(E)-3-(3-Cyano-phenyl)-2-fluoro-but-2-enoic acid ethyl ester | 534576-06-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3-Cyano-phenyl)-2-fluoro-but-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-3-(3-cyanophenyl)-2-fluorobut-2-enoate
• CAS: 534576-06-2
• 化学式: C₁₃H₁₂FNO₂
• 分子量: 233.242
• InChiKey: ZPUGLCBNWGGQSR-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-Cyano-phenyl)-2-fluoro-but-2-enoic acid ethyl ester 在 盐酸 、 羟胺 、 三甲基铝 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (E)-2-fluoro-N-[2-fluoro-4-(2-sulfamoylphenyl)phenyl]-3-[3-(N'-hydroxycarbamimidoyl)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-氟-2-磷酰基乙酸三乙酯 、 3-乙酰苯腈 在 双(三甲基硅烷基)氨基钾 作用下， 生成 (E)-3-(3-Cyano-phenyl)-2-fluoro-but-2-enoic acid ethyl ester 、 ethyl 3-(3-cyanophenyl)-2-fluoro-3-methylacrylate
  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