(2S,5R)-5-(bromomethyl)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one | 1250440-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (2S,5R)-5-(bromomethyl)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one
• CAS: 1250440-74-4
• 化学式: C₉H₁₅BrO₃
• 分子量: 251.12
• InChiKey: RKWCUXZAZWDHNV-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5R)-5-(bromomethyl)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 (2R)-3-溴-2-羟基-2-甲基丙酸
  参考文献：
  名称：

  A New Avenue toward Androgen Receptor Pan-antagonists: C2 Sterically Hindered Substitution of Hydroxy-propanamides

  摘要：

  The androgen receptor (AR) represents the primary target for prostate cancer (PC) treatment even when the disease progresses toward androgen-independent (AIPC) or castration-resistant (CRPC) forms. Because small chemical changes in the structure of nonsteroidal AR ligands determine the pharmacological responses of AR, we developed a novel stereoselective synthetic strategy that allows sterically hindered C2-substituted bicalutamide analogues to be obtained. Biological and theoretical evaluations demonstrate that C2-substitution with benzyl and phenyl moieties is a new, valuable option toward improving pan-antagonist behavior. Among the synthesized compounds, (R)-16m, when compared to casodex, (R)-bicalutamide, and enzalutamide, displayed very promising in vitro activity toward five different prostate cancer cell lines, all representative of CPRC and AIPC typical mutations. Despite being less active than (R)-bicalutamide, (R)-16m also displayed marked in vivo antitumor activity on VCaP xenografts and thus it may serve as starting point for developing novel AR pan-antagonists.

  DOI：

  10.1021/jm5005122
• 作为产物：
  描述：

  2-((2S,4S)-2-tert-butyl-4-methyl-5-oxo-1,3-dioxolan-4-yl)acetic acid 在 三氯溴甲烷 、 N,N'-二环己基碳二亚胺 、 2-巯基吡啶-N-氧化物 作用下， 反应 2.5h， 以88%的产率得到(2S,5R)-5-(bromomethyl)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  [EN] NON-STEROIDAL COMPOUNDS FOR ANDROGEN RECEPTOR MODULATION, PROCESSES FOR THE PREPARATION AND USES THEREOF
  [FR] COMPOSÉS NON STÉROÏDIENS POUR UNE MODULATION DU RÉCEPTEUR AUX ANDROGÈNES

  摘要：

  公开号：

  WO2010116342A8

文献信息

• NON-STEROIDAL COMPOUNDS FOR ANDROGEN RECEPTOR MODULATION
  申请人：Varchi Greta

  公开号：US20120041046A1

  公开（公告）日：2012-02-16

  The present invention concerns compounds of general Formula (I): method of preparation and uses thereof.
• US8741951B2
  申请人：——

  公开号：US8741951B2

  公开（公告）日：2014-06-03