Synthesis and Sympatholytic and Adrenomimetic Activities of Amino Amides and Amino Esters Based on 1-(1,3-Benzodioxol-5-yl)cyclopentane- and 4-(1,3-Benzodioxol-5-yl)tetrahydro-2H-pyran-4-carboxylic Acids

The reactions of 2-(1,3-benzodioxol-5-yl)acetonitrile with 1,4-dibromobuthane and 2,2′-bis(2-chloro­ethyl) ether gave 1-(1,3-benzodioxol-5-yl)cyclopentane- and 4-(1,3-benzodioxol-5-yl)tetrahydro-2H-pyran-4-carbonitriles which were hydrolyzed in alkaline medium to the corresponding carboxylic acids, and the latter were converted to acid chlorides. 1-(1,3-Benzodioxol-5-yl)cyclopentane- and 4-(1,3-benzodioxol-5-yl)­tetrahydro-2H-pyran-4-carbonyl chlorides reacted with N,N-dialkylaminoalkyl- and hetarylalkylamines, as well as with N,N-dialkylaminoalkanols and hetarylalkanols, to afford the target (1,3-benzodioxol-5-yl)cyclo­pentane(tetrahydropyran)carboxamides and (1,3-benzodioxol-5-yl)cyclopentane(tetrahydropyran)carboxylates. The synthesized compounds were evaluated for their effects on the cardiovascular system and blood hemodynamics.

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Journal
Russian Journal of Organic Chemistry
Published
2025-03-01
DOI
https://doi.org/10.1134/s107042802560010x
Primary Topic
Synthesis and biological activity
Type
article
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article

Synthesis and Sympatholytic and Adrenomimetic Activities of Amino Amides and Amino Esters Based on 1-(1,3-Benzodioxol-5-yl)cyclopentane- and 4-(1,3-Benzodioxol-5-yl)tetrahydro-2H-pyran-4-carboxylic Acids

A. S. Tsatinyan, H. А. Panosyan, G. G. Mkryan, R. E. Margaryan et al.
Russian Journal of Organic Chemistry
Synthesis and biological activity
article

Synthesis and Sympatholytic and Adrenomimetic Activities of Amino Amides and Amino Esters Based on 1-(1,3-Benzodioxol-5-yl)cyclopentane- and 4-(1,3-Benzodioxol-5-yl)tetrahydro-2H-pyran-4-carboxylic Acids

A. S. Tsatinyan, H. А. Panosyan, G. G. Mkryan, R. E. Margaryan, А. А. Aghekyan, M. S. Grigoryan, S. A. Arutyunyan, G. V. Stepanyan
article en

Abstract

The reactions of 2-(1,3-benzodioxol-5-yl)acetonitrile with 1,4-dibromobuthane and 2,2′-bis(2-chloro­ethyl) ether gave 1-(1,3-benzodioxol-5-yl)cyclopentane- and 4-(1,3-benzodioxol-5-yl)tetrahydro-2H-pyran-4-carbonitriles which were hydrolyzed in alkaline medium to the corresponding carboxylic acids, and the latter were converted to acid chlorides. 1-(1,3-Benzodioxol-5-yl)cyclopentane- and 4-(1,3-benzodioxol-5-yl)­tetrahydro-2H-pyran-4-carbonyl chlorides reacted with N,N-dialkylaminoalkyl- and hetarylalkylamines, as well as with N,N-dialkylaminoalkanols and hetarylalkanols, to afford the target (1,3-benzodioxol-5-yl)cyclo­pentane(tetrahydropyran)carboxamides and (1,3-benzodioxol-5-yl)cyclopentane(tetrahydropyran)carboxylates. The synthesized compounds were evaluated for their effects on the cardiovascular system and blood hemodynamics.

Russian Journal of Organic ChemistryVol. 61(3)
Institute of Fine Organic Chemistry of Scientific - Technological Center of Organic and Pharmaceutical Chemistry (AM), National Academy of Sciences of Armenia (AM)
Openalex Percentile: Top 93%
Synthesis and biological activity
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Synthesis and Sympatholytic and Adrenomimetic Activities of Amino Amides and Amino Esters Based on 1-(1,3-Benzodioxol-5-yl)cyclopentane- and 4-(1,3-Benzodioxol-5-yl)tetrahydro-2H-pyran-4-carboxylic Acids — A. S. Tsatinyan, H. А. Panosyan, et al. · Russian Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS