Syntheses and calcium channel antagonist activity of nifedipine analogues with methylsulfonylimidazolyl substituent

Shafiee, Abbas; Dehpour, Ahmad Reza; Hadizadeh, Fatemeh; Azimi, Maryam

doi:10.1016/s0031-6865(98)00004-1

Cited by 27 publications

(34 citation statements)

References 8 publications

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“…In addition, the same conclusions have been reported for 5-phenyl-2-imidazolyl and 1-methyl-5-methylsulfonyl-2-imidazolyl groups positioned at C-4 of nifedipine analogs [24,25]. However, studies dealing with the effects of substituents at the C-3 and C-5 positions of DHP ring on the biological activity of these compounds have not yet been reported.…”

Section: Full Papersupporting

confidence: 63%

“…These three classes of DHP compounds have substituents at the C-3 (-COOR 1 ) and C-5 (-COO(CH 2 ) n R 2 ) positions. Also, some compounds are symmetric and have the same substituent (-COO(CH 2 ) n R) at C-3 and C-5.The synthesis and determination of the activity of these compounds have already been reported in the literature by one of us (R. Miri) and by others [19][20][21][22][23][24][25].…”

Section: Methodsmentioning

confidence: 99%

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Quantitative Structure‐Activity Relationship Study of Recently Synthesized 1, 4‐Dihydropyridine Calcium Channel Antagonists. Application of the Hansch Analysis Method

Hemmateenejad

Miri

Akhond

et al. 2002

Archiv der Pharmazie

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The Hansch analysis method was applied to a series of recently synthesized nifedipine analogues containing nitroimidazolyl, phenylimidazolyl, and methylsulphonylimidazolyl groups at the C-4 position and different ester substituents at C-3 and C-5 positions of the dihydropyridine ring. Hydrophobic, electronic, inductive, and resonance substituent constants were used. The effect of these parameters on the biological activity of 1,4-dihydropyridines (calcium channel antagonist activity in Guinea-pig ileal cells, log (1/IC50)) was determined by multiple linear regression analysis. Linear and quadratic relationships were obtained between the activity and these parameters. It was found that both electronic and hydrophobic interactions occur between the nifedipine analogues and the receptor.

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Section: Full Papersupporting

confidence: 63%

Section: Methodsmentioning

confidence: 99%

Quantitative Structure‐Activity Relationship Study of Recently Synthesized 1, 4‐Dihydropyridine Calcium Channel Antagonists. Application of the Hansch Analysis Method

Hemmateenejad

Miri

Akhond

et al. 2002

Archiv der Pharmazie

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“…Oxidation of alkylthio group with m-chloroperbenzoic acid gave compound 3 [15]. Oxidation of hydroxyl group at 5 position of compound 3 with activated manganese (IV) oxide yielded the desired aldehyde 4 [16].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel 2‐(2‐methylsulfonyl‐1‐methyl‐1H‐imidazol‐5‐yl)‐5‐(alkylsulfonyl)‐1,3,4‐thiadiazoles

Javidnia

Akbarzadeh

Firoozpour

et al. 2010

Journal of Heterocyclic Chem

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Starting from 5‐hydroxymethyl‐2‐mercapto‐1‐methyl‐1H‐imidazole (1), a series of 2‐(1‐methyl‐2‐methylsulfonyl‐1H‐imidazol‐5‐yl)‐5‐alkylthio and 5‐alkylsulfonyl‐1,3,4‐thiadiazole derivatives (9a, 9b, 9c, 9d and 10a, 10b, 10c, 10d) were prepared as potential antimicrobial agents. The structure of the obtained compounds was confirmed by NMR, IR, Mass spectroscopy, and elemental analysis. J. Heterocyclic Chem., (2010)

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“…In previous studies we synthesized some compounds in which a C-4 imidazolyl substituent was isosteric with a nitrophenyl substituent; they were potent calcium channel blockers (Akula et al, 1990;Pourmorad et al, 1997;Shafiee et al, 1987Shafiee et al, , 1996. In this paper, we report docking, molecular modeling, and quantitative structure-activity relationship (QSAR) analysis of the DHPs containing a 4-[4-(5)-chloro-2-ethyl-5-(4)-imidazolyl] moiety.…”

Section: Introductionmentioning

confidence: 95%

Computational studies of new 1,4-dihydropyridines containing 4-(5)-chloro-2-ethyl-5-(4)-imidazolyl substituent: QSAR and docking

et al. 2009

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1,4-Dihydropyridine has been recognized as calcium channel blocker agents. In this research we did computational studies of some newly synthesized dihydropyridine containing 4-[4-(5)-chloro-2-ethyl-5-(4)-imidazolyl] moiety. DHPs were built by the HYPERCHEM program and conformational studies were performed through semi-empirical method followed by PM3 method. QSAR descriptors were obtained from E-DRAGON. QSAR equations were obtained from multilinear regression method. This simple equation can be used to estimate the CCBs activity for new compounds of this series of compounds. The sum of the energy of the highest occupied molecular orbital (HOMO), molecular volume (MV), the GETAWAY, and the WHIM were identified as the most significant descriptors. Docking study was performed by using AutoDock4 program on the all compounds which have already been reported by Davood et al. The obtained results show that experimental PIC50 agree with docking results for potent compounds (10a, 6b). These computational studies can offer some useful references for understanding the action mechanism and performing the molecular design or modification of this series of CCB agents.

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Syntheses and calcium channel antagonist activity of nifedipine analogues with methylsulfonylimidazolyl substituent

Cited by 27 publications

References 8 publications

Quantitative Structure‐Activity Relationship Study of Recently Synthesized 1, 4‐Dihydropyridine Calcium Channel Antagonists. Application of the Hansch Analysis Method

Quantitative Structure‐Activity Relationship Study of Recently Synthesized 1, 4‐Dihydropyridine Calcium Channel Antagonists. Application of the Hansch Analysis Method

Synthesis of novel 2‐(2‐methylsulfonyl‐1‐methyl‐1H‐imidazol‐5‐yl)‐5‐(alkylsulfonyl)‐1,3,4‐thiadiazoles

Computational studies of new 1,4-dihydropyridines containing 4-(5)-chloro-2-ethyl-5-(4)-imidazolyl substituent: QSAR and docking

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