6-{[4-(3-{2-carboxy-2-[3-(1,3-dicarboxypropyl)ureido]ethylsulfanyl}-2,5-dioxo-pyrrolidin-1-yl)cyclohexanecarbonyl]amino}hexylammonium chloride | 1374847-79-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-{[4-(3-{2-carboxy-2-[3-(1,3-dicarboxypropyl)ureido]ethylsulfanyl}-2,5-dioxo-pyrrolidin-1-yl)cyclohexanecarbonyl]amino}hexylammonium chloride
• CAS: 1374847-79-6
• 化学式: C₂₇H₄₃N₅O₁₀S*ClH
• 分子量: 666.193
• InChiKey: UVBJNFCKMCBJFT-LRHHMFBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  44.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  245.53
• 氢给体数：
  7.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2-[3-(2-{1-[4-(6-tert-butoxycarbonylaminohexylcarbamoyl)cyclohexyl]-2,5-dioxopyrrolidin-3-ylsulfanyl}-1-carboxyethyl)ureido]pentanedioic acid 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以97%的产率得到6-{[4-(3-{2-carboxy-2-[3-(1,3-dicarboxypropyl)ureido]ethylsulfanyl}-2,5-dioxo-pyrrolidin-1-yl)cyclohexanecarbonyl]amino}hexylammonium chloride
  参考文献：
  名称：

  Structure-Activity Relationships of 2′,5′-Oligoadenylate Analogue Modifications of Prostate-Specific Membrane Antigen (PSMA) Antagonists

  摘要：

  Prostate-specific membrane antigen (PSMA) is an ideal biomarker for prostate cancer. A previously reported 2-5A conjugate RBI1033 (3) showed binding affinity more than 10 times higher than the parent urea-based compound (S)-2-(3-((S)-5-amino-1-carboxypentyl) ureido) pentanedioic acid (1). The purpose of this work is to further optimize the structure of 3 to identify highly selective ligands of PSMA. It was found that conjugates having 2-5A in their structure showed extraordinary improved binding affinity to PSMA compared with compound 1. Removal of 2-5A significantly reduced its biological activity. The results will provide a path to agents for targeted imaging and treatment of prostate cancer.

  DOI：

  10.1080/15257770.2012.671988