5-chloro-11-cyclohexyl-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium | 1186324-27-5

• 英文名称: 5-chloro-11-cyclohexyl-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium
• CAS: 1186324-27-5
• 化学式: C₂₀H₂₃BiClN
• 分子量: 521.843
• InChiKey: VDPHBCRUNGFZKL-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-cyclohexyl-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94%的产率得到11-cyclohexyl-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 、 环己胺 在 n-BuLi 作用下， 以 乙醚 、 正己烷 为溶剂， 以92%的产率得到5-chloro-11-cyclohexyl-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

• 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。
• Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water
  作者：Xiaowen Zhang、Shuangfeng Yin、Renhua Qiu、Jun Xia、Weili Dai、Zhenying Yu、Chak-Tong Au、Wai-Yeung Wong

  DOI：10.1016/j.jorganchem.2009.07.018

  日期：2009.10

  An air-stable hypervalent organobismuth (III) perfluorooctanesulfonate was synthesized and characterized by spectroscopic and X-ray crystallographic techniques, and found to exhibit high catalytic efficiency towards one-pot Mannich-type reaction of ketones with aromatic aldehydes and aromatic amines in water. This catalyst also shows good recyclability and reusability. This catalytic system would provide a simple, efficient and 'green' avenue towards the synthesis of beta-amino ketones. (C) 2009 Published by Elsevier B.V.