JOURNAL BROWSE
Search
Advanced SearchSearch Tips
Design and Synthesis of p-hydroxybenzohydrazide Derivatives for their Antimycobacterial Activity
facebook(new window)  Pirnt(new window) E-mail(new window) Excel Download
 Title & Authors
Design and Synthesis of p-hydroxybenzohydrazide Derivatives for their Antimycobacterial Activity
Bhole, Ritesh.P.; Borkar, Deepak.D.; Bhusari, Kishore.P.; Patil, Prashant.A.;
  PDF(new window)
 Abstract
The main mycobacterial infection in human is tuberculosis caused by Mycobacterium tuberculosis. Tuberculosis is the leading infectious cause of death in the world. Therefore there is continuing and compelling need for new and improved treatment for tuberculosis. The entire logic towards design of new compounds containing 4-hydroxy-N`-(1,3-thiazoldin- 2-yldene)benzohydrazide moiety is basically for superior antimycobacterial activity. The recent advances in QSAR and computer science have provided a systematic approach to design a structure of any compound and further, the biological activity of the compound can be predicted before synthesis. The 3D-QSAR studies for the set of 4-hydroxy-N`-(1,3-thiazoldin- 2-yldene)benzohydrazide and their derivatives were carried out by using V-life MDS (3.50). The various statistical methods such as Multiple Linear Regression (MLR), Partial Least Square Regression (PLSR), Principle Component Regression(PCR) and K nearest neighbour (kNN) were used. The kNN showed good results having cross validated 0.9319, for external test set 0.8561 and standard error of estimate 0.2195. The docking studies were carried out by using Schrodinger GLIDE module which resulted in good docking score in comparison with the standard isoniazid. The designed compounds were further subjected for synthesis and biological evaluation. Antitubercular evaluation of these compounds showed that (4.a), (4.d) and (4.g) found as potent inhibitor of H37RV.
 Keywords
3D QSAR;GLIDE;Benzohydrazide;
 Language
English
 Cited by
1.
(E)-N′-(4-Chlorobenzylidene)-, (E)-N′-(4-bromobenzylidene)- and (E)-N′-[4-(diethylamino)benzylidene]- derivatives of 4-hydroxybenzohydrazide, Acta Crystallographica Section C Crystal Structure Communications, 2012, 68, 10, o408  crossref(new windwow)
2.
Synthesis,In VivoAnti-Inflammatory Activity, and Molecular Docking Studies of New Isatin Derivatives, International Journal of Medicinal Chemistry, 2016, 2016, 1  crossref(new windwow)
3.
Molecular modelling studies on flavonoid derivatives as dual site inhibitors of human acetyl cholinesterase using 3D-QSAR, pharmacophore and high throughput screening approaches, Medicinal Chemistry Research, 2014, 23, 4, 2122  crossref(new windwow)
 References
1.
Delgado, J. N.; Remers, W. A. Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 11th ed.; Lippincott-Raven: Philadelphia, 2002, pp 1-3.

2.
Peter, G.; Maggiora, Synder, J. P.; Cohen, C. N. Guide Book on Molecular Modeling In Drug Design, 1st ed.; Academic Press: 1966, pp 216-32.

3.
Gerhard, K.; Abrahum, U. J. Computer Aided Molecular Designs, 1st ed.; Harward Press: London, 1999, pp 473-98.

4.
http://www.netsci.org/science/compchem/drugdesign2.htm.

5.
Carter, R. C.; Grassy, G.; Kubinyl, H.; Martin, Y. C.; Willett, P. Annual Reports in Medicinal Chemistry 1998, 33, 397. crossref(new window)

6.
Propst, C. L.; Perun, T. J. Computer Aided Drug Design Methods and Application; Marcel Dekker: New york, 1989; Vol. 4, p 12.

