3-(19-methoxy-8,10-dioxa-2-aza-21-azoniahexacyclo[14.7.1.02,14.05,13.07,11.020,24]tetracosa-1(23),5,7(11),12,14,16(24),17,19,21-nonaen-21-yl)-N,N-dimethylpropan-1-amine;chloride | 1300029-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(19-methoxy-8,10-dioxa-2-aza-21-azoniahexacyclo[14.7.1.02,14.05,13.07,11.020,24]tetracosa-1(23),5,7(11),12,14,16(24),17,19,21-nonaen-21-yl)-N,N-dimethylpropan-1-amine;chloride
• CAS: 1300029-29-1
• 化学式: C₂₆H₂₈N₃O₃*Cl
• 分子量: 465.98
• InChiKey: CXBWGDNXCITXBV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙醇 、 盐酸小檗碱 、 N,N-二甲基-1,3-二氨基丙烷 以29%的产率得到3-(19-methoxy-8,10-dioxa-2-aza-21-azoniahexacyclo[14.7.1.02,14.05,13.07,11.020,24]tetracosa-1(23),5,7(11),12,14,16(24),17,19,21-nonaen-21-yl)-N,N-dimethylpropan-1-amine;chloride
  参考文献：
  名称：

  Quinolino-benzo-[5, 6]-dihydroisoquindolium compounds derived from berberine: A new class of highly selective ligands for G-quadruplex DNA in c-myc oncogene

  摘要：

  A series of quinolino-benzo-[5, 6]-dihydroisoquindolium compounds (3a, 3f, 3g, and 3j) derived from alkaloid berberine were designed and synthesized as novel G-quadruplex ligands. Subsequent biophysical and biochemical evaluation demonstrated that the addition of pyridine ring and amino group into berberine improved the binding ability and selectivity towards G-quadruplex DNA in comparison with the previously reported 9-N-substituted berberine derivatives. Furthermore, qRT-PCR assay showed compound 3j led the down-regulation of c-myc gene transcription in leukemia cell line HL60, while little effect on normal cell line ECV-304, which was consistent with the behavior of an effective G-quadruplex ligand targeting c-myc oncogene. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.020

文献信息

• Quinolino-benzo-[5, 6]-dihydroisoquindolium compounds derived from berberine: A new class of highly selective ligands for G-quadruplex DNA in c-myc oncogene
  作者：Yan Ma、Tian-Miao Ou、Jia-Heng Tan、Jin-Qiang Hou、Shi-Liang Huang、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2011.02.020

  日期：2011.5

  A series of quinolino-benzo-[5, 6]-dihydroisoquindolium compounds (3a, 3f, 3g, and 3j) derived from alkaloid berberine were designed and synthesized as novel G-quadruplex ligands. Subsequent biophysical and biochemical evaluation demonstrated that the addition of pyridine ring and amino group into berberine improved the binding ability and selectivity towards G-quadruplex DNA in comparison with the previously reported 9-N-substituted berberine derivatives. Furthermore, qRT-PCR assay showed compound 3j led the down-regulation of c-myc gene transcription in leukemia cell line HL60, while little effect on normal cell line ECV-304, which was consistent with the behavior of an effective G-quadruplex ligand targeting c-myc oncogene. (C) 2011 Elsevier Masson SAS. All rights reserved.