5-O-butyroyl-2-methyl-1,4-naphthoquinone | 1238220-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-O-butyroyl-2-methyl-1,4-naphthoquinone
• 英文别名: butyrate plumbagin；(6-Methyl-5,8-dioxo-1-naphthyl) butanoate；(6-methyl-5,8-dioxonaphthalen-1-yl) butanoate
• CAS: 1238220-25-1
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: SZGCXYBIRPZAAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  兰雪醌 、 丁酸 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-O-butyroyl-2-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  Inhibition of Mycobacterial Growth by Plumbagin Derivatives

  摘要：

  Electron transport and respiratory pathways are active in both latent and rapidly growing mycobacteria and remain conserved in all mycobacterial species. In mycobacteria, menaquinone is the sole electron carrier responsible for electron transport. Menaquinone biosynthesis pathway is found to be essential for the growth of mycobacteria. Structural analogs of the substrate or product of this pathway are found to be inhibitory for the growth of Mycobacterium smegmatis and M. tuberculosis. Several plumbagin [5‐hydroxy‐2‐methyl‐1, 4‐naphthaquinone] derivatives have been analyzed for their inhibitory effects of which butyrate plumbagin was found to be most effective on M. smegmatis mc2155, whereas crotonate plumbagin showed greater activity on M. tuberculosis H37Rv. Effect on electron transport and respiration was demonstrated by butyrate plumbagin inhibiting oxygen consumption in M. smegmatis. Structural modifications of these molecules can further be improved upon to generate new molecules against mycobacteria.

  DOI：

  10.1111/j.1747-0285.2010.00987.x

文献信息

• Inhibition of Mycobacterial Growth by Plumbagin Derivatives
  作者：Ritta Mathew、Anil K. Kruthiventi、Jalli V. Prasad、Sadula P. Kumar、Garlapati Srinu、Dipankar Chatterji

  DOI：10.1111/j.1747-0285.2010.00987.x

  日期：——

  Electron transport and respiratory pathways are active in both latent and rapidly growing mycobacteria and remain conserved in all mycobacterial species. In mycobacteria, menaquinone is the sole electron carrier responsible for electron transport. Menaquinone biosynthesis pathway is found to be essential for the growth of mycobacteria. Structural analogs of the substrate or product of this pathway are found to be inhibitory for the growth of Mycobacterium smegmatis and M. tuberculosis. Several plumbagin [5‐hydroxy‐2‐methyl‐1, 4‐naphthaquinone] derivatives have been analyzed for their inhibitory effects of which butyrate plumbagin was found to be most effective on M. smegmatis mc2155, whereas crotonate plumbagin showed greater activity on M. tuberculosis H37Rv. Effect on electron transport and respiration was demonstrated by butyrate plumbagin inhibiting oxygen consumption in M. smegmatis. Structural modifications of these molecules can further be improved upon to generate new molecules against mycobacteria.