N-(4-(methylthio)phenyl)pyridin-3-amine | 1268526-04-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(4-(methylthio)phenyl)pyridin-3-amine
• 英文别名: N-(4-methylsulfanylphenyl)pyridin-3-amine
• CAS: 1268526-04-0
• 化学式: C₁₂H₁₂N₂S
• 分子量: 216.307
• InChiKey: MKMPGZUTTJWDIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-(methylthio)phenyl)pyridin-3-amine 在 palladium diacetate 、 三氟乙酸 、 氨 作用下， 以 水 为溶剂， 反应 6.0h， 以40%的产率得到8-(methylthio)-5H-pyrido[3,2-b]indole
  参考文献：
  名称：

  δ-Carbolines and their ring-opened analogs: Synthesis and evaluation against fungal and bacterial opportunistic pathogens

  摘要：

  Previous studies have indicated that the delta-carboline (2) ring system derived from the natural product cryptolepine (1) may represent a pharmacophore for anti-infective activity. This paper describes the design and synthesis of a small library of substituted delta-carbolines and the evaluation of the anti-fungal and anti-bacterial activities. An evaluation of the anti-bacterial activity of a previously reported library of ring-opened analogs was also conducted to provide an opportunity to test the hypothesis that both group of compounds may have the same biological target. Results indicate that against a selected group of fungal pathogens, substituted delta-carbolinium analogs displayed higher potency and several fold lower cytotoxicity than cryptolepine the parent natural product. Both the delta-carbolinium compounds and their ring-opened analogs, exhibited equally high anti-bacterial activity against the selected pathogens and especially against the gram positive bacteria evaluated. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.03.021
• 作为产物：
  描述：

  3-氨基吡啶 、 4-甲硫基苯硼酸 在 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-(methylthio)phenyl)pyridin-3-amine
  参考文献：
  名称：

  Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens

  摘要：

  Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.10.065