Synthesis of Some 6-Substituted 5-Azacytidines

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Title:Synthesis of Some 6-Substituted 5-Azacytidines
Creators:
Hanna, Naeem B.
Masojídková, Milena
Fiedler, Pavel
Pískala, Alois
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 2, pp. 222-230
Uncontrolled Keywords:Circular dichroism, Nucleosides, Antibacterial activity, 1,3,5-Triazines, 5-Azapyrimidines

Abstract

Protected 6-substituted benzyl, phenyl and chloromethyl derivatives of 5-azacytidine <strong>8-10</strong> have been prepared by addition of phenylacetyl- (<strong>2</strong>), benzoyl- (<strong>3</strong>) or (chloroacetyl)guanidine (<strong>4</strong>) to 2,3,5-tri-<i>O</i>-benzoyl-β-D-ribosyl isocyanate (<strong>1</strong>) and subsequent silylation-mediated cyclization of the obtained acyl(carbamoyl)guanidines <strong>5-7</strong>. 4-Amino-6-phenyl-1,3,5-triazin-2(1<i>H</i>)-one (<strong>12</strong>) was obtained by condensation of carbamoylguanidine (<strong>13</strong>) with methyl benzoate in presence of methanolic sodium methoxide or by condensation of <strong>13</strong> with triethyl orthobenzoate in <i>N</i>,<i>N</i>-dimethylformamide. Stannic chloride catalyzed condensation of silylated 6-phenyl derivative <strong>11</strong> with 1-<i>O</i>-acetyl-2,3,5-tri-<i>O</i>-benzoyl-β-D-ribose (<strong>14</strong>) in 1,2-dichloroethane afforded a 1.2 : 1 mixture of N<sup>1</sup> and N<sup>3</sup> nucleosides <strong>9</strong> and <strong>15</strong>, respectively. Methanolysis of the protected compounds <strong>8-10</strong> and <strong>15</strong> gave the respective free nucleosides <strong>16-19</strong>. The latter compounds inhibited the growth of bacteria <i>E. coli</i> B to a much lower extent than the unsubstituted 5-azacytidine.

Title:Synthesis of Some 6-Substituted 5-Azacytidines
Creators:
Hanna, Naeem B.
Masojídková, Milena
Fiedler, Pavel
Pískala, Alois
Uncontrolled Keywords:Circular dichroism, Nucleosides, Antibacterial activity, 1,3,5-Triazines, 5-Azapyrimidines
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:63
Number:2
Page Range:pp. 222-230
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980222UNSPECIFIED
ID Code:1290
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Hanna, Naeem B.; Masojídková, Milena; Fiedler, Pavel; Pískala, Alois (1998) Synthesis of Some 6-Substituted 5-Azacytidines. Collection of Czechoslovak Chemical Communications, 63 (2). pp. 222-230. ISSN 0010-0765

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