4-氯-8-氰基喹啉-3-甲酸乙酯 | 77173-67-2

• 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: 4-氯-8-氰基喹啉-3-甲酸乙酯
• 英文名称: 4-Chloro-8-cyano-quinoline-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-chloro-8-cyanoquinoline-3-carboxylate
• CAS: 77173-67-2
• 化学式: C₁₃H₉ClN₂O₂
• 分子量: 260.68
• InChiKey: MHOFAUCLSGVKOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  8-氰基-4-氧代-1H-喹啉-3-羧酸乙酯	ethyl 8-cyano-4-hydroxyquinoline-3-carboxylate	77156-79-7	C13H10N2O3	242.234

反应信息

• 作为反应物：
  描述：

  4-氯-8-氰基喹啉-3-甲酸乙酯 在 钯 氢气 、 三乙胺 、 肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 8-Aminomethyl-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents

  摘要：

  A novel series of substituted quinoline analogs were designed and synthesized as potent and selective melanin concentrating hormone (MCH) antagonists. These analogs show potent (nM) activity (12a-k) with a moderate selectivity. Conversely, the conformationally constrained thienopyrimidinone analogs (1 8a-g) showed improved activity in MCH-1R and selectivity over 5 HT2C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.006
• 作为产物：
  描述：

  8-氰基-4-氧代-1H-喹啉-3-羧酸乙酯 在 氯化亚砜 作用下， 以80%的产率得到4-氯-8-氰基喹啉-3-甲酸乙酯
  参考文献：
  名称：

  Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents

  摘要：

  A novel series of substituted quinoline analogs were designed and synthesized as potent and selective melanin concentrating hormone (MCH) antagonists. These analogs show potent (nM) activity (12a-k) with a moderate selectivity. Conversely, the conformationally constrained thienopyrimidinone analogs (1 8a-g) showed improved activity in MCH-1R and selectivity over 5 HT2C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.006

文献信息

• [EN] CYCLIC AMINE AZAHETEROCYCLIC CARBOXAMIDES<br/>[FR] CARBOXAMIDES AZAHÉTÉROCYCLIQUES D'AMINES CYCLIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2012016001A1

  公开（公告）日：2012-02-02

  The invention provides novel cyclic amine azaheterocyclic carboxamide according to Formula (I), Formula (II) and Formula (III) their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.

  这项发明提供了根据式(I)、式(II)和式(III)制备的新型环胺氮杂杂环羧酰胺，以及它们用于治疗高增殖性疾病，如癌症的用途。
• Cyclic Amine Azaheterocyclic Carboxamides
  申请人：Huck Bayard R.

  公开号：US20130217709A1

  公开（公告）日：2013-08-22

  The invention provides novel cyclic amine azaheterocyclic carboxamide according to Formula (I), Formula (II) and Formula (III) their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.

  该发明提供了新型的环状胺氮杂杂环羧酰胺，其化学式为(I)、(II)和(III)，以及它们的制造和用于治疗高增殖性疾病，如癌症的用途。
• A novel procedure for the synthesis of borylated quinolines and its application in the development of potential boron-based homeodomain interacting protein kinase 2 (HIPK2) inhibitors
  作者：Bhaskar C. Das、Pratik Yadav、Sasmita Das、John Cijiang He

  DOI：10.1039/d2ra05063c

  日期：——

  we demonstrate a Pd catalyzed C-4 borylation of structurally complex chloroquinolines with bis(pinacolato)diboron under relatively simple and efficient conditions. Moreover, the borylated quinolines were converted into oxaborole, trifluoroborate salt and boronic acid and also rendered in the Suzuki reaction successfully. The method was also applied for the synthesis of potential boron-based homeodomain

  在这里，我们展示了在相对简单和有效的条件下，结构复杂的氯喹啉与双（频哪醇）二硼的 Pd 催化 C-4 硼化。此外，硼化喹啉被转化为氧杂硼杂环戊二烯、三氟硼酸盐和硼酸，并成功地用于铃木反应。该方法还用于合成潜在的基于硼的同源域相互作用蛋白激酶 2 (HIPK2) 抑制剂。该策略为喹啉作为未来生物医学研究的潜在探针和药理学试剂的功能化开辟了新途径。
• One-pot borylation/arylation of 4-chloroquinolines and its application for the synthesis of various quinoline-based pharmacophores
  作者：Pratik Yadav、Sasmita Das、Mariko Saito、Todd Evans、Bhaskar C. Das

  DOI：10.1016/j.tetlet.2023.154780

  日期：2023.11

  and H2O furnish synthesis of C-4 arylated quinolines. This method gives access to various structurally interesting and pharmaceutically relevant C-4 arylated quinolines through CC bond formation under simple and efficient condition. Additionally, it offers a new synthetic protocol for future functionalization of quinolines at C-4 position which has been encountered in various quinoline based drugs and

  在此，我们描述了一种 4-氯喹啉一锅硼化/芳基化的新方案。该反应通过钯催化的一锅两步过程进行。在第一步中，用双(频那醇)二硼(B 2 pin 2 )或双(新戊基乙醇)二硼(B 2 neo 2 )与Pd(PPh 3 ) 2 Cl 2和KOAc进行不同取代的4-氯喹啉的硼基化，并在第二步在PPh 3、K 3 PO 4和H 2 O存在下用芳基卤化物进行芳基化，合成C-4芳基化喹啉。该方法可以在简单有效的条件下通过CC键形成获得各种结构有趣且药学相关的C-4芳基化喹啉。此外，它还为未来 C-4 位喹啉的功能化提供了一种新的合成方案，这在各种基于喹啉的药物和生物学上重要的支架中都遇到过。
• Cyclic amine azaheterocyclic carboxamides
  申请人：Merck Patent GmbH

  公开号：US10087166B2

  公开（公告）日：2018-10-02

  The invention provides novel cyclic amine azaheterocyclic carboxamide according to Formula (I), Formula (II) and Formula (III) their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.

  本发明提供了根据式(I)、式(II)和式(III)制造和使用的新型环胺杂杂环羧酰胺，用于治疗过度增殖性疾病，如癌症。