5-羟基-2-氰基喹啉 | 586413-05-0

• 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
• 中文名称: 5-羟基-2-氰基喹啉
• 英文名称: 2-cyano-5-hydroxylquinoline
• 英文别名: 5-Hydroxyquinoline-2-carbonitrile
• CAS: 586413-05-0
• 化学式: C₁₀H₆N₂O
• 分子量: 170.17
• InChiKey: PBXWFTPUPUVGHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 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：
  56.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  5-羟基-2-氰基喹啉 在 氨 、 氢气 、 镍 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 16.5h， 生成 N-[(5-methoxyquinolin-2-yl)methyl]propionamide
  参考文献：
  名称：

  Highly Potent and Selective MT₂ Melatonin Receptor Full Agonists from Conformational Analysis of 1-Benzyl-2-acylaminomethyl-tetrahydroquinolines

  摘要：

  Molecular superposition models guided the design of novel melatonin receptor ligands characterized by a 2-acylaminomethyltetrahydroquinoline scaffold. Starting from the structure of N-anilinoethylamide ligands, the flexible chain was conformationally constrained to reproduce the bioactive conformation of melatonin. Structure activity relationships were investigated, focusing on the substituent at the nitrogen atom, the position of the methoxy group, and the replacement of the amide side chain by urea and thiourea groups. The compounds were tested for binding affinity and intrinsic activity at human MT1, and MT2 receptors. Structural optimization resulted in N-[(1-benzyl-1,2,3,4-tetrahydro-5-methoxyquinolin-2-yl)methyl]propionamide (UCM1014), with picomolar MT2 binding affinity (K-i = 0.001 nM), more than 10000-fold selectivity over the MT1 receptor, and a full agonist profile (GTP gamma S test), being the most potent MT2-selective full agonist reported to date. Molecular dynamics simulations provided a rationale for high binding affinity, stereoselectivity, and agonist behavior of these novel melatonin receptor ligands based on superposition models and conformational preference.

  DOI：

  10.1021/acs.jmedchem.5b01066
• 作为产物：
  描述：

  三甲基氰硅烷 、 5-hydroxylquinoline N-oxide 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 5-羟基-2-氰基喹啉
  参考文献：
  名称：

  Bicyclo 4.4.0 antiviral derivatives

  摘要：

  这项发明提供了具有药物和生物影响特性的化合物，它们的药物组合物和使用方法。具体而言，该发明涉及酰胺哌嗪衍生物。这些化合物具有独特的抗病毒活性，无论是单独使用还是与其他抗病毒药物、抗感染剂、免疫调节剂或HIV进入抑制剂结合使用。更具体地说，本发明涉及治疗HIV和艾滋病。

  公开号：

  US20040009985A1

文献信息

• Compound possessing affinity at 5ht1-type receptors and use thereof in therapy of cns disorders
  申请人：Smith W Paul

  公开号：US20050107410A1

  公开（公告）日：2005-05-19

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein: A is optionally substituted phenyl, naphthyl, indolyl, quinolinyl, quinazolinyl, indazolyl, isoquinolinyl or benzofuranyl; X is carbon, Y is CH and is a double bond; or X is CH, Y is CH 2 or oxygen and is a single bond; or X is nitrogen, Y is CH 2 and is a single bond; is halogen, hydroxy, cyano, C 1-6 alkyl, haloC 1-6 alkyl or C 1-6 alkoxy; a is 0, 1, 2, 3 or 4; R2 and R3, together with the nitrogen atom to which they are attached, form a nitro group or an optionally substituted 3 to 7 membered heterocyclic group, or R2 and R3 are independently hydrogen, aroyl, C 1-6 alkyl, C 1-6 alkanoyl, fluoroC 1-6 alkanoyl, C 1-6 alkylsulfonyl, fluoroC 1-6 alkylsulfonyl, carbamoyl, C 1-6 alkylcarbamoyl, arylC 1-6 alkyl or a group CO(CH 2 )bNR4R5 wherein b is 1, 2, 3 or 4; and R4 and R5 are independently hydrogen or C 1-6 alkyl, or R4 and R5, together with the nitrogen atom to they are attached, form part of an optionally substituted 3 to 7 membered heterocyclic group. Methods of preparing the compounds and uses of the compounds in therapy, in particular for CNS disorders such as depression and anxiety, are also disclosed.

  公开了式（I）的化合物及其药学上可接受的盐：其中，A是可选取的取代苯基、萘基、吲哚基、喹啉基、喹唑啉基、吲唑基、异喹啉基或苯并呋喃基；X是碳，Y是CH且为双键；或X是CH，Y是CH2或氧且为单键；或X是氮，Y是 且为单键；R1是卤素、羟基、氰基、C1-6烷基、卤代C1-6烷基或C1-6烷氧基；a是0、1、2、3或4；R2和R3与它们所连接的氮原子一起形成硝基基团或可选取的取代的3到7元杂环基团，或R2和R3分别是氢、芳香基、C1-6烷基、C1-6酰基、氟代C1-6酰基、C1-6烷基磺酰基、氟代C1-6烷基磺酰基、氨基、C1-6烷基氨基、芳基C1-6烷基或CO( )bNR4R5基团，其中b是1、2、3或4；R4和R5分别是氢或C1-6烷基，或R4和R5与它们所连接的氮原子一起形成可选取的取代的3到7元杂环基团。还公开了制备该化合物的方法以及该化合物在治疗中的用途，特别是在中枢神经系统疾病如抑郁症和焦虑症方面的用途。
• COMPOUNDS POSSESSING AFFINITY AT 5HT1-TYPE RECEPTORS AND USE THEREOF IN THERAPY OF CNS DISORDERS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1480972A2

  公开（公告）日：2004-12-01
• EP1499319A4
  申请人：——

  公开号：EP1499319A4

  公开（公告）日：2006-02-08
• BICYCLO 4.4.0 ANTIVIRAL DERIVATIVES
  申请人：Bristol-Myers Squibb Company

  公开号：EP1499319A1

  公开（公告）日：2005-01-26
• PYRROLIDINE AND PIPERIDINE COMPOUNDS
  申请人：Yuhan Corporation

  公开号：EP4055014A1

  公开（公告）日：2022-09-14