(E)-3-(4-Bromo-phenyl)-2-[(1-tert-butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-acrylic acid methyl ester | 791836-16-3

• 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-(4-Bromo-phenyl)-2-[(1-tert-butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-acrylic acid methyl ester
• CAS: 791836-16-3
• 化学式: C₂₅H₃₇BrNO₆P
• 分子量: 558.45
• InChiKey: VGUGHJUHSHNQAE-HKWRFOASSA-N

物化性质

• 密度：
  1.267±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-Bromo-phenyl)-2-[(1-tert-butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-acrylic acid methyl ester 在 盐酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 (E)-2-[(1-Amino-2-cyclohexyl-ethyl)-hydroxy-phosphinoylmethyl]-3-(4-bromo-phenyl)-acrylic acid
  参考文献：
  名称：

  Synthesis and evaluation of aminophosphinic acid derivatives as inhibitors of renal dipeptidase

  摘要：

  Renal dipeptidase (RDP) is an enzyme overexpressed in benign and malignant colorectal tumors. In an effort to identify potent inhibitors of this enzyme, a series of aminophosphinic acid derivatives were synthesized. Compounds 3a and 3c in which the phenyl ring was para substituted with F and Br and olefin with Z geometry, showed better inhibitory activity against RDP enzyme (IC50 = 5-6 nM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.057
• 作为产物：
  描述：

  2-(二甲氧基亚膦酰)-2-丙烯酸甲酯 、 对溴苯甲醛 、 (1-tert-butoxycarbonylamino-2-cyclohexyl-ethyl)phosphinic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 31.17h， 生成 (Z)-3-(4-Bromo-phenyl)-2-[(1-tert-butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-acrylic acid methyl ester 、 (E)-3-(4-Bromo-phenyl)-2-[(1-tert-butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis and evaluation of aminophosphinic acid derivatives as inhibitors of renal dipeptidase

  摘要：

  Renal dipeptidase (RDP) is an enzyme overexpressed in benign and malignant colorectal tumors. In an effort to identify potent inhibitors of this enzyme, a series of aminophosphinic acid derivatives were synthesized. Compounds 3a and 3c in which the phenyl ring was para substituted with F and Br and olefin with Z geometry, showed better inhibitory activity against RDP enzyme (IC50 = 5-6 nM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.057