2-amino-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}acetamide | 117280-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}acetamide
• 英文别名: 2-amino-N-[3-(2-chlorobenzoyl)-5-[2-[4-(2-methylpropyl)phenyl]ethyl]thiophen-2-yl]acetamide
• CAS: 117280-07-6
• 化学式: C₂₅H₂₇ClN₂O₂S
• 分子量: 455.021
• InChiKey: QKHDDHAMHAKWHE-UHFFFAOYSA-N

物化性质

• 沸点：
  647.5±55.0 °C(predicted)
• 密度：
  1.245±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}acetamide 在 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 20.0h， 生成 5-(2-chlorophenyl)-7-[2-(4-isobutylphenyl)ethyl-]1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepin-2-one
  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 、 氨 、 sulfur 、 一水合肼 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 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 17.5h， 生成 2-amino-N-{3-(2-chlorobenzoyl)-5-[2-(4-isobutylphenyl)ethyl]-2-thienyl}acetamide
  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

• PAF-antagonistic thienotriazolodiazepine compounds and pharmaceutical uses thereof
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：EP0268242A1

  公开（公告）日：1988-05-25

  A thienotriazolodiazepine compound of the general formula (I): wherein each symbol is as defined in the specification and a pharmaceutically acceptable acid addition salt thereof, and pharmaceutical uses thereof. Said compounds exhibit PAF-antagonistic activity and are useful for the prevention or treatment of various PAF-induced diseases.

  通式(I)的噻吩三唑二氮杂卓化合物： 其中各符号如说明书中所定义及其药学上可接受的酸加成盐，以及它们的药物用途。 所述化合物具有 PAF 拮抗活性，可用于预防或治疗各种 PAF 引起的疾病。
• Verfahren zur Herstellung von 4-(4-Isobutylphenyl)-butyraldehyd
  申请人：BOEHRINGER INGELHEIM KG

  公开号：EP0428854A2

  公开（公告）日：1991-05-29

  Die Erfindung betrifft eine einfache, wirtschaftliche Synthese von 4-(4-Isobutylphenyl)-butyraldehyd und seine Verwendung zur Herstellung von (-)-4-(2-Chlorphenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-­thieno[3,2-f][1,2,4]triazolo[4,3-a]-1,4-diazepin.

  本发明涉及一种简单、经济的 4-(4-异丁基苯基)-丁醛合成方法及其在制备 (-)-4-(2-氯苯基)-2-[2-(4-异丁基苯基)乙基]-6,9-二甲基-6H-噻吩并[3,2-f][1,2,4]三唑并[4,3-a]-1,4-二氮杂卓中的应用。
• TAHARA, TETSUYA;MORIWAKI, MINORU;ABE, MASAO;YUASA, SHUJI
  作者：TAHARA, TETSUYA、MORIWAKI, MINORU、ABE, MASAO、YUASA, SHUJI

  DOI：——

  日期：——
• TAVARA, TEHTSUDZI;MORIVAKI, MINORU;ABEH, MASAO;YUASA, SYUNDZI
  作者：TAVARA, TEHTSUDZI、MORIVAKI, MINORU、ABEH, MASAO、YUASA, SYUNDZI

  DOI：——

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

  DOI：——

  日期：——