4-methyl (2-(1,4-dihydro-2-methoxy-1,4-dioxonaphthalen-3-ylthio)acetamido)butanoate | 1620127-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methyl (2-(1,4-dihydro-2-methoxy-1,4-dioxonaphthalen-3-ylthio)acetamido)butanoate
• 英文别名: Methyl 4-[[2-[(3-methoxy-1,4-dioxo-2-naphthyl)sulfanyl]acetyl]amino]butanoate；methyl 4-[[2-(3-methoxy-1,4-dioxonaphthalen-2-yl)sulfanylacetyl]amino]butanoate
• CAS: 1620127-09-4
• 化学式: C₁₈H₁₉NO₆S
• 分子量: 377.418
• InChiKey: ADPBTOYJQCOVNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲氧基-1,4-萘醌 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 4-methyl (2-(1,4-dihydro-2-methoxy-1,4-dioxonaphthalen-3-ylthio)acetamido)butanoate
  参考文献：
  名称：

  Synthesis and SAR study of novel anticancer and antimicrobial naphthoquinone amide derivatives

  摘要：

  A series of novel naphthoquinone amide derivatives of the bioactive quinones, plumbagin, juglone, menadione and lawsone, with various amino acids were synthesized. The compounds were characterized by H-1 NMR, C-13 NMR, Mass, IR and elemental analysis. All the compounds were evaluated for their anticancer activity against HeLa and SAS cancer cell lines and 3D-QSAR indicated the presence of electron donating group near sulphur enhanced the activity against HeLa cells. Among the derivatives synthesized, compounds 11f, 10a, 10b and 10g were the most active with IC50 values of 16, 12, 14 and 24.5 mu M respectively. The analogues were also screened for antimicrobial activity against two human bacterial pathogens, the Gram-positive Methicillin resistant Staphylococcus aureus (MRSA) and the Gram-negative Pseudomonas aeruginosa and a human yeast pathogen, Fluconazole resistant Candida albicans (FRCA). Among the synthesized compounds, 8g, 10g and 11g exhibited maximum antibacterial activity towards MRSA and antifungal activity against FRCA in well diffusion method. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.080

文献信息

• Synthesis and SAR study of novel anticancer and antimicrobial naphthoquinone amide derivatives
  作者：Thonthula Sreelatha、Subramani Kandhasamy、Raghu Dinesh、Suresh Shruthy、Sinha Shweta、Doble Mukesh、Devarajan Karunagaran、Ravichandran Balaji、Narayanasamy Mathivanan、Paramasivan Thirumalai Perumal

  DOI：10.1016/j.bmcl.2014.04.080

  日期：2014.8

  A series of novel naphthoquinone amide derivatives of the bioactive quinones, plumbagin, juglone, menadione and lawsone, with various amino acids were synthesized. The compounds were characterized by H-1 NMR, C-13 NMR, Mass, IR and elemental analysis. All the compounds were evaluated for their anticancer activity against HeLa and SAS cancer cell lines and 3D-QSAR indicated the presence of electron donating group near sulphur enhanced the activity against HeLa cells. Among the derivatives synthesized, compounds 11f, 10a, 10b and 10g were the most active with IC50 values of 16, 12, 14 and 24.5 mu M respectively. The analogues were also screened for antimicrobial activity against two human bacterial pathogens, the Gram-positive Methicillin resistant Staphylococcus aureus (MRSA) and the Gram-negative Pseudomonas aeruginosa and a human yeast pathogen, Fluconazole resistant Candida albicans (FRCA). Among the synthesized compounds, 8g, 10g and 11g exhibited maximum antibacterial activity towards MRSA and antifungal activity against FRCA in well diffusion method. (C) 2014 Elsevier Ltd. All rights reserved.