5-(naphthalen-2-yl)furan-2-carboxylic acid | 488816-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(naphthalen-2-yl)furan-2-carboxylic acid
• 英文别名: 5-(Naphthalin-2-yl)-furan-2-carboxylic acid；5-naphthalen-2-ylfuran-2-carboxylic acid
• CAS: 488816-68-8
• 化学式: C₁₅H₁₀O₃
• mdl: MFCD02812468
• 分子量: 238.243
• InChiKey: OJLLEPSSEQSYKK-UHFFFAOYSA-N

物化性质

• 沸点：
  448.1±33.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 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：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(naphthalen-2-yl)furan-2-carboxylic acid 在 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 6,7-dimethoxy-2-[(5-naphthalen-2-ylfuran-2-yl)methyl]-3,4-dihydro-1H-isoquinoline
  参考文献：
  名称：

  Naphthalenyl derivatives for hitting P-gp/MRP1/BCRP transporters

  摘要：

  Substituted naphthalenyl derivatives bearing oxazole, or thiazole or furyl heteronuclei have been carried out as bioisosters of aryl-oxazoles and -thiazoles derivatives previously reported in order to investigate the role of the hindrance on the activity towards P-gp/BCRP/and MRP1 transporters. In addition, the role of naphthalenyl group to modulate P-gp intrinsic activity of these compounds was ascertained.The results demonstrated that all naphthalenyl derivatives displayed comparable P-gp activity with respect to lead compounds previously characterized in our SAR studies but were less active towards BCRP and MRP1 pumps. In terms of intrinsic activity, the replacement of aryl with naphthalenyl moiety led to P-gp inhibitors, unambiguous or ambiguous substrates on the base of the heteronucleus and the substituent on the naphthalenyl fragment. Indeed, oxazole derivatives were: inhibitors (R = H, F, OH), unambiguous substrates (R = OCH3), or ambiguous substrate (R = Br); thiazole derivatives were: unambiguous substrates (R = OCH3, Br), or ambiguous substrates (R = H, F). Finally furyl derivatives were ambiguous substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.021
• 作为产物：
  描述：

  5-溴-2-糠酸甲酯 在 四(三苯基膦)钯 、 sodium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 生成 5-(naphthalen-2-yl)furan-2-carboxylic acid
  参考文献：
  名称：

  NS6740衍生物的设计，合成和电生理评估：探索alpha7烟碱型乙酰胆碱受体沉默激活的结构活性关系。

  摘要：

  能够诱导受体脱敏并促进α7代谢功能的α7烟碱型乙酰胆碱受体（nAChR）沉默激动剂，正在成为新兴的新型治疗性抗炎药。在这里，我们报告原型沉默激动剂NS6740（1,4-二氮杂双环[3.2.2]壬南-4-基（5-（3-（三氟甲基）-苯基）-呋喃-2-基）的结构-活性关系研究）（甲酮）（1）阐明负责α7沉默激活的配体-受体相互作用。在这项研究中，NS6740片段11 - 16和类似物17 - 32设计，合成，并测定对表达的人α7烟碱受体爪蟾两电极电压钳制实验的卵母细胞。NS6740的所有结构部分对于产生其独特的活性谱至关重要。二氮杂双环核是必需的，但不足以诱导α7沉默激活。中央氢键受体核和芳族部分对于促进延长的α7受体结合和持续的脱敏至关重要。化合物13和17是有效的部分激动剂。化合物12，21，23 - 26，和30α7nAChR高度脱敏，因此可能对炎症反应的其他研究感兴趣。我们获得了有助于进一步沉默激动剂发展的关键结构信息。

  DOI：

  10.1016/j.ejmech.2020.112669

文献信息

• Carboxylic acid derivatives, medicaments comprising these compounds, their use and processes for their production
  申请人：Boehringer Ingelheim Pharma KG

  公开号：US20030055263A1

  公开（公告）日：2003-03-20

  The present application relates to the use of the carboxylic acid derivatives of general formula R 1 —A—B—R 2 (I) wherein R 1 , R 2 , A and B are defined as in claim 1 , the isomers and the salts thereof, particularly the physiologically acceptable salts thereof, which have an inhibitory effect on telomerase, processes for the preparation thereof, pharmaceutical compositions containing these compounds and the use thereof as well as the preparation thereof.

