3,6-dioxo-7-oxa-B-homo-5α-cholestane | 20104-92-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,6-dioxo-7-oxa-B-homo-5α-cholestane
• 英文别名: (1S,2R,7S,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-9-oxatetracyclo[9.7.0.02,7.012,16]octadecane-5,8-dione
• CAS: 20104-92-1
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: DKZDODZIBUXSCK-PWNVBJGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,6-dioxo-7-oxa-B-homo-5α-cholestane 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到3-hydroximino-6-oxo-7-oxa-B-homo-5α-cholestane
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some steroidal lactone compounds

  摘要：

  Using cholesterol as starting material, some steroidal lactone compounds with the structures of 3-substituted-6-oxo-7-oxa-B-homo-cholestane or 3-substituted-7-oxo-6-oxa-B-homo-cholestane were synthesized by oxidation, reduction, Baeyer-Villiger reaction and condensation reaction. The cytotoxicity of these compounds against MGC 7901 (human gastric carcinoma), HeLa (human cervical carcinoma) and SMMC 7404 (human liver carcinoma) cells was investigated. Our results showed that the synthesized compounds displayed a distinct cytotoxicity against these cancer cells. In particular, compounds 8 and 9 have similar cytotoxic capability as cisplatin does. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.11.013
• 作为产物：
  描述：

  3β-hydroxy-6-oxo-7-oxa-B-homo-5α-cholestane 在 Collins reagent 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以84.5%的产率得到3,6-dioxo-7-oxa-B-homo-5α-cholestane
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some steroidal lactone compounds

  摘要：

  Using cholesterol as starting material, some steroidal lactone compounds with the structures of 3-substituted-6-oxo-7-oxa-B-homo-cholestane or 3-substituted-7-oxo-6-oxa-B-homo-cholestane were synthesized by oxidation, reduction, Baeyer-Villiger reaction and condensation reaction. The cytotoxicity of these compounds against MGC 7901 (human gastric carcinoma), HeLa (human cervical carcinoma) and SMMC 7404 (human liver carcinoma) cells was investigated. Our results showed that the synthesized compounds displayed a distinct cytotoxicity against these cancer cells. In particular, compounds 8 and 9 have similar cytotoxic capability as cisplatin does. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.11.013

文献信息

• Synthesis and antiproliferative activity of some steroidal lactone compounds
  作者：Chunfang Gan、Jianguo Cui、Yanmin Huang、Linyi Jia、Wanxin Wei

  DOI：10.1016/j.steroids.2011.11.013

  日期：2012.2

  Using cholesterol as starting material, some steroidal lactone compounds with the structures of 3-substituted-6-oxo-7-oxa-B-homo-cholestane or 3-substituted-7-oxo-6-oxa-B-homo-cholestane were synthesized by oxidation, reduction, Baeyer-Villiger reaction and condensation reaction. The cytotoxicity of these compounds against MGC 7901 (human gastric carcinoma), HeLa (human cervical carcinoma) and SMMC 7404 (human liver carcinoma) cells was investigated. Our results showed that the synthesized compounds displayed a distinct cytotoxicity against these cancer cells. In particular, compounds 8 and 9 have similar cytotoxic capability as cisplatin does. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.