9-methoxy-5-methylbenzothieno[3,2-b]quinolin-5-ium iodide | 1265087-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-methoxy-5-methylbenzothieno[3,2-b]quinolin-5-ium iodide
• 英文别名: 9-Methoxy-5-methyl-[1]benzothiolo[3,2-b]quinolin-5-ium;iodide
• CAS: 1265087-06-6
• 化学式: C₁₇H₁₄NOS*I
• 分子量: 407.275
• InChiKey: WNCKUYDXEPFIFG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-methoxybenzothieno[3,2-b]quinoline 、 碘甲烷 以 环丁砜 为溶剂， 反应 24.0h， 以68%的产率得到9-methoxy-5-methylbenzothieno[3,2-b]quinolin-5-ium iodide
  参考文献：
  名称：

  Benzothieno[3,2-b]quinolinium and 3-(phenylthio)quinolinium compounds: Synthesis and evaluation against opportunistic fungal pathogens

  摘要：

  Substitution around 5-methyl benzothieno[3,2-b] quinolinium (2) ring system was explored in order to identify positions of substitution that could improve its antifungal profile. The 3-methoxy (10b) was active against C. albicans, C. neoformans, and A. fumigatus and the 4-chloro (10f) analog showed moderate increases in anti-cryptococcal and anti-aspergillus activities. The effectiveness of 10b and 10f were validated in murine models of candidiasis and cryptococcosis, respectively. The efficacy of 10f in reducing brain cryptococcal infection and its observation in the brain of mice injected with this quaternary compound confirm the capacity of these compounds to cross the blood-brain barrier of mice. Overall, several of the chloro and methoxy substituted compounds showed significant improvements in activity against A. fumigatus, the fungal pathogen prevalent in patients receiving organ transplant. Opening the benzothiophene ring of 2 to form 1-(5-cyclohexylpentyl)-3-(phenylthio) quinolinium compound (3) resulted in the identification of several novel compounds with over 50-fold increases in potency (cf. 2) while retaining low cytotoxicities. Thus, compound 3 constitutes a new scaffold for development of drugs against opportunistic infections. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.11.008

文献信息

• Benzothieno[3,2-b]quinolinium and 3-(phenylthio)quinolinium compounds: Synthesis and evaluation against opportunistic fungal pathogens
  作者：Comfort A. Boateng、Suresh V.K. Eyunni、Xue Y. Zhu、Jagan R. Etukala、Barbara A. Bricker、M.K. Ashfaq、Melissa R. Jacob、Shabana I. Khan、Larry A. Walker、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2010.11.008

  日期：2011.1

  Substitution around 5-methyl benzothieno[3,2-b] quinolinium (2) ring system was explored in order to identify positions of substitution that could improve its antifungal profile. The 3-methoxy (10b) was active against C. albicans, C. neoformans, and A. fumigatus and the 4-chloro (10f) analog showed moderate increases in anti-cryptococcal and anti-aspergillus activities. The effectiveness of 10b and 10f were validated in murine models of candidiasis and cryptococcosis, respectively. The efficacy of 10f in reducing brain cryptococcal infection and its observation in the brain of mice injected with this quaternary compound confirm the capacity of these compounds to cross the blood-brain barrier of mice. Overall, several of the chloro and methoxy substituted compounds showed significant improvements in activity against A. fumigatus, the fungal pathogen prevalent in patients receiving organ transplant. Opening the benzothiophene ring of 2 to form 1-(5-cyclohexylpentyl)-3-(phenylthio) quinolinium compound (3) resulted in the identification of several novel compounds with over 50-fold increases in potency (cf. 2) while retaining low cytotoxicities. Thus, compound 3 constitutes a new scaffold for development of drugs against opportunistic infections. Published by Elsevier Ltd.