N-[(R)-2-amino-3-(p-nitrophenyl)propyl]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N'',N''-penta-tert-butyl acetate | 880644-82-6

• 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: N-[(R)-2-amino-3-(p-nitrophenyl)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-nitrophenyI)propyI]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N',N'',N''-pentaethyl-t-butanoate；tert-butyl 2-[[(1S,2S)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]cyclohexyl]-[(2R)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-(4-nitrophenyl)propyl]amino]acetate
• CAS: 880644-82-6
• 化学式: C₄₅H₇₄N₄O₁₂
• 分子量: 863.102
• InChiKey: ANPPQKPKEXUWQM-PLJDCMBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  61
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  187
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-[(R)-2-amino-3-(p-nitrophenyl)propyl]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N'',N''-penta-tert-butyl acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以97%的产率得到N-[(R)-2-amino-3-(p-aminophenyl)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 、 N-[(R)-2-amino-3-(p-nitrophenyl)propyl]-trans-(S,S)-cyclohexane-1,2-diamine trihydrochloride 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-[(R)-2-amino-3-(p-nitrophenyl)propyl]-trans-(S,S)-cyclohexane-1,2-diamine-N,N,N',N'',N''-penta-tert-butyl acetate
  参考文献：
  名称：

  立体化学对体内放射性金属配合物稳定性的影响。2-（对硝基苄基）-反式-CyDTPA的四种立体异构体的合成和评价。

  摘要：

  两种非对映体C功能化CyDTPA螯合剂（CHX-A DTPA和CHX-B DTPA，均为外消旋物）在体内稳定性方面存在明显差异，正如最近报道的那样，这促使人们进一步进行调查，以研究为什么构型差异会对内含子产生显着影响钇配合物的体内稳定性。为此，合成了CHX-A和CHX-B的四个单独的组分立体异构体，并在体外和体内研究了结合钇的能力。

  DOI：

  10.1016/s0968-0896(97)00130-2

文献信息

• Stereochemical influence on the stability of radio-metal complexes in vivo. Synthesis and evaluation of the four stereoisomers of 2-(p-nitrobenzyl)-trans-CyDTPA
  作者：C. Wu、H. Kobayashi、B. Sun、T.M. Yoo、C.H. Paik、O.A. Gansow、J.A. Carrasquillo、I. Pastan、M.W. Brechbiel

  DOI：10.1016/s0968-0896(97)00130-2

  日期：1997.10

  stability of the two diastereomeric C-Functionalized CyDTPA chelating agents, (CHX-A DTPA and CHX-B DTPA, both racemates), as recently reported prompted further investigation as to why differences in configuration produced striking effects on the in vivo stability of their yttrium complexes. To this end, the four individual component stereoisomers of CHX-A and CHX-B were synthesized and ability to bind

  两种非对映体C功能化CyDTPA螯合剂（CHX-A DTPA和CHX-B DTPA，均为外消旋物）在体内稳定性方面存在明显差异，正如最近报道的那样，这促使人们进一步进行调查，以研究为什么构型差异会对内含子产生显着影响钇配合物的体内稳定性。为此，合成了CHX-A和CHX-B的四个单独的组分立体异构体，并在体外和体内研究了结合钇的能力。
• [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