2-aminoacetamido-3-(2-chlorobenzoyl)-5-hexylthiophene | 120135-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoacetamido-3-(2-chlorobenzoyl)-5-hexylthiophene
• 英文别名: 2-amino-N-[3-(2-chlorobenzoyl)-5-hexylthiophen-2-yl]acetamide
• CAS: 120135-39-9
• 化学式: C₁₉H₂₃ClN₂O₂S
• 分子量: 378.923
• InChiKey: METDKKNUYBIREW-UHFFFAOYSA-N

物化性质

• 沸点：
  592.6±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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-aminoacetamido-3-(2-chlorobenzoyl)-5-hexylthiophene 在 tetraphosphorus decasulfide 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 异丙醇 为溶剂， 反应 25.0h， 生成 [5-(2-Chloro-phenyl)-7-hexyl-1,3-dihydro-thieno[2,3-e][1,4]diazepin-(2Z)-ylidene]-hydrazine
  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：

  2-amino-3-(2-chlorobenzoyl)-5-hexylthiophene 在 氨 、 sodium iodide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 8.0h， 生成 2-aminoacetamido-3-(2-chlorobenzoyl)-5-hexylthiophene
  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

• THIENO(TRIAZOLO)DIAZEPINE COMPOUNDS AND MEDICINAL APPLICATION OF THE SAME
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：EP0315698A1

  公开（公告）日：1989-05-17

  A thienotriazolodiazepine compound represented by general formula (l), wherein Ar is phenyl, pyridyl, substituted phenyl or substituted pyridyl. R1 and R3 which may be the same or different are each hydrogen or alkyl having 1 to 4 carbon atoms, R2 is hydrogen, alkyl having 1 to 4 carbon atoms or trifluoromethyl and R' is straight-chain or branched alkyl alkenyl or alkinyl having 6 to 18 carbon atoms, or a thienodiazepine compound represented by general formula (ll), wherein Ar, R1, R2 and R' are as defined above, a pharmaceutically acceptable salt thereof, and a medicinal application thereof. These compounds are useful as a therapeutic agent for circulatory diseases and various diseases induced by a platelet activating factor. Further, the compound (ll) is also useful as an intermediate for synthesis of the compound (l).

  通式(l)代表的噻吩三唑二氮杂卓化合物，其中 Ar 是苯基、吡啶基、取代苯基或取代吡啶基。R1和R3可以相同或不同，各自为氢或具有1至4个碳原子的烷基，R2为氢、具有1至4个碳原子的烷基或三氟甲基，R'为具有6至18个碳原子的直链或支链烷基烯基或烷基，或通式(ll)代表的噻二氮卓化合物，其中Ar、R1、R2和R'如上定义，其药学上可接受的盐，及其医药应用。这些化合物可作为循环系统疾病和由血小板活化因子诱发的各种疾病的治疗剂。此外，化合物(ll)还可用作合成化合物(l)的中间体。
• VERFAHREN ZUR HERSTELLUNG VON 6-ARYL-4H-S-TRIAZOLO[3,4-C]-THIENO[2,3-E]-1,4-DIAZEPINEN
  申请人：Boehringer Ingelheim Pharma GmbH & Co.KG

  公开号：EP1392698B1

  公开（公告）日：2004-10-13
• US4960770A
  申请人：——

  公开号：US4960770A

  公开（公告）日：1990-10-02
• 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.