methyl 3,4,5-tris(3-((tert-butoxycarbonyl)amino)propoxy)benzoate | 190589-69-6

• 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 3,4,5-tris(3-((tert-butoxycarbonyl)amino)propoxy)benzoate
• 英文别名: 3,4,5-tris[3-(N-tert-butoxycarbonyl)amino-1-propanoxy]benzoic acid methyl ester；3,4,5-Tris-(3-t-butoxycarbonylaminopropoxy)benzoic acid methyl ester；methyl 3,4,5-tris[3-[(2-methylpropan-2-yl)oxycarbonylamino]propoxy]benzoate
• CAS: 190589-69-6
• 化学式: C₃₂H₅₃N₃O₁₁
• 分子量: 655.786
• InChiKey: LUPHVBVCMCGKHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  730.8±55.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  46
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 3,4,5-tris(3-((tert-butoxycarbonyl)amino)propoxy)benzoate 在 三氟乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3,4,5‐tris[3‐(2‐aminoiminomethyl)amino]propyloxybenoic acid
  参考文献：
  名称：

  A Guanidyl‐Based Bivalent Peptidomimetic Inhibits K‐Ras Prenylation and Association with c‐Raf

  摘要：

  AbstractUnusual lipid modification of K‐Ras makes Ras‐directed cancer therapy a challenging task. Aiming to disrupt electrostatic‐driven protein–protein interactions (PPIs) of K‐Ras with FTase and GGTase I, a series of bivalent dual inhibitors that recognize the active pocket and the common acidic surface of FTase and GGTase I were designed. The structure‐activity‐relationship study resulted in 8 b, in which a biphenyl‐based peptidomimetic FTI‐277 was attached to a guanidyl‐containing gallate moiety through an alkyl linker. Cell‐based evaluation demonstrated that 8 b exhibited substantial inhibition of K‐Ras processing without apparent interference with Rap‐1A processing. Fluorescent imaging showed that 8 b disrupts localization of K‐Ras to the plasma membrane and impairs interaction with c‐Raf, whereas only FTI‐277 was found to be inactive. These results suggest that targeting the PPI interface of K‐Ras may provide an alternative method of inhibiting K‐Ras.

  DOI：

  10.1002/chem.201903129
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 methyl 3,4,5-tris(3-((tert-butoxycarbonyl)amino)propoxy)benzoate
  参考文献：
  名称：

  基于氨基酸的树枝状聚合物的聚合合成和多样性

  摘要：

  以氨基酸为基础的树枝状聚合物 25（第五代，32 个端基）、30（第四代，81 个端基）、手性树枝状聚合物 23（第三代，8 个端基）以及核心修饰的树枝状聚合物 34 和 38 的聚合方法的合成是描述。氨基酸结构单元源自羟基苯甲酸衍生物和氨基醇衍生物，并且可以获得这些新型树枝状聚合物的相当大的分子多样性。合成可以相对大规模地进行，并且树枝状聚合物的这种容易获得可能导致许多潜在的应用。

  DOI：

  10.1002/1099-0690(200105)2001:10<1903::aid-ejoc1903>3.0.co;2-w

文献信息

• Module Assembly for Protein-Surface Recognition: Geranylgeranyltransferase I Bivalent Inhibitors for Simultaneous Targeting of Interior and Exterior Protein Surfaces
  作者：Shinnosuke Machida、Kakeru Usuba、Michelle A. Blaskovich、Akiko Yano、Kazuo Harada、Saïd M. Sebti、Nobuo Kato、Junko Ohkanda

  DOI：10.1002/chem.200701634

  日期：2008.2.8

  probes designed to simultaneously targeting multiple sites of protein surfaces are of interest owing to their potential application as site specific modulators of protein-protein interactions. A new approach toward bivalent inhibitors of mammalian type I geranylgeranyltransferase (GGTase I) based on module assembly for simultaneous recognition of both interior and exterior protein surfaces is reported. The

