β-D-ribofuranosyl-3-spiro-5'-(4'-amino-1',2'-oxathiole 2',2'-dioxide) azide | 170080-15-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: β-D-ribofuranosyl-3-spiro-5'-(4'-amino-1',2'-oxathiole 2',2'-dioxide) azide
• 英文别名: (5S,6R,8R,9R)-4-amino-8-azido-6-(hydroxymethyl)-2,2-dioxo-1,7-dioxa-2lambda6-thiaspiro[4.4]non-3-en-9-ol；(5S,6R,8R,9R)-4-amino-8-azido-6-(hydroxymethyl)-2,2-dioxo-1,7-dioxa-2λ6-thiaspiro[4.4]non-3-en-9-ol
• CAS: 170080-15-6
• 化学式: C₇H₁₀N₄O₆S
• 分子量: 278.246
• InChiKey: GWRVBEVNYALKOC-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  β-D-ribofuranosyl-3-spiro-5'-(4'-amino-1',2'-oxathiole 2',2'-dioxide) azide 在 4-二甲氨基吡啶 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 34.0h， 生成 <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-5-<(methyloxy)carbonyl>-1,2,3-triazole>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide)
  参考文献：
  名称：

  1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) Analogs: Synthesis and Anti-HIV-1 Activity

  摘要：

  Several 4- or 5-monosubsituted and 4,5-disubstituted 1,2,3-triazole analogues of the anti-HIV-1 lead com pound [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]thymine]-3'-spiro-5''(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO-T) have been prepared and evaluated as inhibitors of HIV-1-induced cytopathicity. These analogues have been prepared by 1,3-diplar cycloaddition of [2,5-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3-spiro-5'-(4'-amino- and and 4'-(N-acetylamino)1',2'-oxathiole 2',2'-dioxide) (TSAO) azides to various substituted acetylenes. Several 4- and 5-substituted 1,2,3-triazole-TSAO analogues proved superior to the unsubstituted derivative by 1-2 orders of magnitude. In particular the 5-substituted amido-, (methylamido)-, and (dimethylamido)-1,2,3-triazole derivatives of TSAO were endowed with potent anti-HIV-1 activity (50% effective concentration: 0.056-0.52 mu M). They show a similar resistance spectrum as previously noted for TSAO-T and related derivatives.

  DOI：

  10.1021/jm00050a015
• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-C-cyano-3-O-mesyl-D-ribofuranose 在 叠氮基三甲基硅烷 、 氨 、 四氯化锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 193.0h， 生成 β-D-ribofuranosyl-3-spiro-5'-(4'-amino-1',2'-oxathiole 2',2'-dioxide) azide
  参考文献：
  名称：

  1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) Analogs: Synthesis and Anti-HIV-1 Activity

  摘要：

  Several 4- or 5-monosubsituted and 4,5-disubstituted 1,2,3-triazole analogues of the anti-HIV-1 lead com pound [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]thymine]-3'-spiro-5''(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO-T) have been prepared and evaluated as inhibitors of HIV-1-induced cytopathicity. These analogues have been prepared by 1,3-diplar cycloaddition of [2,5-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3-spiro-5'-(4'-amino- and and 4'-(N-acetylamino)1',2'-oxathiole 2',2'-dioxide) (TSAO) azides to various substituted acetylenes. Several 4- and 5-substituted 1,2,3-triazole-TSAO analogues proved superior to the unsubstituted derivative by 1-2 orders of magnitude. In particular the 5-substituted amido-, (methylamido)-, and (dimethylamido)-1,2,3-triazole derivatives of TSAO were endowed with potent anti-HIV-1 activity (50% effective concentration: 0.056-0.52 mu M). They show a similar resistance spectrum as previously noted for TSAO-T and related derivatives.

  DOI：

  10.1021/jm00050a015

文献信息

• Synthesis and Anti-HIV-1 Activity of 4- and 5-Substituted 1,2,3-Triazole-TSAO Derivatives
  作者：Ana San-Féalix、Rosa Alvarez、Sonsoles Veláazquez、Erik De Clercq、Jan Balzarini、María José Camarasa

  DOI：10.1080/15257779508012433

  日期：1995.5.1

  Several 4- or 5-monosubstituted and 4,5-disubstituted 1,2,3-triazole analogues of the anti-HIV-1 lead compound [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]thymine]-3'-spiro-5 ''-(4 ''-amino-1 '',2 ''-oxathiole-2 '',2 ''-dionide) (TSAO-T) have been prepared and evaluated for their inhibitory effect against HIV-1-induced cytopathicity.
• 1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) Analogs: Synthesis and Anti-HIV-1 Activity
  作者：Rosa Alvarez、Sonsoles Velazquez、Ana San-Felix、Stefano Aquaro、Erik De Clercq、Carlo-Federico Perno、Anna Karlsson、Jan Balzarini、Maria Jose Camarasa

  DOI：10.1021/jm00050a015

  日期：1994.11

  Several 4- or 5-monosubsituted and 4,5-disubstituted 1,2,3-triazole analogues of the anti-HIV-1 lead com pound [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]thymine]-3'-spiro-5''(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO-T) have been prepared and evaluated as inhibitors of HIV-1-induced cytopathicity. These analogues have been prepared by 1,3-diplar cycloaddition of [2,5-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3-spiro-5'-(4'-amino- and and 4'-(N-acetylamino)1',2'-oxathiole 2',2'-dioxide) (TSAO) azides to various substituted acetylenes. Several 4- and 5-substituted 1,2,3-triazole-TSAO analogues proved superior to the unsubstituted derivative by 1-2 orders of magnitude. In particular the 5-substituted amido-, (methylamido)-, and (dimethylamido)-1,2,3-triazole derivatives of TSAO were endowed with potent anti-HIV-1 activity (50% effective concentration: 0.056-0.52 mu M). They show a similar resistance spectrum as previously noted for TSAO-T and related derivatives.