Methanesulfonic acid (S)-9-(2,5-dioxo-4-phenylamino-2,5-dihydro-1H-pyrrol-3-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-ylmethyl ester | 257876-37-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methanesulfonic acid (S)-9-(2,5-dioxo-4-phenylamino-2,5-dihydro-1H-pyrrol-3-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-ylmethyl ester
• CAS: 257876-37-2
• 化学式: C₂₃H₂₁N₃O₅S
• 分子量: 451.503
• InChiKey: QXLWRGNNASUFBW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  106.5
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (S)-9-(2,5-dioxo-4-phenylamino-2,5-dihydro-1H-pyrrol-3-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-ylmethyl ester 在 氨 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 N-[[(2R)-4-(4-anilino-2,5-dioxopyrrol-3-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-yl]methyl]acetamide
  参考文献：
  名称：

  Synthesis, SAR studies, and pharmacological evaluation of 3-anilino-4-(3-indolyl) maleimides with conformationally restricted structure as orally bioavailable PKCβ-selective inhibitors

  摘要：

  Conformationally restricted 3-anilino-4-(3-indolyl)maleimide derivatives were designed and synthesized aiming at discovery of novel protein kinase C beta (PKC beta)-selective inhibitors possessing oral bioavailability. Among them, compounds having a fused five-membered ring at the indole 1,2-position inhibited PKC beta 2 with IC50 of nM-order and showed good oral bioavailability. One of the most potent compounds was found to be PKC beta-selective over other 6 isozymes and exhibited ameliorative effects in a rat diabetic retinopathy model via oral route. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.033
• 作为产物：
  描述：

  2-(1H-indol-2-ylmethyl)propane-1,3-diol 在 Lipase PS 吡啶 、 咪唑 、 三乙基硅烷 、 sodium tetrahydroborate 、 potassium tert-butylate 、 四丁基氟化铵 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.67h， 生成 Methanesulfonic acid (S)-9-(2,5-dioxo-4-phenylamino-2,5-dihydro-1H-pyrrol-3-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis, SAR studies, and pharmacological evaluation of 3-anilino-4-(3-indolyl) maleimides with conformationally restricted structure as orally bioavailable PKCβ-selective inhibitors

  摘要：

  Conformationally restricted 3-anilino-4-(3-indolyl)maleimide derivatives were designed and synthesized aiming at discovery of novel protein kinase C beta (PKC beta)-selective inhibitors possessing oral bioavailability. Among them, compounds having a fused five-membered ring at the indole 1,2-position inhibited PKC beta 2 with IC50 of nM-order and showed good oral bioavailability. One of the most potent compounds was found to be PKC beta-selective over other 6 isozymes and exhibited ameliorative effects in a rat diabetic retinopathy model via oral route. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.033