3-cyano-2,4-dihydroxy-6-nitroquinoline | 84884-27-5

• 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: 3-cyano-2,4-dihydroxy-6-nitroquinoline
• 英文别名: 4-Hydroxy-6-nitro-2-oxo-1,2-dihydroquinoline-3-carbonitrile；4-hydroxy-6-nitro-2-oxo-1H-quinoline-3-carbonitrile
• CAS: 84884-27-5
• 化学式: C₁₀H₅N₃O₄
• 分子量: 231.167
• InChiKey: HFXKJHGSGAHNDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  504.9±50.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-cyano-2,4-dihydroxy-6-nitroquinoline 在 苄基三乙基氯化铵 、 铁粉 、 氯化铵 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 16.17h， 生成 6-Amino-4-(3-chloro-4-fluoro-phenylamino)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  Inhibition of Tpl2 kinase and TNFα production with quinoline-3-carbonitriles for the treatment of rheumatoid arthritis

  摘要：

  The synthesis and structure-activity studies of a series of quinoline-3-carbonitriles as inhibitors of Tpl2 kinase are described. Potent inhibitors of Tpl2 kinase with selectivity against a panel of selected kinases in enzymatic assays and specificity in cell-based phosphorylation assays in LPS-treated human monocytes were identified. Selected inhibitors with moderate activity in human whole blood assay effectively inhibited LPS/D-Gal induced TNFalpha release when administered intraperitoneally in mice.

  DOI：

  10.1016/j.bmcl.2006.08.102
• 作为产物：
  描述：

  2-氨基-5-硝基苯甲酸 在 硫酸 、 sodium 作用下， 以 甲醇 为溶剂， 反应 56.0h， 生成 3-cyano-2,4-dihydroxy-6-nitroquinoline
  参考文献：
  名称：

  Inhibition of Tpl2 kinase and TNFα production with quinoline-3-carbonitriles for the treatment of rheumatoid arthritis

  摘要：

  The synthesis and structure-activity studies of a series of quinoline-3-carbonitriles as inhibitors of Tpl2 kinase are described. Potent inhibitors of Tpl2 kinase with selectivity against a panel of selected kinases in enzymatic assays and specificity in cell-based phosphorylation assays in LPS-treated human monocytes were identified. Selected inhibitors with moderate activity in human whole blood assay effectively inhibited LPS/D-Gal induced TNFalpha release when administered intraperitoneally in mice.

  DOI：

  10.1016/j.bmcl.2006.08.102

文献信息

• 3-cyanoquinoline derivatives
  申请人：BASF Aktiengesellschaft

  公开号：US04927935A1

  公开（公告）日：1990-05-22

  A compound of the formula I ##STR1## where A is nitro, amino, halocarbonyl or halosulfonyl, R is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkanoylamino, hydroxyl, C.sub.1 -C.sub.4 -alkoxy phenoxy which is unsubstituted by methyl or chloro, mercapto, C.sub.1 -C.sub.4 -alkylthio, phenylthio which is unsubstituted or substituted by ethyl, fluoro, or methoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenoxycarbonyl which is unsubstituted or substituted by isopropyl, bromo, or methoxy, carbamoyl, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl which is unsubstituted or substituted by ethyl, chloro, or isopropoxy, sulfamoyl or trifluoromethyl or is C.sub.1 -C.sub.4 -alkyl which may be substituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy or halogen, and X and Y are each, independently of one another, halogen, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkoxy or phenoxy which is unsubstituted or substituted by methyl or chloro, phenoxy, subject to the proviso that at least one of X and Y is halogen.

  化合物的公式为I ##STR1## 其中A为硝基、氨基、卤代羰基或卤代磺酰基，R为氢、卤素、硝基、氰基、C.sub.1-C.sub.4烷酰氨基、羟基、未被甲基或氯代取代的C.sub.1-C.sub.4烷氧基苯氧基、巯基、C.sub.1-C.sub.4烷基硫基、乙基、氟代或甲氧基取代或未被取代的苯基硫基、羧基、C.sub.1-C.sub.4烷氧羰基、未被取代或被异丙基、溴代或甲氧基取代的苯氧羰基、氨基甲酰基、羟基磺酰基、C.sub.1-C.sub.4烷基磺酰基、未被取代或被乙基、氯代或异丙氧基取代的苯基磺酰基、磺酰氨基或三氟甲基或为C.sub.1-C.sub.4烷基，该基团可能被羟基、C.sub.1-C.sub.4烷氧基或卤素取代，X和Y各自独立地为卤素、羟基磺酰基、C.sub.1-C.sub.4烷氧基或未被甲基或氯代取代的苯氧基，或未被取代或被甲基或氯代取代的苯氧基，但至少X和Y中的一个为卤素。
• Preparation of dihydroxyquinoline and certain derivatives
  申请人：The Sherwin-Williams Company