  本申请涉及一般公式R1—A—B—R2(I)的羧酸衍生物的使用，其中R1、R2、A和B的定义如权利要求1中所述，其异构体和盐，特别是其生理上可接受的盐，对端粒酶具有抑制作用，其制备方法，含有这些化合物的药物组合物以及其用途，以及其制备方法。
• [DE] CARBONSÄUREDERIVATE, DIESE VERBINDUNGEN ENTHALTENDE ARZNEIMITTEL, DEREN VERWENDUNG UND HERSTELLUNG<br/>[EN] CARBOXYLIC ACID DERIVATIVES, MEDICAMENTS CONTAINING THESE COMPOUNDS, THEIR USE AND THE PRODUCTION THEREOF<br/>[FR] DERIVES D'ACIDE CARBOXYLIQUE, MEDICAMENTS CONTENANT CES COMPOSES, LEUR UTILISATION ET LEUR PRODUCTION
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2003006443A2

  公开（公告）日：2003-01-23

  Die vorliegende Anmeldung betrifft die Verwendung der Carbonsäurederivate der allgemeinen Formel R1 - A - B - R2 (I), in der R1, R2, A und B wie im Anspruch 1 definiert sind, deren Isomere und deren Salze, insbesondere deren physiologisch verträglichen Salze, welche eine Hemmwirkung auf die Telomerase aufweisen, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie deren Herstellung.
• Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation
  作者：Maria Chiara Pismataro、Nicole A. Horenstein、Clare Stokes、Marta Quadri、Marco De Amici、Roger L. Papke、Clelia Dallanoce

  DOI：10.1016/j.ejmech.2020.112669

  日期：2020.11

  The α7 nicotinic acetylcholine receptor (nAChR) silent agonists, able to induce receptor desensitization and promote the α7 metabotropic function, are emerging as new promising therapeutic anti-inflammatory agents. Herein, we report the structure–activity relationship investigation of the archetypal silent agonist NS6740 (1,4-diazabicyclo[3.2.2]nonan-4-yl(5-(3-(trifluoromethyl)-phenyl)-furan-2-yl)methanone)

  能够诱导受体脱敏并促进α7代谢功能的α7烟碱型乙酰胆碱受体（nAChR）沉默激动剂，正在成为新兴的新型治疗性抗炎药。在这里，我们报告原型沉默激动剂NS6740（1,4-二氮杂双环[3.2.2]壬南-4-基（5-（3-（三氟甲基）-苯基）-呋喃-2-基）的结构-活性关系研究）（甲酮）（1）阐明负责α7沉默激活的配体-受体相互作用。在这项研究中，NS6740片段11 - 16和类似物17 - 32设计，合成，并测定对表达的人α7烟碱受体爪蟾两电极电压钳制实验的卵母细胞。NS6740的所有结构部分对于产生其独特的活性谱至关重要。二氮杂双环核是必需的，但不足以诱导α7沉默激活。中央氢键受体核和芳族部分对于促进延长的α7受体结合和持续的脱敏至关重要。化合物13和17是有效的部分激动剂。化合物12，21，23 - 26，和30α7nAChR高度脱敏，因此可能对炎症反应的其他研究感兴趣。我们获得了有助于进一步沉默激动剂发展的关键结构信息。
• Naphthalenyl derivatives for hitting P-gp/MRP1/BCRP transporters
  作者：Nicola A. Colabufo、Marialessandra Contino、Mariangela Cantore、Elena Capparelli、Maria Grazia Perrone、Giuseppe Cassano、Giuseppe Gasparre、Marcello Leopoldo、Francesco Berardi、Roberto Perrone

  DOI：10.1016/j.bmc.2012.12.021

  日期：2013.3

  Substituted naphthalenyl derivatives bearing oxazole, or thiazole or furyl heteronuclei have been carried out as bioisosters of aryl-oxazoles and -thiazoles derivatives previously reported in order to investigate the role of the hindrance on the activity towards P-gp/BCRP/and MRP1 transporters. In addition, the role of naphthalenyl group to modulate P-gp intrinsic activity of these compounds was ascertained.The results demonstrated that all naphthalenyl derivatives displayed comparable P-gp activity with respect to lead compounds previously characterized in our SAR studies but were less active towards BCRP and MRP1 pumps. In terms of intrinsic activity, the replacement of aryl with naphthalenyl moiety led to P-gp inhibitors, unambiguous or ambiguous substrates on the base of the heteronucleus and the substituent on the naphthalenyl fragment. Indeed, oxazole derivatives were: inhibitors (R = H, F, OH), unambiguous substrates (R = OCH3), or ambiguous substrate (R = Br); thiazole derivatives were: unambiguous substrates (R = OCH3, Br), or ambiguous substrates (R = H, F). Finally furyl derivatives were ambiguous substrates. (C) 2013 Elsevier Ltd. All rights reserved.