Synthesis and Biological Activity of Some 17a-Substituted Homolactones of Androst-5-ene Derivatives

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Title:Synthesis and Biological Activity of Some 17a-Substituted Homolactones of Androst-5-ene Derivatives
Creators:
Penov Gaši, Katarina M.
Stojanović, Srdjan Z.
Sakač, Marija N.
Djurendić, Evgenija A.
Csanádi, János J.
Molnar-Gabor, Dora
Lazar, Dušan
Kovačević, Radmila M.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 9, pp. 1387-1396
Uncontrolled Keywords:Aromatase inhibitors, Oximes, X-Ray analysis, D-ring cleavage, Steroids, Steroidal lactones, D-homoandrostene derivatives

Abstract

Some new 17a-homolactones were prepared from 3β-hydroxy-16-(hydroxyimino)androst-5-en-17-one (<strong>1</strong>) as a starting compound, which was transformed first to the corresponding 17α-phenyl and 17α-benzyl derivatives <strong>2</strong> and <strong>3</strong>. The structure of compound <strong>3</strong> was confirmed by X-ray structure analysis. Beckmann fragmentation of compounds <strong>2</strong> and <strong>3</strong> yielded 16,17-seco-cyano ketones <strong>4</strong>-<strong>7</strong>, whose reduction with NaBH<sub>4</sub> gave 16,17-seco-cyano alcohols <strong>8</strong>-<strong>11</strong>, whereby the structure of compound <strong>7</strong> was established by X-ray structural analysis. Compounds <strong>8</strong>-<strong>11</strong> served as the starting compounds for obtaining lactones <strong>12</strong> and <strong>13</strong> in a reaction with potassium hydroxide in ethylene glycol. One-pot procedures were also developed for preparing 17a-homolactones <strong>12</strong>, <strong>13</strong> and <strong>16</strong> from the hydroxyimino alcohols <strong>2</strong>, <strong>3</strong> and <strong>14</strong>. Compounds <strong>12</strong> and <strong>13</strong> showed an inhibitory activity against the enzyme aromatase (63 and 59%, respectively). <p>

Title:Synthesis and Biological Activity of Some 17a-Substituted Homolactones of Androst-5-ene Derivatives
Creators:
Penov Gaši, Katarina M.
Stojanović, Srdjan Z.
Sakač, Marija N.
Djurendić, Evgenija A.
Csanádi, János J.
Molnar-Gabor, Dora
Lazar, Dušan
Kovačević, Radmila M.
Uncontrolled Keywords:Aromatase inhibitors, Oximes, X-Ray analysis, D-ring cleavage, Steroids, Steroidal lactones, D-homoandrostene derivatives
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:70
Number:9
Page Range:pp. 1387-1396
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20051387UNSPECIFIED
ID Code:2418
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Penov Gaši, Katarina M.; Stojanović, Srdjan Z.; Sakač, Marija N.; Djurendić, Evgenija A.; Csanádi, János J.; Molnar-Gabor, Dora; Lazar, Dušan; Kovačević, Radmila M. (2005) Synthesis and Biological Activity of Some 17a-Substituted Homolactones of Androst-5-ene Derivatives. Collection of Czechoslovak Chemical Communications, 70 (9). pp. 1387-1396. ISSN 0010-0765

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