3-(bromomethyl)-2-chloroquinoline | 35740-82-0

• 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
• 英文名称: 3-(bromomethyl)-2-chloroquinoline
• CAS: 35740-82-0
• 化学式: C₁₀H₇BrClN
• 分子量: 256.529
• InChiKey: FWGQIOWOFSUCMM-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  343.1±27.0 °C(Predicted)
• 密度：
  1.621±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(bromomethyl)-2-chloroquinoline 在 palladium diacetate 、 potassium tert-butylate 、 四丁基溴化铵 、 potassium acetate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 喜树碱
  参考文献：
  名称：

  A 10-step, asymmetric synthesis of (S)-camptothecin

  摘要：

  DOI：

  10.1021/ja00053a049
• 作为产物：
  描述：

  N-(2-chloroquinolin-3-yl)acetamide 在 sodium tetrahydroborate 、 三溴化磷 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-(bromomethyl)-2-chloroquinoline
  参考文献：
  名称：

  Tetrazolylmethyl quinolines: Design, docking studies, synthesis, anticancer and antifungal analyses

  摘要：

  A new series of 2,5 and 1,5-regioisomers of the tetrazolyl group viz., 3-[(5-benzyl/benzylthio-2H-tetrazol-2- yl) methyl]-2-chloro-6-substituted quinoline 6h-q and 3-[(5-benzyl/benzylthio-1H-tetrazol-1-yl) methyl]-2-chloro-6-substituted quinolines 7h-q were synthesized. Docking studies of all these compounds with DNA as target using PDB: 1AU5 and 453D revealed that the compounds 6h and 6i act as covalent cross linker on the DNA helix of the former and intercalate the latter both with higher C score values. Another set of docking studies in the active pocket of dihydrofolate reductase and N-myristoyl transferase as targets to assess antifungal activity revealed that compounds 6k, 6l, 6p and 7q (with bromo and fluro substituents) showcases different binding modes and hydrogen bonding. Further, the compounds were screened for anticancer activity (primary cytotoxicity) against NCI-60 Human tumor cell line at a single high dose (10(-5) M) concentration assay. Among the tested compounds, 6h has shown 99.28% of GI against Melanoma (SK-MEL-5) and compound 6i has shown 97.56% of GI against Breast Cancer (T-47D). Further, in vitro antifungal assay against A. fumigatus and C. albicans for these compounds 6h-q and 7h-q revealed potential to moderate activities as compared to the standard. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.01.043

文献信息

• Synthesis and Antibacterial Evaluation of Some Novel 1,3,4-oxadiazol Derivatives Incorporated with Quinoline Moiety
  作者：Priyanka G. Mandhane、Ratnadeep S. Joshi、Wajid Khan、Charansingh H. Gill

  DOI：10.5012/jkcs.2011.55.4.656

  日期：2011.8.20

  5-(3,4,5-Triethoxyphenyl)-1,3,4-oxadiazole-2-thiol 6을 3-(bromomethyl)-2-chloroquinoline or 2-(p-tolyloxy)-3-(bromomethyl) quinoline 4a-j 화합물과 반응시켜서 3-((5-(3,4,5-triethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-2-chloroquinoline 또는 3-((5-(3,4,5-triethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-2-(p-tolyloxy)quinoline 7a-j를 합성하였다. 합성한 화합물들에 대한 항균활성을 측정하였으며, 화합물 7d, 7i 및 7j 은 우수한 활성을 나타내었다. 5-(3,4,5-Triethoxyphenyl)-1,3,4-oxadiazole-2-thiol 6 on treatment with substituted 3-(bromomethyl)-2-chloroquinoline or 2-(p-tolyloxy)-3-(bromomethyl)quinoline 4a-j afforded the corresponding 3-((5-(3,4,5-triethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-2-chloroquinoline or 3-((5-(3,4,5-triethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-2-(p-tolyloxy)quinoline 7a-j, in the presence of $K_2CO_3$ and DMF under stirring at ambient temperature. All the synthesized compounds were further screened for their antibacterial activities. Some of our compounds showed excellent antibacterial activities against test organisms and reference standard.

  5-(3,4,5-三乙氧基苯基)-1,3,4-噁二唑-2-硫醇6与3-(溴甲基)-2-氯喹啉或2-(对甲苯氧基)-3-(溴甲基)喹啉4a-j反应，合成了3-((5-(3,4,5-三乙氧基苯基)-1,3,4-噁二唑-2-硫代)甲基)-2-氯喹啉或3-((5-(3,4,5-三乙氧基苯基)-1,3,4-噁二唑-2-硫代)甲基)-2-(对甲苯氧基)喹啉7a-j。测定了合成的化合物的抗菌活性，化合物7d、7i和7j表现出优秀的活性。在与取代的3-(溴甲基)-2-氯喹啉或2-(对甲苯氧基)-3-(溴甲基)喹啉4a-j反应时，加入K2CO3和DMF，在室温下搅拌，得到了相应的3-((5-(3,4,5-三乙氧基苯基)-1,3,4-噁二唑-2-硫代)甲基)-2-氯喹啉或3-((5-(3,4-三乙氧基苯基)-1,3,4-噁二唑-2-硫代)甲基)-2-(对甲苯氧基)喹啉7a-j。所有合成的化合物都进一步进行了抗菌活性筛选，一些化合物对测试生物和参考标准表现出极佳的抗菌活性。
• Expeditious Synthesis of the Topoisomerase I Inhibitors Isoindolo[2,1-b]isoquinolin-7(5H)-one and the Alkaloid Rosettacin Based on Aryl Radical Cyclization of Enamide Generated by Using N-Acyl­iminium Chemistry
  作者：Adam Daïch、Lahssen El Blidi、Aurélie Namoune、Alexandre Bridoux、Vijaykumar Nimbarte、Ata Lawson、Sébastien Comesse

