ethyl (4-chloro-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate | 912669-27-3

• 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: ethyl (4-chloro-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate
• 英文别名: ethyl 2-(4-chloro-2,3-dioxoindol-1-yl)acetate
• CAS: 912669-27-3
• 化学式: C₁₂H₁₀ClNO₄
• mdl: MFCD13457933
• 分子量: 267.669
• InChiKey: LZEWZHVQVIVCDV-UHFFFAOYSA-N

物化性质

• 沸点：
  422.4±55.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (4-chloro-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate 在 盐酸 、 溶剂黄146 、 二乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-ethyl 2-(4-chloro-2-oxo-3-(2-oxo-2-(pyridin-3-yl)ethylidene)indolin-1-yl)acetate
  参考文献：
  名称：

  Acylideneoxoindoles: A new class of reversible inhibitors of human transglutaminase 2

  摘要：

  Inhibitors of human transglutaminase 2 (TG2) are anticipated to be useful in the therapy of a variety of diseases including celiac sprue as well as certain CNS disorders and cancers. A class of 3-acylidene-2-oxoindoles was identified as potent reversible inhibitors of human TG2. Structure-activity relationship analysis of a lead compound led to the generation of several potent, competitive inhibitors. Analogs with significant non-competitive character were also identified, suggesting that the compounds bind at one or more allosteric regulatory sites on this multidomain enzyme. The most active compounds had K(i) values below 1.0 mu M in two different kinetic assays for human TG2, and may therefore be suitable for investigations into the role of TG2 in physiology and disease in animals. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.037
• 作为产物：
  描述：

  4-氯靛红 、 碘代醋酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl (4-chloro-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate
  参考文献：
  名称：

  Acylideneoxoindoles: A new class of reversible inhibitors of human transglutaminase 2

  摘要：

  Inhibitors of human transglutaminase 2 (TG2) are anticipated to be useful in the therapy of a variety of diseases including celiac sprue as well as certain CNS disorders and cancers. A class of 3-acylidene-2-oxoindoles was identified as potent reversible inhibitors of human TG2. Structure-activity relationship analysis of a lead compound led to the generation of several potent, competitive inhibitors. Analogs with significant non-competitive character were also identified, suggesting that the compounds bind at one or more allosteric regulatory sites on this multidomain enzyme. The most active compounds had K(i) values below 1.0 mu M in two different kinetic assays for human TG2, and may therefore be suitable for investigations into the role of TG2 in physiology and disease in animals. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.037

文献信息

• Spiro-oxindole compounds and their uses as therapeutic agents
  申请人：Chafeev Mikhail

  公开号：US20060252812A1

  公开（公告）日：2006-11-09

  This invention is directed to spiro-oxindole compounds of formula (I): wherein k, j, Q, R 1 , R 2a , R 2b , R 2c , R 2d , R 3a , R 3b , R 3c , and R 3d are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, which are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of preparing and using the compounds are also disclosed.

  本发明涉及式（I）的螺环-氧吲哚化合物： 其中k，j，Q，R1，R2a，R2b，R2c，R2d，R3a，R3b，R3c和R3d如本说明书中所定义的那样，作为立体异构体，对映异构体，互变异构体或其混合物；或其药学上可接受的盐，溶剂化合物或前药，这些化合物对治疗和/或预防钠通道介导的疾病或病症，如疼痛，有用。还公开了包含这些化合物的制药组合物和制备和使用这些化合物的方法。
• Oxindole compounds and their uses as therapeutic agents
  申请人：Chafeev Mikhail

  公开号：US20070105820A1

  公开（公告）日：2007-05-10

  This invention is directed to oxindole compounds that are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of using the compounds are also disclosed.

  本发明涉及氧化吲哚化合物，其对钠通道介导的疾病或病状，如疼痛的治疗和/或预防有用。还公开了包含该化合物的制药组合物和使用该化合物的方法。
• USE OF SPIRO-OXINDOLE COMPOUNDS AS THERAPEUTIC AGENTS
  申请人：Chafeev Mikhail

  公开号：US20110172282A9

  公开（公告）日：2011-07-14

  This invention is directed to methods of using spiro-oxindole compounds of formula (I): wherein k, j, Q, R 1 , R 2a , R 2b , R 2c , R 2d , R 3a , R 3b , R 3c , and R 3d are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of hypercholesterolemia, benign prostatic hyperplasia, pruritis and cancer.

  本发明涉及使用式（I）的螺环氧吲哚化合物的方法： 其中k，j，Q，R1，R2a，R2b，R2c，R2d，R3a，R3b，R3c和R3d的定义如本文所述，作为立体异构体、对映异构体、互变异构体或其混合物；或其药学上可接受的盐、溶剂或前药，用于治疗和/或预防高胆固醇血症、良性前列腺增生、瘙痒和癌症。
• SPIRO-OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS
  申请人：Chafeev Mikhail

  公开号：US20100125072A1

  公开（公告）日：2010-05-20

  This invention is directed to spiro-oxindole compounds of formula (I): wherein k, j, Q, R 1, R 2a , R 2b , R 2c , R 2d , R 3a , R 3b , R 3c , and R 3d are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, which are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of preparing and using the compounds are also disclosed.

  本发明涉及式（I）的螺环氧吲哚化合物： 其中k，j，Q，R1，R2a，R2b，R2c，R2d，R3a，R3b，R3c和R3d如本文所定义，作为立体异构体，对映异构体，互变异构体或其混合物；或其药学上可接受的盐，溶剂化合物或前药，其用于治疗和/或预防钠通道介导的疾病或病症，如疼痛。还公开了包含该化合物的药物组合物以及制备和使用该化合物的方法。
• Use of spiro-oxindole compounds as therapeutic agents
  申请人：Chafeev Mikhail

  公开号：US08466188B2

  公开（公告）日：2013-06-18

  This invention is directed to methods of using spiro-oxindole compounds of formula (I): wherein k, j, Q, R1, R2a, R2b, R2c, R2d, R3a, R3b, R3c, and R3d are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of hypercholesterolemia, benign prostatic hyperplasia, pruritis and cancer.

  本发明涉及使用式（I）的螺环氧吲哚化合物的方法：其中k，j，Q，R1，R2a，R2b，R2c，R2d，R3a，R3b，R3c和R3d如本文所定义，作为立体异构体，对映异构体，互变异构体或其混合物；或其药学上可接受的盐，溶剂合物或前药，用于治疗和/或预防高胆固醇血症，良性前列腺增生，瘙痒和癌症。