4-methylpent-3-enyl thioacetate | 162132-23-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: 4-methylpent-3-enyl thioacetate
• CAS: 162132-23-2
• 化学式: C₈H₁₄OS
• 分子量: 158.265
• InChiKey: LQNIONSDORGFPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-methylpent-3-enyl thioacetate 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 四正辛基溴化铵 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 10.5h， 生成 16,17-epoxy-4,9,13,17-tetramethyl-4(E),8(E),12(E)-octadecatetraenyl 4'-methylpent-3'-enyl sulfide
  参考文献：
  名称：

  Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.

  DOI：

  10.1021/ja00107a011
• 作为产物：
  描述：

  甲基-3-戊烯-1-醇 、 硫代乙酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 4-methylpent-3-enyl thioacetate
  参考文献：
  名称：

  Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.

  DOI：

  10.1021/ja00107a011