In vitro Antitubercular Activity of Dihydropyridine-Dicarboxamide and Pyrazole Derivatives against Mycobacterium tuberculosis
DOI:
https://doi.org/10.48165/Keywords:
Antitubercular, Dihydropyridine, Pyrazole, Mycobacterium tuberculosis, MIC and ZIAbstract
The 1,4-dihydropyridine (DHP) is the most feasible heterocyclic ring with various substitutions at several positions. The DHP and pyrazole are ever-growing due to their varied biological, pharmaceutical and therapeutic applications. The antitubercular activity of some DHP and pyrozole derivatives (BPD, CMBPD, NMBPD, DPD, DNDDP, DMDDP, BEMPMP, OMEMPMP, KPEMPMP, CEMTDP and NEPMCP) have been documented in the present study. The in vitro activity of selected compounds as antitubercular agents have been measured in term of zone of inhibition (ZI) and minimum inhibitory concentration value (MIC, MIC50 and MIC90). The compounds BPD, DNDDP, CEMTDP, NEPMCP showed good antitubercular activity against Mycobacterium tuberculosis with zone of inhibition 20-21mm and MIC value ranged between 5-12. The other derivatives DPD, CMBPD, OMEMPMP demonstrated moderate antitubercular activity against M. tuberculosis with zone of inhibition 14 to 17mm with MIC value 10 to 14. However, compounds NMBPD, DMDDP showed remarkable antitubercular activity against M. tuberculosis with zone of inhibition 21mm and MIC value 4-5. While the compounds BEMPMP, KPEMPMP showed mild activity against M. tuberculosis with zone of inhibition 11-12mm and MIC value between 17- 20.
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Andrews, J.M., Ashby, J.P., Jevons, G.M. and Wise, R. (1999). Tentative minimum inhibitory concentration and zone diameter breakpoints for moxifloxacin using BSAC criteria. J. Antimicob. Chemother. 44(6): 819–822.
Bahekar, S.K. and Shinde, D. (2002). Synthesis and anti-inflammatory activity of 1,4- dihydropyridines. Acta Pharma. (Zagreb) 52(4): 281–287.
Eby, G.A., Davis, D.R. and Holcomb, W. (1984). Reduction in duration of common colds by zinc gluconate lozenges in a double-blind study. Antimicrob. Agents Chemother. 25: 20–24.
Chang, C.I., Liu, W., and Shyu, C.Z. (2000). Use of prawn blood agar hemolysis to screen for bacteria pathogenic to cultured tiger prawns Pennaeus monodon. Dis. Aquat. Org. 43: 153–157. 5. Chohan, Z.H. and Kausar, S. (2000). Synthesis, characterization and biological properties of tridentate NNO, NNS and NNN donor thiazol-derived furanyl, thiophenyl and pyrrolyl Schiff bases and their Co (II), Cu (II), Ni (II) and Zn (II) metal chelates. Met. Based Drugs 7(1): 17–22.
Daryabari, N., Akbarzadeh, T., Amini, M., Miri, R., Mirkhani, H. and Shafiee, A. (2007). Synthesis and calcium channel antagonist activities of new derivatives of dialkyl 1, 4- Dihydro-2, 6-dimethyl-4-(5-3-yl) pyridine-3,5-dicarboxylates. J. Iran Chem. Soc. 4: 30–36.
Das, A.K. (1990). Medicinal aspects of bioinorganic chemistry. CBS, Shahdara, Delhi. 8. David, J.T. (2007). Calcium channel antagonists: Clinical uses—Past, present and future. Biochem. Pharmacol. 74: 1–9.
Desai, B., Surja, D., Nalapara, Y., Shah, A. and Saxena, A.K. (2001). Synthesis and QSAR studies of 4-phenyl-2, 6-dimethyl-3, 5-bis-N-(substituted phenyl) carbamoyl-1,4- dihydropyridines as potential antitubercular agents. Bioorg. Med.Chem. 9: 1993–1998.
Dover, L.G, Cerden˜o-Ta´rraga, A.M., Pallen, M.J., Parkhill, J. and Besra, G.S. (2004). Comparative cell wall core biosynthesis in the mycolated pathogens, Mycobacterium tuberculosis and Corynebacterium diphtheriae. FEMS Microbiol. Rev. 28: 225–250.
Eharkar, P.S., Desai, B., Gaveria, H., Varu, B., Loriya, R., Naliapara, Y., Shah, A. and Kulkarni, V.M. (2002). Three dimensional quantitative structure-activity relationship of 1,4- dihydropyridines as antitubercular agent. J. Med. Chem. 45: 4858–4867.
Fassihi, A., Zahra, A., Neda, D., Lotfollah, S., Hamid, R., Memarian, Razieh, S. Abdolvahab, A., Ramin, M., Bahman, P., Jalal, M., Pegah, M., Behzad, M., Hojjat, S. (2009). Synthesis and antitubercular activity of novel 4-substituted imidazoly l-2, 6-dimethyl-N3, N5-bisaryl-1,4- dihydropyridine-3,5-dicarboxamides. Eur. J. Med. Chem. 44: 3253–3258.
