(S)-(-)-2-hydroxypropyl triphenylmethylsulfide

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-(-)-2-hydroxypropyl triphenylmethylsulfide
• 英文别名: (2S)-1-tritylsulfanylpropan-2-ol
• 化学式: C₂₂H₂₂OS
• 分子量: 334.482
• InChiKey: SNOBQENERZMBEB-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-hydroxypropyl triphenylmethylsulfide 在 碘 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以51%的产率得到(S)-(+)-2-hydroxypropyl disulfide
  参考文献：
  名称：

  Preparation and Evaluation of Sulfide Derivatives of the Antibiotic Brefeldin A as Potential Prodrug Candidates with Enhanced Aqueous Solubilities

  摘要：

  Several sulfide (+)-brefeldin A (BFA) analogues were prepared through the Michael addition of various thiols. Many of the sulfides were also oxidized to the corresponding sulfoxide with m-CPBA. The sulfides were designed to act as BFA prodrugs via the metabolic oxidation to the sulfoxide and subsequent syn elimination. Kinetic experiments were used to prove that the syn elimination of the sulfoxides prepared did in fact take place. Five selenide BFA prodrugs were also prepared that are envisioned to act in the same manner as the sulfides. As expected, when oxidation of the selenide to selenoxide was attempted, in situ syn elimination was observed. All of the compounds prepared were evaluated for antiproliferative activity against human cancer cell lines in the National Cancer Institute screen. The sulfoxides were much more potent than either the sulfides or selenides. Especially notable were sulfoxide 21, which possessed a cytotoxicity mean graph midpoint value (MGM) value lower than BFA itself, and sulfoxide 22, which possessed an MGM value slightly less potent than that of BFA. The sulfide analogues were shown to possess increased aqueous solubilty with respect to BFA.

  DOI：

  10.1021/jm010054z
• 作为产物：
  描述：

  三苯甲硫醇 、 (S)-(+)-2-羟丙基对甲苯磺酸盐 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以69%的产率得到(S)-(-)-2-hydroxypropyl triphenylmethylsulfide
  参考文献：
  名称：

  Preparation and Evaluation of Sulfide Derivatives of the Antibiotic Brefeldin A as Potential Prodrug Candidates with Enhanced Aqueous Solubilities

  摘要：

  Several sulfide (+)-brefeldin A (BFA) analogues were prepared through the Michael addition of various thiols. Many of the sulfides were also oxidized to the corresponding sulfoxide with m-CPBA. The sulfides were designed to act as BFA prodrugs via the metabolic oxidation to the sulfoxide and subsequent syn elimination. Kinetic experiments were used to prove that the syn elimination of the sulfoxides prepared did in fact take place. Five selenide BFA prodrugs were also prepared that are envisioned to act in the same manner as the sulfides. As expected, when oxidation of the selenide to selenoxide was attempted, in situ syn elimination was observed. All of the compounds prepared were evaluated for antiproliferative activity against human cancer cell lines in the National Cancer Institute screen. The sulfoxides were much more potent than either the sulfides or selenides. Especially notable were sulfoxide 21, which possessed a cytotoxicity mean graph midpoint value (MGM) value lower than BFA itself, and sulfoxide 22, which possessed an MGM value slightly less potent than that of BFA. The sulfide analogues were shown to possess increased aqueous solubilty with respect to BFA.

  DOI：

  10.1021/jm010054z

文献信息

• Preparation and Evaluation of Sulfide Derivatives of the Antibiotic Brefeldin A as Potential Prodrug Candidates with Enhanced Aqueous Solubilities
  作者：Brian M. Fox、Jeffrey A. Vroman、Phillip E. Fanwick、Mark Cushman

  DOI：10.1021/jm010054z

  日期：2001.11.1

  Several sulfide (+)-brefeldin A (BFA) analogues were prepared through the Michael addition of various thiols. Many of the sulfides were also oxidized to the corresponding sulfoxide with m-CPBA. The sulfides were designed to act as BFA prodrugs via the metabolic oxidation to the sulfoxide and subsequent syn elimination. Kinetic experiments were used to prove that the syn elimination of the sulfoxides prepared did in fact take place. Five selenide BFA prodrugs were also prepared that are envisioned to act in the same manner as the sulfides. As expected, when oxidation of the selenide to selenoxide was attempted, in situ syn elimination was observed. All of the compounds prepared were evaluated for antiproliferative activity against human cancer cell lines in the National Cancer Institute screen. The sulfoxides were much more potent than either the sulfides or selenides. Especially notable were sulfoxide 21, which possessed a cytotoxicity mean graph midpoint value (MGM) value lower than BFA itself, and sulfoxide 22, which possessed an MGM value slightly less potent than that of BFA. The sulfide analogues were shown to possess increased aqueous solubilty with respect to BFA.