Synthesis of 24-(Piperidin-1-yl, Morpholin-4-yl and 4-Methylpiperazin-1-yl)-5β-cholan-3α-ols and Four Hydroxylated 23-(4,5-Dihydroimidazol-2-yl)-24-nor-5β-cholanes

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Title:Synthesis of 24-(Piperidin-1-yl, Morpholin-4-yl and 4-Methylpiperazin-1-yl)-5β-cholan-3α-ols and Four Hydroxylated 23-(4,5-Dihydroimidazol-2-yl)-24-nor-5β-cholanes
Creators:
Nguyen, Thi Thu Huong
Protiva, Jiří
Klinotová, Eva
Urban, Jiří
Protiva, Miroslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 3, pp. 471-478
Uncontrolled Keywords:Synthesis, 24-Heterocyclylcholanes

Abstract

Lithocholic (<strong>1a</strong>), chenodeoxycholic (<strong>1b</strong>), deoxycholic (<strong>1c</strong>) and cholic acid (<strong>1d</strong>) were used for the synthesis of the title compouds. Reactions of <i>O</i>-acetyllithocholic acid chloride with piperidine, morpholine and 1-methylpiperazine gave the corresponding amides <strong>2a-2c</strong> which were reduced with lithium aluminium hydride to 24-(piperidin-1-yl)-5β-cholan-3α-ol (<strong>3a</strong>) and analogues <strong>3b</strong> and <strong>3c</strong>. Heating of the acids <strong>1a-1d</strong> with ethylenediamine monotosylate afforded 23-(4,5-dihydroimidazol-2-yl)-24-nor-5β-cholan-3α-ol (<strong>4a</strong>) and analogues <strong>4b-4d</strong>. Compound <strong>4a</strong> was similarly obtained from 3α-acetoxy-24-nor-5β-cholane-23-carbonitrile. Identity of the products was corroborated by spectral characterization. Some of the products (in the form of salts) were tested for cancerostatic and antimicrobial activities <i>in vitro</i> with partially promising results.

Title:Synthesis of 24-(Piperidin-1-yl, Morpholin-4-yl and 4-Methylpiperazin-1-yl)-5β-cholan-3α-ols and Four Hydroxylated 23-(4,5-Dihydroimidazol-2-yl)-24-nor-5β-cholanes
Creators:
Nguyen, Thi Thu Huong
Protiva, Jiří
Klinotová, Eva
Urban, Jiří
Protiva, Miroslav
Uncontrolled Keywords:Synthesis, 24-Heterocyclylcholanes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:3
Page Range:pp. 471-478
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19970471UNSPECIFIED
ID Code:1131
Item Type:Article
Deposited On:06 Feb 2009 17:06
Last Modified:06 Feb 2009 16:06

Citation

Nguyen, Thi Thu Huong; Protiva, Jiří; Klinotová, Eva; Urban, Jiří; Protiva, Miroslav (1997) Synthesis of 24-(Piperidin-1-yl, Morpholin-4-yl and 4-Methylpiperazin-1-yl)-5β-cholan-3α-ols and Four Hydroxylated 23-(4,5-Dihydroimidazol-2-yl)-24-nor-5β-cholanes. Collection of Czechoslovak Chemical Communications, 62 (3). pp. 471-478. ISSN 0010-0765

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