3-((4-methoxyphenyl)thio)quinoline | 1299398-49-4

• 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-((4-methoxyphenyl)thio)quinoline
• 英文别名: 3-(4-Methoxyphenyl)sulfanylquinoline
• CAS: 1299398-49-4
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: ZFESOQDIORPJCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((4-methoxyphenyl)thio)quinoline 在 吡啶盐酸盐 作用下， 以 环丁砜 为溶剂， 反应 6.0h， 生成 3-(4-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-溴喹啉 在 copper(l) iodide 、 potassium carbonate 、 乙二醇 、 sodium iodide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 78.0h， 生成 3-((4-methoxyphenyl)thio)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

• Visible-Light-Driven Halogen-Bond-Assisted Direct Synthesis of Heteroaryl Thioethers Using Transition-Metal-Free One-Pot C–I Bond Formation/C–S Cross-Coupling Reaction
  作者：Anuradha Nandy、Imran Kazi、Somraj Guha、Govindasamy Sekar

  DOI：10.1021/acs.joc.0c02672

  日期：2021.2.5

  involves two sequential reactions in a single pot where the formation of the iodinated heteroarene is followed by a transition-metal-free C–S coupling reaction. A wide range of heteroarene and thiol partners (including aliphatic thiols) have been used for the synthesis of thioethers. NMR studies and DFT calculations revealed the presence of a halogen bond between the thiolate anion (halogen bond acceptor)

  在可见光存在下，在室温下以单锅方式开发了一种直接从杂芳烃直接合成硫醚的有效方法。该方法涉及在一个罐中进行两个顺序的反应，在该反应中，形成碘化杂芳烃，然后进行无过渡金属的CS偶联反应。广泛的杂芳烃和硫醇伙伴（包括脂肪族硫醇）已用于合成硫醚。NMR研究和DFT计算表明，硫醇盐阴离子（卤素键受体）和碘杂芳烃（卤素键供体）之间存在卤素键。在光激发下，这种卤素键合的配合物有助于在室温下将电子从硫醇根阴离子转移到碘杂芳烃。
• Nickel-Catalyzed Site-Selective C3–H Functionalization of Quinolines with Electrophilic Reagents at Room Temperature
  作者：Xinghao Sheng、Mingpan Yan、Bo Zhang、Wai-Yeung Wong、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acscatal.3c01553

  日期：2023.7.21

  Herein, we disclose a mild and versatile nickel-catalyzed method for exclusive C3-selective thioetherification, alkylation, arylation, acylation, and phosphorylation of quinolines with a variety of electrophiles. Unactivated quinolines can be functionalized without directing groups at room temperature. Control experiments indicated that quinolines underwent 1,4-addition with nickel hydride species

  在此，我们公开了一种温和且通用的镍催化方法，用于喹啉与各种亲电子试剂的排他性C3选择性硫醚化、烷基化、芳基化、酰化和磷酸化。未活化的喹啉可以在室温下无需定向基团即可官能化。对照实验表明，喹啉与烷基镍中间体β-H消除产生的氢化镍物质进行1,4-加成反应生成1,4-二氢喹啉，进一步通过随后对外部亲电试剂的亲核攻击和氧化芳构化生成C3-H功能化产物。
• Nucleophilic Aromatic Substitution of Heteroaryl Halides with Thiols
  作者：Weiqi Liu、Xinghao Jin、Dawei Ma

  DOI：10.1021/acs.joc.4c00645

  日期：2024.6.21

  The nucleophilic aromatic substitution (SNAr) between heteroaryl halides (Cl, Br) and thiols proceeds smoothly in DMAc under the action of K2CO3 at rt–100 °C. For most electron-deficient heteroarenes, reaction takes place without introducing an additional electron-withdrawing group. For electron-rich heteroarenes, an additional electron-withdrawing group such as a simple ester, keto, cyano, and nitro

  在 rt–100 °C 的 K 2 CO 3作用下，杂芳基卤化物 (Cl, Br) 和硫醇之间的亲核芳香取代 (S N Ar) 在 DMAc 中顺利进行。对于大多数缺电子杂芳烃，反应的发生无需引入额外的吸电子基团。对于富电子杂芳烃，需要额外的吸电子基团（例如简单的酯基、酮基、氰基和硝基）以确保反应完成。杂芳基卤化物的反应性趋势高度依赖于杂芳烃的电子性质和卤素的方向。除了硫醇之外，一些官能化的硫脲和硫代酰胺也与这些条件相容，以良好的产率提供相应的杂芳基硫醚。
• Metallaphotoredox-Catalyzed C–S Cross-Coupling between Heteroaryl Bromides and α-Thioacetic Acids to Access Biaryl Thioethers
  作者：Alec H. Christian

  DOI：10.1021/acs.joc.1c01309

  日期：2021.8.6
• Structural Simplification of Cryptolepine to Obtain Novel Antifungal Quinoline Derivatives against Phytopathogenic Fungi
  作者：Hai-Xin Li、Xiong-Fei Luo、Peng Deng、Shao-Yong Zhang、Han Zhou、Yan Yan Ding、Yi-Rong Wang、Ying-Qian Liu、Zhi-Jun Zhang

  DOI：10.1021/acs.jafc.2c07575

  日期：2023.2.8