(12S)-12-[2-(dimethylamino)ethyl]-3,7,18,22-tetraoxa-11,14,35,36,37,38-hexazaheptacyclo[27.3.1.12,5.16,9.116,19.120,23.124,28]octatriaconta-1(32),2(38),4,6(37),8,16,19(36),20,23(35),24,26,28(34),29(33),30-tetradecaene-10,13-dione | 1447274-33-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (12S)-12-[2-(dimethylamino)ethyl]-3,7,18,22-tetraoxa-11,14,35,36,37,38-hexazaheptacyclo[27.3.1.12,5.16,9.116,19.120,23.124,28]octatriaconta-1(32),2(38),4,6(37),8,16,19(36),20,23(35),24,26,28(34),29(33),30-tetradecaene-10,13-dione
• CAS: 1447274-33-0
• 化学式: C₃₂H₂₇N₇O₆
• 分子量: 605.61
• InChiKey: FUJMLRVGPZPFCD-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  45
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (12S)-12-(2-aminoethyl)-3,7,18,22-tetraoxa-11,14,35,36,37,38-hexazaheptacyclo[27.3.1.12,5.16,9.116,19.120,23.124,28]octatriaconta-1(32),2(38),4,6(37),8,16,19(36),20,23(35),24,26,28(34),29(33),30-tetradecaene-10,13-dione 在 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.17h， 以47%的产率得到(12S)-12-[2-(dimethylamino)ethyl]-3,7,18,22-tetraoxa-11,14,35,36,37,38-hexazaheptacyclo[27.3.1.12,5.16,9.116,19.120,23.124,28]octatriaconta-1(32),2(38),4,6(37),8,16,19(36),20,23(35),24,26,28(34),29(33),30-tetradecaene-10,13-dione
  参考文献：
  名称：

  Macrocyclic biphenyl tetraoxazoles: Synthesis, evaluation as G-quadruplex stabilizers and cytotoxic activity

  摘要：

  A series of macrocyclic biphenyl tetraoxazoles was synthesized. The latter stages of the synthetic approach allowed for the addition of varied N-protected alpha-amino acids, which were subsequently deprotected and condensed to provide the desired macrocycles. Improved yields could be realized in the macrocyclization step of their synthesis relative to other macrocyclic G-quadruplex stabilizers. These 24-membered macrocycles were evaluated for their ability to stabilize G-quadruplex DNA and for their relative cytotoxicity against human tumor cells. These biphenyl tetraoxazoles were not strong ligands for G-quadruplex DNA relative to other macrocyclic polyoxazoles. This reduced stabilizing potential did correlate with their comparatively lower cytotoxic activity as observed in the human tumor cell lines, RPMI 8402 and KB3-1. These studies provide useful insights into the conformational requirements for the development of selective and more potent G-quadruplex ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.033

文献信息

• Macrocyclic biphenyl tetraoxazoles: Synthesis, evaluation as G-quadruplex stabilizers and cytotoxic activity
  作者：Gifty A. Blankson、Daniel S. Pilch、Angela A. Liu、Leroy F. Liu、Joseph E. Rice、Edmond J. LaVoie

  DOI：10.1016/j.bmc.2013.05.033

  日期：2013.8

  A series of macrocyclic biphenyl tetraoxazoles was synthesized. The latter stages of the synthetic approach allowed for the addition of varied N-protected alpha-amino acids, which were subsequently deprotected and condensed to provide the desired macrocycles. Improved yields could be realized in the macrocyclization step of their synthesis relative to other macrocyclic G-quadruplex stabilizers. These 24-membered macrocycles were evaluated for their ability to stabilize G-quadruplex DNA and for their relative cytotoxicity against human tumor cells. These biphenyl tetraoxazoles were not strong ligands for G-quadruplex DNA relative to other macrocyclic polyoxazoles. This reduced stabilizing potential did correlate with their comparatively lower cytotoxic activity as observed in the human tumor cell lines, RPMI 8402 and KB3-1. These studies provide useful insights into the conformational requirements for the development of selective and more potent G-quadruplex ligands. (C) 2013 Elsevier Ltd. All rights reserved.