methyl 3-((4-bromophenyl)thio)-2-hydroxy-2-methylpropanoate | 1343799-97-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 3-((4-bromophenyl)thio)-2-hydroxy-2-methylpropanoate
• 英文别名: Methyl 3-(4-bromophenyl)sulfanyl-2-hydroxy-2-methylpropanoate
• CAS: 1343799-97-2
• 化学式: C₁₁H₁₃BrO₃S
• 分子量: 305.192
• InChiKey: IXRKWKNSKPKGCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-((4-bromophenyl)thio)-2-hydroxy-2-methylpropanoate 在 水 、 1-羟基苯并三唑 、 1,2-二氯乙烷 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 生成 1-(4-Bromophenyl)sulfanyl-2-[3-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5-yl]propan-2-ol
  参考文献：
  名称：

  1,2,4-Oxadiazoles: A new class of anti-prostate cancer agents

  摘要：

  Sulfide and sulfonyl derivatives of 1,2,4-oxadiazoles were synthesized and screened by MTT assay on the prostate cancer cells, DU-145. Six compounds were identified as potential anti-prostate cancer agents with IC50 values ranging from 0.5 to 5.1 mu M. These compounds exhibited good activity on the androgen independent cells PC-3, while the results were moderate on androgen dependent LNCaP cells, suggesting the possibility of a mechanism of action different from that of the bioisosteric bicalutamide. Also a very low cytotoxicity was observed on non-cancerous cells MCF-10A. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.059
• 作为产物：
  描述：

  4-溴苯硫酚 、 甲基丙烯酸甲酯 在 三苯基膦 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 8.5h， 以81%的产率得到methyl 3-((4-bromophenyl)thio)-2-hydroxy-2-methylpropanoate
  参考文献：
  名称：

  Auto-oxidative hydroxysulfenylation of alkenes

  摘要：

  一锅法介导的电子不足和电子富集烯烃与苯硫醇的羟基硫醚化反应被探索。

  DOI：

  10.1039/c6cc01937d

文献信息

• Auto-oxidative hydroxysulfenylation of alkenes
  作者：Congde Huo、Yajun Wang、Yong Yuan、Fengjuan Chen、Jing Tang

  DOI：10.1039/c6cc01937d

  日期：——

  One-pot auto-oxidation mediated hydroxysulfenylation of electron-deficient and electron-rich olefins with phenthiols was explored.

  一锅法介导的电子不足和电子富集烯烃与苯硫醇的羟基硫醚化反应被探索。
• 1,2,4-Oxadiazoles: A new class of anti-prostate cancer agents
  作者：Gopal L. Khatik、Jasmine Kaur、Varun Kumar、Kulbhushan Tikoo、Vipin A. Nair

  DOI：10.1016/j.bmcl.2012.01.059

  日期：2012.3

  Sulfide and sulfonyl derivatives of 1,2,4-oxadiazoles were synthesized and screened by MTT assay on the prostate cancer cells, DU-145. Six compounds were identified as potential anti-prostate cancer agents with IC50 values ranging from 0.5 to 5.1 mu M. These compounds exhibited good activity on the androgen independent cells PC-3, while the results were moderate on androgen dependent LNCaP cells, suggesting the possibility of a mechanism of action different from that of the bioisosteric bicalutamide. Also a very low cytotoxicity was observed on non-cancerous cells MCF-10A. (c) 2012 Elsevier Ltd. All rights reserved.