1,2-二氢-1-氧代-5-异喹啉甲酸 | 212374-18-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 异喹啉类化合物
• 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: 1,2-二氢-1-氧代-5-异喹啉甲酸
• 中文别名: 1-氧代-1,2-二氢异喹啉-5-羧酸
• 英文名称: 1-oxoisoquinoline-5-carboxylic acid
• 英文别名: 1-oxo-1,2-dihydro-isoquinoline-5-carboxylic acid；1-Oxo-1,2-dihydroisoquinoline-5-carboxylic acid；1-oxo-2H-isoquinoline-5-carboxylic acid
• CAS: 212374-18-0
• 化学式: C₁₀H₇NO₃
• 分子量: 189.17
• InChiKey: MLQUDHWCGDWPDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  532.6±50.0 °C(Predicted)
• 密度：
  1.405

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1,2-二氢-1-氧代-5-异喹啉甲酸 、 1-金刚烷甲胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 1-羟基苯并三唑 、 三乙胺 、 N,N-二甲基甲酰胺 在 水 、 乙酸乙酯 、 Sodium sulfate-III 作用下， 反应 18.0h， 生成 1-Oxo-1,2-dihydro-isoquinoline-5-carboxylic acid (adamantan-1-ylmethyl)-amide
  参考文献：
  名称：

  Bicycloheteroaryl Compounds As P2X7 Modulators and Uses Thereof

  摘要：

  公开了具有化学式（I）的双环杂芳基化合物。这些化合物可以制备为药物组成物，并可用于预防和治疗哺乳动物，包括人类的多种疾病条件，例如疼痛、炎症、创伤性损伤等。

  公开号：

  US20110118287A1
• 作为产物：
  描述：

  1-氧代-1,2-二氢异喹啉-5-甲腈 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以83%的产率得到1,2-二氢-1-氧代-5-异喹啉甲酸
  参考文献：
  名称：

  Synthesis of 3-Substituted Benzamides and 5-Substituted Isoquinolin-1(2H)-ones and Preliminary Evaluation as Inhibitors of Poly(ADP-ribose)polymerase (PARP)

  摘要：

  Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. 3-Substituted benzamides and 5-substituted isoquinolin-1-ones have been synthesised and evaluated for inhibition of PARP. Reduction of 3-(bromoacetyl)benzamide, followed by treatment with base, gave RS-3-oxiranylbenzamide. Reduction of 3-(hydroxyacetyl)benzonitrile with bakers' yeast gave 'the R-diol which was converted to R-3-(1,2-dihydroxyethyl)benzamide. Similar reduction of 3-(acetoxyacetyl)benzonitrile led towards the S-diol which was converted to its cyclic acetonide. E-2-(2,6-Dicyanophenyl)-N,N-dimethylethenamine was formed by condensation of 2,6-dicyanotoluene with dimethylformamide dimethyl acetal (DMFDMA); cyclisation under acidic conditions afforded 5-cyanoisoquinolin-1-one. Heck coupling of 5-iodoisoquinolin-1-one with propenoic acid formed E-3-(1-oxoisoquinolin-5-yl)propenoic acid. 3-Oxiranylbenzamide, 5-bromoisoquinolin-1-one and 5-iodoisoquinolin-1-one were among the most potent inhibitors of PARP activity in a preliminary screen in vitro. (C) 1998 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00029-7

文献信息

• Bicycloheteroaryl compounds as P2X7 modulators and uses thereof
  申请人：Kelly Michael G.

  公开号：US08779144B2

  公开（公告）日：2014-07-15

  Bicycloheteroaryl compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.

  公开了具有以下公式表示的双环杂芳基化合物：这些化合物可以制备为药物组合物，并可用于预防和治疗哺乳动物，包括人类的各种病症，例如疼痛、炎症、创伤性损伤等。
• 5-Benzamidoisoquinolin-1-ones and 5-(ω-Carboxyalkyl)isoquinolin-1-ones as Isoform-Selective Inhibitors of Poly(ADP-ribose) Polymerase 2 (PARP-2)
  作者：Peter T. Sunderland、Esther C. Y. Woon、Archana Dhami、Aoife B. Bergin、Mary F. Mahon、Pauline J. Wood、Louise A. Jones、Sophie R. Tully、Matthew D. Lloyd、Andrew S. Thompson、Hashim Javaid、Niall M. B. Martin、Michael D. Threadgill

  DOI：10.1021/jm1010918

  日期：2011.4.14

  PARP-2 is a member of the poly(ADP-ribose) polymerase family, with some activities similar to those of PARP-1 but with other distinct roles. Two series of isoquinolin-1-ones were designed, synthesized, and evaluated as selective inhibitors of PARP-2, using the structures of the catalytic sites of the isoforms. A new efficient synthesis of 5-aminoisoquinolin-1-one was developed, and acylation with acyl chlorides gave 5-acylaminoisoquinolind-1-ones. By examination of isoquinolin-1-ones with carboxylates tethered to the 5-position, Heck coupling of 5-iodoisoquinolin-1-one furnished the 5-CH = CHCO(2)H compound for reduction to the 5-propanoic acid. Alkylation of 5-aminoisoquinolin-1-one under mildly basic conditions, followed by hydrolysis, gave 5-(carboxymethylamino)isoquinolin-1-one, whereas it was alkylated at 2-N with methyl propenoate and strong base. Compounds were assayed in vitro for inhibition of PARP-1 and PARP-2, using Flash Plate and solution-phase assays, respectively. The 5-benzamidoisoquinolin-1-ones were more selective for inhibition of PARP-2, whereas the 5-(omega-carboxyalkl)isoquinolin-1-ones were less so. 5-Benzamidoisoquinolin-1-one is the most PARP-2-selective compound (IC(50(PARP-1))/IC(50(PARP-2)) = 9.3) to date, in a comparative study.
• BICYCLOHETEROARYL COMPOUNDS AS P2X7 MODULATORS AND USES THEREOF
  申请人：Second Genome, Inc.

  公开号：EP1937643B1

  公开（公告）日：2016-07-13
• US8779144B2
  申请人：——

  公开号：US8779144B2

  公开（公告）日：2014-07-15
• [EN] BICYCLOHETEROARYL COMPOUNDS AS P2X7 MODULATORS AND USES THEREOF<br/>[FR] COMPOSÉS DE BICYCLOHÉTÉROARYLE EN TANT QUE MODULATEURS DE P2X7 ET LEURS UTILISATIONS
  申请人：RENOVIS INC

  公开号：WO2007109160A2

  公开（公告）日：2007-09-27

  (EN) Bicycloheteroaryl compounds are disclosed that have formula (I). The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.(FR) La présente invention concerne des composés de bicyclohétéroaryle de formule (I). Ces composés peuvent être préparés sous la forme de compositions pharmaceutiques et peuvent être utilisés pour prévenir et traiter chez des mammifères, y compris chez l'homme, un certain nombre d'états pathologiques comprenant, entre autres, la douleur, l'inflammation, les blessures traumatiques, etc.