4-oxo-1,4-dihydrocinnoline-3-carboxylic acid | 18514-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-oxo-1,4-dihydrocinnoline-3-carboxylic acid
• 英文别名: 4(1H)-oxocinnoline 3-carboxylic acid；4-oxo-1,4-dihydro-cinnoline-3-carboxylic acid；4-Oxo-1,4-dihydro-cinnolin-3-carbonsaeure；4-oxo-1,4-dihydro-3-cinnoline-carboxylic acid；4-Oxo-1,4-dihydro-3-cinnolinecarboxylic acid；1,4-dihydro-4-cinnolinone-3-carboxylic acid；4-Hydroxycinnoline-3-carboxylic acid；4-oxo-1H-cinnoline-3-carboxylic acid
• CAS: 18514-85-7
• 化学式: C₉H₆N₂O₃
• mdl: MFCD04111189
• 分子量: 190.158
• InChiKey: ZIPLRYYWAXPVMG-UHFFFAOYSA-N

物化性质

• 熔点：
  >200 °C
• 沸点：
  427.6±28.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  78.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-oxo-1,4-dihydrocinnoline-3-carboxylic acid 在 五氯化磷 、 硫酸 、 硝酸 、 三氯氧磷 作用下， 生成 (6-nitro-cinnolin-4-yl)-phenyl-amine
  参考文献：
  名称：

  131. Cinnolines。第三部分 里希特反应

  摘要：

  DOI：

  10.1039/jr9450000512
• 作为产物：
  描述：

  2-硝基苯基丙炔酸 在 iron(II) sulfate 作用下， 生成 4-oxo-1,4-dihydrocinnoline-3-carboxylic acid
  参考文献：
  名称：

  131. Cinnolines。第三部分 里希特反应

  摘要：

  DOI：

  10.1039/jr9450000512

文献信息

• Drug efflux pump inhibitor
  申请人：DAIICHI PHARMACEUTICAL CO., LTD

  公开号：US20030092720A1

  公开（公告）日：2003-05-15

  A medicament for preventive and/or therapeutic treatment of a microbial infection which comprises as an active ingredient a compound represented by the following general formula (I): 1 wherein, R 1 and R 2 represent hydrogen atom, a halogen atom, hydroxyl group or the like, W 1 represents —CH═CH—, —CH 2 O—, —CH 2 CH 2 — or the like; R 3 represents hydrogen atom, a halogen atom, hydroxyl group or an amino group; R 4 represents hydrogen atom, a group of —OZ 0-4 R 5 (Z 0-4 represents an alkylene group, a fluorine-substituted alkylene group or a single bond, and R 5 represents a cyclic alkyl group, an aryl group or the like); W 2 represents a single bond or —C(R 8 )═C(R 9 )— (R 8 and R 9 represent hydrogen atom, a halogen atom, a lower alkyl group or the like, Q represents an acidic group, but W 2 and Q may together form vinylidenethiazolidinedione or an equivalent heterocyclic ring; m and n represent an integer of 0 to 2, and q represents an integer of 0 to 3.

  一种用于预防和/或治疗微生物感染的药物，其活性成分表示为以下一般式(I)的化合物： 其中，R1和R2代表氢原子、卤素原子、羟基或类似物，W1代表—CH═CH—、—CH2O—、—CH2CH2—或类似物；R3代表氢原子、卤素原子、羟基或氨基；R4代表氢原子、—OZ0-4R5（Z0-4代表烷基链、氟取代的烷基链或单键，R5代表环烷基、芳基或类似物）；W2代表单键或—C(R8)═C(R9)—（R8和R9代表氢原子、卤素原子、较低烷基或类似物，Q代表酸性基团，但W2和Q可以共同形成乙烯基噻唑二酮或等效的杂环环；m和n代表0到2的整数，q代表0到3的整数。
• [EN] NOVEL CANNABINOID RECEPTOR LIGANDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND PROCESS FOR THEIR PREPARATION<br/>[FR] NOUVEAUX LIGANDS DU RÉCEPTEUR CANNOBINOÏDE, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2009053799A1

  公开（公告）日：2009-04-30

  The present invention relates to compounds of f formula (I) as cannabinoid receptor modulators, in particular cannabinoid 1 (CB1) or cannabinoid 2 (CB2 ) receptor modulators, and uses thereof f or treating diseases, conditions and/or disorders modulated by a cannabinoid receptor ( such as pain, neurodegenrative disorders, eating disorders, weight loss or control, and obesity).

  本发明涉及公式（I）的化合物作为大麻素受体调节剂，特别是大麻素1（CB1）或大麻素2（CB2）受体调节剂，以及它们的用途用于治疗由大麻素受体调节的疾病、症状和/或障碍（如疼痛、神经退行性疾病、进食障碍、体重减轻或控制以及肥胖症）。
• 4-hydroxycinnoline-3-carboxyamides as antiviral agents
  申请人：——

  公开号：US20020042397A1

  公开（公告）日：2002-04-11

  Certain novel 4-hydroxycinnoline-3-carboxyamides. The compounds are particularly effective in the treatment or prevention of viral infections, particularly infections caused by herpes viruses including herpes simplex virus types 1 and 2, human herpes virus types 6, 7 and 8, varicello zoster virus, human cytomegalovirus or Epstein-Barr virus.

  某些新型4-羟基肉桂酰胺基喹啉化合物。这些化合物在治疗或预防病毒感染方面特别有效，尤其是对由疱疹病毒引起的感染，包括单纯疱疹病毒类型1和2、人类疱疹病毒类型6、7和8、水痘-带状疱疹病毒、人类巨细胞病毒或EB病毒感染。
• Cinnoline-carboxamides and process for their preparation
  申请人：Farmitalia Carlo Erba s.r.l.

