1,7-dimethyl-α-oxo-3-indoleacetyl chloride | 143137-57-9

• 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: 1,7-dimethyl-α-oxo-3-indoleacetyl chloride
• 英文别名: 2-(1,7-Dimethylindol-3-yl)-2-oxoacetyl chloride
• CAS: 143137-57-9
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: TUTLGFVRDACFMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  407.0±37.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,7-dimethyl-α-oxo-3-indoleacetyl chloride 在 ammonium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3-(1,7-dimethyl-3-indolyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Inhibitors of protein kinase C. 1. 2,3-bisarylmaleimides

  摘要：

  The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) is described. These 2,3-bisarylznaleimides were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a. Optimum activity required the imide NH, both carbonyl groups, and the olefinic bond of the maleimide ring. 2,3-Bisindolylmaleimides were the most active, and the potency of these was improved by a chloro substituent at the 5-position of one indole ring (compound 28, IC50 0.11-mu-M). In a series of (phenylindolyl)maleimides, nitro compound 74 was most active (IC50 0.67-mu-M). Naphthalene 19 and benzothiophene 21 showed greater than 100-fold selectivity for inhibition of PKC over the closely related cAMP-dependent protein kinase (PKA).

  DOI：

  10.1021/jm00079a024
• 作为产物：
  描述：

  7-甲基吲哚 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 1,7-dimethyl-α-oxo-3-indoleacetyl chloride
  参考文献：
  名称：

  Inhibitors of protein kinase C. 1. 2,3-bisarylmaleimides

  摘要：

  The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) is described. These 2,3-bisarylznaleimides were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a. Optimum activity required the imide NH, both carbonyl groups, and the olefinic bond of the maleimide ring. 2,3-Bisindolylmaleimides were the most active, and the potency of these was improved by a chloro substituent at the 5-position of one indole ring (compound 28, IC50 0.11-mu-M). In a series of (phenylindolyl)maleimides, nitro compound 74 was most active (IC50 0.67-mu-M). Naphthalene 19 and benzothiophene 21 showed greater than 100-fold selectivity for inhibition of PKC over the closely related cAMP-dependent protein kinase (PKA).

  DOI：

  10.1021/jm00079a024

文献信息

• Serotonergic alpha-oxoacetamides
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05192770A1

  公开（公告）日：1993-03-09

  .alpha.-Oxoacetamides of the formula R.sup.1 C(O)C(O)NR.sup.2 R.sup.3 in which R.sup.1 is optionally substituted phenyl, 1-indolyl, 2,3-dihydro-1-indolyl, 1-benzimidazolidinonyl, 3-benzofuranyl, 3-benzothiophenyl, 3-indolyl, and 1,2-alkano-3-indolyl; R.sup.2 is selected from: ##STR1## and R.sup.3 is selected from hydrogen or lower alkyl; and the pharmaceutically acceptable salts, individual isomers, mixtures of isomers, processes for preparation, compositions, and methods of use thereof.

  该文献描述了式为R.sup.1 C(O)C(O)NR.sup.2 R.sup.3的.alpha.-羰基乙酰胺，其中R.sup.1为可选取代的苯基、1-吲哚基、2,3-二氢-1-吲哚基、1-苯并咪唑啉基、3-苯并呋喃基、3-苯并硫杂苯基、3-吲哚基和1,2-烷基-3-吲哚基；R.sup.2选自：##STR1## R.sup.3选自氢或低碳基；以及其药学上可接受的盐、单体异构体、异构体混合物、制备过程、组合物和使用方法。
• Alpha-oxoacetamide derivatives
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0490263A1

  公开（公告）日：1992-06-17

  α-Oxoacetamides represented by Formula I wherein R¹ is selected from in which: the dashed line denotes an optional bond; X and Y are independently selected from hydrogen, halo, cyano, hydroxy, lower alkoxy, benzyloxy, lower alkyl, nitro, amino, aminocarbonyl, (lower alkyl)amino, di(lower alkyl)amino, and (lower alkanoyl)amino; Z is -O-, -S- or -N(R⁴)-; and R⁴ and R⁵ are independently selected from hydrogen or lower alkyl or (lower cycloalkyl) lower alkyl or are together -(CH₂)n- wherein n is an integer from 3 to 5; R² is selected from in which: p is 0 or 1; q is 1, 2 or 3; and R⁶ is C₁₋₇ alkyl; and R³ is selected from hydrogen or lower alkyl; their pharmaceutically acceptable salts, individual isomers and mixtures of isomers, processes for their preparation, compositions, and methods of use thereof.

  由式 I 代表的 α-氧代乙酰胺 其中 R¹ 选自 其中 虚线表示任选键； X和Y独立地选自氢、卤素、氰基、羟基、低级烷氧基、苄氧基、低级烷基、硝基、氨基、氨基羰基、(低级烷基)氨基、二(低级烷基)氨基和(低级烷酰基)氨基； Z 是-O-、-S-或-N(R⁴)-；以及 R⁴ 和 R⁵ 独立选自氢或低级烷基或（低级环烷基）低级烷基，或共同为-(CH₂)n-，其中 n 为 3 至 5 的整数； R² 选自 其中 p 是 0 或 1 q 是 1、2 或 3；以及 R⁶ 是 C₁₋₇ 烷基；以及 R³ 选自氢或低级烷基； 它们的药学上可接受的盐、单个异构体和异构体混合物、制备工艺、组合物及其使用方法。
• US5192770A
  申请人：——

  公开号：US5192770A

  公开（公告）日：1993-03-09
• Inhibitors of protein kinase C. 1. 2,3-bisarylmaleimides
  作者：Peter D. Davis、Christopher H. Hill、Geoffrey Lawton、John S. Nixon、Sandra E. Wilkinson、Steven A. Hurst、Elizabeth Keech、Susan E. Turner

  DOI：10.1021/jm00079a024

  日期：1992.1

  The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) is described. These 2,3-bisarylznaleimides were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a. Optimum activity required the imide NH, both carbonyl groups, and the olefinic bond of the maleimide ring. 2,3-Bisindolylmaleimides were the most active, and the potency of these was improved by a chloro substituent at the 5-position of one indole ring (compound 28, IC50 0.11-mu-M). In a series of (phenylindolyl)maleimides, nitro compound 74 was most active (IC50 0.67-mu-M). Naphthalene 19 and benzothiophene 21 showed greater than 100-fold selectivity for inhibition of PKC over the closely related cAMP-dependent protein kinase (PKA).