5-(4-氟苯甲酰基)呋喃-2-甲酸甲酯 | 170632-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-(4-氟苯甲酰基)呋喃-2-甲酸甲酯
• 英文名称: 4'-Fluorophenyl 5-methoxycarbonyl-2-furyl ketone
• 英文别名: p-Fluorophenyl 5-methoxycarbonyl-2-furyl ketone；4-Fluorphenyl 5-methoxycarbonyl-2-furyl ketone；methyl 5-(4-fluorobenzoyl)furan-2-carboxylate
• CAS: 170632-16-3
• 化学式: C₁₃H₉FO₄
• 分子量: 248.21
• InChiKey: VWUXSQCSRLZRRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-氟苯甲酰基)呋喃-2-甲酸甲酯 在 lead(IV) acetate 、 calcium borohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-benzyl-3-(5'-hydroxymethyl-2'-furyl)-6-fluoroindazole
  参考文献：
  名称：

  1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole (YC-1) Derivatives as Novel Inhibitors Against Sodium Nitroprusside-Induced Apoptosis

  摘要：

  Antiapoptotic agents based on 1-benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (22, YC-1) derivatives were explored for effective treatment of sepsis and septic shock. We found that compound 22, 1-benzyl-3-(5'-methoxymethyl-2'-furyl)indazole (27), and 1-phenyl-3-(5'-hydroxymethyl-2'-furyl)-indazole (23) were the most effective inhibitors of sodium nitroprusside-induced vascular smooth muscle cell apoptosis. These three compounds are proposed as potential therapeutic agents for the treatment of sepsis.

  DOI：

  10.1021/jm020070b
• 作为产物：
  描述：

  2-糠酸甲酯 、 对氟苯甲酰氯 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以58.1%的产率得到5-(4-氟苯甲酰基)呋喃-2-甲酸甲酯
  参考文献：
  名称：

  1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole (YC-1) Derivatives as Novel Inhibitors Against Sodium Nitroprusside-Induced Apoptosis

  摘要：

  Antiapoptotic agents based on 1-benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (22, YC-1) derivatives were explored for effective treatment of sepsis and septic shock. We found that compound 22, 1-benzyl-3-(5'-methoxymethyl-2'-furyl)indazole (27), and 1-phenyl-3-(5'-hydroxymethyl-2'-furyl)-indazole (23) were the most effective inhibitors of sodium nitroprusside-induced vascular smooth muscle cell apoptosis. These three compounds are proposed as potential therapeutic agents for the treatment of sepsis.

  DOI：

  10.1021/jm020070b

文献信息

• Method of treating disorders related to protease-activated receptors-induced cell activation
  申请人：——

  公开号：US20020004518A1

  公开（公告）日：2002-01-10

  A method of treating a disorder related to cell activation induced by protease-activated receptors. The method includes administering to a subject in need thereof a compound having a pyrazolyl core; an aryl group, via an via an alkylene linker, bonded to 1-N of the pyrazolyl core; a second aryl group fused at 4-C and 5-C of the pyrazolyl core; and a third aryl group bonded directly to 3-C of the pyrazolyl core.

  一种治疗与蛋白酶激活受体引起的细胞活化相关障碍的方法。该方法包括向需要的受试者施用具有吡唑基核的化合物；通过烷基连接剂与吡唑基核的1-N键合的芳基团；在吡唑基核的4-C和5-C处融合的第二个芳基团；以及直接与吡唑基核的3-C键合的第三个芳基团。
• Preferential inhibition of release of pro-inflammatory cytokines
  申请人：Yung Shin Pharm. Ind. Co. Ltd.

