3-(羟基-甲氧基亚甲基)-2H-异喹啉-7,8-二酮 | 146515-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 3-(羟基-甲氧基亚甲基)-2H-异喹啉-7,8-二酮
• 英文名称: Methyl 7,8-dihydroxyisoquinoline-3-carboxylate
• 英文别名: methyl 7,8-dihydroxyisoquinoline-3-carboxylate
• CAS: 146515-39-1
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: FYZSTQBJIYNWIC-UHFFFAOYSA-N

物化性质

• 沸点：
  468.3±40.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  79.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(羟基-甲氧基亚甲基)-2H-异喹啉-7,8-二酮 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 7,8-二羟基-3-异喹啉甲酰胺
  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

• Quinoline derivatives and preparation thereof
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：US10227355B2

  公开（公告）日：2019-03-12

  The patent discloses novel quinoline derivatives of formula (I), (Formula should be inserted here) and process for preparing the same. The compounds of formula (I) can be further used for the synthesis of Inhibitors like Kinase Tyrosine Inhibitors.

  该专利公开了式 (I) 的新型喹啉衍生物（此处应插入式）及其制备方法。式 (I) 化合物可进一步用于合成激酶酪氨酸抑制剂等抑制剂。
• 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
• NOVEL QUINOLINE DERIVATIVES AND PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：US20180237448A1

  公开（公告）日：2018-08-23

  The patent discloses novel quinoline derivatives of formula (I), (Formula should be inserted here) and process for preparing the same. The compounds of formula (I) can be further used for the synthesis of Inhibitors like Kinase Tyrosine Inhibitors.
• US5610185A
  申请人：——

  公开号：US5610185A

  公开（公告）日：1997-03-11
• [EN] POLYHYDROXYLATED NAPHTHYL 2-CARBOXYLATE, AND QUINOLYL AND ISOQUINOLYL 3-CARBOXYLATE DERIVATIVES AS PROTEIN TYROSINE KINASE INHIBITORS<br/>[FR] DERIVES DE 2-CARBOXYLATE DE NAPHTYLE POLYHYDROXYLE ET DE 3-CARBOXYLATE DE QUINOLYLE ET D'ISOQUINOLYLE UTILISES COMME INHIBITEURS DE LA PROTEINE-TYROSINE-KINASE
  申请人：THE GOVERNMENT OF THE UNITED STATES as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：WO1994003432A1

  公开（公告）日：1994-02-17

  (EN) Polyhydroxylated naphthyl 2-carboxylate, and isoquinoline and quinoline 3-carboxylate derivatives are provided which possess protein tyrosine kinase inhibitory activity. Pharmaceutical compositions containing the compounds as well as methods of treating neoplastic and immune diseases, which diseases require protein tyrosine kinase for cell proliferation, are also provided.(FR) L'invention concerne des dérivés de 2-carboxylate de naphtyle polyhydroxylé et de 3-carboxylate d'isoquinoléine et de quinoléine possédant une efficacité d'inhibition de la protéine-tyrosine-kinase. L'invention concerne également des compositions pharmaceutiques contenant les composés, ainsi que des procédés de traitement de maladies néoplasiques et immunes, lesdites maladies nécessitant la protéine-tyrosine-kinase pour la prolifération cellulaire.