5'-methylspiro[[1,3]dithiolane-2,3'-indolin]-2'-one

• 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: 5'-methylspiro[[1,3]dithiolane-2,3'-indolin]-2'-one
• 英文别名: 5'-methylspiro[1,3-dithiolane-2,3'-indol]-2'(1'H)-one；5'-methylspiro[1,3-dithiolane-2,3'-1H-indole]-2'-one
• 化学式: C₁₁H₁₁NOS₂
• 分子量: 237.346
• InChiKey: ZEUBZCDNTJHGFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-methylspiro[[1,3]dithiolane-2,3'-indolin]-2'-one 在 双氧水 作用下， 反应 2.0h， 生成 5'-methylspiro[[1,3]dithiolane-2,3'-indolin]-2'-one 1-oxide
  参考文献：
  名称：

  螺二硫杂环戊二烯-吲哚酮对映选择性钌催化的硫氧化中的协同立体控制

  摘要：

  开发了手性钌催化剂用于标题化合物的对映选择性磺氧化。该催化剂结合了两个手性元素，一个手性pybox配体和一个与该配体连接的手性双环内酰胺单元。后者被证明可以通过氢键介导的配位作用将两个对映体硫原子之一暴露于活性位点，从而显着提高催化剂的性能。十个不同取代的底物转化成相应的亚砜中的52-71％的产率和以≥90％ee值。

  DOI：

  10.1002/chem.201501780
• 作为产物：
  描述：

  5-甲基靛红 、 1,2-乙二硫醇 在 三氟化硼乙醚 、 溶剂黄146 作用下， 生成 5'-methylspiro[[1,3]dithiolane-2,3'-indolin]-2'-one
  参考文献：
  名称：

  吲哚酮乙酰胺作为新型SV2A配体的发现，具有增强的抑制癫痫发作效力的能力。

  摘要：

  利用左乙拉西坦作为抗癫痫药的久经验证的临床功效，药物发现计划导致鉴定出与左乙拉西坦具有相同或更好耐受性的新一代SV2A配体，并提高了在动物模型中抑制癫痫发作的能力。

  DOI：

  10.1002/cmdc.200900436

文献信息

• [EN] INDOLONE-ACETAMIDE DERIVATIVES, PROCESSES FOR PREPARING THEM AND THEIR USES<br/>[FR] DERIVES D'INDOLONE-ACETAMIDE, LEURS PROCEDES DE PREPARATION ET LEURS UTILISATIONS
  申请人：UCB SA

  公开号：WO2004087658A1

  公开（公告）日：2004-10-14

  The present invention relates to indolone-acetamide derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as for the treatment of epilepsy, epileptogenesis, seizure disorders and convulsion.

  本发明涉及吲哚酮-乙酰胺衍生物，其制备方法，含有它们的药物组合物以及它们用于治疗癫痫、癫痫发作、抽搐障碍的用途。
• Discovery of Indolone Acetamides as Novel SV2A Ligands with Improved Potency Toward Seizure Suppression
  作者：Anne Frycia、Jean-Philippe Starck、Sophie Jadot、Bénédicte Lallemand、Karine Leclercq、Patrick Lo Brutto、Alain Matagne、Valérie Verbois、Joël Mercier、Benoit Kenda

  DOI：10.1002/cmdc.200900436

  日期：2010.2.1

  Capitalizing on the proven clinical efficacy of levetiracetam as an antiepileptic drug, a drug discovery program lead to the identification of a new generation of SV2A ligands with equal or better tolerability profiles than levetiracetam, and improved potency toward seizure suppression in animal models.

  利用左乙拉西坦作为抗癫痫药的久经验证的临床功效，药物发现计划导致鉴定出与左乙拉西坦具有相同或更好耐受性的新一代SV2A配体，并提高了在动物模型中抑制癫痫发作的能力。
• Indolone-acetamide derivatives, processes for preparing them and their uses
  申请人：Starck Jean-Philippe

  公开号：US20070043038A1

  公开（公告）日：2007-02-22

  The present invention relates to indolone-acetamide derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as for the treatment of epilepsy, epileptogenesis, seizure disorders and convulsion.

  本发明涉及吲哚酮乙酰胺衍生物、其制备方法、含有其的药物组合物以及其作为治疗癫痫、癫痫发生、癫痫发作和惊厥的用途。
• Indolone-Acetamide Derivatives, Processes for Preparing Them and Their Uses
  申请人：Starck Jean-Philippe

  公开号：US20100069375A1

  公开（公告）日：2010-03-18

  The present invention relates to indolone-acetamide derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as for the treatment of epilepsy, epileptogenesis, seizure disorders and convulsion.

  本发明涉及吲哚酮乙酰胺衍生物，其制备方法，包含它们的药物组合物以及它们用于治疗癫痫、癫痫发作、惊厥障碍和抽搐的用途。
• Novel 2-oxoindoline-based hydroxamic acids: synthesis, cytotoxicity, and inhibition of histone deacetylation
  作者：Tran Thi Lan Huong、Do Thi Mai Dung、Phan Thi Phuong Dung、Phung Thanh Huong、Tran Khac Vu、Hyunggu Hahn、Byung Woo Han、Jisung Kim、Minji Pyo、Sang-Bae Han、Nguyen-Hai Nam

  DOI：10.1016/j.tetlet.2015.09.147

  日期：2015.11

  In a continuation of a research program to discover novel small molecules targeting histone deacetylases, a series of 2'-oxospiro[1,3]dioxolane/dithiolane-2,3'-indoline-based hydroxamic acids have been designed and synthesized. These 2-oxoindoline-based hydroxamic acids displayed potent cytotoxicity against three human cancer cell lines, including SW620 (colon cancer), PC-3 (prostate cancer) and AsPC-1 (pancreatic cancer), with IC50 values as low as 0.05-0.07 mu M, 74-fold lower than that of SAHA (1.64-3.70 mu M). Additionally, compounds in this series exhibited good inhibition against histone-H3 and histone-H4 deacetylation, as evaluated by Western blot assay. These compounds also strongly inhibited HDAC2 with IC50 values as low as 0.03 mu M. Docking studies performed using Autodock Vina showed all compounds bound to HDAC2 with relatively higher affinities (from -7.7 to -8.0 kcal/mol) compared to SAHA (-7.4 kcal/mol). (C) 2015 Elsevier Ltd. All rights reserved.