(Z)-2-[(1-tert-Butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-3-(4-iodo-phenyl)-acrylic acid methyl ester | 533935-33-0

• 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: (Z)-2-[(1-tert-Butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-3-(4-iodo-phenyl)-acrylic acid methyl ester
• CAS: 533935-33-0
• 化学式: C₂₅H₃₇INO₆P
• 分子量: 605.45
• InChiKey: XVLGUVCHMPGMJV-HMMYKYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 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：

  (Z)-2-[(1-tert-Butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-3-(4-iodo-phenyl)-acrylic acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (Z)-2-[(1-Amino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-3-(4-iodo-phenyl)-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
• 作为产物：
  描述：

  2-(二甲氧基亚膦酰)-2-丙烯酸甲酯 、 4-碘苯甲醛 、 (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)-2-[(1-tert-Butoxycarbonylamino-2-cyclohexyl-ethyl)-methoxy-phosphinoylmethyl]-3-(4-iodo-phenyl)-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

文献信息

• Design and synthesis of renal dipeptidase inhibitors
  申请人：The Johns Hopkins University

  公开号：US20040091422A1

  公开（公告）日：2004-05-13

  Aminophosphinic acid derivatives were synthesized as potential inhibitors of renal dipeptidase, an enzyme overexpressed in benign and malignant colon tumors. Several compounds showed potent enzyme-inhibitory activity. These compounds can be used therapeutically and diagnostically for treatment and detection of tumors.

  氨基膦酸衍生物被合成为肾脏二肽酶的潜在抑制剂，该酶在良性和恶性结肠肿瘤中过度表达。几种化合物显示出强大的酶抑制活性。这些化合物可用于治疗和检测肿瘤的治疗和诊断。
• Design, synthesis and evaluation of new RDP inhibitors
  作者：Hallur Gurulingappa、Phillip Buckhaults、Srinivas K. Kumar、Kenneth W. Kinzler、Bert Vogelstein、Saeed R. Khan

  DOI：10.1016/s0040-4039(03)00082-0

  日期：2003.2

  Aminophosphinic acid derivatives were synthesized as potential inhibitors of renal dipeptidase, an enzyme over-expressed in benign and malignant colon tumors. Several compounds showed potent enzyme-inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.