  设计用于同时靶向蛋白质表面多个位点的合成化学探针由于其作为蛋白质-蛋白质相互作用的位点特异性调节剂的潜在应用而受到关注。报道了一种基于模块组装同时识别内部和外部蛋白质表面的针对哺乳动物I型香叶基香叶基转移酶（GGTase I）的二价抑制剂的新方法。在这项研究中合成的抑制剂由通过烷基间隔基连接的两个模块组成。一个是四肽CVIL模块，用于与内部蛋白质表面（活性口袋）结合，另一个是3,4,5-烷氧基取代的苯甲酰基基序，其中包含三个氨基烷基，旨在与活性区域附近的带负电荷的蛋白质外表面结合地点。通过基于荧光光谱法的两种不同的酶抑制试验以及将[（3H）]标记的异戊二烯基结合到蛋白质底物上来筛选化合物。二价抑制剂以亚微摩尔范围的K（i）值阻断GGTase I的酶促活性，分别比四肽CVIL和苯甲酸甲酯衍生物高一个数量级，并且效力高出150倍以上。二价化合物6和8被证明是竞争性抑制剂，表明CVIL模块将整个分子锚定在GGTase
• AMPHIPHILIC JANUS-DENDRIMERS
  申请人：Percec Virgil

  公开号：US20120308640A1

  公开（公告）日：2012-12-06

  The invention concerns compounds of the formula: X—(Y) t wherein: X is Formula (X), each Y is the same or different and is Formula (Y) —O—[CH 2 —CH(OH)—CH 2 —O—] m —H; or —C(OR 5 ) 3 ; R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 9 , R 10 are each, independently, —(CH 2 CH 2 O) m —R 4 , —[CH 2 CH(OH)CH 2 O] n H, OR 11 , —O(CH 2 ) P R 13 , or —(CH 2 )R 12 ; each R 4 is independently OR 5 or OH; R 5 , R 11 and R 12 are each, independently, H or C 1 -C 30 alkyl; R 13 is —NH 3 + Cl − or —NHBoc; t is an integer from 2 to 6; m, n, and p are each, independently, an integer from 1 to 12; and each q, r, and s is 0 or 1 and the sum of q+r+s is at least 2.

  本发明涉及以下式的化合物：X—（Y）t其中：X是式（X），每个Y相同或不同，是式（Y）—O—[CH2—CH（OH）—CH2—O—]m—H；或—C（OR5）3；R1、R2、R3、R6、R7、R8、R9、R10各自独立地为—（CH2CH2O）m—R4，—[CH2CH（OH）CH2O]nH，OR11，—O（CH2）PR13或—（CH2）R12；每个R4独立地为OR5或OH；R5、R11和R12各自独立地为H或C1-C30烷基；R13为—NH3+Cl−或—NHBoc；t为2至6的整数；m、n和p各自独立地为1至12的整数；每个q、r和s为0或1，且q+r+s的总和至少为2。
• Molecular Diversity of Novel Amino Acid Based Dendrimers
  作者：Suzanne J.E. Mulders、Arwin J. Brouwer、Rob M.J. Liskamp*

  DOI：10.1016/s0040-4039(97)00551-0

  日期：1997.4

  We have expanded the recently introduced methodology for the preparation of a novel amino acid based dendrimer in order to be able to synthesize a diversity of dendrimers. For this purpose different hydroxybenzoic acids and amino alcohols were used to prepare the required monomers, necessary for construction of the respective dendrimers. (C) 1997 Elsevier Science Ltd.
• Synthesis of novel dendrimers incorporating a dye into the core
  作者：Jidong Zhang、Gérémy Drugeon、Nathalie L'hermite

  DOI：10.1016/s0040-4039(01)00533-0

  日期：2001.5

  Dendrimers 1a and 1b, with six and nine terminal tert-butyloxycarbonyl (t-Boc) protected amine groups, respectively, have been prepared by an efficient divergent synthetic approach. These novel dendrimers contain a dye Red-1 incorporated into the core, which adds to them, in addition to their physicochemical properties proper to dendrimers. an additional one that is the visibility perceptible to human eyes. This new property was particularly interesting in relation to our research of new carriers for active entities and/or antibodies. (C) 2001 Elsevier Science Ltd. All rights reserved.
• US9623046B2
  申请人：——

  公开号：US9623046B2

  公开（公告）日：2017-04-18