10-(azulene-1-carboxy)phenothiabismine 5,5-dioxide | 1442441-70-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 10-(azulene-1-carboxy)phenothiabismine 5,5-dioxide
• 英文别名: (5,5-dioxobenzo[b][1,4]benzothiabismin-10-yl) azulene-1-carboxylate
• CAS: 1442441-70-4
• 化学式: C₂₃H₁₅BiO₄S
• 分子量: 596.416
• InChiKey: YKPDLTBUANKOKI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  10-(4-methylphenyl)phenothiabismine 5,5-dioxide 在 三氟化硼乙醚 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 10-(azulene-1-carboxy)phenothiabismine 5,5-dioxide
  参考文献：
  名称：

  Heterocyclic bismuth carboxylates based on a diphenyl sulfone scaffold: Synthesis and antifungal activity against Saccharomyces cerevisiae

  摘要：

  A series of heterocyclic organobismuth(III) carboxylates 4 and 5 [RCO2Bi(C6H4-2-SO2C6H4-1'-)] derived from diphenyl sulfone was synthesized to determine the influence of the carboxylate ligand structure on the lipophilicity and antifungal activity against the yeast Saccharomyces cerevisiae. In contrast to the clear structure-activity relationship between the size of the inhibition zone and the value of ClogP for specific substitution on diphenyl sulfone scaffold 1 [ClBi(5-RC6H3-2-SO2C6H4-1'-)], scaffolds 4 and 5 showed similar inhibition activities irrespective of the ClogP value. This suggests that these molecules function inside the yeast cell by separating into the cationic heterocyclic bismuth scaffold and the anionic carboxylate moiety, and that the bismuth scaffold plays an important role in the inhibition activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.036

文献信息

• Heterocyclic bismuth carboxylates based on a diphenyl sulfone scaffold: Synthesis and antifungal activity against Saccharomyces cerevisiae
  作者：Toshihiro Murafuji、Kunito Kitagawa、Daisuke Yoshimatsu、Kei Kondo、Katsuya Ishiguro、Ryo Tsunashima、Isamu Miyakawa、Yuji Mikata

  DOI：10.1016/j.ejmech.2013.02.036

  日期：2013.5

  A series of heterocyclic organobismuth(III) carboxylates 4 and 5 [RCO2Bi(C6H4-2-SO2C6H4-1'-)] derived from diphenyl sulfone was synthesized to determine the influence of the carboxylate ligand structure on the lipophilicity and antifungal activity against the yeast Saccharomyces cerevisiae. In contrast to the clear structure-activity relationship between the size of the inhibition zone and the value of ClogP for specific substitution on diphenyl sulfone scaffold 1 [ClBi(5-RC6H3-2-SO2C6H4-1'-)], scaffolds 4 and 5 showed similar inhibition activities irrespective of the ClogP value. This suggests that these molecules function inside the yeast cell by separating into the cationic heterocyclic bismuth scaffold and the anionic carboxylate moiety, and that the bismuth scaffold plays an important role in the inhibition activity. (C) 2013 Elsevier Masson SAS. All rights reserved.