5-(2-fluorophenyl)furan-2-carboxylic acid methyl ester | 852145-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-(2-fluorophenyl)furan-2-carboxylic acid methyl ester
• 英文别名: methyl 5-(2-fluorophenyl)furan-2-carboxylate
• CAS: 852145-96-1
• 化学式: C₁₂H₉FO₃
• mdl: MFCD09030561
• 分子量: 220.2
• InChiKey: WCKJUEPCTHGYLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-fluorophenyl)furan-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 5-(2-氟苯基)-2-糠酸
  参考文献：
  名称：

  5-芳基-呋喃-2-羧酰胺衍生物的合成和合成孔径雷达作为有效的尿紧张素-II受体拮抗剂。

  摘要：

  一系列4-（3-氯-4-（哌啶丁-4-基氧基）苄基）哌嗪-1的5-芳基呋喃-2-羧酰胺衍生物1的合成和生物学评价，作为潜在的尿紧张素II受体拮抗剂。描述了基团。对具有C-5芳基且具有多个芳环取代基的呋喃-2-甲酰胺进行系统SAR研究的结果导致鉴定3,4-二氟苯基类似物1y为高效UT拮抗剂，IC50值为6 nM。另外，发现该物质表现出高的代谢稳定性，低的hERG抑制和细胞毒性，并具有可接受的PK曲线。

  DOI：

  10.1016/j.bmcl.2018.12.058
• 作为产物：
  描述：

  2-糠酸甲酯 、 2-氟苯胺 在 盐酸 、 sodium nitrite 、 copper(II) chloride dihydrate 作用下， 以 水 、 丙酮 为溶剂， 以57%的产率得到5-(2-fluorophenyl)furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  由不饱和化合物的芳基化产物合成杂环：XVIII。5-芳基呋喃-2-羧酸及其在1,2,4-噻二唑，1,3,4-恶二唑和[1,2,4]三唑[3,4-b] [1， 3,4]噻二唑衍生物

  摘要：

  在氯化铜（II）存在下，将呋喃-2-甲酸或其甲酯与氯化芳二氮鎓进行氯化，得到相应的5-芳基呋喃-2-羧酸或5-芳基呋喃-2-羧酸甲酯。5-芳基呋喃-2-羰基氯与硫氰酸钾反应，然后与5-甲基-1,2-恶唑-3-胺反应，得到5-芳基-N- [3-（2-氧丙基）-1,2,4 -噻二唑-5-基]呋喃-2-甲酰胺是中间体异恶唑基硫脲衍生物再循环的结果。5-芳基呋喃-2-羰基氯化物与5-（2-呋喃基）-1 H-四唑的反应涉及四唑环的打开并消除了氮分子，并导致了2-（5-芳基呋喃-2-基）的形成。 yl）-5-（2-呋喃基）-1,3,4-恶二唑。3-取代的6-（5-芳基呋喃-2-基）-[1,2,4]三唑[3,4- b] [1,3,4]噻二唑是通过将5-芳基呋喃-2-羧酸与5-取代的4-氨基-4 H -1,2,4-三唑-3-硫醇在磷酰氯中缩合而获得的。

  DOI：

  10.1134/s1070428009040125

文献信息

• Methyl 2-Furoate: An Alternative Reagent to Furan for Palladium-Catalysed Direct Arylation
  作者：Hai Yan Fu、Henri Doucet

  DOI：10.1002/ejoc.201101102

  日期：2011.12

  The palladium-catalysed direct arylation of methyl 2-furoate with aryl bromides was studied. The use of KOAc as the base, dimethylacetamide (DMAc) as the solvent and Pd(OAc)2 as the catalyst was found to give 5-arylfurans regioselectively and without decarboxylation. These methyl 5-aryl-2-furoates gave 2,5-diarylfurans by decarboxylative coupling by using Pd(OAc)2 as the catalyst. Methyl 2-furoate

  研究了钯催化的 2-糠酸甲酯与芳基溴化物的直接芳基化反应。发现使用 KOAc 作为碱、二甲基乙酰胺 (DMAc) 作为溶剂和 Pd(OAc) 2 作为催化剂可以区域选择性地得到 5-芳基呋喃并且没有脱羧。这些5-芳基-2-糠酸甲酯通过使用Pd(OAc) 2 作为催化剂的脱羧偶联得到2,5-二芳基呋喃。因此，2-糠酸甲酯代表了一种方便的替代呋喃的底物，用于合成单或多芳基化呋喃。
• [EN] [4-(3-AMINOMETHYLPHENYL) PIPERIDIN-1-YL]- [5-(2-FLUOROPHENYLETHYNYL)FURAN-2-YL]-METHANONE AS AN INHIBITOR OF MAST CELL TRYPTASE<br/>[FR] [4-(3-AMINOMETHYLPHENYL)PIPERIDIN-1-YL]-[5-(2-FLUOROPHENYLETHYNYL)FURAN-2-YL]-METHANONE EN TANT QU'INHIBITEUR DE LA TRYPTASE MASTOCYTAIRE
  申请人：AVENTIS PHARMA INC

  公开号：WO2004060884A1

  公开（公告）日：2004-07-22

  The present invention extends to the compund of formula (I): (I) or a prodrug, pharmaceutically acceptable salt, or solvate of said compound; to a pharmaceutical composition comprising a pharmaceutically effective amount of the compound of forumula (I), and a pharmaceutically acceptable carrier; the use of a compound of formula (I) as an inhibitor of tryptase, comprising introducing the compound into a composition comprising tryptase.

