Ethyl 2-[1(S)-t-butoxycarbonylamino-2-(4-fluorophenyl)ethyl]thiazole-4-carboxylate | 212756-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 2-[1(S)-t-butoxycarbonylamino-2-(4-fluorophenyl)ethyl]thiazole-4-carboxylate
• 英文别名: ethyl 2-[(1S)-2-(4-fluorophenyl)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-thiazole-4-carboxylate
• CAS: 212756-38-2
• 化学式: C₁₉H₂₃FN₂O₄S
• 分子量: 394.467
• InChiKey: FWHMAUWYXUNETG-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[1(S)-t-butoxycarbonylamino-2-(4-fluorophenyl)ethyl]thiazole-4-carboxylate 在 N-甲基吗啉 、 lithium hydroxide 、 苯甲醚 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-[(S)-2-(4-Fluoro-phenyl)-1-(2-methylamino-acetylamino)-ethyl]-thiazole-4-carboxylic acid [(S)-1-((S)-1-benzylcarbamoyl-4-guanidino-butylcarbamoyl)-2-cyclohexyl-ethyl]-amide
  参考文献：
  名称：

  Thrombin receptor (PAR-1) antagonists. Heterocycle-based peptidomimetics of the SFLLR agonist motif

  摘要：

  The thrombin receptor (PAR-I) is activated by a-thrombin to stimulate various cell types, including platelets, through the tethered-ligand sequence SFLLRN. A series of azole-based carboxamides, designed after SFLLR, were synthesized and evaluated in vitro. The compounds inhibited platelet aggregation induced by SFLLRN-NH2 or a-thrombin, and blocked the binding of [H-3]-S-(p-F-Phe)-Har-L-Har-KY-NH2 to a CHRF membrane preparation of PAR-I. Oxazole 30 bound to PAR-I with an IC50 Of 1.6 mu M, and gave IC50 values of 25 mu M and 6.6 mu M against alpha-thrombin- and SFLLRN-NH2-induced platelet aggregation, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00292-3
• 作为产物：
  描述：

  Boc-p-F-Phe-NH2 在 劳森试剂 、 吡啶 、 碳酸氢钠 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 生成 Ethyl 2-[1(S)-t-butoxycarbonylamino-2-(4-fluorophenyl)ethyl]thiazole-4-carboxylate
  参考文献：
  名称：

  Thrombin receptor (PAR-1) antagonists. Heterocycle-based peptidomimetics of the SFLLR agonist motif

  摘要：

  The thrombin receptor (PAR-I) is activated by a-thrombin to stimulate various cell types, including platelets, through the tethered-ligand sequence SFLLRN. A series of azole-based carboxamides, designed after SFLLR, were synthesized and evaluated in vitro. The compounds inhibited platelet aggregation induced by SFLLRN-NH2 or a-thrombin, and blocked the binding of [H-3]-S-(p-F-Phe)-Har-L-Har-KY-NH2 to a CHRF membrane preparation of PAR-I. Oxazole 30 bound to PAR-I with an IC50 Of 1.6 mu M, and gave IC50 values of 25 mu M and 6.6 mu M against alpha-thrombin- and SFLLRN-NH2-induced platelet aggregation, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00292-3

文献信息

• US6017890A
  申请人：——

  公开号：US6017890A

  公开（公告）日：2000-01-25
• US6156732A
  申请人：——

  公开号：US6156732A

  公开（公告）日：2000-12-05
• Thrombin receptor (PAR-1) antagonists. Heterocycle-based peptidomimetics of the SFLLR agonist motif
  作者：William J. Hoekstra、Becky L. Hulshizer、David F. McComsey、Patricia Andrade-Gordon、Jack A. Kauffman、Michael F. Addo、Donna Oksenberg、Robert M. Scarborough、Bruce E. Maryanoff

  DOI：10.1016/s0960-894x(98)00292-3

  日期：1998.7

  The thrombin receptor (PAR-I) is activated by a-thrombin to stimulate various cell types, including platelets, through the tethered-ligand sequence SFLLRN. A series of azole-based carboxamides, designed after SFLLR, were synthesized and evaluated in vitro. The compounds inhibited platelet aggregation induced by SFLLRN-NH2 or a-thrombin, and blocked the binding of [H-3]-S-(p-F-Phe)-Har-L-Har-KY-NH2 to a CHRF membrane preparation of PAR-I. Oxazole 30 bound to PAR-I with an IC50 Of 1.6 mu M, and gave IC50 values of 25 mu M and 6.6 mu M against alpha-thrombin- and SFLLRN-NH2-induced platelet aggregation, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.