methyl 3,5-bis(aminomethyl)benzoate dihydrochloride

• 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: methyl 3,5-bis(aminomethyl)benzoate dihydrochloride
• 英文别名: Methyl 3,5-bis(aminomethyl)benzoate;hydrochloride
• 化学式: C₁₀H₁₄N₂O₂*2ClH
• 分子量: 267.155
• InChiKey: PKFILMGOFLIKMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3,5-bis(aminomethyl)benzoate dihydrochloride 、 cholic acid N-succinimidyl ester 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以50%的产率得到methyl 3,5-bis[[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]methyl]benzoate
  参考文献：
  名称：

  Solvent-Induced Amphiphilic Molecular Baskets:  Unimolecular Reversed Micelles with Different Size, Shape, and Flexibility

  摘要：

  Amphiphilic molecular baskets were obtained by attaching facially amphiphilic cholate groups to a covalent scaffold (calix[4] arene or 1,3,5-2,4,6-hexasubstituted benzene). In a solvent mixture consisting of mostly a nonpolar solvent (i.e., CCl4) and a polar solvent (i.e., DMSO), the hydrophilic faces of cholates turned inward to form a reversed-micelle-like conformer whose stability was strongly influenced by the number of the cholates and the topology of the scaffold. Preferential solvation of the hydrophilic faces of cholates within the molecule by the polar solvent was cooperative and gave the fundamental driving force to the conformational change. The reversed-micelle-like conformer was most stable in structures that allowed multiple cholates to form a microenvironment that could efficiently enrich the polar solvent molecules from the bulk solvent mixture.

  DOI：

  10.1021/jo0607663
• 作为产物：
  描述：

  3,5-双(溴甲基)苯甲酸甲酯 、 methyl-3,5-bis(azidomethyl)benzoate 在 盐酸 、 四丁基溴化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 生成 methyl 3,5-bis(aminomethyl)benzoate dihydrochloride
  参考文献：
  名称：

  Amplifier molecules for enhancement of diagnosis and therapy

  摘要：

  揭示了放大器分子：各种具有分支结构并以胺基终止的有机化合物，可在其上化学地连接药理活性基团。合成了多种MRI增强对比剂，每种包含多个活性基团，如稳定的亚硝基和三价金属阳离子的络合物。使用具有不同分支结构的多种放大器成功地进行了这些合成，展示了相关化学在合成具有各种药理活性基团的放大器方面的普遍实用性。还合成了具有终止于化学反应性基团（如异硫氰酸酯）的连接剂的放大器，使放大器具有双功能性：可连接到聚合物、生物大分子或其他具有多个反应位点（如末端胺基）的生物兼容实体。通过这种化学方法，可以将放大器连接到单克隆抗体，以便将药理活性基团浓集在体内所需的部位。

  公开号：

  US05135737A1

文献信息

• US5135737A
  申请人：——

  公开号：US5135737A

  公开（公告）日：1992-08-04
• US5252317A
  申请人：——

  公开号：US5252317A

  公开（公告）日：1993-10-12
• US5412148A
  申请人：——

  公开号：US5412148A

  公开（公告）日：1995-05-02
• [EN] AMPLIFIER MOLECULES FOR ENHANCEMENT OF DIAGNOSIS AND THERAPY<br/>[FR] MOLECULES AMPLIFICATRICES PERMETTANT D'AMELIORER LE DIAGNOSTIC ET LA THERAPIE
  申请人：THE STATE OF OREGON ACTING BY AND THROUGH THE STATE BOARD OF HIGHER EDUCATION ON BEHALF OF THE UNIVERSITY OF OREGON

  公开号：WO1994003593A1

  公开（公告）日：1994-02-17

  (EN) Disclosed are amplifier molecules: various organic compounds having branched structures terminating with amine groups to which pharmacologically active groups can be chemically attached. A number of MRI contrast-enhancing agents were synthesized, each comprising plural active groups, such as stable nitroxides and complexes of trivalent metal cations. Such syntheses were successfully performed using a number of amplifiers having different branched structures, demonstrating the general utility of the pertinent chemistry in the synthesis of amplifiers having any of a wide variety of pharmacologically active groups. Amplifiers were also synthesized having linkers terminating with chemically reactive groups such as isothiocyanates, which render the amplifier bifunctional: attachable to polymers, biomacromolecules, or other biocompatible entity possessing multiple reactive sites such as terminal amines. Via such chemistry, the amplifiers are attachable to monoclonal antibodies for concentration of pharmacologically active groups at a desired site in the body.(FR) L'invention se rapporte à des molécules d'amplification qui peuvent être divers composés organiques à structures ramifiées se terminant par des groupes d'amines auxquels des groupes pharmacologiquement actifs peuvent être liés chimiquement. Plusieurs agents de contraste à RNM comprenant chacun plusieurs groupes actifs tels que des oxydes azotés stables et des complexes de cations métalliques trivalents ont été synthétisés. Ces synthèses ont été réalisées avec succès à l'aide d'un certain nombre d'amplificateurs présentant des structures ramifiées différentes, ce qui a permis de démontrer l'utilité générale de la chimie pertinente dans la synthèse d'amplificateurs comprenant une grande variété de groupes pharmacologiquement actifs. On a également synthétisé des amplificateurs comprenant des segments de liaison se terminant par des groupes chimiquement réactifs tels que les isothiocyanates qui rendent l'amplificateur bifonctionnel, c'est-à-dire liable à des polymères, des biomacromolécules ou d'autres entités biocompatibles possédant de multiples sites réactifs tels que les amines terminales. Grâce à ce type de chimie, les amplificateurs peuvent être liés à des anticorps monoclonaux pour la concentration de groupes pharmacologiquement actifs dans un site choisi du corps.
• Solvent-Induced Amphiphilic Molecular Baskets:  Unimolecular Reversed Micelles with Different Size, Shape, and Flexibility
  作者：Eui-Hyun Ryu、Jie Yan、Zhenqi Zhong、Yan Zhao

  DOI：10.1021/jo0607663

  日期：2006.9.1

  Amphiphilic molecular baskets were obtained by attaching facially amphiphilic cholate groups to a covalent scaffold (calix[4] arene or 1,3,5-2,4,6-hexasubstituted benzene). In a solvent mixture consisting of mostly a nonpolar solvent (i.e., CCl4) and a polar solvent (i.e., DMSO), the hydrophilic faces of cholates turned inward to form a reversed-micelle-like conformer whose stability was strongly influenced by the number of the cholates and the topology of the scaffold. Preferential solvation of the hydrophilic faces of cholates within the molecule by the polar solvent was cooperative and gave the fundamental driving force to the conformational change. The reversed-micelle-like conformer was most stable in structures that allowed multiple cholates to form a microenvironment that could efficiently enrich the polar solvent molecules from the bulk solvent mixture.