3-溴-5-羟基喹啉 | 1123738-15-7

• 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: 3-溴-5-羟基喹啉
• 中文别名: 3-溴喹啉-5-醇
• 英文名称: 3-bromoquinolin-5-ol
• 英文别名: 3-Bromoquinolin-5-ol
• CAS: 1123738-15-7
• 化学式: C₉H₆BrNO
• 分子量: 224.057
• InChiKey: NJBHLUVEQVTPCC-UHFFFAOYSA-N

物化性质

• 沸点：
  348.4±22.0 °C(Predicted)
• 密度：
  1.705±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

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：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  3-溴-5-羟基喹啉 在 copper(l) iodide 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium iodide 、 N,N'-二甲基乙二胺 作用下， 以 2-甲基四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 3-(morpholine-4-carbonyl)quinolin-5-yl dimethylcarbamate
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate

  摘要：

  An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)(2)/Xantphos catalyst system.

  DOI：

  10.1021/acs.joc.5b01119
• 作为产物：
  描述：

  3-溴-5-硝基喹啉 在 铁粉 、 溶剂黄146 、 硫酸 、 sodium nitrite 、 水 作用下， 以 水 为溶剂， 以30%的产率得到3-溴-5-羟基喹啉
  参考文献：
  名称：

  Synthesis and c-Met Kinase Inhibition of 3,5-Disubstituted and 3,5,7-Trisubstituted Quinolines: Identification of 3-(4-Acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a Novel Anticancer Agent

  摘要：

  By use of an improved synthetic strategy, a series of 3,5-disubstituted and 3,5,7-trisubstituted quinolines were readily prepared. 3,5,7-Trisubstituted quinolines 21a-c, 211, and 27a-c were identified as the most potent c-Met inhibitors with IC50 of less than 1.0 nM. Compound 21b showed the most promising overall PK profile and has high potency and extraordinary selectivity to c-Met against c-Met family member Ron and 12 other tyrosine kinases. It produced constitutive inhibition of c-Met phosphorylation in c-Met dependent cell lines. At doses of 100 mg/kg, compound 21b showed statistically significant tumor growth inhibition (68-69%) in both NIH-3T3-TPR-Met and U-87 MG human gliobastoma xenograft models. These results clearly indicated that compound 21b is a potent and highly selective c-Met inhibitor. Its favorable in vitro and in vivo profiles warrant further investigation.

  DOI：

  10.1021/jm101340q

文献信息

• [EN] SPIRO-FUSED TRICYCLIC MAP4K1 INHIBITORS<br/>[FR] INHIBITEURS DE MAP4K1 TRICYCLIQUES SPIRO FUSIONNÉS
  申请人：BAYER AG

  公开号：WO2021074279A1

  公开（公告）日：2021-04-22

  The present invention relates to Map4K1 inhibitors of formula (I) to pharmaceutical compositions and combinations comprising the compounds according to the invention, and to the prophylactic and therapeutic use of the inventive compounds, respectively to the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular for neoplastic disorders, repectively cancer or conditions with dysregulated immune responses or other disorders associated with aberrant MAP4K1 signaling, as a sole agent or in combination with other active ingredients. The present invention further relates to the use, respectively to the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of protein inhibitors in benign hyperplasias, atherosclerotic disorders, sepsis, autoimmune disorders, vascular disorders, viral infections, in neurodegenerative disorders, in inflammatory disorders, in atherosclerotic disorders and in male fertility control.

  本发明涉及式(I)的Map4K1抑制剂，以及包含根据本发明的化合物的药物组合物和组合物，以及创新化合物的预防性和治疗性用途，分别用于制造用于治疗或预防疾病的药物组合物，特别是用于肿瘤性疾病，癌症或与异常MAP4K1信号相关的其他紊乱免疫反应或其他紊乱的疾病，作为单一药剂或与其他活性成分组合使用。本发明还涉及使用，分别用于制造用于治疗或预防良性增生、动脉粥样硬化疾病、败血症、自身免疫疾病、血管疾病、病毒感染、神经退行性疾病、炎症性疾病、动脉粥样硬化疾病和男性生育控制的蛋白抑制剂的药物组合物的用途。
• Anti-Mycobacterial N-(2-Arylethyl)quinolin-3-amines Inspired by Marine Sponge-Derived Alkaloid
  作者：Junya Mukomura、Hiroki Nonaka、Hiromasa Sato、Maho Kishimoto、Masayoshi Arai、Naoyuki Kotoku

