Various pyrrole and pyrrolidine derivatives acts as new trends in development of antimycobacterial agents

  • Mohammad Asif Department of Pharmacy, GRD (PG) Institute of Management & Technology, 248009, Dehradun, (Uttarakhand)
Keywords: Pyrrole derivatives, Anti-tubercular activity, MDR-TB

Abstract

Pyrrole and pyrrolidine derivatives are important antimicrobial agents. Some pyrrole and pyrrolidine derivatives are under investigation for the treatment of tuberculosis and multidrug-resistant tuberculosis. In this article, study the pyrrole and pyrrolidine derivatives with anti-mycobacterial properties, mode of action and structure activity relationship studies of the pyrrole derivatives. Furthermore, we update the synthesis and activity of pyrrole and pyrrolidine derivatives as a new class of potent anti-mycobacterial agents. Furthermore, particularly interesting is their activity against MDR-TB.

Downloads

Download data is not yet available.

References

WHO Global Tuberculosis Control Report, Geneva: World Health Organization, March 2002.

Global Tuberculosis Control, Geneva: World Health Organization, 2011.

Medical Research Council. Streptomycin treatment of pulmonary tuberculosis. Medical Research Council investigation. Br Med J, 1948; 2: 769-82.

Pyle MM. Relative numbers of resistant tubercle bacilli in sputa of patients before and during treatment with streptomycin. Proc Staff Meet Mayo Clin 1947; 22: 465-72.

Youmans GP, Williston EH, Feldman WH, Hinshaw HC. Increase in resistance of tubercle bacilli to streptomycin: a preliminary report. Proc Staff Meet Mayo Clin, 1946; 21: 126-7.

Medical Research Council. Treatment of pulmonary tuberculosis with streptomycin and para-aminosalicylic acid. Medical Research Council investigation. Br Med J, 1950; 2: 1073-86.

Gilman AG. In: Gilman AG Ed, Antimicrobial agents, The pharmacologic basis of therapeutics. Pergamon Press, New York. 1990; 1061-62.

Goldberger MJ. Antituberculous agents. Med Clin North Am, 1988; 72: 661-8.

Iseman MD. Treatment of multidrug-resistant tuberculosis. N Engl J Med, 1993; 329: 784-91.

Duncan K, Sacchettini JC. In: Hatfull GF, Jacobs WRJ Ed, Approaches to tuberculosis drug development. Molecular genetics of mycobacteria. Washington DC, ASM Press. 2000; 297-307.

Anti-tuberculosis drug resistance in the world: Third Global Report, Geneva: World Health Organization, 2008.

Ginsburg, A.S, Grosset, J.H, Bishai, W.R. Fluoroquinolones, tuberculosis, and resistance. Lancet Infect. Dis, 2003; 3: 432.

Alland, D, Kalkut, G.E, Moss, A.R, McAdam, R.A, Hahn, J.A, Bosworth, W, Drucker, E, Bloom, B.R. Transmission of tuberculosis in New York City. An analysis by DNA fingerprinting and conventional epidemiologic methods. N. Engl. J. Med, 1994, 330, 1710-1716.

Global tuberculosis control: a short update to the 2010 Report. Geneva: World Health Organization, 2010.

Getahun H, Gunneberg C, Granich R, Nunn P. HIV infectionassociated tuberculosis: the epidemiology and the response. Clin. Infect. Dis, 2010, 50(3), 201-207.

Guidelines for intensified tuberculosis case-finding and Isoniazid preventive therapy for people living with HIV in resourceconstrained settings, Geneva: World Health Organization, 2011.

Whalen, C, Horsburgh, C.R, Hom, D, Lahart, C, Simberkoff, M, Ellner, J. Accelerated course of human immunodeficiency virus infection after tuberculosis. Am. J. Respir. Crit. Care Med, 1995; 51: 129-135.

Hart, C.A, Beeching, N.J, Duerden, B.I. Tuberculosis into the next century. Proceedings of a symposium held on 4 February 1995 at the Liverpool School of Medicine. J. Med. Microbiol, 1996, 44, 1-34.

