1,5-二氯异喹啉 | 70810-23-0

• 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: 1,5-二氯异喹啉
• 英文名称: 1,5-dichloroisoquinoline
• 英文别名: 1,5-dichloro-isoquinoline；1,5-Dichlor-isochinolin；1,5-Dichlorisochinolin
• CAS: 70810-23-0
• 化学式: C₉H₅Cl₂N
• 分子量: 198.051
• InChiKey: IKLNCVLTIQMRDB-UHFFFAOYSA-N

物化性质

• 熔点：
  147℃
• 沸点：
  327.7±22.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

1,5-二氯异喹啉是一种有机中间体，可以通过从2-氯肉桂酸开始的两步反应制得。它主要用于合成NS3/4A抑制剂。

反应信息

• 作为反应物：
  描述：

  1,5-二氯异喹啉 在 四甲基乙二胺 、 1,5-双(二苯基膦)戊烷 、 palladium diacetate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (2S,2'S)-N,N'-(4,4'-((E)-ethene-1,2-diyl)bis(4,1-phenylene))bis(1-(5-chloroisoquinoline-1-carbonyl)pyrrolidine-2-carboxamide)
  参考文献：
  名称：

  HCV NS5A Replication Complex Inhibitors. Part 4.1 Optimization for Genotype 1a Replicon Inhibitory Activity

  摘要：

  A series of symmetrical E-stilbene prolinamides that originated from the library-synthesized lead 3 was studied with respect to HCV genotype 1a (G-1a) and genotype 1b (G-1b) replicon inhibition and selectivity against BVDV and cytotoxicity. SAR emerging from an examination of the prolinamide cap region revealed 11 to be a selective HCV NS5A inhibitor exhibiting submicromolar potency against both G-1a and G-1b replicons. Additional structural refinements resulted in the identification of 30 as a potent, dual G-1a/1b HCV NS5A inhibitor.

  DOI：

  10.1021/jm301796k
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 1,5-二氯异喹啉
  参考文献：
  名称：

  1-Dialkylaminoalkylaminoisoquinolines¹

  摘要：

  DOI：

  10.1021/ja01200a028

文献信息

• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HEPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099274A1

  公开（公告）日：2003-12-04

  Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

  丙型肝炎病毒抑制剂公开了具有以下通式：其中R1、R2、R3、R'、B、Y和X在描述中有所描述。还公开了包含该化合物的组合物以及使用该化合物抑制HCV的方法。
• Hepatitis C Virus Inhibitors
  申请人：Bachand Carol

  公开号：US20090202483A1

  公开（公告）日：2009-08-13

  The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本公开涉及化合物、组合物和治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及在治疗HCV感染中使用这些化合物的方法。
• Design and Synthesis of Piperazinylpyridine Derivatives as Novel 5-HT1A Agonists/5-HT3 Antagonists for the Treatment of Irritable Bowel Syndrome (IBS)
  作者：Akira Asagarasu、Teruaki Matsui、Hiroyuki Hayashi、Satoru Tamaoki、Yukinao Yamauchi、Michitaka Sato

  DOI：10.1248/cpb.57.34

  日期：——

  We have prepared a series of piperazinylpyridine derivatives for the treatment of irritable bowel syndrome (IBS). These compounds, which were designed by pharmacophore analysis, bind to both serotonin subtype 1A (5-HT1A) and subtype 3 (5-HT3) receptors. The nitrogen atom of the isoquinoline, a methoxy group and piperazine were essential to the pharmacophore for binding to these receptors. We also synthesized furo- and thienopyridine derivatives according to structure–activity relationship analyses. Compound 17c (TZB-20810) had high affinities to these receptors and exhibited 5-HT1A agonistic activity and 5-HT3 antagonistic activity concurrently, and is a promising drug for further development in the treatment of IBS.

  我们已准备了一系列哌嗪吡啶衍生物用于治疗肠易激综合征（IBS）。这些化合物通过药效团分析设计，能够同时与血清素亚型1A（5-HT1A）和亚型3（5-HT3）受体结合。异喹啉的氮原子、一个甲氧基和哌嗪是与这些受体结合的药效团的重要组成部分。我们还根据结构-活性关系分析合成了呋喃和噻吡啶衍生物。化合物17c（TZB-20810）对这些受体具有很高的亲和力，同时展现出5-HT1A激动剂活性和5-HT3拮抗剂活性，是治疗IBS方面具有进一步开发潜力的有前景药物。
• [EN] HETEROARYLAMINOISOQUINOLINES, METHODS FOR THEIR PREPARATION AND THERAPEUTIC USES THEREOF<br/>[FR] HÉTÉROARYLAMINOISOQUINOLINES, PROCÉDÉS POUR LES PRÉPARER ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：MINORYX THERAPEUTICS S L

  公开号：WO2016120808A1

  公开（公告）日：2016-08-04

  The application is directed to compounds of formula (IA) : and specifically compounds of formula (I) and their salts and solvates, wherein R1, R11, R12, R13, R4, R5, n, A1, A2, and A3 are as set forth in the specification, as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of conditions associated with the alteration of the activity of β-galactosidase, specially galactosidase beta-1 or GLB1, including GM1 gangliosidoses and Morquio syndrome, type B.

  该申请涉及式（IA）的化合物，特别涉及式（I）的化合物及其盐和溶剂合物，其中R1、R11、R12、R13、R4、R5、n、A1、A2和A3如规范中所述，以及它们的制备方法，包含它们的药物组合物，以及用于治疗和/或预防与β-半乳糖苷酶活性改变相关的病症的用途，特别是β-半乳糖苷酶1或GLB1，包括GM1神经节苷脂症和莫尔基奥综合征B型。
• Macrocyclic isoquinoline peptide inhibitors of Hepatitis C virus
  申请人：McPhee Fiona

  公开号：US20050090432A1

  公开（公告）日：2005-04-28

  Macrocyclic isoquinoline peptides are disclosed having the general formula: A compound of formula I: wherein R 1 to R 9 , Q and W are described in the description. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  本发明揭示了具有一般式的大环异喹啉肽： 式I的化合物： 其中R1至R9，Q和W在说明书中描述。还揭示了包含该化合物的组合物以及使用该化合物抑制HCV的方法。

表征谱图