh, R. (2015). Microwave-Assisted Synthesis, in silico ADME Prediction and Antibacterial Study of 2-(Substituted acetamido)-5-Nitrobenzophenone Derivatives. Asian Journal of Chemistry, 27(7), 2452–2456. https://doi.org/10.14233/ajchem.2015.17914

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References

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References

D.A. Walsh, Synthesis, 677 (1980); doi:10.1055/s-1980-29169.

L.H. Sternbach, R.I. Fryer, W. Metlesics, E. Reeder, G. Sach, G. Saucy and A. Stempel. J. Org. Chem., 27, 3788 (1962); doi:10.1021/jo01058a010.

R.V. Coombs, R.P. Danna, M. Denzer, G.E. Hardtmann, B. Huegi, G. Koletar, J. Koletar, H. Ott and E. Jukniewicz, J. Med. Chem., 16, 1237 (1973); doi:10.1021/jm00269a006.

W.J. Welstead Jr., J.H.W. Moran, H.F. Stauffer, L.B. Turnbull and L.F. Sancilio, J. Med. Chem., 22, 1074 (1979); doi:10.1021/jm00195a012.

E.R. Ottosen, M.D. Sørensen, F. Björkling, T. Skak-Nielsen, M.S. Fjording, H. Aaes and L. Binderup, J. Med. Chem., 46, 5651 (2003); doi:10.1021/jm030851s.

S. Cortez-Maya, E. Cortes, S. Hernández-Ortega, T.R. Apan and M. Martínez-García, Syn. Commun., 42, 46 (2012); doi:10.1080/00397911.2010.521435.

J.P. Liou, C.W. Chang, J.S. Song, Y.N. Yang, C.F. Yeh, H.Y. Tseng, Y.K. Lo, Y.L. Chang, C.M. Chang and H.P. Hsieh, J. Med. Chem., 45, 2556 (2002); doi:10.1021/jm010365+.

R.K. Singh, S. Devi and D.N. Prasad, Arab. J. Chem.; doi:10.1016/j.arabjc.2011.11.013.

R.K. Singh, D.N. Prasad and T.R. Bhardwaj, Med. Chem. Res., 22, 5901 (2013); doi:10.1007/s00044-013-0582-8.

P. Cheng, Q. Zhang, Y.-B. Ma, Z-Y. Jiang, X.M. Zhang, F.X. Zhang and J.J. Chen, Bioorg. Med. Chem. Lett., 18, 3787 (2008); doi:10.1016/j.bmcl.2008.05.065.

J.-P. Liou, J.-Y. Chang, C.-W. Chang, C.-Y. Chang, N. Mahindroo, F.-M. Kuo and H.-P. Hsieh, J. Med. Chem., 47, 2897 (2004); doi:10.1021/jm0305974.

J.P. Liou, Y.L. Chang, F.M. Kuo, C.W. Chang, H.Y. Tseng, C.C. Wang, Y.N. Yang, J.Y. Chang, S.-J. Lee and H.-P. Hsieh, J. Med. Chem., 47, 4247 (2004); doi:10.1021/jm049802l.

L. Sun, J. Wu, M. Luo, X. Wang, M. Pan, Z. Gou and D. Sun, Molecules, 16, 9739 (2011); doi:10.3390/molecules16119739.

A. Sakunpak and P. Panichayupakaranant, Food Chem., 130, 826 (2012); doi:10.1016/j.foodchem.2011.07.088.

Molinspiration Cheminformatics, Bratislava, Slovak Republic, Available from: http://www.molinspiration.com/cgi-bin/properties.

C.A. Lipinski, F. Lombardo, B.W. Dominy and P.J. Feeney, Adv. Drug Deliv. Rev., 23, 3 (1997); doi:10.1016/S0169-409X(96)00423-1.

Indian Pharmacopoeia. Government of India, Ministry of Health and Welfare, Published by Controller of Publication, New Delhi, vol. II, A105 (1996).

Issue

Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015

Microwave-Assisted Synthesis, in silico ADME Prediction and Antibacterial Study of 2-(Substituted acetamido)-5-Nitrobenzophenone Derivatives

Corresponding Author(s) : Xiangqi Meng

Abstract

Keywords

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