5,6-Dihydroxy-naphthalene-2-carboxylic acid methyl ester | 146515-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,6-Dihydroxy-naphthalene-2-carboxylic acid methyl ester
• 英文别名: Methyl 5,6-dihydroxynaphthalene-2-carboxylate
• CAS: 146515-44-8
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: OHWJXNLECYLABW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-bromo-1,2-dimethoxynaphthalene 在 正丁基锂 、 三溴化硼 作用下， 反应 1.83h， 生成 5,6-Dihydroxy-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Bicyclic compounds as ring-constrained inhibitors of protein-tyrosine kinase p56lck

  摘要：

  A study was undertaken to prepare inhibitors of the lymphocyte protein-tyrosine kinase p56lck. Using the known p56lck inhibitor 3,4-dihydroxy-alpha-cyanocinnamamide (4) as a lead compound, bicyclic analogues were designed as conformationally constrained mimetics in which the phenyl ring and vinyl side chain of the cinnamamide are locked into a coplanar orientation. Such planarity was rationalized to be an important determinant for binding within a putative flat, cleftlike catalytic cavity. Bicyclic analogues were prepared using the naphthalene, quinoline, isoquinoline, and 2-iminochromene ring systems and examined for their ability to inhibit autophosphorylation of immunopurified p56lck. The most potent analogues were methyl 7,8-dihydroxyisoquinoline-3-carboxylate (12) (IC50 = 0.2 muM) and 7,8-dihydroxyisoquinoline-3-carboxamide (13) (IC50 = 0.5 muM). Inhibition by 12 was not competitive with respect to ATP. These compounds may represent important new structural motifs for the development of p56lck inhibitors.

  DOI：

  10.1021/jm00056a001

文献信息

• Burke (Jr) Terrence R., Lim Benjamin, Marquez Victor E., Li Zhen-Hong, Bo+, J. Med. Chem., 36 (1993) N 4, S 425-432
  作者：Burke (Jr) Terrence R., Lim Benjamin, Marquez Victor E., Li Zhen-Hong, Bo+

  DOI：——

  日期：——
• A METHOD FOR THE TREATMENT OF HYPERPROLIFERATIVE EPITHELIAL SKIN DISEASES BY TOPICAL APPLICATION OF HYDROXYLATED AROMATIC PROTEIN CROSS-LINKING COMPOUNDS
  申请人：THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP0809493A1

  公开（公告）日：1997-12-03
• US5610185A
  申请人：——

  公开号：US5610185A

  公开（公告）日：1997-03-11
• [EN] A METHOD FOR THE TREATMENT OF HYPERPROLIFERATIVE EPITHELIAL SKIN DISEASES BY TOPICAL APPLICATION OF HYDROXYLATED AROMATIC PROTEIN CROSS-LINKING COMPOUNDS<br/>[FR] PROCEDE POUR TRAITER LES LESIONS EPITHELIALES HYPERPROLIFERATIVES DE LA PEAU PAR APPLICATION TOPIQUE DE COMPOSES DE RETICULATION DE PROTEINES AROMATIQUES HYDROXYLES
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：WO1996025159A1

  公开（公告）日：1996-08-22

  (EN) The present invention relates to a method of treating hyperproliferative epithelial lesions by topical administration. The method prevents growth and actively cross-links these aberrant cells, thereby killing the cells. The present invention is useful in control and prevention of hyperproliferative epithelial disorders, such as HPV-infected cell lesions, actinic keratosis, melanomas, and malignant and pre-malignant carcinomas.(FR) Cette invention se rapporte à un procédé pour traiter les lésions épithéliales hyperprolifératives de la peau par administration topique. Ce procédé empêche la croissance et entraîne la réticulation active de ces cellules aberrantes, afin de les détruire. Cette invention permet de combattre et prévenir les troubles épithéliaux hyperprolifératifs, telles que les lésions cellulaires infectées par HPV, la kératose actinique, les mélanomes et les carcinomes malins et prémalins.