  公开号：US04826837A1

  公开（公告）日：1989-05-02

  The invention relates to compounds having the general formula (I) ##STR1## wherein n is zero, 1 or 2; each of R.sub.1 and R.sub.2 is independently: (a) hydrogen, halogen, trifluoromethyl or C.sub.1 -C.sub.6 alkyl; (b) hydroxy, C.sub.1 -C.sub.6 alkoxy or C.sub.3 -C.sub.4 alkenyloxy; (c) nitro, amino, formylamino or C.sub.2 -C.sub.8 alkanoylamino; R.sub.3 represents hydrogen or C.sub.1 -C.sub.8 alkyl; R.sub.4 is: (a') C.sub.1 -C.sub.20 alkyl, unsubstituted or substituted by ##STR2## wherein each of R.sub.a and R.sub.b is independently phenyl or C.sub.1 -C.sub.6 alkyl, or R.sub.a and R.sub.b, taken together with the nitrogen atom to which they are linked, form a N-pyrrolidinyl, N-piperazinyl, hexahydroazepin-1-yl, thiomorpholino, morpholino or piperidino ring, wherein said heterocyclic rings may be unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl or phenyl; (b') C.sub.5 -C.sub.10 cycloalkyl, unsubstituted or substituted by methyl; (c') 2- or 3-pyrrolidinyl, piperidyl of 2-piperazinyl, wherein said heterocyclic rings may be unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl; (d') isoxazolyl or thiazolyl, wherein said heterocyclic rings may be unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl; (e') pyridyl, unsubstituted or substituted by one or two substituents chosen independently from halogen, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy; or (f') phenyl, unsubstituted or substituted by one or two substituents chosen independently from halogen, CF.sub.3,C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, amino, nitro, formylamino and C.sub.2 -C.sub.8 alkanoylamino, and the pharmaceutically acceptable salts thereof, which possess immunomodulating activity and are useful e.g. in the treatment of neoplastic diseases and acute and chronic infections of both bacterial and viral origin in mammals.

  本发明涉及具有通式(I)的化合物 ##STR1## 其中n为0、1或2；每个R1和R2独立地为：(a)氢、卤素、三氟甲基或C1-C6烷基；(b)羟基、C1-C6烷氧基或C3-C4烯氧基；(c)硝基、氨基、甲酰氨基或C2-C8烷酰氨基；R3代表氢或C1-C8烷基；R4为：(a')C1-C20烷基，未被取代或被##STR2##取代，其中每个Ra和Rb独立地为苯基或C1-C6烷基，或者Ra和Rb与它们所连接的氮原子一起形成N-吡咯烷基、N-哌嗪基、六氢氮杂环庚三烯-1-基、硫代吗啉基、吗啉基或哌啶基环，其中所述杂环环可未被取代或被C1-C6烷基或苯基取代；(b')C5-C10环烷基，未被取代或被甲基取代；(c')2-或3-吡咯烷基、哌啶基或2-哌嗪基，其中所述杂环环可未被取代或被C1-C6烷基取代；(d')异噁唑基或噻唑基，其中所述杂环环可未被取代或被C1-C6烷基取代；(e')吡啶基，未被取代或被一个或两个独立地选自卤素、C1-C6烷基和C1-C6烷氧基的取代基取代；或(f')苯基，未被取代或被一个或两个独立地选自卤素、CF3、C1-C6烷基、C1-C6烷氧基、氨基、硝基、甲酰氨基和C2-C8烷酰氨基的取代基取代，以及其药学上可接受的盐，它们具有免疫调节活性，并且例如在治疗哺乳动物的肿瘤疾病以及由细菌和病毒引起的急性和慢性感染方面有用。
• Medicine for inhibiting drug elimination pump
  申请人：Nakayama Kiyoshi

  公开号：US20050009843A1

  公开（公告）日：2005-01-13

  A medicament for preventive and/or therapeutic treatment of a microbial infection which comprises as an active ingredient a compound represented by the following general formula (I): wherein, R 1 and R 2 represent hydrogen atom, a halogen atom, hydroxyl group or the like, W 1 represents —CH═CH—, —CH 2 O—, —CH 2 CH 2 — or the like; R 3 represents hydrogen atom, a halogen atom, hydroxyl group or an amino group; R 4 represents hydrogen atom, a group of —OZ 0-4 R 5 (Z 0-4 represents an alkylene group, a fluorine-substituted alkylene group or a single bond, and R 5 represents a cyclic alkyl group, an aryl group or the like); W 2 represents a single bond or —C(R 8 )═C(R 9 )—(R 8 and R 9 represent hydrogen atom, a halogen atom, a lower alkyl group or the like, Q represents an acidic group, but W 2 and Q may together form vinylidenethiazolidinedione or an equivalent heterocyclic ring; m and n represent an integer of 0 to 2, and q represents an integer of 0 to 3.

  预防和/或治疗微生物感染的药物，其活性成分为以下通用式（I）所表示的化合物：其中，R1和R2表示氢原子、卤原子、羟基或类似物，W1表示—CH═CH—、—CH2O—、—CH2CH2—或类似物；R3表示氢原子、卤原子、羟基或氨基；R4表示氢原子、—OZ0-4R5（Z0-4表示烷基、氟代烷基或单键，R5表示环烷基、芳基或类似物）；W2表示单键或—C（R8）═C（R9）—（R8和R9表示氢原子、卤原子、低烷基或类似物，Q表示酸性基团，但W2和Q可以共同形成乙烯基噻唑烷二酮或等效的杂环环；m和n表示0至2的整数，q表示0至3的整数。