5-O-propionoyl-2-methyl-1,4-naphthoquinone | 1238220-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-O-propionoyl-2-methyl-1,4-naphthoquinone
• 英文别名: 5-propanoyloxy-2-methyl-1,4-naphthoquinone；propionate plumbagin；plumbagin propionic acid ester；(6-Methyl-5,8-dioxo-1-naphthyl) propanoate；(6-methyl-5,8-dioxonaphthalen-1-yl) propanoate
• CAS: 1238220-30-8
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: ISLUOBCWKRZHJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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 、 丙酸 在 4-二甲氨基吡啶 、 2-甲基-6-硝基苯甲酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到5-O-propionoyl-2-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  JP2015/54842

  摘要：

  公开号：

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.
• ANTI-CANCER LEAD MOLECULE
  申请人：KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20140107196A1

  公开（公告）日：2014-04-17

  Derivatives of plumbagin can be selectively cytotoxic to breast cancer cells. Derivative ‘A’ (Acetyl Plumbagin) has emerged as a lead molecule for testing against estrogen positive breast cancer and has shown low hepatotoxicity as well as overall lower toxicity in nude mice model. The toxicity of derivative ‘A’ was determined to be even lower than vehicle control (ALT and AST markers). The possible mechanism of action identified based on the microarray experiments and pathway mapping shows that derivative ‘A’ could be acting by altering the cholesterol-related mechanisms. The low toxicity profile of derivative ‘A’ highlights its possible role'as future anti-cancer drug and/or as an adjuvant drug to reduce the toxicity of highly toxic chemotherapeutic'drugs.
• CHOLESTERYL ESTER TRANSFER PROTEIN (CETP) INHIBITION IN THE TREATMENT OF CANCER
  申请人：KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20180049997A1

  公开（公告）日：2018-02-22

  In one embodiment, the invention provides methods of treatment which use therapeutically effective amounts of Cholesteryl Ester Transfer Protein (CETP) inhibitors to treat a variety of cancers. In certain embodiments, the inhibitor is a CETP-inhibiting small molecule, CETP-inhibiting antisense oligonucleotide, CETP-inhibiting siRNA or a CETP-inhibiting antibody. Related pharmaceutical compositions, kits, diagnostics and screens are also provided.
• US9890106B2
  申请人：——

  公开号：US9890106B2

  公开（公告）日：2018-02-13
• [EN] CHOLESTERYL ESTER TRANSFER PROTEIN (CETP) INHIBITION IN THE TREATMENT OF CANCER<br/>[FR] INHIBITION DE PROTÉINE DE TRANSFERT D'ESTER DE CHOLESTÉRYLE (CETP) DANS LE TRAITEMENT DE CANCER
  申请人：KING ABDULLAH UNIV OF SCIENCE & TECH

  公开号：WO2016135633A1

  公开（公告）日：2016-09-01

  In one embodiment, the invention provides methods of treatment which use therapeutically effective amounts of Choleste ryl Ester Transfer Protein (CETP) inhibitors to treat a variety of cancers. In certain embodiments, the inhibitor is a CETP-inhibiting small molecule, CETP-inhibiting antisense oligonucleotide, CETP-inhibiting siRNA or a CETP- inhibiting antibody. Related pharmaceutical compositions, kits, diagnostics and screens are also provided.