  本发明涉及到式(I)的化合物：(I)或者该化合物的前药、药学上可接受的盐或溶剂；一种包含式(I)化合物的药物组合物，以及药学上有效量的该化合物和药学上可接受的载体；将式(I)化合物用作色氨酸蛋白酶抑制剂的用途，包括将该化合物引入含有色氨酸蛋白酶的组合物中。
• [EN] FURANCARBONYLGUANIDINE DERIVATIVES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DERIVES DE FURANCARBONYLGUANIDINE, LEUR PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2005063727A1

  公开（公告）日：2005-07-14

  The present invention relates to furancarbonylguanidine derivatives, a preparation method thereof and a pharmaceutical composition comprising the same. Furancarbonylguanidine derivatives of the present invention inhibit NHE-1 (sodium-hydrogen exchanger isoform 1), which helps recovery of heart function damaged from ischemia/ reperfusion and decreases myocardial infarction rate, indicating that they have protective effect on myocardial cells. Thus, furancarbonylguanidine derivatives of the present invention can be ef­fectively used for the prevention and the treatment of ischemic heart diseases such as myocardial infarction, arrhythmia, angina pectoris, etc, and also a promising candidate for a heart protecting agent applied to reperfusion therapy including thrombolytics or cardiac surgery including coronary artery bypass graft, percutaneous transluminal coronary angioplasty, etc.

  本发明涉及呋喃羰基胍衍生物，其制备方法以及包含这些衍生物的药物组合物。本发明的呋喃羰基胍衍生物抑制NHE-1（钠氢交换体异构体1），有助于恢复因缺血/再灌注而受损的心脏功能，降低心肌梗死率，表明它们对心肌细胞具有保护作用。因此，本发明的呋喃羰基胍衍生物可以有效用于预防和治疗心肌梗死、心律失常、心绞痛等缺血性心脏疾病，并且是应用于再灌注疗法（包括溶栓疗法或心脏手术，如冠状动脉旁路移植术、经皮冠状动脉成形术等）的心脏保护剂的有前景的候选药物。
• Furancarbonylguanidine Derivatives, Their Preparation and Pharmaceutical Compositions Containing Them
  申请人：Yi Yang Kyu

  公开号：US20070299131A1

  公开（公告）日：2007-12-27

  The present invention relates to furancarbonylguanidine derivatives, a preparation method thereof and a pharmaceutical composition comprising the same. Furancarbonylguanidine derivatives of the present invention inhibit NHE-1 (sodium-hydrogen exchanger isoform 1), which helps recovery of heart function damaged from ischemia/reperfusion and decreases myocardial infarction rate, indicating that they have protective effect on myocardial cells. Thus, furancarbonylguanidine derivatives of the present invention can be effectively used for the prevention and the treatment of ischemic heart diseases such as myocardial infarction, arrhythmia, angina pectoris, etc, and also a promising candidate for a heart protecting agent applied to reperfusion therapy including thrombolytics or cardiac surgery including coronary artery bypass graft, percutaneous transluminal coronary angioplasty, etc.

  本发明涉及呋喃羰基胍衍生物、其制备方法和包含它们的药物组合物。本发明的呋喃羰基胍衍生物抑制NHE-1（钠-氢交换体型1），有助于恢复因缺血/再灌注而受损的心脏功能，并降低心肌梗死率，表明它们对心肌细胞具有保护作用。因此，本发明的呋喃羰基胍衍生物可有效用于预防和治疗缺血性心脏病，如心肌梗死、心律失常、心绞痛等，并且是再灌注治疗（包括溶栓治疗）或冠状动脉搭桥手术、经皮冠状动脉成形术等心脏手术的心脏保护剂的有前途的候选物。
• (5-Arylfuran-2-ylcarbonyl)guanidines as Cardioprotectives through the Inhibition of Na⁺/H⁺ Exchanger Isoform-1
  作者：Sunkyung Lee、Kyu Yang Yi、Sun Kyung Hwang、Byung Ho Lee、Sung-eun Yoo、Kyunghee Lee

  DOI：10.1021/jm0492305

  日期：2005.4.1

  A series of (5-arylfuran-2-ylcarbonyl)guanidines was synthesized and evaluated for the NHE-1 inhibitory activity and cardiprotective efficacy against ischemia-reperfusion injury. Starting with (5-phenylfuran-2-ylcarbonyl)guanidine 47 with a moderate inhibitory effect on NHE-1, the compounds with various substituents at the phenyl ring were investigated with the aim to optimize the potency. In this study, the 2,5-disubstituted compounds appeared to have better activities than the other analogues, and the 2-methoxy-5-chlorophenyl compound 85 was found as a potent inhibitor of NHE-1 (IC50 = 0.081 mu M). Furthermore, 85 showed a marked reduction of infarct size in the rat myocardial infarction model in vivo and significant improvement of cardiac contractile function in the isolated rat heart ischemia model in vitro.