(1H-Indol-4-yl)(3,4,5-trimethoxyphenyl)methanone | 143259-55-6

• 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: (1H-Indol-4-yl)(3,4,5-trimethoxyphenyl)methanone
• 英文别名: 1H-indol-4-yl-(3,4,5-trimethoxyphenyl)methanone
• CAS: 143259-55-6
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: CLUMHWYRLGICLP-UHFFFAOYSA-N

物化性质

• 熔点：
  94.8-95.2 °C(Solv: dichloromethane (75-09-2); ethyl acetate (141-78-6))
• 沸点：
  526.9±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1H-Indol-4-yl)(3,4,5-trimethoxyphenyl)methanone 、 碘甲烷 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 以86%的产率得到(1-Methylindol-4-yl)-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  4- and 5-Aroylindoles as Novel Classes of Potent Antitubulin Agents

  摘要：

  A novel series of 4- and 5-aroylindole derivatives was prepared and evaluated for antitumor activity. Several compounds showed excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 13, 14, 15, and 18, with IC50 values of 1.9, 1.1, 1.2, and 1.8 mu M, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine. They also displayed antiproliferative activity, with IC50 values ranging from 10 to 43 nM in a variety of human cell lines from different organs.

  DOI：

  10.1021/jm070557q
• 作为产物：
  描述：

  4-吲哚甲醛 在 氢氧化钾 、 sodium hydroxide 、 重铬酸吡啶 、 4 A molecular sieve 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 (1H-Indol-4-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  4- and 5-Aroylindoles as Novel Classes of Potent Antitubulin Agents

  摘要：

  A novel series of 4- and 5-aroylindole derivatives was prepared and evaluated for antitumor activity. Several compounds showed excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 13, 14, 15, and 18, with IC50 values of 1.9, 1.1, 1.2, and 1.8 mu M, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine. They also displayed antiproliferative activity, with IC50 values ranging from 10 to 43 nM in a variety of human cell lines from different organs.

  DOI：

  10.1021/jm070557q

文献信息

• Platelet activating factor antagonists
  申请人：ABBOTT LABORATORIES

  公开号：EP0499987A1

  公开（公告）日：1992-08-26

  Indole compounds substituted at the 1- or 3-position by a (pyrid-3-yl)thiazolid-4-yl)alkyl-, (pyrid-3-yl)thiazolid-4-oyl)-, (pyrid-3-yl)dithiolan-4-yl)alkyl- or (pyrid-3-yl)dithiolan-4-oyl)- group are potent inhibitors of PAF and are useful in the treatment of PAF-related disorders including septic shock, respiratory distress syndrome, acute inflammation, delayed cellular immunity, parturtition, fetal lung maturation, and cellular differentiation.

  在 1 位或 3 位被(吡啶-3-基)噻唑-4-基)烷基、(吡啶-3-基)噻唑-4-酰基、(吡啶-3-基)二硫环戊-4-基)烷基或(吡啶-3-基)二硫环戊-4-酰基取代的吲哚化合物是 PAF 的强效抑制剂，可用于治疗与 PAF 有关的疾病，包括脓毒性休克、呼吸窘迫综合征、急性炎症、细胞免疫延迟、妊娠、胎儿肺成熟和细胞分化、可用于治疗与 PAF 有关的疾病，包括脓毒性休克、呼吸窘迫综合征、急性炎症、细胞免疫延迟、部分喷射、胎儿肺成熟和细胞分化。
• INDOLES USEFUL AS PLATELET ACTIVATING FACTOR ANTAGONISTS
  申请人：ABBOTT LABORATORIES

  公开号：EP0574494A1

  公开（公告）日：1993-12-22
• EP0574494A4
  申请人：——

  公开号：EP0574494A4

  公开（公告）日：1994-07-06
• US5382670A
  申请人：——

  公开号：US5382670A

  公开（公告）日：1995-01-17
• [EN] INDOLES USEFUL AS PLATELET ACTIVATING FACTOR ANTAGONISTS
  申请人：——

  公开号：WO1992014732A1

  公开（公告）日：1992-09-03

  [FR] L'invention se rapporte à des composés d'indole, qui sont substitués aux positions 1 ou 3 par un groupe (pyrid-3-yl)thiazolid-4-yl alkyl-, (pyrid-3-yl)thiazolid-4-oyl)-, (pyrid-3-yl)dithiolan-4-yl)alkyl- ou (pyrid-3-yl)dithiolan-4-oyl)- et qui constituent de puissants inhibiteurs du facteur d'activation des plaquettes et sont utiles dans le traitement des troubles associés au facteur d'activation des plaquettes, tels que choc septique, syndrome de la détresse respiratoire, inflammations aiguës, immunité cellulaire retardée, parturition, maturation des poumons du foetus et différenciation cellulaire.
  [EN] Indole compounds substituted at the 1- or 3-position by a (pyrid-3-yl)thiazolid-4-yl)alkyl-, (pyrid-3-yl)thiazolid-4-oyl)-, (pyrid-3-yl)dithiolan-4-yl)alkyl- or (pyrid-3-yl)dithiolan-4-oyl)- group are potent inhibitors of PAF and are useful in the treatment of PAF-related disorders including septic shock, respiratory distress syndrome, acute inflammation, delayed cellular immunity, parturition, fetal lung maturation, and cellular differentiation.