ethyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)propanoate | 916250-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)propanoate
• 英文别名: Ethyl 2-[(3-chloro-1,4-dioxo-2-naphthyl)sulfanyl]propanoate；ethyl 2-(3-chloro-1,4-dioxonaphthalen-2-yl)sulfanylpropanoate
• CAS: 916250-48-1
• 化学式: C₁₅H₁₃ClO₄S
• 分子量: 324.785
• InChiKey: AGHHCOMITRGOLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  83 °C
• 沸点：
  411.7±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)propanoate 在 氨 作用下， 以 乙醇 为溶剂， 生成 Ethyl 2-[(3-amino-1,4-dioxo-2-naphthyl)sulfanyl]propanoate
  参考文献：
  名称：

  Naphtho[2,3-b][1,4]-thiazine-5,10-diones and 3-substituted-1,4-dioxo-1,4-dihydronaphthalen-2-yl-thioalkanoate derivatives: Synthesis and biological evaluation as potential antibacterial and antifungal agents

  摘要：

  A series of 3-substituted-1,4-dioxo-1,4-dihydronaphthalen-2-yl-thio-alkanoate derivatives 3-21 and naphtho[2,3-b][1,4]thiazine-5,10-diones 24 were synthesized and evaluated for their antibacterial and antifungal activities. The structure-activity relationships of these compounds were studied and the results show that the compound 24a exhibited better antibacterial activity than Gentamycin in vitro against Staphylococcus aureus. In addition 24a also imparted marked antifungal activity in vitro against Cryptococcus neoformans, Sporothrix schenckii, and Trichophyton mentagraphytes when compared with Fluconazole. Compounds 15, 18, 19, and 21 also exhibited significant antibacterial activity in vitro against S. aureus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.060
• 作为产物：
  描述：

  2-巯基丙酸乙酯 、 萘茜 以 水 为溶剂， 反应 2.0h， 以93%的产率得到ethyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)propanoate
  参考文献：
  名称：

  ‘On water’ assisted synthesis and biological evaluation of nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents

  摘要：

  2-Chloro-3-(4-methylpiperazin-1-yl)naphthalene-1,4-dione (3a), 2-chloro-3-(pyrrolidin-1-yl)naphthalene-1,4-dione (3b), 2-chloro-3-(piperidin-1-yl)naphthalene-1,4-dione (3c), 2-chloro-3-morpholinonaphthalene-1,4-dione (3d), 2-chloro-3-(2-phenylhydrazinyl)naphthalene-1,4-dione (3e), 2-(allylamino)-3-chloronaphthalene-1,4-dione (3f), 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetic acid (3g), 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)succinic acid (3h), methyl 2-(3-chloro-1,4-choxo-1,4-dihydronaphthalen-2-ylthio)acetate (3i), 2-chloro-3-(2-mercaptoethylthio)naphthalene-1,4-dione (3j), 3-hydroxy-4-methyl-4H-naphtho[2,3-b][1,4]thiazine-5,10-dione (3k) and compounds 31-q have been synthesized by a green methodology approach using water as solvent and evaluated for their antifungal and antibacterial activity. The antifungal profile of 3a-n indicated that compounds 3a-d, 3j, 3e and 3k have potent antifungal activity. Amongst the most promising antifungal compounds, 3a-g, 3j, 3k showed better antifungal activity than clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Trichophyton mentagraphytes and compounds 3j and 3k have been found to be lead antifungal bicyclic and tricyclic 1,4-naphthoquinones. Compound 3k also exhibited pronounced antibacterial activity.

  DOI：

  10.1016/j.ejmech.2010.02.023