5‐Oxo‐1,4‐dihydroindenopyridines: Calcium modulators with partial calcium agonistic activity

Rose, Ulrich

doi:10.1002/jhet.5570270223

Cited by 27 publications

(11 citation statements)

References 11 publications

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“…Similar results were obtained in 5-oxo-1,4-indenopyridine (I) and furoquinoline (II) derivatives [66,79]. The 4-arylhexahydroquinoline derivatives having an electron withdrawing substituent on the phenyl ring showed high calcium antagonist activity.…”

Section: Structure-activity Relationshipssupporting

confidence: 82%

Fused 1,4-Dihydropyridines as Potential Calcium Modulatory Compounds

Şafak¹,

Şimşek²

2006

MRMC

119

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1,4-Dihydropyridine (1,4-DHP) derivatives nifedipine of which the prototype, are the most popular drugs having calcium antagonistic activity. Fused 1,4-dihydropyridines (DHPs) have also exhibit calcium modulatory activities. In this article, we emphasize calcium channels and fused 1,4-DHP derivatives affecting calcium channels. In addition, the basic considerations of synthesis, metabolism, structure-activity relationships and the latest developments on fused 1,4-DHP derivatives will be reviewed. This review also has extended examples of fused 1,4-DHP derivatives having cited activities synthesized by our group.

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Section: Structure-activity Relationshipssupporting

confidence: 82%

Fused 1,4-Dihydropyridines as Potential Calcium Modulatory Compounds

Şafak¹,

Şimşek²

2006

MRMC

119

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“…1D and 2D-NMR spectra Bruker AMX-600 MHz FT NMR. 13 C-NMR Spectra: 13 C AMX 150 MHz FT NMR Spectrophotometer. Chemical shift values are given as ppm.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Evaluation of the Calcium Antagonistic Activity and Biotransformation of Hexahydroquinoline and Furoquinoline Derivatives

Şimşek

Şafak

Erol

et al. 2011

Arzneimittelforschung

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The objective of this study was to synthesise new condensed 1,4-dihydropyridine derivatives and investigate their calcium channel blocking activity. In addition, the in vitro hepatic microsomal biotransformation of one hexahydroquinoline derivative was studied. 2,6,6-Trimethyl-3-carbmethoxy (carbethoxy)-4-aryl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives were synthesised by modified Hantzsch synthesis. 1,3,4,5,6,7,8,9-octahydro-7,7-dimethyl-9-arylfuro [3,4-b]quinoline-1,8-dione derivatives were synthesised the reaction of hexahydroquinoline derivatives with pyridinium bromide perbromide. The calcium antagonistic activities of the compounds were determined by tests performed on isolated rat ileum and lamb carotid artery. In vitro hepatic biotransformation of one compound was studied in rat microsomes.Although compounds 3, 18 and 28 showed promising relaxant activity, they were less active than nicardipine (CAS 55985-32-5) in isolated rat ileum. In all studied concentrations, compounds 5 and 20 were more active than nicardipine in lamb carotid artery. These compounds showed high tissue selectivity compared with nicardipine. In addition, in vitro hepatic microsomal biotransformation of compound 2 produced its lactone derivative (compound 34). This metabolite was verified by HPLC.In the hexahydroquinoline series, the compounds having ortho substituted phenyl substituent were more active than the meta isomers. Lactone derivatives were found less active than hexahydroquinoline derivatives in respect to calcium antagonistic activity. Key wordsFuroquinoline derivatives, calcium antagonistic activity, synthesis Hexahydroquinoline derivatives, calcium antagonistic activity, synthesis Arzneim.-Forsch./Drug Res. 53, No. 3, 159−166 (2003) Arzneim.-Forsch./Drug Res. 53, No. 3, 159−166 (2003) Şimşek et al. − Hexahydroquinolines and furoquinolines Scheme 3: Mass fragmentation of hexahydroquinoline derivatives. Arzneim.-Forsch./Drug Res. 53, No. 3, 159−166 (2003) Şimşek et al. − Hexahydroquinolines and furoquinolines

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“…In addition, in order to fix one carbonyl group in an antiperiplanar position, the 1,4-DHP structure has been annelated. Thus condensed 1,4-DHP derivatives have been obtained and these analogs showed calcium antagonistic activity [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%