2-[1-(3-Cyano-phenyl)-eth-(Z)-ylidene]-succinic acid 1-ethyl ester | 534575-99-0

• 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: 2-[1-(3-Cyano-phenyl)-eth-(Z)-ylidene]-succinic acid 1-ethyl ester
• 英文别名: (Z)-4-(3-cyanophenyl)-3-ethoxycarbonylpent-3-enoic acid
• CAS: 534575-99-0
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: WIKBMLPLBYNGQM-RAXLEYEMSA-N

物化性质

• 沸点：
  444.1±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1-(3-Cyano-phenyl)-eth-(Z)-ylidene]-succinic acid 1-ethyl ester 在 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-{1-[2,5-Dioxo-1-(2'-sulfamoyl-biphenyl-4-yl)-pyrrolidin-(3Z)-ylidene]-ethyl}-benzimidic acid methyl ester
  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：

  3-乙酰苯腈 、 丁二酸二乙酯 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 2-[1-(3-Cyano-phenyl)-eth-(Z)-ylidene]-succinic acid 1-ethyl ester 、 2-[1-(3-Cyano-phenyl)-eth-(E)-ylidene]-succinic acid 1-ethyl ester
  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

文献信息

• Design and synthesis of factor Xa inhibitors and their prodrugs
  作者：Yonghong Song、Lane Clizbe、Chhaya Bhakta、Willy Teng、Paul Wong、Brian Huang、Katherine Tran、Uma Sinha、Gary Park、Andrea Reed、Robert M Scarborough、Bing-Yan Zhu

  DOI：10.1016/s0960-894x(02)00921-6

  日期：2003.1

  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.