N-[(R)-2-amino-3-(p-aminophenyl-N-{5-oxopentanoic acid})-propyl]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N'',N''-penta-tert-butyl acetate | 905825-53-8

• 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: N-[(R)-2-amino-3-(p-aminophenyl-N-{5-oxopentanoic acid})-propyl]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N'',N''-penta-tert-butyl acetate
• 英文别名: N-[(R)-2-amino-3-(p-aminophenyI-N-{5-oxopentanoic acid})propyI]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N',N'',N''-pentaethyl-t-butanoate；5-[4-[(2R)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-[[(1S,2S)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]cyclohexyl]-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propyl]anilino]-5-oxopentanoic acid
• CAS: 905825-53-8
• 化学式: C₅₀H₈₂N₄O₁₃
• 分子量: 947.22
• InChiKey: XNHGATAGFAGSLT-XWTVRQILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  67
• 可旋转键数：
  32
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  208
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N-[(R)-2-amino-3-(p-aminophenyl-N-{5-oxopentanoic acid})-propyl]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N'',N''-penta-tert-butyl acetate 、 N-羟基丁二酰亚胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到N-[(R)-2-amino-3-(p-5-[(2,5-dioxopyrrolidin-1-yl)oxy]-5-oxo-N-phenylpentanamide)-propyl]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N'',N''-penta-tert-butyl acetate
  参考文献：
  名称：

  Validation of a Novel CHX-A‘ ‘ Derivative Suitable for Peptide Conjugation:  Small Animal PET/CT Imaging Using Yttrium-86-CHX-A‘ ‘-Octreotide

  摘要：

  A versatile bifunctional chelating reagent based on a preorganized cyclohexyl derivative of DTPA (CHX-A ") has been developed for the convenient N-terminal labeling of peptides with metal ion radionuclides of Bi(III), In(III), Lu(III), or Y(III). This was achieved via the synthesis of a mono-N-hydroxysuccinimidyl penta-tert-butyl ester derivative of CHX-A" (trans-cyclohexyldiethylenetriaminepenta-acetic acid) featuring a glutaric acid spacer. Commercially obtained octreotide was modified at its N-terminus by this reagent in the solution phase, and its subsequent radiolabeling with In-111 (T-1/2 = 2.8 d) and Y-86 (T-1/2 = 14.7 h) demonstrated. Small animal PET/CT imaging results of Y-86-CHX-A"-octreotide in a somatostatin receptor-positive tumor-bearing rat model are presented for the validation of the novel agent.

  DOI：

  10.1021/jm060317v
• 作为产物：
  描述：

  溴乙酸叔丁酯 在 palladium on activated charcoal K₂O₃ 、 氢气 作用下， 以 乙醇 、 乙腈 、 苯 为溶剂， 反应 80.0h， 生成 N-[(R)-2-amino-3-(p-aminophenyl-N-{5-oxopentanoic acid})-propyl]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N'',N''-penta-tert-butyl acetate
  参考文献：
  名称：

  Validation of a Novel CHX-A‘ ‘ Derivative Suitable for Peptide Conjugation:  Small Animal PET/CT Imaging Using Yttrium-86-CHX-A‘ ‘-Octreotide

  摘要：

  A versatile bifunctional chelating reagent based on a preorganized cyclohexyl derivative of DTPA (CHX-A ") has been developed for the convenient N-terminal labeling of peptides with metal ion radionuclides of Bi(III), In(III), Lu(III), or Y(III). This was achieved via the synthesis of a mono-N-hydroxysuccinimidyl penta-tert-butyl ester derivative of CHX-A" (trans-cyclohexyldiethylenetriaminepenta-acetic acid) featuring a glutaric acid spacer. Commercially obtained octreotide was modified at its N-terminus by this reagent in the solution phase, and its subsequent radiolabeling with In-111 (T-1/2 = 2.8 d) and Y-86 (T-1/2 = 14.7 h) demonstrated. Small animal PET/CT imaging results of Y-86-CHX-A"-octreotide in a somatostatin receptor-positive tumor-bearing rat model are presented for the validation of the novel agent.

  DOI：

  10.1021/jm060317v

文献信息

• [EN] METAL CHELATORS AND METHODS OF THEIR USE<br/>[FR] CHELATEURS METALLIQUES ET LEURS PROCEDES D'UTILISATION
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2006033714A3

  公开（公告）日：2006-05-04
• Validation of a Novel CHX-A‘ ‘ Derivative Suitable for Peptide Conjugation:  Small Animal PET/CT Imaging Using Yttrium-86-CHX-A‘ ‘-Octreotide
  作者：Thomas Clifford、C. Andrew Boswell、Gráinne B. Biddlecombe、Jason S. Lewis、Martin W. Brechbiel

  DOI：10.1021/jm060317v

  日期：2006.7.1

  A versatile bifunctional chelating reagent based on a preorganized cyclohexyl derivative of DTPA (CHX-A ") has been developed for the convenient N-terminal labeling of peptides with metal ion radionuclides of Bi(III), In(III), Lu(III), or Y(III). This was achieved via the synthesis of a mono-N-hydroxysuccinimidyl penta-tert-butyl ester derivative of CHX-A" (trans-cyclohexyldiethylenetriaminepenta-acetic acid) featuring a glutaric acid spacer. Commercially obtained octreotide was modified at its N-terminus by this reagent in the solution phase, and its subsequent radiolabeling with In-111 (T-1/2 = 2.8 d) and Y-86 (T-1/2 = 14.7 h) demonstrated. Small animal PET/CT imaging results of Y-86-CHX-A"-octreotide in a somatostatin receptor-positive tumor-bearing rat model are presented for the validation of the novel agent.