Synthesis and in vitro evaluation of new hydrazones as pyrrole derivatives with anti-tubercular activity

Arzneimittel-Forschung/Drug Research

Volumn 59, Issue 1, 2009, Pages 34-41

  Bijev, Atanas ^a  

^a UNIVERSITY OF CHEMICAL TECHNOLOGY AND METALLURGY   (Bulgaria)

Author keywords

Carbohydrazides; Pyrrole derivatives, hydrazones, synthesis, tuberculostatic activity; Tuberculostatics

Indexed keywords

CARBONYL DERIVATIVE; ETHYL 1 [2 [2 [1 [4 (DIMETHYLAMINO)PHENYL]METHYLIDENE]HYDRAZINO] 2 OXOETHYL] 2 METHYL 5 (3 NITROPHENYL) 1H 3 PYRROLECARBOXYLATE; ETHYL 1 [2 [2 [1 [4 (ETHOXYCARBONYL) 2,5 DIMETHYL 1H 3 PYRROLYL]METHYLIDENE]HYDRAZINO] 2 OXOETHYL] 2 METHYL 5 (4 NITROPHENYL) 1H 3 PYRROLECARBOXYLATE; ETHYL 2 METHYL 1 [2 [2 [1 (5 NITRO 2 FURYL)METHYLIDENE]HYDRAZINO] 2 OXOETHYL) 5 (3 NITROPHENYL) 1H 3 PYRROLECARBOXYLATE; ETHYL 2 METHYL 5 (3 NITROPHENYL) 1 [2 OXO 2 [2 [1 (2 THIENYL)METHYLIDENE]HYDRAZINO]ETHYL] 1H 3 PYRROLECARBOXYLATE; ETHYL 5 (4 CHLOROPHENYL) 1 [3 [2 [1 [4 (DIMETHYLAMINO)PHENYL]METHYLIDENE]HYDRAZINO] 3 OXOPROPYL] 2 METHYL 1H 3 PYRROLECARBOXYLATE; ETHYL 5 (4 CHLOROPHENYL) 2 METHYL 1 [2 OXO 2,2 [1 (2 THIENYL)METHYLIDENE]HYDRAZINOETHYL] 1H 3 PYRROLECARBOXYLATE; ETHYL 5 (4 FLUOROPHENYL) 1 [2 [2 [1 (2 HYDROXYPHENYL)METHYLIDENE]HYDRAZINO] 2 OXOETHYL] 2 METHYL 1H 3 PYRROLECARBOXYLATE; HYDRAZIDE; HYDRAZONE DERIVATIVE; N' 4 [1 (4 ACETYL 3,5 DIMETHYL 1H 2 PYRROLYL)METHYLIDENE] 4 PYRIDINECARBOHYDRAZIDE; PYRROLE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; BACTERIOSTASIS; DIPOLE; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH THROUGHPUT SCREENING; IC 50; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STRUCTURE ACTIVITY RELATION; TUBERCULOSTATIC ACTIVITY;

EID: 59849084170     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296362     Document Type: Article

References (18)

1. Tripathi RP, Tewari N, Dwivedi N, Tiwari VK. Fighting tuberculosis: An old disease with new challenges. Med Res Rev. 2005 Jan; 25(l):93-131.
2. Zhang Y, Post-Martens K, Denkin S. New drug candidates and therapeutic targets for tuberculosis therapy. Drug Discov. Today. 2006; 11(1-2):21-7.
3. Janin YL. Antituberculosis drugs: Ten years of research; Review. Bioorg Med Chem. 2007; 15(7):2479-513.
4. García-García A, Gálvez J, Julián-Ortiz JV, García-Domenech R, Muñoz C, Guna R, et al. Search of Chemical Scaf-folds for Novel Antituberculosis Agents. J Biomol Screen. 2005; 10(3):206-14.
5. Ragno R, Marshall GR, Di Santo R, Costi R, Massa S, Rom-pei R, et al. Antimycobacterial Pyrroles: Synthesis, Anti-Mycobacterium tuberculosis Activity and QSAR Studies. Bioorg Med Chem. 2000; 8:1423-32.
6. Bijev A. Synthesis and preliminary screening of carbohydrazides and hydrazones of pyrrole as potential tuberculostatics. Arzneimittelforschung. 2006; 56(2):96-103.
7. Bijev A. New hydrazones as pyrrole derivatives with higher inhibitory activity against Mycobacterium tuberculosis. Lett Drug Des Discov. 2006; 3(7):506-12.
8. Bijev A. Synthesis, in vitro evaluations and structure-activity assessment of pyrrole hydrazones. Lett Drug Des Discov. 2008; 5(1):15-24.
9. Bijev A, Yaneva D, Nankov A. Synthesis and preliminary screening of new N-pyrrolylcarboxylic hydrazides as prospective antituberculosis agents. J Univ Chem Technol Met (Sofia). 2003; 38:257-63.
10. Gossauer A. Die Chemie der Pyrrole. Berlin: Springer-Verlag; 1974, p. 289-300.
11. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev. 2001; 46:3-26.
12. Molinspiration Cheminformatics. [Cited 2008 March 11]. Available from: http://www.molinspiration.com/.
13. Chem3D Ultra, Molecular modeling and analyses, Version 8.0.3, CambridgeSoft.
14. Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) [home page]. [Cited 2008 March 11]. Available from: http://www.taacf.org/.
15. TAACF Data Interpretation on-line. [Cited 2008 March 11]. Available from: http://www.taacf.org/data-interpretation.htm.
16. Collins L, Franzblau SG. Microplate Alamar Blue Assay versus BACTEE 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Chemother. 1997; 41:1004-9.
17. Costa MS, Boechat N, Rangel EA et al. Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-l,2,3-triazole derivatives. Bioorg Med Chem. 2006; 14(24):8644-53.
18. Tiwari V, Pande R. Molecular Descriptors of N-Arylhy-droxamic Acids: A Tool in Drug Design. Chem Biol Drug Des. 2006; 68:225-8.