(2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-fluorobut-2-enamide | 288309-84-2

• 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: (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-fluorobut-2-enamide
• 英文别名: N-{4-[(2-tert-butylaminosulfonyl)phenyl]phenyl}-3-(3-cyanophenyl)-2-fluoro-3-methylacrylamide；(E)-N-[4-[2-(tert-butylsulfamoyl)phenyl]phenyl]-3-(3-cyanophenyl)-2-fluorobut-2-enamide
• CAS: 288309-84-2
• 化学式: C₂₇H₂₆FN₃O₃S
• 分子量: 491.586
• InChiKey: DVJWBEXUWMCGRR-XIEYBQDHSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-fluorobut-2-enamide 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 (E)-2-fluoro-3-[3-(N'-methylcarbamimidoyl)phenyl]-N-[4-(2-sulfamoylphenyl)phenyl]but-2-enamide
  参考文献：
  名称：

  Design and synthesis of factor Xa inhibitors and their prodrugs

  摘要：

  In addition to our previously reported fluoro acrylamides Xa inhibitors 2 and 3, a series of potent and novel cyclic diimide amidine compounds has been identified. In efforts to improve their oral bioavailability, replacement of the amidine group with methyl amidrazone: gives compounds of moderate potency (14, IC50 = 0.028 muM). In the amidoxime prodrug approach, the amidoxime compounds show good oral bioavailability in rats and dogs. High plasma level of prodrug 26 and significant concentration of active drug 26a were obtained upon oral administration of prodrug 26 in rats. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00921-6
• 作为产物：
  描述：

  2-(4-氨基苯基)-N-叔丁基苯磺酰胺 、 (E)-3-(3-Cyano-phenyl)-2-fluoro-but-2-enoic acid ethyl ester 在 三甲基铝 作用下， 以 二氯甲烷 为溶剂， 生成 (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-fluorobut-2-enamide
  参考文献：
  名称：

  Design, synthesis, and SAR of substituted acrylamides as factor Xa inhibitors

  摘要：

  Substituted acrylamides were used as templates that bridge P1 and P4 binding elements, resulting in a series of potent sub-nanomolar) and selective factor Xa inhibitors. In this template, cis-geometry of P1 and P4 ligands is highly preferred. SAR on the substituting groups, as well as on modification of P1 and P4 moieties is described. Compounds in this series show good in vivo efficacy in animal models. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00199-3

文献信息

• Inhibitors of factor Xa
  申请人：Cor Therapeutics, Inc.

  公开号：US06399627B1

  公开（公告）日：2002-06-04

  Novel compounds, their salts and compositions related thereto having activity against mammalian factor Xa are disclosed. The compounds are useful in vitro or in vivo for preventing or treating coagulation disorders.

  披露了新型化合物、它们的盐和与它们相关的组合物，这些化合物对哺乳动物因子Xa具有活性。这些化合物在体外或体内用于预防或治疗凝血障碍。
• INHIBITORS OF FACTOR Xa
  申请人：COR THERAPEUTICS, INC.

  公开号：EP1159264A2

  公开（公告）日：2001-12-05
• US6399627B1
  申请人：——

  公开号：US6399627B1

  公开（公告）日：2002-06-04
• [EN] INHIBITORS OF FACTOR Xa<br/>[FR] INHIBITEURS DU FACTEUR Xa
  申请人：COR THERAPEUTICS INC

  公开号：WO2000047554A2

  公开（公告）日：2000-08-17

  Novel compounds of formula in which A is a substituted or unsubstituted phenyl, naphthyl or monocyclic heterocyclic ring, D is a substituted or unsubstituted phenyl or aromatic six-membered heterocyclic ring, K is a substituted or unsubstituted phenyl, naphthyl or bicyclic heterocyclic ring, and the other variables are as defined in the claims, their salts and other derivatives and compositions related thereto having activity against mammalian Factor Xa are disclosed. The coumpounds are useful in vitro or in vivo for preventing or treating coagulation disorders.