2,3-bis(3-methoxyphenylthio)naphthalene-1,4-dione | 1146961-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-bis(3-methoxyphenylthio)naphthalene-1,4-dione
• 英文别名: 2,3-Bis[(3-methoxyphenyl)sulfanyl]naphthalene-1,4-dione
• CAS: 1146961-27-4
• 化学式: C₂₄H₁₈O₄S₂
• 分子量: 434.537
• InChiKey: ADQDMFBIHUXFLT-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C(Solvent: Ethyl acetate; Hexane)
• 沸点：
  575.5±50.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 3-甲氧基苯硫酚 以 乙醇 为溶剂， 以93%的产率得到2,3-bis(3-methoxyphenylthio)naphthalene-1,4-dione
  参考文献：
  名称：

  2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents

  摘要：

  A series of 2-chloro-3-arylsulfanyl-[1,4]naphthoquinones (2), 2,3-bis-arylsulfanyl-[1,4]naphthoquinones (3) and 12H-benzo[b]phenothiazine-6,11-diones and their analogs 6-8 were synthesized and evaluated for their antiproliferative activity against human cervical cancer (HeLa) cells. Compounds 3a and 3b were found to possess most potent antiproliferative and cell killing ability. Compounds 1-8 were also evaluated for antifungal activities. The structure-activity relationship of these compounds was studied and the results show that compound 2a (MIC50 = 1.56 mu g/mL) exhibited in vitro potent antifungal activity compared to the clinically useful antifungal. drug Fluconazole (MIC50 = 2.0 mu g/mL) against Sporothrix. schenckii. Compound 2a (MIC50 = 1.56 mu g/mL) also exhibited same antifungal activity compared to clinically useful drug Amphotericin-B (MIC50 = 1.56 mu g/mL) against Trichophyton. mentagraphytes. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.06.025

文献信息

• 2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Ashutosh Tripathi、G.B. ShivaKeshava、Praveen K. Shukla、Pallavi Srivastava、Dulal Panda

  DOI：10.1016/j.ejmech.2008.06.025

  日期：2009.3

  A series of 2-chloro-3-arylsulfanyl-[1,4]naphthoquinones (2), 2,3-bis-arylsulfanyl-[1,4]naphthoquinones (3) and 12H-benzo[b]phenothiazine-6,11-diones and their analogs 6-8 were synthesized and evaluated for their antiproliferative activity against human cervical cancer (HeLa) cells. Compounds 3a and 3b were found to possess most potent antiproliferative and cell killing ability. Compounds 1-8 were also evaluated for antifungal activities. The structure-activity relationship of these compounds was studied and the results show that compound 2a (MIC50 = 1.56 mu g/mL) exhibited in vitro potent antifungal activity compared to the clinically useful antifungal. drug Fluconazole (MIC50 = 2.0 mu g/mL) against Sporothrix. schenckii. Compound 2a (MIC50 = 1.56 mu g/mL) also exhibited same antifungal activity compared to clinically useful drug Amphotericin-B (MIC50 = 1.56 mu g/mL) against Trichophyton. mentagraphytes. (C) 2008 Elsevier Masson SAS. All rights reserved.