  公开号：US04362876A1

  公开（公告）日：1982-12-07

  There is disclosed a process for the preparation of dihydroxyquinoline and certain derivatives thereof. The compounds have the structure: ##STR1## where X=Cl, Br, I, NO.sub.2, H Y=--CN, --H --COOH The process comprises the reaction of isatoic anhydride or its derivatives with alkyl esters of cyanoacetic acid to form an intermediate compound such as 2-(2'-aminobenzoyl)cyanoacetate which subsequently undergoes cyclization to form 3-cyano-2,4-diydroxyquinoline (when X is hydrogen) or its derivatives (where X is Cl, Br, I or NO.sub.2). The cyano group may be cleaved under alkaline conditions to convert Y from --CN to --H or under acid conditions to convert Y from --CN to --COOH.

  本发明揭示了一种制备二羟基喹啉及其某些衍生物的方法。该化合物的结构为：##STR1##其中X = Cl，Br，I，NO.sub.2，H，Y = --CN，--H，--COOH。该方法包括将异香草酸酐或其衍生物与氰乙酸烷基酯反应，形成一个中间化合物，例如2-(2'-氨基苯甲酰)氰乙酸酯，随后发生环化反应，形成3-氰基-2,4-二羟基喹啉（当X为氢）或其衍生物（其中X为Cl、Br、I或NO.sub.2）。氰基可以在碱性条件下裂解，将Y从--CN转换为--H，或在酸性条件下裂解，将Y从--CN转换为--COOH。
• 3-Cyanochinolinderivate
  申请人：BASF Aktiengesellschaft

  公开号：EP0252350A1

  公开（公告）日：1988-01-13

  Die Erfindung betrifft Verbindungen der Formel I in der A Nitro, Amino, Halogencarbonyl oder Halogensulfonyl, R Wasserstoff, Halogen, Nitro, Cyano, C₁-C₄-Alkanoylamino, Hydroxy, C₁-C₄-Alkoxy, gegebenenfalls substituiertes Phenoxy, Mercapto, C₁-C₄-­Alkylthio, gegebenenfalls substituiertes Phenylthio, Carboxyl, C₁-C₄-­Alkoxycarbonyl, gegebenenfalls substituiertes Phenoxycarbonyl, Carbamoyl, Hydroxysulfonyl, C₁-C₄-Alkylsulfonyl, gegebenenfalls sub­stituiertes Phenylsulfonyl, Sulfamoyl, Trifluormethyl oder gegebenen­falls durch Hydroxy, C₁-C₄-Alkoxy oder Halogen substituiertes C₁-C₄-Alkyl und X und Y jeweils unabhängig voneinander Halogen, Hydroxysulfonyl, C₁-C₄-­Alkoxy oder gegebenenfalls substituiertes Phenoxy bedeuten, mit der Maßgabe, daß mindestens einer der Reste X und Y für Halogen steht. Die erfindungsgemäßen Verbindungen eignen sich vorzugsweise als Reaktivanker.

  本发明涉及式 I 的化合物 其中 A 是硝基、氨基、卤代羰基或卤代磺酰基、 R 氢、卤素、硝基、氰基、C₁-C₄-烷酰胺基、羟基、C₁-C₄-烷氧基、任选取代的苯氧基、巯基、C₁-C₄-烷硫基、任选取代的苯硫基、羧基、C₁-C₄-烷氧基羰基、任选取代的苯氧基羰基、氨基甲酰基、羟基磺酰基、任选取代的苯氧基羰基、氨基甲酰基、羟基磺酰基、C₁-C₄-烷基磺酰基、任选取代的苯基磺酰基、氨基磺酰基、三氟甲基或任选羟基、C₁-C₄-烷氧基或卤素取代的 C₁-C₄-烷基，以及 X和Y各自独立地为卤素、羟基磺酰基、C₁-C₄-烷氧基或任选取代的苯氧基，但X和Y中至少有一个基为卤素。 根据本发明的化合物最好可用作活性锚。
• HACKENBERGER, ALFRED;PATSCH, MANFRED
  作者：HACKENBERGER, ALFRED、PATSCH, MANFRED

  DOI：——

  日期：——
• US4362876A
  申请人：——

  公开号：US4362876A

  公开（公告）日：1982-12-07