  公开号：EP1576954A1

  公开（公告）日：2005-09-21

  A method for preferentially inhibiting release of pro-inflammatory cytokines over release of anti-inflammatory cytokines using a fused pyrazolyl compound of formula (I): A is R or in which R is H, alkyl, aryl, cyclyl, heteroaryl, or heterocyclyl; each of Ar1, Ar2, and Ar3, independently, is phenyl, thienyl, furyl, or pyrrolyl; each of R1, R2, R3, R4, R5, and R6, independently, is R', nitro, halogen, -C(O)-OR', -C(O)-SR', -C(O)-NR'R", -(CH2)mOR', -(CH2)mSR', -(CH2)mNR'R", -(CH2)mCN, -(CH2)mC(O)-OR', -(CH2)mC(O)H, or R1 and R2 together, R3 and R4 together, or R5 and R6 together are -O(CH2)mO-, in which each of R' and R", independently, is H, alkyl, cyclyl, aryl, heteroaryl, heterocyclyl; and m is 0, 1, 2, 3, 4, 5, or 6; and n is 1, 2, or 3. This invention also covers a method of inhibiting activity of NF-κB with such a compound.

  使用式(I)的融合吡唑基化合物优先抑制释放促炎细胞因子而不是抗炎细胞因子的方法：其中A为R或其中R为H，烷基，芳基，环烷基，杂芳基或杂环烷基；Ar1，Ar2和Ar3中的每一个独立地为苯基，噻吩基，呋喃基或吡咯基；R1，R2，R3，R4，R5和R6中的每一个独立地为R'，硝基，卤素，-C(O)-OR'，-C(O)-SR'，-C(O)-NR'R"，-(CH2)mOR'，-(CH2)mSR'，-(CH2)mNR'R"，-(CH2)mCN，-(CH2)mC(O)-OR'，-(CH2)mC(O)H，或者R1和R2一起，R3和R4一起，或者R5和R6一起为-O(CH2)mO-，其中R'和R"中的每一个独立地为H，烷基，环烷基，芳基，杂芳基，杂环烷基；m为0，1，2，3，4，5或6；n为1，2或3。该发明还涵盖了使用这种化合物抑制NF-κB活性的方法。
• Use of pyrazole derivatives for inhibiting thrombin-induced platelet aggregation
  申请人：Yung Shin Pharmeutical Ind. Co., Ltd.

  公开号：EP1166785A1

  公开（公告）日：2002-01-02

  A method of treating a disorder or disease related to thrombin-induced platelet aggregation. The method includes administering to a subject in need thereof a compound having a pyrazolyl core; an aryl group, via an via an alkylene linker, bonded to 1-N of the pyrazolyl core; a second aryl group fused at 4-C and 5-C of the pyrazolyl core; and a third aryl group bonded directly to 3-C of the pyrazolyl core.

  一种治疗与凝血酶诱导的血小板聚集有关的紊乱或疾病的方法。该方法包括向有需要的受试者施用一种化合物，该化合物具有吡唑基核心；通过亚烷基连接体与吡唑基核心的1-N键合的芳基；在吡唑基核心的4-C和5-C处融合的第二芳基；以及直接与吡唑基核心的3-C键合的第三芳基。
• Synthesis of 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole Analogues as Novel Antiplatelet Agents
  作者：Fang-Yu Lee、Jin-Cherng Lien、Li-Jiau Huang、Tsang-Miao Huang、Sheng-Chung Tsai、Che-Ming Teng、Chin-Chung Wu、Fong-Chi Cheng、Sheng-Chu Kuo

  DOI：10.1021/jm010001h

  日期：2001.10.1

  1-Benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (28, YC-1) was selected as the lead compound for systemic structural modification. After screening for antiplatelet activity, SARs of YC-1 analogues were established. Among these potent active derivatives, compounds 29, 30, 31, 44, and 45 functioned as potent activators of sGC and inhibitors of PDE5 with potency comparable to that of YC-1. In addition, compound 58 was found to be a selective and potent inhibitor of protease-activated receptor type 4 (PAR4)-dependent platelet activation.
• 1-Benzyl-3-(substituted aryl)-condensed pyrazole derivatives as inhibitors of platelet aggregation
  申请人：Yung Shin Pharm. Ind. Co. Ltd.

  公开号：EP0667345B1

  公开（公告）日：1999-09-29