(Z)-Octadec-9-enoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester | 92006-70-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (Z)-Octadec-9-enoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
• CAS: 92006-70-7
• 化学式: C₄₂H₆₉ClO₃
• 分子量: 657.461
• InChiKey: JCSCSORTKCXJLH-LTCVZZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  46.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (Z)-Octadec-9-enoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 苯 为溶剂， 反应 0.25h， 生成 4-<3β-(oleoyloxy)androst-5-en-17β-yl>pentanol chlorambucil ester
  参考文献：
  名称：

  Selective delivery of cytotoxic compounds to cells by the LDL pathway

  摘要：

  Cancer cells need cholesterol to make new membrane. They get it either by de novo synthesis or from low-density lipoprotein (LDL), or both. Some types of cancer have very high LDL requirements. LDL particles, which circulate in the blood, contain a cholesteryl ester core surrounded by a phospholipid coat containing apoproteins that are recognized by LDL receptors on cell surfaces. After attachment to cells, LDL is endocytosed into lysosomes, where the core is exposed and hydrolyzed. A technique is known whereby LDL can be isolated, its core removed and replaced by a compatible lipophilic substance, and then reconstituted into intact LDL particles that are recognized and internalized by cells in the normal manner. A series of cytotoxic compounds has been synthesized, designed to be compatible with reconstituted LDL, and directed against cancers that copiously internalize LDL. They were evaluated by measuring the toxicity of reconstituted LDL toward test cells bearing LDL receptors. Selectivity was determined by comparison, either with mutant cells with few LDL receptors or with reconstituted methylated LDL (which is not recognized by LDL receptors) on normal cells. Two compounds, 19 and 25, were found that reconstitute well, kill or arrest the test cells at reasonably low concentrations, and are completely selective, suggesting that they are delivered to cells exclusively via the LDL pathway.

  DOI：

  10.1021/jm00374a017
• 作为产物：
  描述：

  3B-羟基-D5-胆烯酸 在 4-二甲氨基吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 、 lithium iodide 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 (Z)-Octadec-9-enoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Selective delivery of cytotoxic compounds to cells by the LDL pathway

  摘要：

  Cancer cells need cholesterol to make new membrane. They get it either by de novo synthesis or from low-density lipoprotein (LDL), or both. Some types of cancer have very high LDL requirements. LDL particles, which circulate in the blood, contain a cholesteryl ester core surrounded by a phospholipid coat containing apoproteins that are recognized by LDL receptors on cell surfaces. After attachment to cells, LDL is endocytosed into lysosomes, where the core is exposed and hydrolyzed. A technique is known whereby LDL can be isolated, its core removed and replaced by a compatible lipophilic substance, and then reconstituted into intact LDL particles that are recognized and internalized by cells in the normal manner. A series of cytotoxic compounds has been synthesized, designed to be compatible with reconstituted LDL, and directed against cancers that copiously internalize LDL. They were evaluated by measuring the toxicity of reconstituted LDL toward test cells bearing LDL receptors. Selectivity was determined by comparison, either with mutant cells with few LDL receptors or with reconstituted methylated LDL (which is not recognized by LDL receptors) on normal cells. Two compounds, 19 and 25, were found that reconstitute well, kill or arrest the test cells at reasonably low concentrations, and are completely selective, suggesting that they are delivered to cells exclusively via the LDL pathway.

  DOI：

  10.1021/jm00374a017