Young, L.S. Mycobacterial infections in immunocompromised patients. Curr. Opin. Infect. Dis, 1996; 9: 240-245.

Tomioka, H, Sato, K, Kajitani, H, Akaki, T, Shishido, S. Comparative antimicrobial activities of the newly synthesized quinolone WQ-3034, levofloxacin, sparfloxacin, and ciprofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex. Antimicrob. Agents Chemother, 2000, 44, 283-286.

Cole ST, Brosch R, Parkhill J, et al. Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature, 1998; 393: 537-44.

Biavaa M, Porrettaa GC, Deiddab D, Pompeib R. New trends in development of antimycobacterial compounds. Infectious Disorders-Drug Targets 2006, 6, 159-172.

Di Santo R, Costi R, Artico M, Massa S, Lampis G, Deidda D, Pompei R. Pyrrolnitrin and related pyrroles endowed with antibacterial activities against Mycobacterium tuberculosis. Bioorg Med Chem Lett, 1998; 8:2931–2936.

Deidda D, Lampis G, Fioravanti R, Biava M, Porretta GC, Zanetti S, Pompei R. Bactericidal activities of the pyrrole derivative BM212 against multidrug-resistant and intramacrophagic Mycobacterium tuberculosis strains. Antimicrob Agents Chemother, 1998; 42:3035–3037

Biava M, Porretta GC, Deidda D, Pompei R, Tafi A, Manetti F. Importance of the Thiomorpholine Introduction in New Pyrrole Derivatives as Antimycobacterial Agents Analogues of BM 212. Bioorg. Med. Chem., 2003; 11(4), 515-520.

Biava M, Porretta GC, Deidda D, Pompei R, Tafi A, Manetti F. Antimycobacterial compounds. New pyrrole derivatives of BM212. Bioorg Med Chem, 2004; 12:1453–1458

Biava M, Porretta GC, Poce G, Deidda D, Pompei R, Tafi A, Manetti F. Antimycobacterial compounds. Optimization of the BM 212 structure, the lead compound for a new pyrrole derivative class. Bioorg Med Chem, 2005; 13:1221–1230

Biava M, Porretta GC, Poce G, Supino S, Deidda D, Pompei R, Molicotti P, Manetti F, Botta M. Antimycobacterial agents. Novel diarylpyrrole derivatives of BM212 endowed with high activity toward Mycobacterium tuberculosis and low cytotoxicity. J Med Chem, 2006; 49(16): 4946–4952.

Biava M, Porretta GC, Manetti F. New derivatives of BM212: a class of antimycobacterial compounds based on the pyrrole ring as a scaffold. Mini Rev Med Chem, 2007; 7:65–78

Pichota A, Duraiswamy J, Yin Z et al. Peptide deformylase inhibitors of Mycobacterium tuberculosis: Synthesis, structural investigations, and biological results. Bioorg. Med. Chem. Lett., 2008; 18(24), 6568-6572.

Faugeroux V, Genisson Y, Salma Y, Constant P, Baltasa M. Synthesis and biological evaluation of conformationally constrained analogues of the antitubercular agent ethambutol. Bioorg. Med. Chem., 2007; 15(17), 5866-5876.

Kumar RR, Perumal S, Manju SC, Bhatt P, Yogeeswari P, Sriram D. An atom economic synthesis and antitubercular evaluation of novel spiro-cyclohexanones. Bioorg. Med. Chem. Lett., 2009; 19(13): 3461-3465.

Kumar RR, Perumal S, Senthilkumar P, Yogeeswari P, Sriram D. A facile synthesis and antimycobacterial evaluation of novel spiro-pyrido-pyrrolizines and pyrrolidines. Eur. J. Med. Chem., 2009; 44(9), 3821-3829.

Nefzi A, Appel J, Arutyunyan S, Houghten RA. Parallel synthesis of chiral pentaamines and pyrrolidine containing bis-heterocyclic libraries. Multiple scaffolds with multiple building blocks: A double diversity for the identification of new antitubercular compounds. Bioorg. Med. Chem. Lett., 2009; 19(17), 5169-5175.

