[2-(3-Amino-propoxy)-1,1-bis-(3-amino-propoxymethyl)-ethyl]-carbamic acid benzyl ester | 510753-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-(3-Amino-propoxy)-1,1-bis-(3-amino-propoxymethyl)-ethyl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[1,3-bis(3-aminopropoxy)-2-(3-aminopropoxymethyl)propan-2-yl]carbamate
• CAS: 510753-80-7
• 化学式: C₂₁H₃₈N₄O₅
• 分子量: 426.557
• InChiKey: DKCUPGIHWXJAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [2-(3-Amino-propoxy)-1,1-bis-(3-amino-propoxymethyl)-ethyl]-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-[3-[2-amino-3-[3-[[2-[diethoxy(oxido)phosphaniumyl]acetyl]amino]propoxy]-2-[3-[[2-[diethoxy(oxido)phosphaniumyl]acetyl]amino]propoxymethyl]propoxy]propyl]-2-[diethoxy(oxido)phosphaniumyl]acetamide
  参考文献：
  名称：

  CMP(O) tripodands: synthesis, potentiometric studies and extractions

  摘要：

  含有三个羧甲基膦酸酯（CMP）或-膦氧化物（CMPO）基团的配体系统通过连接在三脚架平台上，已合成用于金属络合并从HNO3溶液中提取。结合到离子选择性电极（ISE）和苦味酸盐萃取中，与Na+、K+、Ag+、Ca2+、Cd2+、Hg2+、Pb2+、Cu2+、Eu3+和Fe3+的实验表明，CMPO三脚配体3对Eu3+非常选择性，并形成非常稳定的络合物（log βML = 28.3）。通过Eu3+和Am3+进行的液-液萃取显示CMP（O）三脚配体3、11和13在1,1,2,2-四氯乙烷中具有合理的萃取性能，而在1-辛醇中所有研究的三脚配体的分配系数都较低。在加入协同剂六溴化钴双（二碳硼烷）阴离子（溴-COSAN）后，CMP（O）三脚配体3和4对Am3+和Eu3+的萃取分配系数显著增加。共价连接的COSAN仅在0.001-0.01 M HNO3中增强Am3+和Eu3+的萃取。利用CMP（O）三脚配体功能化的树枝状磁性硅基粒子，导致从0.01 M HNO3溶液中有效去除Am3+和Eu3+的粒子（31和32）。

  DOI：

  10.1039/b600412a
• 作为产物：
  描述：

  tris(cyanoethoxymethyl)aminomethane 在 sodium tetrahydroborate 、 碳酸氢钠 、 cobalt(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 生成 [2-(3-Amino-propoxy)-1,1-bis-(3-amino-propoxymethyl)-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Syntheses of dendritic linkers containing chlorambucil residues for the preparation of antibody–multidrug immunoconjugates

  摘要：

  A novel dendritic molecule with nine chlorambucil (CBL) residues on the surface and a maleimide moiety at the core terminus was synthesized using a convergent synthetic methodology. This molecule is ready for attachment to single-chain Fv antibodies (scFvs) to form antibody-multidrug immunoconjugates in an effort to study the relevance of drug/antibody molar ratio and the potency of these drug antibody immunoconjugates. A monomer and a trimer with a similar structural motif were also prepared for comparative purposes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00361-x

文献信息

• Enabling ScFvs as multi-drug carriers: A dendritic approach
  作者：Chengzao Sun、Peter Wirsching、Kim D Janda

  DOI：10.1016/s0968-0896(03)00057-9

  日期：2003.4

  To enable scFvs as multi-drug carriers, we designed and synthesized dendritic linker molecules bearing up to nine chlorambucil residues at the branch ends. A maleimide group was used at the focal point of the dendron for easy linkage to the scFv. Originally designed molecules showed poor water solubility. To address this problem, a lysine residue with an unprotected carboxylic acid group was inserted into the dendron branches. The new molecules showed excellent water solubility and are now suitable for conjugation. Such dendritic molecules will allow studies to understand the relationship between the drug/antibody ratio and the potency of the immunoconjugates. The dendritic approach could also be applied to drugs other than chlorambucil and carriers other than scFvs to greatly increase the drug/carrier ratio. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A novel 1→3 C-branched isocyanate monomer for resin amplification—a pseudo PS-PEG high-loading resin
  作者：Sylvain Lebreton、Nicholas Newcombe、Mark Bradley

