(1s,3s,5s)-N1,N3,N5-tris(2-aminoethyl)-1,3,5-trimethylcyclohexane-1,3,5-tricarboxamide | 1000289-74-6

• 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: (1s,3s,5s)-N1,N3,N5-tris(2-aminoethyl)-1,3,5-trimethylcyclohexane-1,3,5-tricarboxamide
• CAS: 1000289-74-6
• 化学式: C₁₈H₃₆N₆O₃
• 分子量: 384.522
• InChiKey: XVWPZVGTUAXLNX-BCDXTJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.59
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  165.36
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1s,3s,5s)-N1,N3,N5-tris(2-aminoethyl)-1,3,5-trimethylcyclohexane-1,3,5-tricarboxamide 、 N-甲氧基羰基顺丁烯二酰亚胺 在 四丁基硫酸氢铵 、 碳酸氢钠 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Conformational Analysis of Novel Trimeric Maleimide Cross-Linking Reagents

  摘要：

  Nine homotrifunctional cross-linking reagents are presented. Their synthesis and chemical properties as well as their characterization by classical mechanical conformational searching techniques is reported. Mixed Low Mode and Monte Carlo searching techniques were used to exhaustively sample the OPLS2005/GBSA(water) potential energy surface of trisubstituted cyclohexane and benzene derivatives of C3 symmetry. Geometric structure, molecular length, and hydrogen-bonding patterns were analyzed. Nonaromatic compounds exhibited exclusively chair conformations at low energies, with a preference for axial or equatorial arms depending upon the presence of additional ring substituent Me groups. Increasing chain length often resulted in overall shorter molecular length due to additional chain flexibility. These results were consistent with one- and two-dimensional temperature-dependent NMR studies.

  DOI：

  10.1021/jo0709293
• 作为产物：
  描述：

  KEMP'S TRIACID 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (1s,3s,5s)-N1,N3,N5-tris(2-aminoethyl)-1,3,5-trimethylcyclohexane-1,3,5-tricarboxamide
  参考文献：
  名称：

  Synthesis and Conformational Analysis of Novel Trimeric Maleimide Cross-Linking Reagents

  摘要：

  Nine homotrifunctional cross-linking reagents are presented. Their synthesis and chemical properties as well as their characterization by classical mechanical conformational searching techniques is reported. Mixed Low Mode and Monte Carlo searching techniques were used to exhaustively sample the OPLS2005/GBSA(water) potential energy surface of trisubstituted cyclohexane and benzene derivatives of C3 symmetry. Geometric structure, molecular length, and hydrogen-bonding patterns were analyzed. Nonaromatic compounds exhibited exclusively chair conformations at low energies, with a preference for axial or equatorial arms depending upon the presence of additional ring substituent Me groups. Increasing chain length often resulted in overall shorter molecular length due to additional chain flexibility. These results were consistent with one- and two-dimensional temperature-dependent NMR studies.

  DOI：

  10.1021/jo0709293

文献信息

• Synthesis and anti-HIV activity of trivalent CD4-mimetic miniproteins
  作者：Hengguang Li、Yongjun Guan、Agnieszka Szczepanska、Antonio J. Moreno-Vargas、Ana T. Carmona、Inmaculada Robina、George K. Lewis、Lai-Xi Wang

  DOI：10.1016/j.bmc.2007.03.064

  日期：2007.6

  A series of trivalent CD4-mimetic miniproteins was synthesized, in which three CD4M9 miniprotein moieties were tethered on a threefold-symmetric scaffold. The trivalent miniproteins were designed to target the CD4-binding sites displayed in the trimeric gp120 complex of HIV-1. The synthesis takes advantage of the highly efficient ligation between a cysteine-tagged CD4M9 miniprotein and a suitable trivalent maleimide that varied in the nature and length of spacer. Antiviral assay revealed that most of the synthetic trivalent miniproteins demonstrated significantly enhanced anti-HIV activities over the monomeric CD4M9 against both R5- and X4-tropic viruses, indicating the beneficial multivalent effects. One compound that possesses a hydrophobic linker was shown to be 140-fold more active than CD4M9 against HIV-1 (Bal) infection, implicating a positive contribution of the lipid portion to the antiviral activity. It was also found that most of the trivalent miniproteins showed comparable anti-HIV activities in comparison with a typical bivalent miniprotein, regardless of the length of the linker. The results implicate a novel mechanism of the interactions between the multivalent inhibitors and the trimeric gpl20 complex. (C) 2007 Elsevier Ltd. All rights reserved.