9-(2,3-di-O-acetyl-5(Z)-chloro-5-deoxy-β-D-erythro-pent-4-enofuranosyl)adenine | 144494-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(2,3-di-O-acetyl-5(Z)-chloro-5-deoxy-β-D-erythro-pent-4-enofuranosyl)adenine
• 英文别名: [(2R,3R,4S,5Z)-4-acetyloxy-2-(6-aminopurin-9-yl)-5-(chloromethylidene)oxolan-3-yl] acetate
• CAS: 144494-07-5
• 化学式: C₁₄H₁₄ClN₅O₅
• 分子量: 367.749
• InChiKey: RWOZJRGIBNFIKD-IFSIVEHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-(2,3-di-O-acetyl-5(Z)-chloro-5-deoxy-β-D-erythro-pent-4-enofuranosyl)adenine 在 甲醇 、 氨 作用下， 反应 1.0h， 生成 9-[5-(Z)-chloro-5-deoxy-β-D-erythro-pent-4-enofuranosyl]adenine 、 9-<5(E)-chloro-5-deoxy-β-D-erythro-pent-4-enofuranosyl>adenine
  参考文献：
  名称：

  Nucleic acid related compounds. 76. Synthesis of 5'(E and Z)-chloro-4',5'-didehydro-5'-deoxyadenosines via chlorination and thermolysis of adenosine 5'-sulfoxides. Mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase

  摘要：

  Treatment of 2',3'-di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thioadenosine (1a), or its sulfoxides 2a(S(R)) and 3a(S(S)), with iodobenzene dichloride and potassium carbonate in acetonitrile resulted in formation of the 5'-chloro(and 5',5'-dichloro)-5'-deoxy-5'-[(4-methoxyphenyl)sulfinyl]adenosines 4a, 5a, 6a, and minor diastereomers. Deprotection of 5a gave 5'(S)-chloro-5'-deoxy-5'-[(4-methoxyphenyl)-sulfinyl(S(S))]adenosine [5b(5'S,S(S))] whose stereochemistry and conformation were established by X-ray crystallography. The alpha-chlorination of sulfoxides 2a(S(R)) and 3a (S(S)) occurred with predominant retention of configuration at sulfur. Thermolysis of the alpha-chloro sulfoxides and deprotection gave the chloromethylene derivatives. The 5'(Z)-chloro-4',5'-didehydro-5'-deoxyadenosine [9b(5'Z)] diastereomer was found to be a potent time-dependent inhibitor of S-adenosyl-L-homocysteine hydrolase.

  DOI：

  10.1021/jo00053a022
• 作为产物：
  描述：

  2',3'-Di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thioadenosine 在 2,3-二氯碘苯 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二乙二醇二甲醚 、 乙腈 为溶剂， 反应 21.0h， 生成 9-(2,3-di-O-acetyl-5(Z)-chloro-5-deoxy-β-D-erythro-pent-4-enofuranosyl)adenine
  参考文献：
  名称：

  Nucleic acid related compounds. 76. Synthesis of 5'(E and Z)-chloro-4',5'-didehydro-5'-deoxyadenosines via chlorination and thermolysis of adenosine 5'-sulfoxides. Mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase

  摘要：

  Treatment of 2',3'-di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thioadenosine (1a), or its sulfoxides 2a(S(R)) and 3a(S(S)), with iodobenzene dichloride and potassium carbonate in acetonitrile resulted in formation of the 5'-chloro(and 5',5'-dichloro)-5'-deoxy-5'-[(4-methoxyphenyl)sulfinyl]adenosines 4a, 5a, 6a, and minor diastereomers. Deprotection of 5a gave 5'(S)-chloro-5'-deoxy-5'-[(4-methoxyphenyl)-sulfinyl(S(S))]adenosine [5b(5'S,S(S))] whose stereochemistry and conformation were established by X-ray crystallography. The alpha-chlorination of sulfoxides 2a(S(R)) and 3a (S(S)) occurred with predominant retention of configuration at sulfur. Thermolysis of the alpha-chloro sulfoxides and deprotection gave the chloromethylene derivatives. The 5'(Z)-chloro-4',5'-didehydro-5'-deoxyadenosine [9b(5'Z)] diastereomer was found to be a potent time-dependent inhibitor of S-adenosyl-L-homocysteine hydrolase.

  DOI：

  10.1021/jo00053a022