  DOI：10.1016/s0040-4039(02)00295-2

  日期：2002.3

  High loading resins (up to 120 nmoles/bead) were preprared by solid-phase dendrimerisation using a novel 1-->3 C-branched isocyanate monomer. (C) 2002 Published by Elsevier Science Ltd.
• Solid-phase construction: high efficiency dendrimer synthesis using AB3 isocyanate-type monomers
  作者：Sylvain Lebreton、Siew-Eng How、Monika Buchholz、Boon-Ek Yingyongnarongkul、Mark Bradley

  DOI：10.1016/s0040-4020(03)00463-0

  日期：2003.5

  Solid-phase synthesis is an ideal tool for reactions that require high concentrations and excess reagents and forcing chemical conditions. One such chemistry is that required for dendrimer construction. In this paper the synthesis of a series of symmetrical AB(3) isocyanate-type monomers is reported and used for the preparation of tri-branched dendrimers on the solid-phase. This method not only allows isolable dendrimer but can generate high-loading supports and devices for multivalent presentation. (C) 2003 Elsevier Science Ltd. All rights reserved.
• CMP(O) tripodands: synthesis, potentiometric studies and extractions
  作者：Marta M. Reinoso-García、Dominik Jańczewski、David N. Reinhoudt、Willem Verboom、Elżbieta Malinowska、Mariusz Pietrzak、Clement Hill、Jiří Báča、Bohumír Grüner、Pavel Selucky、Cordula Grüttner

  DOI：10.1039/b600412a

  日期：——

  Ligand systems containing three carbamoylmethylphosphonate (CMP) or -phosphine oxide (CMPO) moieties attached to a tripodal platform have been synthesized for metal complexation and subsequent extraction from HNO3 solutions. The incorporation into ion selective electrodes (ISE) and picrate extractions with Na+, K+, Ag+, Ca2+, Cd2+, Hg2+, Pb2+, Cu2+, Eu3+ and Fe3+ shows that CMPO tripodand 3 is very selective for Eu3+ and forms a very stable complex (log βML = 28.3). Liquid–liquid extractions performed with Eu3+ and Am3+ show reasonable extraction properties of the CMP(O) tripodands 3, 11 and 13 in 1,1,2,2-tetrachloroethane, while in 1-octanol for all tripodands studied the distribution coefficients are low. Upon addition of the synergistic agent hexabrominated cobalt bis(dicarbollide) anion (bromo-COSAN) the distribution coefficients for Am3+ and Eu3+ extraction increase considerably for CMP(O) tripodands 3 and 4. Covalently linked COSAN only enhances the extraction of Am3+ and Eu3+ at 0.001–0.01 M HNO3. The functionalization of dendrimer coated magnetic silica particles with CMP(O) tripodands led to very effective particles (31 and 32) for Am3+ and Eu3+ removal from 0.01 M HNO3 solutions.

  含有三个羧甲基膦酸酯（CMP）或-膦氧化物（CMPO）基团的配体系统通过连接在三脚架平台上，已合成用于金属络合并从HNO3溶液中提取。结合到离子选择性电极（ISE）和苦味酸盐萃取中，与Na+、K+、Ag+、Ca2+、Cd2+、Hg2+、Pb2+、Cu2+、Eu3+和Fe3+的实验表明，CMPO三脚配体3对Eu3+非常选择性，并形成非常稳定的络合物（log βML = 28.3）。通过Eu3+和Am3+进行的液-液萃取显示CMP（O）三脚配体3、11和13在1,1,2,2-四氯乙烷中具有合理的萃取性能，而在1-辛醇中所有研究的三脚配体的分配系数都较低。在加入协同剂六溴化钴双（二碳硼烷）阴离子（溴-COSAN）后，CMP（O）三脚配体3和4对Am3+和Eu3+的萃取分配系数显著增加。共价连接的COSAN仅在0.001-0.01 M HNO3中增强Am3+和Eu3+的萃取。利用CMP（O）三脚配体功能化的树枝状磁性硅基粒子，导致从0.01 M HNO3溶液中有效去除Am3+和Eu3+的粒子（31和32）。
• Syntheses of dendritic linkers containing chlorambucil residues for the preparation of antibody–multidrug immunoconjugates
  作者：Chengzao Sun、Peter Wirsching、Kim D. Janda

  DOI：10.1016/s0960-894x(02)00361-x

  日期：2002.8

  A novel dendritic molecule with nine chlorambucil (CBL) residues on the surface and a maleimide moiety at the core terminus was synthesized using a convergent synthetic methodology. This molecule is ready for attachment to single-chain Fv antibodies (scFvs) to form antibody-multidrug immunoconjugates in an effort to study the relevance of drug/antibody molar ratio and the potency of these drug antibody immunoconjugates. A monomer and a trimer with a similar structural motif were also prepared for comparative purposes. (C) 2002 Elsevier Science Ltd. All rights reserved.