He X, Alian A, Stroud R, de Montellano PRO. Pyrrolidine Carboxamides as a Novel Class of Inhibitors of Enoyl Acyl Carrier Protein Reductase from Mycobacterium tuberculosis. J. Med. Chem., 2006; 49(21), 6308-6323.

Yendapally R, Hurdle JG, Carson EI, Lee RB, Lee RE. N-Substituted 3-Acetyltetramic Acid Derivatives as Antibacterial Agents. J. Med. Chem. 2008; 51(5): 1487-1491.

Biava M, Porretta GC, Poce G et al. 1,5-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.

Biava M, Porretta GC, Poce G et al. 1,5-Diaryl-2-ethyl pyrrole derivatives as antimycobacterial agents: Design, synthesis, and microbiological evaluation. Eur. J. Med. Chem.. 2009; 44(11), 4734-4738.

Ragno R, Marshall GR, Santo RD et al. Antimycobacterial Pyrroles: Synthesis, Anti-Mycobacterium tuberculosis Activity and QSAR Studies. Bioorg. Med. Chem., 2000, 8(6), 1423-1432.

Joshi SD, Vagdevi HM, Vaidya VP, Gadaginamath GS. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and antitubercular agents. Eur. J. Med. Chem., 2008; 43(9), 1989-1996.

Mai A, Artico M, Esposito M, Ragno R, Sbardella G, Massa S. Synthesis and biological evaluation of enantiomerically pure pyrrolyl-oxazolidinones as a new class of potent and selective monoamine oxidase type A Inhibitors. II Farmaco, 2003; 58(3), 231-241.

Guzel O, Salman A. Synthesis, antimycobacterial and antitumor activities of new (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl N,N-disubstituted dithiocarbamate/O-alkyl dithio-carbonate derivatives. Bioorg. Med. Chem,.2006; 14(23) 7804-7815.

Ukrainets IV, Mospanova EV, Sidorenko LV. 4-hydroxy-2-quinolones. 1-hydroxy-3-oxo-5,6-dihydro-3h-pyrrolo[3,2,1-ij]-Quinoline-2-carboxylic acid hetarylamides as potential anti-tubercular agents. Chem. Heterocycl. Comp., 2007; 43(7), 863-870.

Guillon J, Reynolds RC, Leger J-M et al. Synthesis and Preliminary In Vitro Evaluation of Antimycobacterial Activity of New Pyrrolo[ 1,2-a ] quinoxalinecarboxylic Acid Hydrazide Derivatives. J. Enz. Inhib. Med. Chem., 2004; 19(6), 489-495.

Parai MK, Panda G, Chaturvedi V, Manju YK, Sinha S. Thiophene containing triarylmethanes as antitubercular agents. Bioorg. Med. Chem. Lett. 18(1), 289-292 (2008).

46. Panda G, Parai MK, Das SK et al. Effect of substituents on diarylmethanes for antitubercular activity. Eur. J. Med. Chem., 2007; 42(3): 410-419.

Bijev A. New Heterocyclic Hydrazones in the Search for Antitubercular Agents: Synthesis and In Vitro Evaluations. Lett Drug Design & Discov, 2006; 3(7), 506-512.

Karthikeyan, SV, Bala, BD, Raja, VP, Perumal, S, Yogeeswari, P, Sriram, D. A highly atom economic, chemo-, regio and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents. Bioorg & Med Chem Lett, 2010; 20(1): 350-353.

Published
2015-02-28
How to Cite
1.
Asif M. Various pyrrole and pyrrolidine derivatives acts as new trends in development of antimycobacterial agents. AMS [Internet]. 28Feb.2015 [cited 22Dec.2024];2(2):42-6. Available from: http://asdpub.com/index.php/ams/article/view/70
Section
Review Articles

Most read articles by the same author(s)

Obs.: This plugin requires at least one statistics/report plugin to be enabled. If your statistics plugins provide more than one metric then please also select a main metric on the admin's site settings page and/or on the journal manager's settings pages.