  DOI：10.1055/s-0034-1378811

  日期：——

  approach to the synthesis of the topoisomerase I inhibitor isoindolo[2,1-b]isoquinolin-7(5H)-one and the alkaloid rosettacin belonging to the aromathecin family is presented. The key step of this sequence, which resulted in the formation of a five-membered ring, was the aryl radical cyclization of enamides generated using N-acyliminium chemistry. A short and effective approach to the synthesis of the topoisomerase

  为了纪念我们的同事让·莫雷尔教授，于2012年12月12日在法国勒阿弗尔逝世。 抽象 提出了一种短而有效的方法来合成拓扑异构酶I抑制剂isoindolo [2,1 - b ] isoquinolin -7（5 H）-one和属于阿奇霉素家族的生物碱Rosettacin。该序列的关键步骤导致形成五元环，该步骤是使用N-酰亚胺化学生成的酰胺的芳基环化。 提出了一种短而有效的方法来合成拓扑异构酶I抑制剂isoindolo [2,1 - b ] isoquinolin -7（5 H）-one和属于阿奇霉素家族的生物碱Rosettacin。该序列的关键步骤导致形成五元环，该步骤是使用N-酰亚胺化学生成的酰胺的芳基环化。
• Interrupted CuAAC‐Thiolation for the Construction of 1,2,3‐Triazole‐Fused Eight‐Membered Heterocycles from <i>O</i> ‐/ <i>N</i> ‐Propargyl derived Benzyl Thiosulfonates with Organic Azides
  作者：Raju Jannapu Reddy、Md. Waheed、Arram Haritha Kumari、Gamidi Rama Krishna

  DOI：10.1002/adsc.202101256

  日期：2022.1.18

  click-sulfenylation of O-/N-propargyl benzyl thiosulfonates with organic azides has been disclosed. The unified CuAAC-thiolation provides a wide range of triazole-fused eight-membered heterocycles in good to high (51–94%) yields under mild reaction conditions. Moreover, a three-component reaction is also achieved involving O-/N-propargyl benzyl thiosulfonates, benzyl bromide, and sodium azide to deliver fused-triazoles

  已公开了铜 (I) 催化的O-/N-炔丙基苄基硫代磺酸盐与有机叠氮化物的间断点击亚磺酰化。在温和的反应条件下，统一的 CuAAC-硫醇化提供了范围广泛的三唑稠合八元杂环，产率从好到高（51-94%）。此外，还实现了涉及O-/N-炔丙基苄基硫代磺酸盐、苄基溴和叠氮化钠的三组分反应，以 61-74% 的收率提供稠合三唑。从合成的角度来看，本协议已在克级反应中得到证明。基于实验结果和对照实验，还提出了一种似是而非的机制。
• TRICYCLIC INHIBITORS OF 5-LIPOXYGENASE
  申请人：Hutchinson John Howard

  公开号：US20070173508A1

  公开（公告）日：2007-07-26

  Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of 5-lipoxygenase (5-LO). Also described herein are methods of using such 5-LO inhibitors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions, diseases, or disorders.

  本文描述了含有这些化合物的化合物和药物组合物，这些化合物抑制5-脂氧合酶（5-LO）的活性。本文还描述了使用这种5-LO抑制剂的方法，单独或与其他化合物结合，用于治疗呼吸系统、心血管系统和其他依赖或介导白三烯的状况、疾病或紊乱。
• Substituted oxoazaheterocyclyl compounds
  申请人：AVENTIS PHARMACEUTICALS INC.

  公开号：US20040102450A1

  公开（公告）日：2004-05-27

  This invention is directed to oxoazaheterocycyl compounds which inhibit Factor Xa, to oxoazaheterocycyl compounds which inhibit both Factor Xa and Factor IIa, to pharmaceutical compositions comprising these compounds, to intermediates useful for preparing these compounds, to a method of directly inhibiting Factor Xa and to a method of simultaneously directly inhibiting Factor Xa and Factor IIa..

  这项发明涉及抑制因子Xa的氧杂杂环化合物，抑制同时抑制因子Xa和因子IIa的氧杂杂环化合物，包含这些化合物的药物组合物，用于制备这些化合物的中间体，直接抑制因子Xa的方法，以及同时直接抑制因子Xa和因子IIa的方法。