(5R)-5-[(7-氯-1H-吲哚-3-基)甲基]-3-甲基-2,4-咪唑烷二酮 | 852391-19-6

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (5R)-5-[(7-氯-1H-吲哚-3-基)甲基]-3-甲基-2,4-咪唑烷二酮
• 英文名称: (R)-5-((7-chloro-1H-indol-3-yl)methyl)-3-methylimidazolidine-2,4-dione
• 英文别名: (R)-5-(7'-Chloro-1H-indol-3ylmethyl)-3-methyl-imidazolidine-2,4-dione；(5r)-5-[(7-Chloro-1h-Indol-3-Yl)methyl]-3-Methylimidazolidine-2,4-Dione
• CAS: 852391-19-6
• 化学式: C₁₃H₁₂ClN₃O₂
• 分子量: 277.71
• InChiKey: WIKGAEMMNQTUGL-SNVBAGLBSA-N

物化性质

• 密度：
  1.450±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R)-5-[(7-氯-1H-吲哚-3-基)甲基]-3-甲基-2,4-咪唑烷二酮 在 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 作用下， 以34%的产率得到(5R)-5-[(2-bromo-7-chloro-1H-indol-3-yl)methyl]-3-methylimidazolidine-2,4-dione
  参考文献：
  名称：

  [EN] INHIBITORS OF CELLULAR NECROSIS AND RELATED METHODS
  [FR] INHIBITEURS DE NÉCROSE CELLULAIRE ET PROCÉDÉS ASSOCIÉS

  摘要：

  提供具有以下结构（I）的化合物：或其药用盐、前药、立体异构体或互变异构体。还提供相关化合物、制备方法以及利用这些化合物治疗各种适应症的用途，包括治疗坏死细胞疾病和/或炎症。

  公开号：

  WO2016094846A1
• 作为产物：
  描述：

  7-氯吲哚 在 氯化亚砜 、 phosphate buffer 、 D-酰化氨基酸水解酶 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 76.0h， 生成 (5R)-5-[(7-氯-1H-吲哚-3-基)甲基]-3-甲基-2,4-咪唑烷二酮
  参考文献：
  名称：

  Structure–activity relationship study of novel necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.077

文献信息

• [EN] HETEROCYCLIC INHIBITORS OF NECROPTOSIS<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES DE LA NÉCROPTOSE
  申请人：HARVARD COLLEGE

  公开号：WO2009023272A1

  公开（公告）日：2009-02-19

  The invention features a series of heterocyclic derivatives that inhibit tumor necrosis factor alpha (TNF-α) induced necroptosis. The heterocyclic compounds of the invention are described by Formulas (I) and (Ia)-(Ie) and are shown to inhibit TNF-α induced necroptosis in FADD-deficient variant of human Jurkat T cells. The invention further features pharmaceutical compositions featuring the compounds of the invention. The compounds and compositions of the invention may also be used to treat disorders where necroptosis is likely to play a substantial role.

  该发明涉及一系列杂环衍生物，可以抑制肿瘤坏死因子α（TNF-α）诱导的坏死程序。该发明的杂环化合物由化学式（I）和（Ia）-（Ie）描述，并且已经证明可以抑制人类Jurkat T细胞中FADD缺陷变体中TNF-α诱导的坏死程序。该发明还涉及含有该发明化合物的药物组合物。该发明的化合物和组合物也可用于治疗坏死程序可能起重要作用的疾病。
• Inhibitors of cellular necrosis
  申请人：Cuny D. Gregory

  公开号：US20050119260A1

  公开（公告）日：2005-06-02

  The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.

  本发明涉及化合物、药物制剂及其在预防或治疗与细胞死亡相关的创伤、缺血、中风和退行性疾病中的应用的治疗。本发明的方法和组合物特别适用于治疗与细胞坏死相关的神经系统疾病。
• Compounds, Screens, and Methods of Treatment
  申请人：Yuan Junying

  公开号：US20100190836A1

  公开（公告）日：2010-07-29

  The present invention features compounds, pharmaceutical compositions, and methods for treating trauma, ischemia, stroke, degenerative diseases associated with cellular necrosis, and other conditions. Screening assays for identifying compounds useful for treating these conditions are also described.

  本发明涉及化合物、药物组合物和治疗创伤、缺血、中风、与细胞坏死相关的退行性疾病以及其他疾病的方法。还描述了用于识别治疗这些疾病的化合物的筛选测定方法。
• INHIBITORS OF CELLULAR NECROSIS
  申请人：Cuny Gregory D.

  公开号：US20120149702A1

  公开（公告）日：2012-06-14

  The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.

  本发明涉及化合物和药物制剂及其在预防或治疗与细胞死亡相关的创伤、缺血、中风和退行性疾病中的应用。本发明的方法和组合物特别适用于治疗与细胞坏死相关的神经系统疾病。
• TRICYCLIC NECROSTATIN COMPOUNDS
  申请人：Yuan Junying

  公开号：US20130158024A1

  公开（公告）日：2013-06-20

  The present invention features compounds, pharmaceutical compositions, and methods for treating trauma, ischemia, stroke, degenerative diseases associated with cellular necrosis, and other conditions. Screening assays for identifying compounds useful for treating these conditions are also described.

  本发明涉及化合物、制药组合物和治疗创伤、缺血、中风、与细胞坏死相关的退行性疾病以及其他疾病的方法。还描述了用于鉴定治疗这些疾病的化合物的筛选测定。