6-nitroplumbagin

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-nitroplumbagin
• 英文别名: 5-Hydroxy-2-methyl-6-nitronaphthalene-1,4-dione；5-hydroxy-2-methyl-6-nitronaphthalene-1,4-dione
• 化学式: C₁₁H₇NO₅
• 分子量: 233.18
• InChiKey: IEOBZALONDRWBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  兰雪醌 在 硫酸 、 硝酸 作用下， 反应 1.0h， 以43%的产率得到8-nitroplumbagin
  参考文献：
  名称：

  Preparation of Naphthoquinone Derivatives from Plumbagin and Their Ichthyotoxicity.

  摘要：

  各种萘醌衍生物是从天然产物5-羟基-2-甲基-1,4-萘醌（铅醌）中制备的；这些衍生物主要通过金属氧化剂（如醋酸铅四乙酯）在多种羧酸存在下，通过碳-碳键形成在C-3位进行取代。卤素化化合物的鱼毒性比铅醌更强，但其他衍生物的活性较低。

  DOI：

  10.1248/cpb.45.437

文献信息

• Dinda, B.; Chel, G.; Saha, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 5, p. 502 - 506
  作者：Dinda, B.、Chel, G.、Saha, S.、Patra, A.

  DOI：——

  日期：——
• 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
• Preparation of Naphthoquinone Derivatives from Plumbagin and Their Ichthyotoxicity.
  作者：Kazuhito OGIHARA、Rieko YAMASHIRO、Matsutake HIGA、Seiichi YOGI

  DOI：10.1248/cpb.45.437

  日期：——

  Various naphthoquinone derivatives were prepared from a natural product, 5-hydroxy-2-methyl-1, 4-naphthoquinone (plumbagin); these were mostly substituted at C-3 through carbon-carbon bond formation mediated by a metal-based oxidant such as lead tetraacetate in the presence of various carboxylic acids. The halogenated compounds showed stronger ichthyotoxicity than plumbagin, but other derivatives were less active.

  各种萘醌衍生物是从天然产物5-羟基-2-甲基-1,4-萘醌（铅醌）中制备的；这些衍生物主要通过金属氧化剂（如醋酸铅四乙酯）在多种羧酸存在下，通过碳-碳键形成在C-3位进行取代。卤素化化合物的鱼毒性比铅醌更强，但其他衍生物的活性较低。