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 | 880644-86-0

• 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-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
• 英文别名: N-[(R)-2-amino-3-(p-5-[(2,5-dioxopyrroIidin-1-yI)oxy]-5-oxo-N-phenylpentanamide)propyI]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N',N'',N''-pentaethyl-t-butanoate；(2,5-dioxopyrrolidin-1-yl) 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-oxopentanoate
• CAS: 880644-86-0
• 化学式: C₅₄H₈₅N₅O₁₅
• 分子量: 1044.29
• InChiKey: SIMAPAVTTCDGLI-WKSNTLBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  74
• 可旋转键数：
  34
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  234
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  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 、 生成 tert-butyl 2-[[(2R)-3-[4-[[5-[[(2S)-1-[[(4R,7S,10S,13R,16S,19R)-16-benzyl-4-[[(2R,3R)-1,3-dihydroxybutan-2-yl]carbamoyl]-7-[(1R)-1-hydroxyethyl]-13-(1H-indol-3-ylmethyl)-10-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-19-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-oxopentanoyl]amino]phenyl]-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propyl]-[(1S,2S)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]cyclohexyl]amino]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 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 80.0h， 生成 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

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
• Metal Chelators and Methods of Their Use
  申请人：Brechbiel Martin Wade

  公开号：US20080152588A1

  公开（公告）日：2008-06-26

  Metal chelators of formula (I) and formula (II) are disclosed or a farmaceutically acceptable salt thereof. Also disclosed are metal chelator-targeting moiety complexes, metal chelator-targeting moiety-metal conjugates, kits, and methods of their preparation and use in diagnosis and/or treatment of diseases and conditions, including, inter alia, cancer and thrombosis.
• METAL CHELATORS AND METHODS OF THEIR USE
  申请人：Brechbiel Martin Wade

  公开号：US20100189645A1

  公开（公告）日：2010-07-29

  Metal chelators of Formula I and Formula II are disclosed: or a pharmaceutically acceptable salt thereof. Also disclosed are metal chelator-targeting moiety complexes, metal chelator-targeting moiety-metal conjugates, kits, and methods of their preparation and use in diagnosis and/or treatment of diseases and conditions, including, inter alia, cancer and thrombosis.
• US7785565B2
  申请人：——

  公开号：US7785565B2

  公开（公告）日：2010-08-31
• US8454936B2
  申请人：——

  公开号：US8454936B2

  公开（公告）日：2013-06-04