Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds

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Title:Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds
Creators:
Nguyen, Thi Thu Huong
Urban, Jiří
Klinotová, Eva
Sejbal, Jan
Protiva, Jiří
Drašar, Pavel
Protiva, Miroslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 60, 2, pp. 257-275

Abstract

<p>The bile acids <i>Ia - Id</i> (lithocholic, chenodeoxycholic, deoxycholic, cholic) and their derivatives (<i>O</i>-acetylated acids and <i>O</i>-acetylated acid chlorides) reacted under various conditions with 1,2-diaminobenzene, 2-aminophenol and 2-aminothiophenol and afforded the title benzimidazoles <i>II</i> and <i>VII</i>, benzoxazoles <i>V</i> and benzothiazoles <i>VI</i>. Alkylation of the benzimidazole derivative <i>IIa</i> with 2-dimethylaminoethyl chloride resulted in 3α-hydroxy-23-[1-(2-dimethylaminoethyl)ben zimidazol-2-yl]- norcholane (<i>IVa</i>). The use of 1,2-diamino-4-methylbenzene enabled the preparation of 3α-acetoxy-23-[5(6)-methylbenzimidazol-2-y l]norcholane (<i>VIII</i>). Reactions of the 3α-hydroxy compounds <i>IVa</i>, <i>Va</i> and <i>VIa</i> with succinic anhydride resulted in the hemisuccinates <i>IVi</i> - <i>VIi</i>. The boric acid mediated condensation of <i>O</i>-acetyllithocholic acid (<i>Ie</i>) with 3,4-diaminopyridine gave compound <i>X</i> which was transformed to 3α-acetoxy-23-[1<i>H</i>-imidazo(4,5- <i>c</i>)pyridin-2-yl]norcholane (<i>IX</i>). The structure of the products was corroborated by the mass, IR, <sup>1</sup>H NMR and <sup>13</sup>C NMR spectra. Some of the compounds were tested for antileukemic and for the anti-HIV activity in vitro.

Title:Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds
Creators:
Nguyen, Thi Thu Huong
Urban, Jiří
Klinotová, Eva
Sejbal, Jan
Protiva, Jiří
Drašar, Pavel
Protiva, Miroslav
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:60
Number:2
Page Range:pp. 257-275
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19950257UNSPECIFIED
ID Code:715
Item Type:Article
Deposited On:06 Feb 2009 17:03
Last Modified:06 Feb 2009 16:03

Citation

Nguyen, Thi Thu Huong; Urban, Jiří; Klinotová, Eva; Sejbal, Jan; Protiva, Jiří; Drašar, Pavel; Protiva, Miroslav (1995) Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds. Collection of Czechoslovak Chemical Communications, 60 (2). pp. 257-275. ISSN 0010-0765

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