(+/-)-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}-2-phthalimidopropanamide | 127113-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}-2-phthalimidopropanamide
• 英文别名: N-[3-(2-chlorobenzoyl)-5-[2-[4-(2-methylpropyl)phenyl]ethyl]thiophen-2-yl]-2-(1,3-dioxoisoindol-2-yl)propanamide
• CAS: 127113-12-6
• 化学式: C₃₄H₃₁ClN₂O₄S
• 分子量: 599.15
• InChiKey: TWSFYUCKCWZOBM-UHFFFAOYSA-N

物化性质

• 沸点：
  766.8±60.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}-2-phthalimidopropanamide 在 盐酸 、 一水合肼 作用下， 生成 (+/-)-2-amino-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}propionamide
  参考文献：
  名称：

  Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system

  摘要：

  A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (+/-)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.

  DOI：

  10.1016/0223-5234(96)85877-6
• 作为产物：
  描述：

  异丁基苯 在 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 sodium tetrahydroborate 、 三氯化铝 、 Celite 、 三氟化硼乙醚 、 sulfur 、 一水合肼 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 乙二醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 (+/-)-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}-2-phthalimidopropanamide
  参考文献：
  名称：

  Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system

  摘要：

  A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (+/-)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.

  DOI：

  10.1016/0223-5234(96)85877-6

文献信息

• Eur. J. Med. Chem. 1996, 31, 683-692
  作者：

  DOI：——

  日期：——
• TAVARA, TEHTSUYA;MORIVAKI, MINORU;ABEH, MASAO;YUASA, SYUDZI
  作者：TAVARA, TEHTSUYA、MORIVAKI, MINORU、ABEH, MASAO、YUASA, SYUDZI

  DOI：——

  日期：——
• Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system
  作者：Y Kawakami、H Kitani、S Yuasa、M Abe、M Moriwaki、M Kagoshima、M Terasawa、T Tahara

  DOI：10.1016/0223-5234(96)85877-6

  日期：1996.1

  A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (+/-)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.