7.
Kulkarni, V. M.; Bothara, K. G. Textbook of Drug Design, 2nd ed.; Nirali Prakashan: 2003; pp 189-211.

8.
Claude, C. N. Guidebook on Molecular Modeling In Drug Design, 1st ed.; Elsevier: 2009, pp 94-100.

9.
Richet, M. C. Compt. Rend. Soc. Biol. 1893, 45, 885.

10.
Overton, E.; Lipnick, R. L. Studies on Narcosis; Chapman and Hall: London, 1991.

11.
Rao, R. P. J. Indian. Chem. Soc. 1961, 38, 784.

12.
Wilson, F. J.; Burns, R. J. Chem. Soc. 1922, 121, 870. crossref(new window)

13.
Bhole, R. P.; Bhusari, K. P. QSAR Comb. Sci. 2009, 28, 405.

14.
Joshi, S. D.; Vagdevi, H. M.; Vaidya, V. P. Eur. J. Med. Chem. 2008, 43, 1989. crossref(new window)

15.
Rollas, S.; Kiraz, M. Eur. J. Med. Chem. 1999, 34, 1093. crossref(new window)

16.
Vijaya Raj K. K.; Narayana, B.; Ashalatha, B.; Sarojani, B. K. Eur. J. Med. Chem. 2007, 42, 425. crossref(new window)

17.
Maccari, R.; Ottana, R.; Vigorita, M. G. Bioorg. Med. Chem. 2005, 15, 2509. crossref(new window)

18.
Zhong, X.; Wei. L. H.; Liu, W. S.; Wang, D. Q.; Wang, X. Bioorg. Med. Chem. 2007, 17, 3774. crossref(new window)

19.
Osyanin, V. A.; Purygin, P. P.; Belovsova, Z. P. Rus. J. Gen. Chem. 2005, 75, 111. crossref(new window)

20.
Patole, J.; Sandbhor, U.; Padhye, S.; Deobagkar, D. N.; Anson, C. E.; Powell, A. Bioorg. Med. Chem. 2003, 13, 51. crossref(new window)

21.
Koschucharov, R.; Ivanov, G. Pharmazie 1960, 15, 492.

22.
Paigeen, K. Prog. Nucleic. Acid. Res. Mol. Biol. 1989, 37, 155. crossref(new window)

23.
Ho, J.; Hsu, S. C.; Chen, J. S. Eur. J. Clin. Invest. 1986, 16, 361. crossref(new window)

24.
Inanov, N. Chem. Abst. 1959, 53, 15038.

25.
Mazouz, F.; Gueddari, S.; Burstein, C.; Mansy, D.; Milcent, R. J. Med. Chem. 1993, 36, 1157. crossref(new window)

26.
Ernest, Carron MC. U.S. Patent 3290213.

27.
Davidson, P. T.; Le, H. Q. Drugs 1993, 43, 651.

28.
Vincent, T. A. Int. J. Antimicrob. Agents. 2000, 16, 317. crossref(new window)

29.
Tan, Y. T.; Tillett, D. J.; Mckay, I. A. Mol. Med. Today. 2000, 6, 309. crossref(new window)

30.
PHASE 2.0, Schrodinger, LLC, New York, 2006.

31.
Ligprep 2.0, Schrodinger, LLC, New York, 2006.

32.
Ke, Y. S.; Quin, X. Y.; Wang, N.; Yang, Q. Eur. J. Med. Chem. 2008, 43, 1. crossref(new window)

33.
MacroModel 9.1, Schrodinger, LLC, New York, 2006.

34.
Halgren, T. A. J. Comput. Chem. 1996, 17, 520. crossref(new window)

35.
MacroModel 2.0, User Manual, Schrodinger, LLC, New York, 2006.

36.
Chang, G.; Guida, W.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379. crossref(new window)

37.
Kolossvary, I.; Guida, W. C. J. Am. Chem. Soc. 1996, 118, 5011. crossref(new window)

38.
SMARTS-Language for Describing Molecular Patterns, Daylight Chemical Information Systems, Inc., Aliso Viejo, CA.