Synthesis and antitubercular activity of new N,N-diaryl-4-(4,5- dichloroimidazole-2-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxamides

Daru

Volumn 16, Issue 1, 2008, Pages 9-12

  Amini, M ^a   Navidpour, L ^a   Shafiee, A ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Antituberculosis; Dichloroimidazole; Dihydropyridine

Indexed keywords

AMIDE; AMMONIUM ACETATE; METHANOL; N,N DI 3 BROMOPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DI 3 CHLOROPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DI 3 FLUOROPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DI 3 NITROPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DI 3,4 DICHLOROPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DI 4 BROMOPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DI 4 CHLOROPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DI 4 FLUOROPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DI 4 NITROPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; N,N DIPHENYL 4 (4,5 DICHLOROIMIDAZOLE 2 YL) 1,4 DIHYDRO 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXAMIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

EID: 39449132758     PISSN: 15608115     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. Mannhold R. Medicinal chemistry of DHP-like calcium antagonists. Drugs of Today 1994;30:103-122.
2. Cooper K, Johnathon FM. Dihydropyridine anti-allergic and anti-inflammatory agents. Eur Patent 294074 1988.
3. Johnson RC, Taylor DJ. 4-(Nitorne aryl) dihydropyridines. US Patent 4758669 1998.
4. Godfraind T, Miller R, Wibo M. Calcium antagonism and calcium entry blockade. Pharmacol Rev 1986;38:321-325.
5. Tanabe H, Tasaka S, Ohmori H, Gomi N, Sasaki Y, Machida T, Iino M, Kiue A, Naito S, Kuwano M. Newly synthesized dihydropyridine derivatives as modulators of P-glycoprotein-madiated multidrug resistance. Bioorg Med Chem 1998;6:2219-2227.
6. Tasaka S, Ohmori H, Gomi N, Iino M, Machida T, Kiue A, Naito S, Kuwano M. Synthesis and structure-activity analysis of novel dihydropyridine derivatives to overcome multidrug resistance. Bioorg Med Chem Lett 2001;11:275-277.
7. Eharkar P S, Desai B, Gaveria H, Varu B, Loriya R, Naliapara Y, Shah A, Kulkarni VM. Three-dimensional quantitative structure-activity relationship of 1,4-dihydropyridines as antitubercular agents. J Med Chem 2002;45:4858-4867.
8. Desai B, Sureja D, Nalapara Y, Shah A, Saxena AK. Synthesis and QSAR studies of 4-substituted phenyl-2,6-dimethyl-3,5-bis-N-(substituted phenyl)carbamoyl-1,4-dihydropyridines as potential antitubercular agents. Bioorg Med Chem 2001;9:1993-1998.
9. Gaveriya H, Desai B, Vora V, Shah A. Synthesis and antitbercular avtivity studies of some unsymmetrical 1,4-dihydropyridines. Indian J Pharm Sci 2002;64:59-62.
10. Gevariya H, Desai B, Vora V, Shah A. Synthesis of some new unsymmetrical 1,4-dihydropyridine derivatives as potent antitubercular agents. Heterocycl Commun 2001;5:481-484.
11. Shafiee A, Miri R, Dehpour AR, Soleymani F. Synthesis and calcium-channel antagonist activity of nifedipine analogues containing nitroimidazolyl substituent in guinea-pig ileal smooth muscle. Pharm Sci 1996;2:541-543.
12. Pourmorad F, Hadizadeh F, Shafiee A. Synthesis and calcium-channel antagonist activity of 4-imidazolyl-1,4-dihydropyridines. Pharm Sci 1997;3:165-168.
13. Shafiee A, Dehpour AR , Hadizadeh F, Azimi M. Synthesis and calcium channel antagonist activity of nifedipine analogues containing 4(5)-chloro-2-methyl-5(4)-imidazolyl substituent. Pharm Acta Helv 1998;73:75-79.
14. Amini M, Golabchifar A, Dehpour AR, Pirali Hamedani M, Shafiee A. Synthesis and calcium channel antagonist activity of new 1,4-dihydropyridine derivatives containing dichloroimidazolyl substituents. Arzneim-Forsch/Drug Res 2002;52:21-26.
15. Davood A, Khodarahmi G, Alipour E, Dehpour A, Amini M, Shafiee A. Synthesis and calcium channel antagonist activity of nifedipine analogues containing 4(5)-chloro-2-methyl-5(4)-imidazolyl substituent. Boll Chim Farm 2001;140:381-386.
16. Miri R, Niknahad H, Vazin A, Azarpira A, Shafiee A. Synthesis and smooth muscle calcium channel antagonist effects of new derivatives of 1,4-dihydropyridine containing nitroimidazolyl substituent. DARU 2002;10:130-135.
17. Ghodsi S, Alipour E, Amini M, Miri R, Tagi-Ganji KM, Hosseini M, Mirkhani H, Shafiee A. The synthesis and characterization of new asymmetrical dihydropyridine derivatives containing a 2,4-dichloro-5-thiazolyl substituent. Phosphorus Sulfur and Silicon 2006;181:2435-2444.
18. Clemens RJ, Hyatt JA. Acetoacetylation with 2,2,6-trimethyl-4H-1,3- dioxin-4-one: a convenient alternative to diketene. J Org Chem 1985;50:2431-2433.
19. Collins L, Franzblau SG. 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.