2-(2-bromophenyl)quinoline-4-carboxylic acid | 130987-63-2

• 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
• 英文名称: 2-(2-bromophenyl)quinoline-4-carboxylic acid
• CAS: 130987-63-2
• 化学式: C₁₆H₁₀BrNO₂
• 分子量: 328.165
• InChiKey: HYZHYKDLSCJRMM-UHFFFAOYSA-N

物化性质

• 熔点：
  250.2-253.4 °C(Solv: ethanol (64-17-5))
• 沸点：
  484.8±40.0 °C(Predicted)
• 密度：
  1.556±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)quinoline-4-carboxylic acid 在 吡啶 、 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  Discovering novel chemical inhibitors of human cyclophilin A: Virtual screening, synthesis, and bioassay

  摘要：

  Cyclophilin A (CypA) is a member of cyclophilins, a family of the highly homologous peptidyl prolyl cis-trans isomerases (PPIases), which can bind to cyclosporin A (CsA). CypA plays critical roles in various biological processes, including protein folding, assembly, transportation, regulation of neuron growth, and HIV replication. The discovery of CypA inhibitor is now of a great special interest in the treatment of immunological disorders. In this study, a series of novel small molecular CypA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. The SPECS-1 database containing 85,000 small molecular compounds was searched by virtual screening against the crystal structure of human CypA. After SPR-based binding affinity assay, 15 compounds were found to show binding affinities to CypA at submicro-molar or micromolar level (compounds 1-15). Seven compounds were selected as the starting point for the further structure modification in considering binding activity, synthesis difficulty, and structure similarity. We thus synthesized 40 new small molecular compounds (1-6, 15, 16a-q, 17a-d, and 18a-I), and four of which (compounds 16b, 16h 16k,. and 18g) showed high CypA PPIase inhibition activities with IC50S of 2.5-6,2 mu M. Pharmacological assay indicated that these four Compounds demonstrated somewhat inhibition activities against the proliferation of spleen cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.006
• 作为产物：
  描述：

  2-苯基-4-喹啉羧酸 在 2,6-二甲基吡啶 、 Selectfluor 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 22.0h， 生成 2-(2-bromophenyl)quinoline-4-carboxylic acid
  参考文献：
  名称：

  通过芳基 BF2 络合物进行硼介导的区域选择性芳族 C−H 功能化

  摘要：

  已经实现了2-芳基氮杂芳烃N-杂芳烃和芳基醛的区域选择性功能化。该反应通过 BBr 3促进的 5 元和 6 元硼环进行，该环经过 Selectfluor 促进的配体交换，得到以前稀缺的芳基 BF 2物质。芳基 BF 2是一种稳定的中间体，可用于 2-芳基-氮杂芳烃支架的脱硼功能化。

  DOI：

  10.1002/chem.202203505

文献信息

• A novel synthesis of 3-halo-2-phenylquinoline-4-carboxylic acids
  作者：Luca F. Raveglia、Giuseppe A. M. Giardina、Mario Grugni、Roberto Rigolio、Carlo Farina

  DOI：10.1002/jhet.5570340235

  日期：1997.3

  3-bromo-2-phenylquinoline-4-carboxylic acids were obtained in good yields through a novel procedure, entailing the synthesis of the 3-amino intermediate and the subsequent replacement of the amino group with chlorine or bromine, according to the Sandmeyer reaction.

  通过一种新颖的方法，以高收率获得了3-氯和3-溴-2-苯基喹啉-4-羧酸，需要合成3-氨基中间体，然后用氯或溴取代氨基。桑德迈尔反应。
• Exploration of Isoxazole‐Carboxylic Acid Methyl Ester Based 2‐Substituted Quinoline Derivatives as Promising Antitubercular Agents
  作者：Santosh Kumar Sahoo、Mohammad Naiyaz Ahmad、Grace Kaul、Srinivas Nanduri、Arunava Dasgupta、Sidharth Chopra、Venkata Madhavi Yaddanapudi

  DOI：10.1002/cbdv.202200324

  日期：2022.7

  pursuit of potent anti-TB agents active against drug resistant tuberculosis (DR-TB), herein we report synthesis and bio-evaluation of a new series of isoxazole-carboxylic acid methyl ester based 2-substituted quinoline derivatives. Preliminary evaluation indicated selectivity towards Mtb H37Rv, with no inhibition of non-tubercular mycobacterial (NTM) & bacterial pathogen panel. Out of 36 synthesized compounds

  为了追求对耐药结核病 (DR-TB) 有活性的有效抗结核药物，我们在此报告了一系列基于异恶唑-羧酸甲酯的 2-取代喹啉衍生物的合成和生物评价。初步评估表明对 Mtb H37Rv 具有选择性，对非结核分枝杆菌 (NTM) 和细菌病原体组没有抑制作用。在 36 种合成化合物中，大多数化合物对 Mtb H37Rv 具有显着抑制作用（MIC 0.5-8 μg/mL）。针对 Vero 细胞的细胞活力测试显示没有显着的细胞毒性。此外，针对耐药菌株 (DR-Mtb) 的筛选发现命中化合物显示出有希望的效力 (MIC 1-4 μg/mL)。命中的结构优化导致了先导化合物的鉴定，证明了对药物敏感的 Mtb (MIC 0. 12 μg/mL) 和耐药 Mtb (MIC 0.25-0.5 μg/mL) 以及高选择性指数 (SI) >80。总之，具有可观的选择性和有效的活性，这些化学型显示出有望成为潜在的抗结核病候选者。