6-amino-2-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)-8-thioxo-9H-purine | 170872-43-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-amino-2-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)-8-thioxo-9H-purine
• 英文别名: 6-amino-2-chloro-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-purine-8-thione
• CAS: 170872-43-2
• 化学式: C₁₀H₁₂ClN₅O₃S
• 分子量: 317.756
• InChiKey: RPIFWZOJMPSYPO-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  碘乙烷 、 6-amino-2-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)-8-thioxo-9H-purine 在 potassium carbonate 作用下， 反应 8.0h， 以72%的产率得到6-amino-2-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)-8-ethylthio-9H-purine
  参考文献：
  名称：

  2-Chloro-2′-deoxyadenosine: Synthesis and Antileukemic Activity of 8-Substituted Derivatives

  摘要：

  A series of 8-substituted 2-chloro-2'-deoxyadenosine (2-CdA, 1) derivatives were prepared as potential anticancer agents. They were synthesized stereoselectively by the anion displacement reactions on 8-bromo-2-chloro-2'-deoxyadenosine (3). Within the 8-substituted CdA derivatives the 8-thioxo compound 11 was cytotoxic to several leukemia cell lines.

  DOI：

  10.1080/15257779508010700
• 作为产物：
  描述：

  8-bromo-2-chloro-2'-deoxyadenosine 在 sodium hydrogensulfide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以62%的产率得到6-amino-2-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)-8-thioxo-9H-purine
  参考文献：
  名称：

  2-Chloro-2′-deoxyadenosine: Synthesis and Antileukemic Activity of 8-Substituted Derivatives

  摘要：

  A series of 8-substituted 2-chloro-2'-deoxyadenosine (2-CdA, 1) derivatives were prepared as potential anticancer agents. They were synthesized stereoselectively by the anion displacement reactions on 8-bromo-2-chloro-2'-deoxyadenosine (3). Within the 8-substituted CdA derivatives the 8-thioxo compound 11 was cytotoxic to several leukemia cell lines.

  DOI：

  10.1080/15257779508010700

文献信息

• 2-Chloro-2′-deoxyadenosine: Synthesis and Antileukemic Activity of 8-Substituted Derivatives
  作者：Zygmunt Kazimierczuk、Juhani A. Vilpo、Frank Seela

  DOI：10.1080/15257779508010700

  日期：1995.8

  A series of 8-substituted 2-chloro-2'-deoxyadenosine (2-CdA, 1) derivatives were prepared as potential anticancer agents. They were synthesized stereoselectively by the anion displacement reactions on 8-bromo-2-chloro-2'-deoxyadenosine (3). Within the 8-substituted CdA derivatives the 8-thioxo compound 11 was cytotoxic to several leukemia cell lines.