7-chloro-9-methoxy-5,6-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]acridin-8-yl benzenesulfonate | 1359946-06-7

• 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: 7-chloro-9-methoxy-5,6-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]acridin-8-yl benzenesulfonate
• 英文别名: (14-Chloro-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,13,15(20),16,18-octaen-16-yl) benzenesulfonate
• CAS: 1359946-06-7
• 化学式: C₂₅H₁₈ClNO₆S
• 分子量: 495.94
• InChiKey: AZJNHNBGBGPTMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-chloro-9-methoxy-5,6-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]acridin-8-yl benzenesulfonate 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 56.0h， 生成 9-methoxy-12-methyl-8-(3-(pyrrolidin-1-yl)propoxy)-5,6-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]acridin-12-ium chloride
  参考文献：
  名称：

  12-N-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for c-myc G-quadruplex DNA

  摘要：

  12-N-Methylated and non-methylated 5,6-dihydrobenzo[c]acridine derivatives were designed and synthesized as new series of c-myc G-quadruplex binding ligands. Their interactions with c-myc G-quadruplex were evaluated using fluorescence resonance energy transfer (FRET) melting assay, circular dichroism (CD) spectroscopy, surface plasmon resonance (SPR), polymerase chain reaction (PCR) stop assay, and molecular modeling. Compared with the non-methylated derivatives, 12-N-methylated derivatives had stronger binding affinity and stabilizing ability to c-myc G-quadruplex structure, and could more effectively stack on the G-quartet surface. All these derivatives had high selectivity for c-myc G-quadruplex DNA over duplex DNA. The reverse transcription (RT) PCR assay showed that compound 21c could down-regulate transcription of c-myc gene in Ramos cell line containing NHE III1 element, but had no effect in CA46 cell line with NHE III1 element removed. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.034
• 作为产物：
  描述：

  邻苯二甲醚 在 三乙基硅烷 、 aluminum (III) chloride 、 potassium fluoride 、 氢溴酸 、 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 、 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.17h， 生成 7-chloro-9-methoxy-5,6-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]acridin-8-yl benzenesulfonate
  参考文献：
  名称：

  12-N-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for c-myc G-quadruplex DNA

  摘要：

  12-N-Methylated and non-methylated 5,6-dihydrobenzo[c]acridine derivatives were designed and synthesized as new series of c-myc G-quadruplex binding ligands. Their interactions with c-myc G-quadruplex were evaluated using fluorescence resonance energy transfer (FRET) melting assay, circular dichroism (CD) spectroscopy, surface plasmon resonance (SPR), polymerase chain reaction (PCR) stop assay, and molecular modeling. Compared with the non-methylated derivatives, 12-N-methylated derivatives had stronger binding affinity and stabilizing ability to c-myc G-quadruplex structure, and could more effectively stack on the G-quartet surface. All these derivatives had high selectivity for c-myc G-quadruplex DNA over duplex DNA. The reverse transcription (RT) PCR assay showed that compound 21c could down-regulate transcription of c-myc gene in Ramos cell line containing NHE III1 element, but had no effect in CA46 cell line with NHE III1 element removed. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.034