Dimethyl-(10-thiophen-2-yl-3-selena-17-azapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-1(21),2(11),4,7,9,12-hexaen-6-ylidene)azanium;bromide | 1103256-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Dimethyl-(10-thiophen-2-yl-3-selena-17-azapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-1(21),2(11),4,7,9,12-hexaen-6-ylidene)azanium;bromide
• CAS: 1103256-38-7
• 化学式: Br*C₂₅H₂₅N₂SSe
• 分子量: 544.417
• InChiKey: VFQYCDVAHUEWMN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴噻吩 、 6-(Dimethylamino)-3-selena-17-azapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-1(21),2(11),4(9),5,7,12-hexaen-10-one 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以77%的产率得到Dimethyl-(10-thiophen-2-yl-3-selena-17-azapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-1(21),2(11),4,7,9,12-hexaen-6-ylidene)azanium;bromide
  参考文献：
  名称：

  Substituent control of DNA binding modes in a series of chalcogenoxanthylium photosensitizers as determined by isothermal titration calorimetry and topoisomerase I DNA unwinding assay

  摘要：

  The DNA binding efficacy and preferred mode of binding of a series of rhodamine-related chalcogenoxan-thylium dyes was investigated by isothermal titration calorimetry (ITC) using ctDNA, [poly(dCdG)](2) and [poly(dAdT)](2), and by a topoisomerase I DNA unwinding ( Topo I) assay. The dyes of this study showed tight binding to ctDNA with binding constants, K(b), on the order of 10(6)-10(7) M(-1). The ITC and Topo I assay studies suggested that the 9-substituent has a strong impact on binding modes ranging from an apparent preference for intercalation with a 9-2-thienyl substituent ( similar binding to [poly(dCdG)](2) and [poly(dAdT)](2), re-supercoiling of DNA in the Topo I assay at <10(-5) M dye), to mixed binding modes with 9-phenyl derivatives (2- to 3-fold preference for binding to [poly(dAdT)](2), re-supercoiling of DNA in the Topo I assay at similar to 2 x 10(-5) M dye), to minor groove binding in a 9-(2-thienyl-5-diethylcarboxamide) derivative (strong preference for binding to [poly(dAdT)](2), did not show complete re-supercoiling in the Topo I assay). No binding to ctDNA was observed in one derivative with a 9-(3-thienyl-2-diethylcarboxamide) substituent, which cannot be co-planar with the xanthylium core. In series of dyes where the chalcogen atom was varied, the selenoxanthylium derivatives had 2- to 3-fold higher values of Kb than the corresponding xanthylium, thioxanthylium, or telluroxanthylium derivatives, which all showed comparable values of Kb. The chalcogen atom appeared to have little influence on binding mode. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.051