2-ethyl-3-thioxo-2,3-dihydroimidazo[1,5-a]indol-1-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: 2-ethyl-3-thioxo-2,3-dihydroimidazo[1,5-a]indol-1-one
• 英文别名: 1h-Imidazo[1,5-a]indol-1-one,2-ethyl-2,3-dihydro-3-thioxo-；2-ethyl-1-sulfanylideneimidazo[1,5-a]indol-3-one
• 化学式: C₁₂H₁₀N₂OS
• 分子量: 230.29
• InChiKey: NVUFFRKPYUMDKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚-2-羧酸甲酯 、 异硫氰酸乙酯 在 N,N-二异丙基乙胺 作用下， 生成 2-ethyl-3-thioxo-2,3-dihydroimidazo[1,5-a]indol-1-one
  参考文献：
  名称：

  Both 5-arylidene-2-thioxodihydropyrimidine-4,6(1H,5H)-diones and 3-thioxo-2,3-dihydro-1H-imidazo[1,5-a]indol-1-ones are light-Dependent tumor necrosis factor-α antagonists

  摘要：

  Based on the realization that N-alkyl 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones are tumor necrosis factor-a antagonists, we discovered two additional classes of antagonists: 3-thioxo-2,3-dihydro-1H-imidazo[1,5-a]indol-1-ones (via rational design) and 5-arylidene-2-thioxodihydropyrimidine-4,6(1H,5H)-diones (via computer-guided screening). Chemical modification of the lead structures showed that the structure-activity relationship profiles for both of these series were dependent on the electronic properties of the molecules. Subsequent studies showed that they were light-dependent inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00941-1

文献信息

• Novel Synthesis of Bicycles with Fused Pyrrole, Indole, Oxazole, and Imidazole Rings
  作者：Alan R. Katritzky、Sanjay K. Singh、Sergey Bobrov

  DOI：10.1021/jo0485334

  日期：2004.12.1

  Reactions of benzotriazol-1-yl(1H-pyrrol-2-yl)methanone 10 and benzotriazol-1-yl(1H-indol-2-yl)methanone 11 with diverse ketones, isocyanates, and isothiocyanates in the presence of base afforded pyrrolo[1,2-c]oxazol-1-ones 1, oxazolo[3,4-a]indol-1-ones 2, pyrrolo[1,2-c]imidazoles 3, and imidazo[1,5-a]indoles 4 by a simple one-step procedure.

  在碱存在下，苯并三唑-1-基（1 H-吡咯-2-基）甲酮10和苯并三唑-1-基（1 H-吲哚-2-基）甲酮11在碱的存在下与各种酮，异氰酸酯和异硫氰酸酯的反应得到吡咯并[1,2 - c ]恶唑-1-酮1，恶唑并[3,4- a ]吲哚-1-酮2，吡咯并[1,2- c ]咪唑3和咪唑并[1,5- a通过简单的一步操作即可吲哚4。
• Both 5-arylidene-2-thioxodihydropyrimidine-4,6(1H,5H)-diones and 3-thioxo-2,3-dihydro-1H-imidazo[1,5-a]indol-1-ones are light-Dependent tumor necrosis factor-α antagonists
  作者：Matthew E Voss、Percy H Carter、Andrew J Tebben、Peggy A Scherle、Gregory D Brown、Lorin A Thompson、Meizhong Xu、Yvonne C Lo、Gengjie Yang、Rui-Qin Liu、Paul Strzemienski、J.Gerry Everlof、James M Trzaskos、Carl P Decicco

  DOI：10.1016/s0960-894x(02)00941-1

  日期：2003.2

  Based on the realization that N-alkyl 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones are tumor necrosis factor-a antagonists, we discovered two additional classes of antagonists: 3-thioxo-2,3-dihydro-1H-imidazo[1,5-a]indol-1-ones (via rational design) and 5-arylidene-2-thioxodihydropyrimidine-4,6(1H,5H)-diones (via computer-guided screening). Chemical modification of the lead structures showed that the structure-activity relationship profiles for both of these series were dependent on the electronic properties of the molecules. Subsequent studies showed that they were light-dependent inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.