ethyl 6,7-dimethoxyquinoline-3-carboxylate | 5278-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 6,7-dimethoxyquinoline-3-carboxylate
• 英文别名: 6,7-Dimethoxychinolin-3-carbonsaeureethylester；3-Quinolinecarboxylic acid, 6,7-dimethoxy-, ethyl ester
• CAS: 5278-39-7
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: BSUAOVKVNPPFQI-UHFFFAOYSA-N

物化性质

• 沸点：
  372.9±37.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  ethyl 6,7-dimethoxyquinoline-3-carboxylate 在 氨 、 吡啶盐酸盐 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 96.5h， 生成 6,7-dihydroxyquinoline-3-carboxamide hydrochloride
  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
• 作为产物：
  描述：

  3,4-二甲氧基苯胺 在 palladium on activated charcoal 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 二苯醚 、 乙醇 、 乙腈 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 28.0h， 生成 ethyl 6,7-dimethoxyquinoline-3-carboxylate
  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。
• 10.1021/acs.joc.4c00571
  作者：Agneswaran, Rudrasenan、Mohanakrishnan, Arasambattu K.

  DOI：10.1021/acs.joc.4c00571

  日期：——

  In this study, we present our findings on the synthesis of α-, β-, γ-carbolines via PIFA/BF3·OEt2-mediated intramolecular cyclization of isomeric azidomethyl(indolyl)acrylates. Alternately, 1,5,7-triazabicyclo[4.4.0]dec-5-ene/1,8-diazabicyclo(5.4.0)undec-7-ene (TBD/DBU)-mediated Michael addition followed by intramolecular cyclization of isomeric 2/3-(azidomethyl)indol-3/2-yl)acrylates also furnished

  在本研究中，我们展示了通过 PIFA/BF 3 ·OEt 2介导的异构叠氮甲基（吲哚基）丙烯酸酯的分子内环化合成 α-、β-、γ-咔啉的研究结果。或者，1,5,7-三氮杂双环[4.4.0]dec-5-ene/1,8-二氮杂双环(5.4.0)十一碳-7-烯 (TBD/DBU) 介导的迈克尔加成，然后进行异构体的分子内环化2/3-(叠氮甲基)吲哚-3/2-基)丙烯酸酯还提供了各自的β-和γ-咔啉衍生物。出乎意料的是，2-(叠氮基甲基)-3-(吲哚-3-基)丙烯酸酯的热解导致通过氮宾插入和重排形成5-(2-(苯基磺酰胺基)芳基)烟酸乙酯以及γ-咔啉和环化。异构2-(叠氮基甲基)-3-(吲哚-2-基)丙烯酸酯热解后产生预期的δ-咔啉。热分子内氮烯插入反应也可以扩展到获得吡啶并苯并噻吩、吡啶并噻吩和喹啉。
• [EN] NOVEL QUINOLINE DERIVATIVES AND PREPARATION THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE QUINOLÉINE ET LEUR PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2016125187A4

  公开（公告）日：2016-10-27
• Polythiophene-Encapsulated Bimetallic Au-Fe₃O₄ Nano-Hybrid Materials: A Potential Tandem Photocatalytic System for Nondirected C(sp²)–H Activation for the Synthesis of Quinoline Carboxylates
  作者：Mandeep Kaur、Subhamay Pramanik、Manoj Kumar、Vandana Bhalla

  DOI：10.1021/acscatal.6b02681

  日期：2017.3.3

  Hetero-oligophenylene derivative 3 appended with thiophene moieties has been designed and synthesized which undergoes aggregation to form J-typefluorescent aggregates in in H2O/THF (7/3) media. These aggregates served as reactors for the preparation of bimetallic Au-Fe3O4 NPs. During the reduction process, aggregates of derivative 3 were oxidized to the polythiophene species 4. Interestingly, the polythiophene species 4, having a fibrous morphology, served as a shape-and morphology-directed template for assembly of bimetallic Au-Fe3O4 NPs in a flower-like arrangement. Furthermore, polythiophene-encapsulated bimetallic 4:AuFe3O4 nanohybrid materials served as an efficient and recyclable catalytic system for C(sp(2)) H bond activation of unprotected electron-rich anilines for the construction of synthetically versatile quinoline carboxylates via C H activation, carbonylation, and subsequent annulation under mild and eco-friendly conditions (aqueous media, room temperature, visible-light irradiation, and aerial conditions).
• 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：——