N,N'-(1,8-di(1H-pyrazol-1-yl)-9H-carbazole-3,6-diyl)bis(3-chloropropanamide) | 1375464-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N,N'-(1,8-di(1H-pyrazol-1-yl)-9H-carbazole-3,6-diyl)bis(3-chloropropanamide)
• 英文别名: 3-chloro-N-[6-(3-chloropropanoylamino)-1,8-di(pyrazol-1-yl)-9H-carbazol-3-yl]propanamide
• CAS: 1375464-10-0
• 化学式: C₂₄H₂₁Cl₂N₇O₂
• 分子量: 510.382
• InChiKey: BMWFEKCLVPOOSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  109.63
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N,N'-(1,8-di(1H-pyrazol-1-yl)-9H-carbazole-3,6-diyl)bis(3-chloropropanamide) 、 二乙胺 以 乙醇 为溶剂， 以53%的产率得到N,N'-(1,8-di(1H-pyrazol-1-yl)-9H-carbazole-3,6-diyl)bis(3-(diethylamino)propanamide)
  参考文献：
  名称：

  Disubstituted 1,8-dipyrazolcarbazole derivatives as a new type of c-myc G-quadruplex binding ligands

  摘要：

  A series of 1,8-dipyrazolcarbazole (DPC) derivatives (6a-6d, 7a-7d) designed as G-quadruplex ligands have been synthesized and characterized. The FRET-melting and SPR results showed that the DPC derivatives could well recognize G-quadruplex with strong discrimination against the duplex DNA. In addition, the DPC derivatives showed much stronger stabilization activities and binding affinities for c-myc G-quadruplex rather than telomeric G-quadruplex. Therefore, their interactions with c-myc G-quadruplex were further explored by means of CD spectroscopy, PCR-stop assay, and molecular modeling. In cellular studies, all compounds showed strong cytotoxicity against cancer cells, while weak cytotoxicity towards normal cells. RT-PCR assay showed that compound 7b could down-regulate c-myc gene expression in Ramos cell line, while had no effect on c-myc expression in CA46 cell line with NHE III1 element removed, indicating its effective binding with G-quadruplex on c-myc oncogene in vivo. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.031
• 作为产物：
  描述：

  3,6-dinitro-1,8-di(1H-pyrazol-1-yl)-9H-carbazole 在 盐酸 、 tin 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 38.0h， 生成 N,N'-(1,8-di(1H-pyrazol-1-yl)-9H-carbazole-3,6-diyl)bis(3-chloropropanamide)
  参考文献：
  名称：

  Disubstituted 1,8-dipyrazolcarbazole derivatives as a new type of c-myc G-quadruplex binding ligands

  摘要：

  A series of 1,8-dipyrazolcarbazole (DPC) derivatives (6a-6d, 7a-7d) designed as G-quadruplex ligands have been synthesized and characterized. The FRET-melting and SPR results showed that the DPC derivatives could well recognize G-quadruplex with strong discrimination against the duplex DNA. In addition, the DPC derivatives showed much stronger stabilization activities and binding affinities for c-myc G-quadruplex rather than telomeric G-quadruplex. Therefore, their interactions with c-myc G-quadruplex were further explored by means of CD spectroscopy, PCR-stop assay, and molecular modeling. In cellular studies, all compounds showed strong cytotoxicity against cancer cells, while weak cytotoxicity towards normal cells. RT-PCR assay showed that compound 7b could down-regulate c-myc gene expression in Ramos cell line, while had no effect on c-myc expression in CA46 cell line with NHE III1 element removed, indicating its effective binding with G-quadruplex on c-myc oncogene in vivo. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.031