2-(3-溴苯基)喹啉-4-羧酸 | 298230-83-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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: 2-(3-溴苯基)喹啉-4-羧酸
• 英文名称: 2-(3-bromophenyl)quinoline-4-carboxylic acid
• CAS: 298230-83-8
• 化学式: C₁₆H₁₀BrNO₂
• mdl: MFCD00687529
• 分子量: 328.165
• InChiKey: KBIDGMKRLPPRNG-UHFFFAOYSA-N

物化性质

• 熔点：
  232-234 °C
• 沸点：
  487.8±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

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-(3-溴苯基)喹啉-4-羧酸 在 吡啶 、 氯化亚砜 作用下， 反应 3.0h， 生成 2-(3-bromophenyl)-N-{4-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl}quinoline-4-carboxamide
  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：

  靛红 、 3'-溴苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(3-溴苯基)喹啉-4-羧酸
  参考文献：
  名称：

  2-苯基喹啉-4-甲酰胺连接苯磺酰胺衍生物作为跨膜人碳酸酐酶异构体选择性抑制剂的探索

  摘要：

  使用尾部方法合成了一系列新的含有 32 种磺酰胺的喹啉（5a-j、7a-k和9a-k） ，并测定了它们对四种人 (h) 碳酸酐酶 (CA) 异构体 hCA I、II 的碳酸酐酶抑制效力，九和十二。大多数这些新合成的化合物在纳摩尔范围内对 hCA I、II、IX 和 XII 表现出有趣的抑制效力，其中一些衍生物比标准药物乙酰唑胺 ( AAZ ) 更有效。在 hCA I 上最有效的是9b (91.8 nM)，在 hCA II 上：5b ( 7.1 nM)、9c (9.6 nM) 和在 hCA IX 上：5b (6.5 nM) 、5g (21.4 nM), 5i (9.1 nM) , 9a (22.8 nM) , 9b (9.7 nM)。发现化合物5h (8.8 nM)、7a (9.6 nM)、9d (6.9 nM)、9e (6.7 nM) 对 hCA XII 非常有效。发现这些 4-官能化苯磺酰胺

  DOI：

  10.1016/j.ejmech.2022.114247

文献信息

• Exploration of 2-phenylquinoline-4-carboxamide linked benzene sulfonamide derivatives as isoform selective inhibitors of transmembrane human carbonic anhydrases
  作者：Baijayantimala Swain、Santosh Kumar Sahoo、Priti Singh、Andrea Angeli、Venkata Madhavi Yaddanapudi、Claudiu T. Supuran、Mohammed Arifuddin

  DOI：10.1016/j.ejmech.2022.114247

  日期：2022.4

  A novel series of 32 sulfonamide containing quinolines (5a-j, 7a-k and 9a-k) were synthesized using tail approach and assayed for their carbonic anhydrase inhibitory potency against four human (h) carbonic anhydrase (CA) isoforms hCA I, II, IX and XII. Most of these newly synthesized compounds exhibited interesting inhibition potency against hCA I, II, IX and XII, in the nanomolar range with some derivatives

  使用尾部方法合成了一系列新的含有 32 种磺酰胺的喹啉（5a-j、7a-k和9a-k） ，并测定了它们对四种人 (h) 碳酸酐酶 (CA) 异构体 hCA I、II 的碳酸酐酶抑制效力，九和十二。大多数这些新合成的化合物在纳摩尔范围内对 hCA I、II、IX 和 XII 表现出有趣的抑制效力，其中一些衍生物比标准药物乙酰唑胺 ( AAZ ) 更有效。在 hCA I 上最有效的是9b (91.8 nM)，在 hCA II 上：5b ( 7.1 nM)、9c (9.6 nM) 和在 hCA IX 上：5b (6.5 nM) 、5g (21.4 nM), 5i (9.1 nM) , 9a (22.8 nM) , 9b (9.7 nM)。发现化合物5h (8.8 nM)、7a (9.6 nM)、9d (6.9 nM)、9e (6.7 nM) 对 hCA XII 非常有效。发现这些 4-官能化苯磺酰胺
• 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。
• COMPOUNDS FOR USE IN THE TREATMENT OF VIRAL INFECTIONS BY VIRUS OF THE FAMILY CORONAVIRIDAE
  申请人：Consejo Superior De Investigaciones Científicas

  公开号：EP3939664A1

  公开（公告）日：2022-01-19

  The present invention relates to new derivatives of 2-phenyl-quinoline-4-carboxylic acid or pharmaceutically acceptable salt thereof and to combination of said compounds with other active ingredients, for use in the treatment and/or prevention of viral infections by virus from the family Coronaviridae, to the use of said compound or its combinations in the manufacture of a medicament for the treatment or prevention of said diseases and to a method of treating and/or preventing said diseases by administration of said compound or its combinations.

  本发明涉及 2-苯基-喹啉-4-羧酸的新衍生物或其药学上可接受的盐，以及所述化合物与其他活性成分的组合，用于治疗和/或预防冠状病毒科病毒感染，涉及所述化合物或其组合在制造治疗或预防所述疾病的药物中的用途，以及通过服用所述化合物或其组合治疗和/或预防所述疾病的方法。
• [EN] COMPOUNDS FOR USE IN THE TREATMENT OF VIRAL INFECTIONS BY VIRUS OF THE FAMILY CORONAVIRIDAE<br/>[FR] COMPOSÉS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT D'INFECTIONS VIRALES PAR UN VIRUS DE LA FAMILLE DES CORONAVIRIDAE
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2022013412A1

  公开（公告）日：2022-01-20

  The present invention relates to new derivatives of 2-phenyl-quinoline-4-carboxylic acid or pharmaceutically acceptable salt thereof and to combination of said compounds with other active ingredients, for use in the treatment and/or prevention of viral infections by virus from the family Coronaviridae, to the use of said compound or its combinations in the manufacture of a medicament for the treatment or prevention of said diseases and to a method of treating and/or preventing said diseases by administration of said compound or its combinations.
• [EN] BIFUNCTIONAL MOLECULES FOR SELECTIVE MODIFICATION OF TARGET SUBSTRATES<br/>[FR] MOLÉCULES BIFONCTIONNELLES POUR LA MODIFICATION SÉLECTIVE DE SUBSTRATS CIBLES
  申请人：[en]THE BROAD INSTITUTE, INC.

  公开号：WO2022225728A2

  公开（公告）日：2022-10-27

  The present disclosure relates to bifunctional chemical conjugation molecules, which find utility as modifiers of target substrates. The present disclosure includes multifunctional compounds comprising an enzyme binding moiety, a chemical linker moiety, and a target binding moiety, which may further include an electrophilic reactive group. Molecules according to the present invention find use making substrate modifications such as post- translational modifications to proteins that are not the natural substrate of the enzyme. Diseases or disorders may be treated or prevented with molecules of the present disclosure.