4-[2-(3,4,5,6-tetrahydropyrimidine-2-ylamino)ethyloxy]benzoyl-2-[N-(3-amino-neopenta-1-carbamyl)]aminoethylsulfonyl-amino-β-alanine | 1393934-18-3

• 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: 4-[2-(3,4,5,6-tetrahydropyrimidine-2-ylamino)ethyloxy]benzoyl-2-[N-(3-amino-neopenta-1-carbamyl)]aminoethylsulfonyl-amino-β-alanine
• 英文别名: 2-[2-[(3-amino-2,2-dimethylpropoxy)carbonylamino]ethylsulfonylamino]-3-[[4-[2-(1,4,5,6-tetrahydropyrimidin-2-ylamino)ethoxy]benzoyl]amino]propanoic acid
• CAS: 1393934-18-3
• 化学式: C₂₄H₃₉N₇O₈S
• 分子量: 585.682
• InChiKey: LCNAIFMSOWTUTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  40
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  231
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-(4,7-bis(2-(tert-butoxy)-2-oxoethyl)-1,4,7-triazacyclononan-1-yl)-5-(tert-butoxy)-5-oxopentanoic acid NHS ester 、 4-[2-(3,4,5,6-tetrahydropyrimidine-2-ylamino)ethyloxy]benzoyl-2-[N-(3-amino-neopenta-1-carbamyl)]aminoethylsulfonyl-amino-β-alanine 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以78%的产率得到2-[2-[[3-[[4-[4,7-Bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,4,7-triazonan-1-yl]-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]-2,2-dimethylpropoxy]carbonylamino]ethylsulfonylamino]-3-[[4-[2-(1,4,5,6-tetrahydropyrimidin-2-ylamino)ethoxy]benzoyl]amino]propanoic acid
  参考文献：
  名称：

  Synthesis and characterization of αvβ3-targeting peptidomimetic chelate conjugates for PET and SPECT imaging

  摘要：

  There is growing interest in small peptidomimetic alpha(v)beta(3) integrin antagonists that are readily synthesized and characterized and can be easily handled using physiological conditions. Peptidomimetic 4-[2-(3,4,5,6-tetrahydropyrimidine-2-ylamino)ethyloxy]benzoyl-2-[N-(3-amino-neopenta-1-carbamyl)] -aminoethylsulfonyl-amino-beta-alanine (IAC) was successfully conjugated to 1-(1-carboxy-3-carbo-t-but-oxypropyl)-4,7-(carbo-tert-butoxymethyl)-1,4,7-triazacyclononane (NODA-GA(tBu)(3)) and 1-(1-carboxy-3-carbotertbutoxymethyl)-1,4,7,10-tetraazacyclododecane (DOTA-GA(tBu)(4)) and radiolabeled with In-111, Ga-67 and Pb-203. Results of a radioimmunoassay demonstrated binding to purified alpha(v)beta(3) integrin when 14 equiv of integrin were added to the reaction. Based on this promising result, investigations are moving forward to evaluate the NODA-GA-IAC and DOTA-GA-IAC conjugates for targeting tumor associated angiogenesis and alpha(v)beta(3) integrin positive tumors to define their PET and SPECT imaging qualities as well as their potential for delivery of therapeutic radionuclides. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.07.024