2-(2-Tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)ethanamine | 824937-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 2-(2-Tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)ethanamine
• CAS: 824937-92-0
• 化学式: C₁₇H₁₇N
• 分子量: 235.329
• InChiKey: AEBOTSLGUVHHOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-Tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)ethanamine 、 对氯苯异氰酸酯 以 乙腈 为溶剂， 反应 2.0h， 生成 1-(4-Chlorophenyl)-3-[2-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)ethyl]urea
  参考文献：
  名称：

  Hybrid cholecystokinin-A antagonists based on molecular modeling of lorglumide and L-364,718

  摘要：

  A series of novel nonpeptide cholecystokinin-A (CCK-A) antagonists have been synthesized. Designed on the basis of the structural homology between lorglumide and L-364,718, as investigated with molecular modeling, these compounds constitute a link between the N-acylglutamic acid and 3-amino-5-phenyl-1,4-benzodiazepin-2-one derived antagonists. The prepared compounds were tested in vitro as antagonists of the binding of [H-3]-(+/-)-L-364,718 and [H-3]-CCK-8(S) to rat pancreas and guinea pig brain membranes, respectively. All compounds proved to be selective for the (peripheral) CCK-A receptor, the most potent analogue, 6, having a K(i) value of 90 nM. The structure-activity profile of the series of hybrid compounds relates closest to that of the N-acylglutamic acid derived antagonists.

  DOI：

  10.1021/jm00084a009
• 作为产物：
  描述：

  10,11-二氢二苯并[a,b]环庚烯-5-酮 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 74.33h， 生成 2-(2-Tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)ethanamine
  参考文献：
  名称：

  Hybrid cholecystokinin-A antagonists based on molecular modeling of lorglumide and L-364,718

  摘要：

  A series of novel nonpeptide cholecystokinin-A (CCK-A) antagonists have been synthesized. Designed on the basis of the structural homology between lorglumide and L-364,718, as investigated with molecular modeling, these compounds constitute a link between the N-acylglutamic acid and 3-amino-5-phenyl-1,4-benzodiazepin-2-one derived antagonists. The prepared compounds were tested in vitro as antagonists of the binding of [H-3]-(+/-)-L-364,718 and [H-3]-CCK-8(S) to rat pancreas and guinea pig brain membranes, respectively. All compounds proved to be selective for the (peripheral) CCK-A receptor, the most potent analogue, 6, having a K(i) value of 90 nM. The structure-activity profile of the series of hybrid compounds relates closest to that of the N-acylglutamic acid derived antagonists.

  DOI：

  10.1021/jm00084a009

文献信息

• 2-(4-Methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure–activity relationships in the B and C-regions
  作者：Wei Sun、Keliang Liu、HyungChul Ryu、Dong Wook Kang、Yong Soo Kim、Myeong Seop Kim、Yongsung Cho、Rahul S. Bhondwe、Shivaji A. Thorat、Ho Shin Kim、Larry V. Pearce、Vladimir A. Pavlyukovets、Richard Tran、Matthew A. Morgan、Jozsef Lazar、Christopher B. Ryder、Attila Toth、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmc.2011.12.014

  日期：2012.2

  On the basis of the previous lead N-4-t-butylbenzyl 2-(3-fluoro-4-methylsulfonylaminophenyl) propanamide (3) as a potent TRPV1 antagonist, structure-activity relationships for the B (propanamide part) and C-region (4-t-butylbenzyl part) have been investigated for rTRPV1 in CHO cells. The B-region was modified with dimethyl, cyclopropyl and reverse amides and then the C-region was replaced with 4-substituted phenyl, aryl alkyl and diaryl alkyl derivatives. Among them, compound 50 showed high binding affinity with K-i = 21.5 nM, which was twofold more potent than 3 and compound 54 exhibited potent antagonism with K-i(ant) = 8.0 nM comparable to 3. (C) 2011 Elsevier Ltd. All rights reserved.
• DIPEPTIDYL PEPTIDASE-IV INHIBITORS
  申请人：Kroth Heiko

  公开号：US20100009961A1

  公开（公告）日：2010-01-14

  The present invention relates generally to pyrrolidine and thiazolidine DPP-IV inhibitor compounds. The present invention also provides synthetic methods for preparation of such compounds, methods of inhibiting DPP-IV using such compounds and pharmaceutical formulations containing them for treatment of DPP-IV mediated diseases, in particular, Type-2 diabetes.
• Dipeptidyl Peptidase-IV Inhibitors
  申请人：KROTH Heiko

  公开号：US20110112051A1

  公开（公告）日：2011-05-12

  The present invention relates generally to pyrrolidine and thiazolidine DPP-IV inhibitor compounds. The present invention also provides synthetic methods for preparation of such compounds, methods of inhibiting DPP-IV using such compounds and pharmaceutical formulations containing them for treatment of DPP-IV mediated diseases, in particular, Type-2 diabetes.
• US7553861B2
  申请人：——

  公开号：US7553861B2

  公开（公告）日：2009-06-30
• US8076330B2
  申请人：——

  公开号：US8076330B2

  公开（公告）日：2011-12-13