2-Allyl-6,8-dimethoxy-9-methyl-imidazo[1,5-a]indole-1,3-dione | 521302-24-9

• 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: 2-Allyl-6,8-dimethoxy-9-methyl-imidazo[1,5-a]indole-1,3-dione
• 英文别名: 5,7-Dimethoxy-4-methyl-2-prop-2-enylimidazo[1,5-a]indole-1,3-dione
• CAS: 521302-24-9
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: CVHHYPIWPOFYIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Allyl-6,8-dimethoxy-9-methyl-imidazo[1,5-a]indole-1,3-dione 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 2-Allyl-6,8-dimethoxy-9-methyl-1-thioxo-1,2-dihydro-imidazo[1,5-a]indol-3-one 、 2-Allyl-6,8-dimethoxy-9-methyl-imidazo[1,5-a]indole-1,3-dithione
  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
• 作为产物：
  描述：

  4,6-Dimethoxy-3-methyl-1H-indole-2-carboxylic acid methyl ester 在 氢氧化钾 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-Allyl-6,8-dimethoxy-9-methyl-imidazo[1,5-a]indole-1,3-dione
  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

• 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.