Foroumadi, A., Kargar, Z., Sakhteman, A., Sharifzadeh, A.Z., Feyzmohammadi, R., Kazemi, M., Shafiee, A. (2006). Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)- 1,3,4-2-ylthio]propionates Bioorg. Med. Chem. Lett. 16: 1164–1167.
Gaveriya, H., Desai, B., Vora, V. and Shah, A. (2002). Synthesis and antitubercular activity studies of some unsymmeterical 1, 4-dihydropyridines. Indian J. Pharm. Sci. 64: 59–62. 15. Gavariya, H., Desai, B., Vora, V. and Shah, A. (2001). Synthesis of some new unsymmetical 1,4-derivatives as potent antitubercular agents. Heterocycl. Commun. 5: 481–484. 16. Gould, J.C. and Bowie, J.H. (1952). The determination of bacterial sensitivity to antibiotics. Edinb. Med. J. 59: 178.
Gullapalli, S. and Ramarao, P. (2002). L-type Ca2+ channel modulation by dihydropyridines potentiatesĸ-opioid receptor agonist induced acute analgesia and inhibits development of tolerance in rats. Neuropharmacol. 42: 467–475.
Harikrishna, N., Isloor, A.M., Ananada, K., Parish, T., Jamalis, J., Ghabbour, H.A and Fun, H.K. (2017). Antitubercular and antimicrobial activity of NH4VO3 promoted 1,4- Dihydropyridine incorporated 1,3,4-trisubstituted pyrazole. Lett. Drug Desig. Discov. 14(6): 699–711.
Kawase, M., Shah, A., and Gaveriya, H. (2002). 3,5-dibenzoyl-1,4-dihydropyridines: synthesis and MDR reversal in tumor cells. Bioorg. Med. Chem. 10(4): 1051–1055.
Kumar, P., Upadhyay, S.K. and Singh, R. (2018). A study on recent trends in therapy of air borne communicable disease caused by Mycobacterium tuberculosis: The tuberculosis. Bull. Pure Appl. Sci. (Zool.) 37A (2): 65–74.
Manvar, A., Raghuvir, T. Pissurlenkar, R.S. (2010). Synthesis, in vitro antitubercular activity and 3D-QSAR study of 1, 4-dihydropyridines. Mol. Divers. 14: 285–305.
Mishra L. Said. M.K. and Itokawa, H. (1995). Antitumor and antimicrobial activities of Fe (II)/Fe (III) complexes derived from some heterocyclic compounds. Bioorg. Med. Chem. 33(9): 1241–1255.
Newton, S.M., Lau, C. and Wright, C.W. (2000). A review of antimycobacterial natural products. Phytoter. Res. 14: 303–322.
Satoskar, R.S. and Bhandarkar, S.D. (1933). Pharmacology and Pharmacotherapeutics (13th ed.). Popular Prakash Pvt. Ltd, Bombay 552p.
Shafii, B., Amini, M., Akbarzadeh, T. and Shafiee, A. (2008). Synthesis and antitubercular activity of N3, N5-Diaryl-4-(5-arylisoxazol-3-yl)-1, 4-dihydropyridine-3, 5-dicarboxamide. J. Sci., Islam. Repub. Iran 19(4): 323–328.
Sirisha, K., Achaiah, G. and Reddy, V.M. (2010). Facile synthesis and antibacterial, antitubercular, and anticancer activities of novel 1, 4-Dihydropyridines. Arch. Pharm. Chem. Life Sci. 343: 342–352.
Spinu, C., Pleniceanu, M. and Tigae, C. (2008). Biologically active transition metal chelates with a 2-thiophenecarboxaldehyde-derived Schiff base: Synthesis, characterization, and antibacterial properties. Turk. J. Chem. 32(4): 487–493.
Swarnalatha, G., Prasanthi, G., Sirisha, N., Chetty. C.M. (2011). 1, 4-Dihydropyridines: A multtifunctional molecule- A review. Int. J. Chem. Tech. Res. 3(1): 75–89.
Tanabe, H., Tasaka, S. Ohmori, H., Gomi, N., Sasaki, Y., Machida, T., Iino, M., Kiue, K., Naito, S. and Kuwano, M. (1998). Newly synthesized dihydropyridine derivatives as modulators of P-Glycoprotein-mediated multidrug resistance. Bioorg Med. Chem. 6(11): 2219–2227.
Upadhyay, S.K. (2016). Allelopathic activities of specific microbial metabolites in the inland prawn fisheries off eastern Uttar Pradesh, India. Int. J. Scient. Res. 5(2): 415–416. 31. Wachter .G.A. and Davis, M.C. (1998). Antimycobacterial activity of substituted isosters of pyridines and pyrazine carboxylic acids. J. Med. Chem. 41: 2436–2438.
Xu, Z., Gao, C., Ren, Q.C., Sonq, X.F., Feng, L.S. and Lv, Z.S. (2017). Recent advances of pyrazole-containing derivatives as anti-tubercular agents. Eur. J. Med. Chem. 139: 429–440.
