5-chloro-11-phenyl-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium | 1186324-26-4

• 英文名称: 5-chloro-11-phenyl-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium
• CAS: 1186324-26-4
• 化学式: C₂₀H₁₇BiClN
• 分子量: 515.795
• InChiKey: ADEYJKFXFBWJFN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  b-triphenylgermanylpropionic acid 、 5-chloro-11-phenyl-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium 在 NaOH 作用下， 以 四氢呋喃 、 水 为溶剂， 以93%的产率得到11-phenyl-5-((3-(triphenylgermyl)propanoyl)oxy)-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium
  参考文献：
  名称：

  Synthesis, structure, and in vitro antiproliferative activity of cyclic hypervalent organobismuth(III) chlorides and their triphenylgermylpropionate derivatives

  摘要：

  Six compounds of cyclic hypervalent organobismuth(III) chlorides and triphenylgermylpropionates bearing a nitrogen or sulfur atom as intramolecular coordination atom have been synthesized and characterized. The results of single-crystal X-ray analysis reveal that the eight-membered tetrahydroazabismocine rings are highly flexible. The Bi-S or Bi-N bond lengths in the thiabismocine or azabismocine derivatives are dependent on how the substituted groups are acting on the Bi, S or N atom. The replacement of the chlorine atom in azabismocine and thiabismocine with the triphenylgermylpropionic group (Ph3GeCH2CH2COO-) leads to the lengthening of Bi-N and Bi-S bond. The substituents connected with the nitrogen atom also have an effect on the Bi-N bond length of azabismocine. For example, a cyclohexyl group has electron-donating ability higher than a phenyl group; the replacement of the former by the latter would lead to the decline of Bi-N bond length and increase of CAr-Bi-CAr angle in the eight-membered ring. The in vitro antiproliferative activities of the fabricated materials were compared on gastric carcinoma cells by means of the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl tetrazolium bromide (MTT) method. It was found that the compounds show antiproliferative activity on gastric carcinoma cells (MGC-803) much higher than that of cisplatin. Moreover, there is enhancement of antiproliferative activity when the chlorine atom of the bismocine compounds is replaced by the triphenylgermylpropionic group, giving a low IC50 value of 0.7 mu M for thiabismocine triphenylgermylpropionate. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.05.003
• 作为产物：
  描述：

  氯化铋 、 苯胺 在 n-BuLi 作用下， 以 乙醚 、 正己烷 为溶剂， 以87%的产率得到5-chloro-11-phenyl-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium
  参考文献：
  名称：

  Synthesis, structure, and in vitro antiproliferative activity of cyclic hypervalent organobismuth(III) chlorides and their triphenylgermylpropionate derivatives

  摘要：

  Six compounds of cyclic hypervalent organobismuth(III) chlorides and triphenylgermylpropionates bearing a nitrogen or sulfur atom as intramolecular coordination atom have been synthesized and characterized. The results of single-crystal X-ray analysis reveal that the eight-membered tetrahydroazabismocine rings are highly flexible. The Bi-S or Bi-N bond lengths in the thiabismocine or azabismocine derivatives are dependent on how the substituted groups are acting on the Bi, S or N atom. The replacement of the chlorine atom in azabismocine and thiabismocine with the triphenylgermylpropionic group (Ph3GeCH2CH2COO-) leads to the lengthening of Bi-N and Bi-S bond. The substituents connected with the nitrogen atom also have an effect on the Bi-N bond length of azabismocine. For example, a cyclohexyl group has electron-donating ability higher than a phenyl group; the replacement of the former by the latter would lead to the decline of Bi-N bond length and increase of CAr-Bi-CAr angle in the eight-membered ring. The in vitro antiproliferative activities of the fabricated materials were compared on gastric carcinoma cells by means of the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl tetrazolium bromide (MTT) method. It was found that the compounds show antiproliferative activity on gastric carcinoma cells (MGC-803) much higher than that of cisplatin. Moreover, there is enhancement of antiproliferative activity when the chlorine atom of the bismocine compounds is replaced by the triphenylgermylpropionic group, giving a low IC50 value of 0.7 mu M for thiabismocine triphenylgermylpropionate. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.05.003

文献信息

• Bioinspired zinc-mediated umpolung thiolation of alkyl electrophiles: reaction development, scope and mechanism
  作者：Yuenian Xu、Yan Zhang、Yong Liu、Wen-Wu Sun、Jie Huang、Hui He、Yingjie Wu、Wen Liu、Shao-Fei Ni、Xu-Qiong Xiao、Xinxin Shao

  DOI：10.1007/s11426-023-1795-9

  日期：2024.3

  Zinc-promoted umpolung thiolation of alkyl electrophiles with masked sulfur transfer reagents in the absence of nickel or copper catalysis is described. This protocol proceeds via a SET process of Zn to electrophilic sulfur reagent followed by insertion of Zn into disulfide and nucleophilic thiolation, providing straightforward access to a wide range of alkyl sulfides with broad substrate scope. A

  描述了在没有镍或铜催化的情况下，使用掩蔽硫转移试剂对烷基亲电子试剂进行锌促进的还原硫醇化。该方案通过Zn 与亲电硫试剂的 SET 过程进行，然后将 Zn 插入二硫化物和亲核硫醇化，从而可以直接获得具有广泛底物范围的各种烷基硫醚。合成、分离并通过 NMR、IR 和 X 射线分析充分表征了具有四面体几何形状的中性 TMEDA 连接的四配位硫醇锌。更重要的是，这种活性中间体的化学反应性已经得到研究，能够构建 C-SE、C-Te、Sb-S 和 Bi-S 键，以制备有价值的含硫分子等。
• Facile synthesis and antifungal evaluation of hypervalent organoantimony(iii) and organobismuth(iii) thioates with tridentate C,N,C-coordinating ligands
  作者：Zixiu Wang、Yan Huang、Dandan Deng、Shan Li、Yimei Yu、Yifei Ye、Yi Chen、Jian Lei

  DOI：10.1039/d4ob00702f

  日期：——

  In the present work, a series of organometallic thioates bearing a 5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine or -azabismocine framework were synthesized through the cross-coupling reactions of the corresponding halide precursors with thiols and disulfides at room temperature. The former transformation can be achieved under additive-free conditions, and mild dithiothreitol (DTT) is the only additive

  在本工作中，通过相应卤化物前体与 5,6,7,12-四氢二苯并[ c , f ][1,5]氮杂替博辛或-氮杂双胺骨架的交叉偶联反应合成了一系列带有 5,6,7,12-四氢二苯并[c,f][1,5]氮杂替博辛或-氮杂双胺骨架的有机金属硫酸盐。室温下的硫醇和二硫化物。前者的转化可以在无添加剂的条件下实现，而温和的二硫苏糖醇（DTT）是后者中唯一的添加剂。两种方法均具有操作简单、底物范围广、反应收率好的特点。抗真菌试验表明，合成的硫代有机铋( III )对白色念珠菌的抗菌活性明显高于临床氟康唑，而磺化锑产品的抑制作用低至可忽略不计。此外，还发现了此类含 Bi-S 键化合物的抗生物膜潜力。