3-(2-hydroxyphenylthio)quinoline | 1299398-56-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(2-hydroxyphenylthio)quinoline
• 英文别名: 2-Quinolin-3-ylsulfanylphenol
• CAS: 1299398-56-3
• 化学式: C₁₅H₁₁NOS
• 分子量: 253.324
• InChiKey: ASXAHXMVTGUJCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(iodopentyl) cyclohexane 、 3-(2-hydroxyphenylthio)quinoline 以 环丁砜 为溶剂， 以37%的产率得到3-(2-hydroxyphenylsulfanyl)-1-(5-cyclohexylpentyl)quinolin-1-ium iodide
  参考文献：
  名称：

  Optimization of 3-(phenylthio)quinolinium compounds against opportunistic fungal pathogens

  摘要：

  Ring-opened benzothieno[3,2-b]quinolinium salts (3) were designed and synthesized with substitution on the thiophene moiety. In vitro screenings were carried out against fungal pathogens including Cryptococcus neoformans, Candida albicans, Candida glabrata, Candida krusei and Aspergillus fumigatus. In all, by replacing the N-methyl group (2) with N-omega-phenylpentyl or omega-cyclohexylpentyl group to form substituted 3-(phenylthio)quinolinium compounds produced remarkable potencies, as high as 300-fold (cf. cryptolepine (1) = 250 mu g/mL vs lip = 0.8 mu g/mL for C. albicans) over the starting tetracyclic parent. In addition, all the N-omega-cyclohexylpentyl analogs produced superior activity against all the microorganisms tested than the N-omega-phenylpentyl substituted compounds. The potential of these compounds to induce toxicity in Vero cells was also investigated and the majority of them showed lower or no cytotoxicity at 10 mu g/mL than amphotericin B. the gold standard in antifungal drug development. For instance, the trifluoromethyl substituted analogs (11n-p) have selectivity indices over 2-fold better than those of amphotericin B in C. neoformans. Overall, this ring-opened scafford of benzothienoquinolines, with substitution on the thiophenyl moiety, serves as a new lead for further development. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.02.034
• 作为产物：
  描述：

  3-((2-methoxyphenyl)thio)quinoline 在 吡啶盐酸盐 作用下， 反应 6.0h， 以51%的产率得到3-(2-hydroxyphenylthio)quinoline
  参考文献：
  名称：

  Optimization of 3-(phenylthio)quinolinium compounds against opportunistic fungal pathogens

  摘要：

  Ring-opened benzothieno[3,2-b]quinolinium salts (3) were designed and synthesized with substitution on the thiophene moiety. In vitro screenings were carried out against fungal pathogens including Cryptococcus neoformans, Candida albicans, Candida glabrata, Candida krusei and Aspergillus fumigatus. In all, by replacing the N-methyl group (2) with N-omega-phenylpentyl or omega-cyclohexylpentyl group to form substituted 3-(phenylthio)quinolinium compounds produced remarkable potencies, as high as 300-fold (cf. cryptolepine (1) = 250 mu g/mL vs lip = 0.8 mu g/mL for C. albicans) over the starting tetracyclic parent. In addition, all the N-omega-cyclohexylpentyl analogs produced superior activity against all the microorganisms tested than the N-omega-phenylpentyl substituted compounds. The potential of these compounds to induce toxicity in Vero cells was also investigated and the majority of them showed lower or no cytotoxicity at 10 mu g/mL than amphotericin B. the gold standard in antifungal drug development. For instance, the trifluoromethyl substituted analogs (11n-p) have selectivity indices over 2-fold better than those of amphotericin B in C. neoformans. Overall, this ring-opened scafford of benzothienoquinolines, with substitution on the thiophenyl moiety, serves as a new lead for further development. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.02.034

文献信息

• Optimization of 3-(phenylthio)quinolinium compounds against opportunistic fungal pathogens
  作者：Comfort A. Boateng、Xue Y. Zhu、Melissa R. Jacob、Shabana I. Khan、Larry A. Walker、Seth Y. Ablordeppey

  DOI：10.1016/j.ejmech.2011.02.034

  日期：2011.5

  Ring-opened benzothieno[3,2-b]quinolinium salts (3) were designed and synthesized with substitution on the thiophene moiety. In vitro screenings were carried out against fungal pathogens including Cryptococcus neoformans, Candida albicans, Candida glabrata, Candida krusei and Aspergillus fumigatus. In all, by replacing the N-methyl group (2) with N-omega-phenylpentyl or omega-cyclohexylpentyl group to form substituted 3-(phenylthio)quinolinium compounds produced remarkable potencies, as high as 300-fold (cf. cryptolepine (1) = 250 mu g/mL vs lip = 0.8 mu g/mL for C. albicans) over the starting tetracyclic parent. In addition, all the N-omega-cyclohexylpentyl analogs produced superior activity against all the microorganisms tested than the N-omega-phenylpentyl substituted compounds. The potential of these compounds to induce toxicity in Vero cells was also investigated and the majority of them showed lower or no cytotoxicity at 10 mu g/mL than amphotericin B. the gold standard in antifungal drug development. For instance, the trifluoromethyl substituted analogs (11n-p) have selectivity indices over 2-fold better than those of amphotericin B in C. neoformans. Overall, this ring-opened scafford of benzothienoquinolines, with substitution on the thiophenyl moiety, serves as a new lead for further development. Published by Elsevier Masson SAS.