Structure-activity relationships of pyrrole hydrazones as new anti-tuberculosis agents

Medicinal Chemistry

Volumn 8, Issue 3, 2012, Pages 462-473

  Lessigiarska, Iglika ^a   Pajeva, Ilza ^a   Prodanova, Penka ^b   Georgieva, Maya ^b   Bijev, Atanas ^b  

^a INSTITUTE OF BIOPHYSICS AND BIOMEDICAL ENGINEERING   (Bulgaria)

^b UNIVERSITY OF CHEMICAL TECHNOLOGY AND METALLURGY   (Bulgaria)

Author keywords

Classification trees; Hydrazones; Pharmacophore; Pyrrole; QSAR; Tuberculostatics

Indexed keywords

CHLORINE; FLUORINE; HYDRAZONE DERIVATIVE; ISONIAZID; NITROGEN; PYRROLE HYDRAZONE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; ATOM; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG TARGETING; HYDROGEN BOND; MOUSE; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM MECHANICS;

EID: 84863652822     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/1573406411208030462     Document Type: Article

References (32)

1. Tripathi, R.P.; Tewari, N.; Dwivedi, N.; Tiwari, V.K. Fighting tuberculosis: An old disease with new challenges. Med. Res. Rev., 2005, 25(1), 93-131. (Pubitemid 39642233)
2. Zhang, Y.; Post-Martens, K.; Denkin, S. New drug candidates and therapeutic targets for tuberculosis therapy. Drug Discov. Today, 2006, 11(1-2), 21-27. (Pubitemid 43227848)
3. Janin, Y.L. Antituberculosis drugs: Ten years of research; Review. Bioorg. Med. Chem., 2007, 15(7), 2479-2513. (Pubitemid 46367698)
4. World Health Organization. http://www.who.int/topics/ tuberculosis/en/ (Accessed Mar 31, 2011).
5. García-García, A.; Gálvez, J.; Julián-Ortiz, J.V.; García-Domenech, R.; Muñoz, C.; Guna, R.; Borras, R. Search of chemical scaffolds for novel antituberculosis agents. J. Biomol. Screen., 2005, 10(3), 206-214. (Pubitemid 40617158)
6. Ragno, R.; Marshall, G.R.; Di Santo, R.; Costi, R.; Massa, S.; Rompei, R.; Artico, M. Antimycobacterial pyrroles: synthesis, antimycobacterium tuberculosis activity and QSAR studies. Bioorg. Med. Chem., 2000, 8, 1423-1432. (Pubitemid 30398462)
7. Castagnolo, D.; Radi, M.; Dessi, F.; Manetti, F.; Saddi, M.; Meleddu, R.; De Logu, A.; Botta, M. Synthesis and biological evaluation of new enantiomerically pure azole derivatives as inhibitors of Mycobacterium tuberculosis. Bioorg. Med. Chem. Lett., 2009, 19, 2203-2205.
8. Swamy, B.N.; Suma, T.K.; Rao, G.V.; Reddy, G.C. Synthesis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis. Eur. J. Med. Chem., 2007, 42, 420-424. (Pubitemid 46349365)
9. Sriram, D.; Yogeeswari, P.; Madhu, K. Synthesis and in-vitro antimycobacterial activity of some isonicotinyl hydrazones. Bioorg. Med. Chem. Lett., 2005, 15, 4502-4505. (Pubitemid 41253883)
10. Sriram D.; Yogeeswari, P.; Devakaram, R.V. Synthesis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides. Bioorg. Med. Chem., 2006, 14, 3113-3118.
11. Patole, J.; Sandbhor, U.; Padhye, S.; Deobagkar, D.N.; Anson, C.E.; Powell. A. Structural chemistry and in vitro antitubercular activity of acetylpyridine benzoyl hydrazone and its copper complex against Mycobacterium smegmatis. Bioorg. Med. Chem. Lett., 2003, 13, 51-55. (Pubitemid 35447683)
12. Maccari, R.; Ottana, R.; Vigorita, M.G. In vitro advanced antimycobacterial screening of isoniazid-related hydrazones, hydrazides and cyanoboranes: part 14. Bioorg. Med. Chem. Lett., 2005, 15(10), 2509-2513. (Pubitemid 40614979)
