(2S,4S)-4-(3-chlorophenyl)-2-[(5,6-dimethyl-4H-indeno[1,2-d][1,3]thiazol-8-yl)oxymethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide | 1229578-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,4S)-4-(3-chlorophenyl)-2-[(5,6-dimethyl-4H-indeno[1,2-d][1,3]thiazol-8-yl)oxymethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide
• 英文别名: (2S,4S)-4-(3-chlorophenyl)-2-[(5,6-dimethyl-4H-indeno[1,2-d][1,3]thiazol-8-yl)oxymethyl]-1,3,2λ5-dioxaphosphinane 2-oxide
• CAS: 1229578-27-1
• 化学式: C₂₂H₂₁ClNO₄PS
• 分子量: 461.906
• InChiKey: JMEWMZJZKKQIDU-YRVHBCJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  、 (S)-1-(3-氯苯基)-1,3-丙二醇 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,4S)-4-(3-chlorophenyl)-2-[(5,6-dimethyl-4H-indeno[1,2-d][1,3]thiazol-8-yl)oxymethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide 、 (2R,4S)-4-(3-chlorophenyl)-2-[(5,6-dimethyl-4H-indeno[1,2-d][1,3]thiazol-8-yl)oxymethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide
  参考文献：
  名称：

  A prodrug approach towards the development of tricyclic-based FBPase inhibitors

  摘要：

  For the purpose of reducing the strong CYP3A4 inhibitory potency of diamide prodrug 4, cyclic prodrugs of tricyclic-based FBPase inhibitors were synthesized. Extensive SAR studies led to the discovery of pyridine-containing cyclic prodrug 20, which strongly inhibited glucose production in monkey hepatocytes and also showed weak CYP3A4 inhibitory potency. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.017

文献信息

• A prodrug approach towards the development of tricyclic-based FBPase inhibitors
  作者：Tomoharu Tsukada、Kazuhiko Tamaki、Jun Tanaka、Toshiyuki Takagi、Taishi Yoshida、Akira Okuno、Takeshi Shiiki、Mizuki Takahashi、Takahide Nishi

  DOI：10.1016/j.bmcl.2010.03.017

  日期：2010.5

  For the purpose of reducing the strong CYP3A4 inhibitory potency of diamide prodrug 4, cyclic prodrugs of tricyclic-based FBPase inhibitors were synthesized. Extensive SAR studies led to the discovery of pyridine-containing cyclic prodrug 20, which strongly inhibited glucose production in monkey hepatocytes and also showed weak CYP3A4 inhibitory potency. (C) 2010 Elsevier Ltd. All rights reserved.