(S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione | 872254-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione
• 英文别名: 5-[(2S)-2-(phenoxymethyl)azetidin-1-yl]sulfonyl-1H-indole-2,3-dione
• CAS: 872254-10-9
• 化学式: C₁₈H₁₆N₂O₅S
• 分子量: 372.401
• InChiKey: WWKKPLWKYQGHBF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione 在 copper(ll) sulfate pentahydrate 、 sodium hydride 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 (S)-1-((1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl)methyl)-5-(2-(phenoxymethyl)azetidin-1-ylsulfonyl)indoline-2,3-dione
  参考文献：
  名称：

  Synthesis and evaluation of isatin analogs as caspase-3 inhibitors: Introduction of a hydrophilic group increases potency in a whole cell assay

  摘要：

  A series of isatin analogs containing a hydrophilic group, including a pyridine ring, ethylene glycol group, and a triazole ring, have been synthesized, and their inhibition potency for caspase-3 was measured both in vitro (i.e., recombinant enzyme) and in whole cells (HeLa cells). The analogs having a hydrophilic group, including 12, 13, 16, 38, and 40, have dramatically increased activity in vitro and in HeLa cells compared to the corresponding unsubstituted N-phenyl isatin analogs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.015
• 作为产物：
  描述：

  tert-butyl (S)-2-(phenoxymethyl)azetidine-1-carboxylate 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 (S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione
  参考文献：
  名称：

  N-Benzylisatin Sulfonamide Analogues as Potent Caspase-3 Inhibitors:  Synthesis, in Vitro Activity, and Molecular Modeling Studies

  摘要：

  A number of isatin sulfonamide analogues were prepared and their potencies for inhibiting caspase-1, -3, -6, -7, and -8 were evaluated in vitro. Several compounds displaying a nanomolar potency for inhibiting the executioner caspases, caspase-3 and caspase-7, were identified. These compounds were also observed to have a low potency for inhibiting the initiator caspases, caspase-1 and caspase-8, and caspase-6. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The results of the current study revealed a number of non-peptide-based caspase inhibitors that may be useful in assessing the role of inhibiting the executioner caspases in minimizing tissue damage in disease conditions characterized by unregulated apoptosis.

  DOI：

  10.1021/jm0506625
• 作为试剂：
  描述：

  5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione 、 tert-butyl (S)-2-(phenoxymethyl)azetidine-1-carboxylate 在 (S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione 、 乙醚 作用下， 以to afford 715 mg (63%) of 17 as a yellow solid, mp 173.2-174.5° C的产率得到(S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione
  参考文献：
  名称：

  ISATIN ANALOGUES AND USES THEREFOR

  摘要：

  本发明揭示了新型异喹啉类似物，包括包含迈克尔受体（IMAs）的异喹啉类似物。还揭示了异喹啉类似物的合成方法以及类似物的用途，包括抑制caspase-3和caspase-7，并通过正电子发射断层扫描（PET）或单光子发射计算机断层扫描（SPECT）进行体内细胞凋亡成像。

  公开号：

  US20090068105A1

文献信息

• Isatin analogues and uses therefor
  申请人：Washington University

  公开号：US08329686B2

  公开（公告）日：2012-12-11

  Novel isatin analogues, including isatin analogues comprising Michael Acceptors (IMAs) are disclosed. Further disclosed are methods of synthesis of the isatin analogues, and uses of the analogues, including inhibition of caspase-3 and caspase-7, and in vivo imaging of apoptosis by Positron emission tomography (PET) or Single Photon Emission Computed Tomography (SPECT).

  本发明揭示了新型异色酮类似物，包括包含迈克尔受体（IMAs）的异色酮类似物。进一步揭示了异色酮类似物的合成方法和用途，包括抑制caSPase-3和caSPase-7，以及通过正电子发射断层扫描（PET）或单光子发射计算机断层扫描（SPECT）在体内成像细胞凋亡。
• US8329686B2
  申请人：——

  公开号：US8329686B2

  公开（公告）日：2012-12-11