13. Bijev, A.; Prodanova, P. New hydrazones of 5-methyl-1H-4- imidazolecarbohydrazide as potential tuberculostatics. Pharmacia, 2004, 3-4, 3-8. (Pubitemid 40568102)
14. Bijev, A. Synthesis and preliminary screening of carbohydrazides and hydrazones of pyrrole as potential tuberculostatics. Arzneim.-Forsch./Drug Res., 2006, 56(2), 96-103.
15. Bijev, A. New hydrazones as pyrrole derivatives with higher inhibitory activity against Mycobacterium tuberculosis. Lett. Drug Des. Discov., 2006, 3, 506-512.
16. Bijev, A. Synthesis, In Vitro evaluations and structure-activity assessment of pyrrole hydrazones as potential tuberculostatics. Lett. Drug Des. Discov., 2008, 5, 15-24. (Pubitemid 351225640)
17. Bijev, A. Synthesis and in vitro evaluation of new hydrazones as pyrrole derivatives with anti-tubercular activity. Arzneim.-Forsch./Drug Res., 2009, 59(1), 34-39.
18. Bijev, A.; Georgieva, M. Pyrrole-based hydrazones synthesized and evaluated in vitro as potential tuberculostatics. Lett. Drug Des. Discov., 2010, 7, 430-437.
19. Georgieva, M.; Bijev, A.; Prodanova, P. Synthesis and comparative study of tuberculostatic activity of pyrrole-based hydrazones related to structural variations. Farmacia, 2010, LVII(1-4), 3-14.
20. Tuberculosis Antimicrobial Acquisition and Coordinating Facility. Available at: http://www.taacf.org/ (Accessed Mar 31, 2011).
21. Collins, L.; Franzblau, S.G. Microplate Alamar Blue Assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother., 1997, 41, 1004-1009. (Pubitemid 27194176)
22. SYBYL; Tripos Inc., 1699 South Hanley Road, St. Louis, MO 63144-2917, USA.
23. MOE (Molecular Operating Environment), Chemical Computing Group Inc., 1010 Sherbrooke Street West, Suite 910; Montreal, Quebec; Canada.
24. Cronin, M. In: The Use of Computer Models as Alternatives to Animal Experiments in Chemical Risk Assessment, Summary paper of ECVAM Workshop on The Use of Computer Models as Alternatives to Animal Experiments in Chemical Risk Assessment, Praha, Czech Republic, October 3-4, 2002; I. Lessigiarska and A. Worth; ATLA, 2003, 31, 67-73.
25. STATISTICA 6.0, StatSoft Inc., 2300 East 14th Street, Tulsa, OK 74104, USA.
26. International Programme on Chemical Safety (INCHEM). Available at: http://www.inchem.org/ (Accessed Oct 27, 2011).
27. Hall, L.H.; Kier, L.B. The molecular connectivity chi indices and kappa shape indices in structure-property modeling. In: Reviews of Computational Chemistry, Boyd, D.B.; Lipkowitz, K.; Eds., VCH Publishers, USA, 1991; Vol. 2, pp. 367-422.
28. Cruciani, G.; Crivori, P.; Carrupt, P.-A.; Testa, B. Molecular fields in quantitative structure-permeation relationships: the VolSurf approach. J. Mol. Struct. (Theochem), 2000, 503, 17-30.
29. Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron, 1980, 36, 3219-3228.
30. Zhang, Y.; Amzel, L.M. Tuberculosis drug targets. Curr. Drug Targets, 2002, 3, 131-154. (Pubitemid 34296204)
31. Biava, M.; Porretta, G.C.; Poce, G.; De Logu, A.; Saddi, M.; Meleddu, R.; Manetti, F.; De Rossi, E.; Botta M. Diphenylpyrrole derivatives as antimycobacterial agents. Probing the influence on antimycobacterial activity of lipophilic substituents at the phenyl rings. J. Med. Chem., 2008, 51(12), 3644-3648. (Pubitemid 351875020)
32. Barry, P.J.; O'Connor, T.M. Novel agents in the management of Mycobacterium tuberculosis disease. Curr. Med. Chem., 2007, 14(18), 2000-2008. (Pubitemid 47209109)