3-(2-trifluoromethylphenylsulfanyl)-1-(5-phenylpentyl)quinolin-1-ium iodide | 1299398-83-6

• 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-trifluoromethylphenylsulfanyl)-1-(5-phenylpentyl)quinolin-1-ium iodide
• 英文别名: 1-(5-phenyl-pentyl)-3-(2-trifluoromethyl-phenylsulfanyl)-quinolinium iodide；1-(5-phenylpentyl)-3-[2-(trifluoromethyl)phenyl]sulfanylquinolin-1-ium;iodide
• CAS: 1299398-83-6
• 化学式: C₂₇H₂₅F₃NS*I
• 分子量: 579.468
• InChiKey: VIGKJLIOJGOBMC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯戊醇 在 咪唑 、 碘 、 三苯基膦 作用下， 以 环丁砜 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-(2-trifluoromethylphenylsulfanyl)-1-(5-phenylpentyl)quinolin-1-ium iodide
  参考文献：
  名称：

  3-SUBSTITUTED QUINOLINIUM AND 7H-INDOLO[2,3-c]QUINOLINIUM SALTS AS NEW ANTIINFECTIVES

  摘要：

  本发明涉及喹啉类抗感染剂，其中喹啉核与吲哚环融合，或者喹啉核通过打开的吲哚或苯硫醚或苯并呋喃环与一个环状结构连接。该化合物进一步被各种取代基取代。这些化合物由化学式(I)、(II)和(III)表示。还包括药物组合物和使用方法。

  公开号：

  US20120165369A1

文献信息

• 3-substituted quinolinium and 7H-indolo[2,3-c]quinolinium salts as new antiinfectives
  申请人：Florida Agricultural and Mechanical University

  公开号：US08288410B2

  公开（公告）日：2012-10-16

  The present invention relates to quinolinium antiinfective agents in which the qunolinium nucleus is fused to an indole ring or the qunolinium nucleus is linked to a cyclic structure through an opened indole or a benzothiophene or benzofuran ring. The compound is further substituted with various substituent groups. The compounds are represented by formula (I), (II) and (III): Pharmaceutical compositions and methods of use are also included.

  本发明涉及喹啉类抗感染剂，其中喹啉核融合到吲哚环或通过开放的吲哚环或苯并噻吩或苯并呋喃环连接到环状结构。该化合物进一步被各种取代基取代。所述化合物由公式(I)、(II)和(III)表示：本发明还包括制药组合物和使用方法。
• 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.
• US8288410B2
  申请人：——

  公开号：US8288410B2

  公开（公告）日：2012-10-16