8-chloro-2',3',5'-tri-O-acetyladenosine | 64344-20-3

• 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: 8-chloro-2',3',5'-tri-O-acetyladenosine
• 英文别名: O^2'_,O3'_,O5'-triacetyl-8-chloro-adenosine；2',3',5'-Tri-O-acetyl-8-chloradenosin；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-amino-8-chloropurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 64344-20-3
• 化学式: C₁₆H₁₈ClN₅O₇
• 分子量: 427.801
• InChiKey: VXIPDZGRZNHXTG-SDBHATRESA-N

物化性质

• 沸点：
  624.0±65.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  8-chloro-2',3',5'-tri-O-acetyladenosine 在 亚硝酸特丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以39%的产率得到8-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Synthesis and Biologic Evaluation of 8-Substituted Derivatives of Nebularine (9-β-D-Ribofuranosylpurine)

  摘要：

  A series of 8-substituted purine ribonucleosides were prepared from 2',3',5'-tri-O-acetyl-8-bromoadenosine and evaluated for cytotoxicity and antiviral activity. Four of these nucleosides (6b-9b) were significantly toxic to both HEp-2 and L1210 cells in culture but the most cytotoxic one (9b) was inactive against the P388 leukemia in mice. None of these nucleosides showed significant antiviral activity against Herpes Simplex 1 or 2, vaccinia, or influenza A.

  DOI：

  10.1080/15257779408011875
• 作为产物：
  描述：

  9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-8-chloropurin-6-amine 生成 8-chloro-2',3',5'-tri-O-acetyladenosine
  参考文献：
  名称：

  SHORTNACY, ANITA T.;MONTGOMERY, JOHN A.;SECRIST, JOHN A. (III), NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 911--913

  摘要：

  DOI：

文献信息

• [EN] METHODS OF TREATING CANCER WITH 8-CHLORO-ADENOSINE<br/>[FR] METHODES DE TRAITEMENT DU CANCER A L'AIDE DE 8-CHLORO-ADENOSINE
  申请人：SOPHERION THERAPEUTICS

  公开号：WO2005120521A2

  公开（公告）日：2005-12-22

  A method for treating cancer in a patient is provided comprising administering 8-chloro-adenosine in a daily dose ranging from 500 to 2500 mg/m2, wherein the daily dose is administered at least once and up to five days per week for at least two weeks in a two month period. The method may further comprise administering a second therapeutic agent, such as another anti-cancer agent, GCSF, or erythropoietin. In addition, diagnostic and prognostic methods are provided for determining if a cancer patient is likely to respond to 8-Cl-Ado, which involve determining phosphatase, adenosine kinase, adenosine deaminase, or mRNA levels in cancer cells from the patient.