  DOI：10.3390/molecules27248701

  日期：——

  The synthesis and evaluation of simplified analogs of marine sponge-derived alkaloid 3-(phenethylamino)demethyl(oxy)aaptamine were performed to develop novel anti-mycobacterial substances. Ring truncation of the tricyclic benzo[de][1,6]-naphthyridine skeleton effectively weakened the cytotoxicity of the natural product, and the resulting AC-ring analog exhibited good anti-mycobacterial activity. A

  对海绵衍生生物碱 3-(苯乙氨基)去甲基(氧基)aaptamine 的简化类似物进行了合成和评价，以开发新型抗分枝杆菌物质。三环苯并[de][1,6]-萘啶骨架的截环有效削弱了天然产物的细胞毒性，所得AC环类似物表现出良好的抗分枝杆菌活性。结构-活性关系 (SAR) 研究、合成和评估一些类似物，证明了 N-(2-芳基乙基)喹啉-3-胺骨架作为抗分枝杆菌先导化合物的有前途支架的特异性和重要性。
• Discovery of a novel series of quinoxalines as inhibitors of c-Met kinase
  作者：John Porter、Simon Lumb、Fabien Lecomte、James Reuberson、Anne Foley、Mark Calmiano、Kelly le Riche、Helen Edwards、Jean Delgado、Richard J. Franklin、Jose M. Gascon-Simorte、Alison Maloney、Christoph Meier、Mark Batchelor

  DOI：10.1016/j.bmcl.2008.11.062

  日期：2009.1

  A series of quinoxaline inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and optimisation of the series was performed on the basis of this structure. Future directions for development of the series are discussed together with the identification of a novel quinoline scaffold.
• Synthesis and c-Met Kinase Inhibition of 3,5-Disubstituted and 3,5,7-Trisubstituted Quinolines: Identification of 3-(4-Acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a Novel Anticancer Agent
  作者：Yuanxiang Wang、Jing Ai、Ying Wang、Yi Chen、Lu Wang、Gang Liu、Meiyu Geng、Ao Zhang

  DOI：10.1021/jm101340q

  日期：2011.4.14

  By use of an improved synthetic strategy, a series of 3,5-disubstituted and 3,5,7-trisubstituted quinolines were readily prepared. 3,5,7-Trisubstituted quinolines 21a-c, 211, and 27a-c were identified as the most potent c-Met inhibitors with IC50 of less than 1.0 nM. Compound 21b showed the most promising overall PK profile and has high potency and extraordinary selectivity to c-Met against c-Met family member Ron and 12 other tyrosine kinases. It produced constitutive inhibition of c-Met phosphorylation in c-Met dependent cell lines. At doses of 100 mg/kg, compound 21b showed statistically significant tumor growth inhibition (68-69%) in both NIH-3T3-TPR-Met and U-87 MG human gliobastoma xenograft models. These results clearly indicated that compound 21b is a potent and highly selective c-Met inhibitor. Its favorable in vitro and in vivo profiles warrant further investigation.
• Targeting NOX2 with Bivalent Small-Molecule p47phox–p22phox Inhibitors
  作者：Jie Zang、Felix Peters、Yves Cambet、Eugenia Cifuentes-Pagano、Munira Mohamed Shishay Hissabu、Christopher M. Dustin、Lars Henrik Svensson、Martin Mariboe Olesen、Mathias Feldt Lomholt Poulsen、Stig Jacobsen、Pernille Sønderby Tuelung、Dilip Narayanan、Annette Eva Langkilde、Michael Gajhede、Patrick J. Pagano、Vincent Jaquet、Frederik Vilhardt、Anders Bach

  DOI：10.1021/acs.jmedchem.3c01548

  日期：2023.11.9