5-methoxycarbonylfuryl phenyl ketone benzylhydrazone | 170632-18-5

• 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-methoxycarbonylfuryl phenyl ketone benzylhydrazone
• 英文别名: 5-Methoxycarbonylfuryl phenyl ketone benzylhydrazone；methyl 5-[N-(benzylamino)-C-phenylcarbonimidoyl]furan-2-carboxylate
• CAS: 170632-18-5
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: SSTLDYNLPHSCMS-UHFFFAOYSA-N

物化性质

• 沸点：
  496.1±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonylfuryl phenyl ketone benzylhydrazone 在 calcium borohydride 、 三氟化硼乙醚 作用下， 生成 3-(5-羟基甲基-2-呋喃基)-1-苯基吲哚
  参考文献：
  名称：

  Synthesis of 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole Analogues as Novel Antiplatelet Agents

  摘要：

  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.

  DOI：

  10.1021/jm010001h
• 作为产物：
  描述：

  2-糠酸甲酯 在 三氯化铁 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 5-methoxycarbonylfuryl phenyl ketone benzylhydrazone
  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。
• Novel fused pyrazolyl compound
  申请人：Kuo Sheng-Chu

  公开号：US20050215612A1

  公开（公告）日：2005-09-29

  A fused pyrazolyl compound of the following formula: wherein A, Ar 1 , Ar 2 , R 1 , R 2 , R 3 , and R 4 , are as defined herein. Also disclosed is a pharmaceutical composition containing an effective amount of the above-described fused pyrazolyl compound.

  以下是融合的吡唑化合物的化学式，其中A、Ar1、Ar2、R1、R2、R3和R4的定义如下。还公开了一种含有上述融合的吡唑化合物的有效量的药物组合物。
• Fused pyrazolyl compound
  申请人：Yung Shin Pharmaceutical Ind. Co., Ltd.

  公开号：US07378532B2

  公开（公告）日：2008-05-27

  A fused pyrazolyl compound of the following formula: wherein A, Ar1, Ar2, R1, R2, R3, and R4, are as defined herein. Also disclosed is a pharmaceutical composition containing an effective amount of the above-described fused pyrazolyl compound.

  以下是一种融合了吡唑基的化合物，其化学式为：其中，A，Ar1，Ar2，R1，R2，R3和R4的定义如本文所述。此外，还公开了一种药物组合物，其含有上述融合吡唑基化合物的有效量。
• 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole (YC-1) Derivatives as Novel Inhibitors Against Sodium Nitroprusside-Induced Apoptosis
  作者：Jin-Cherng Lien、Fang-Yu Lee、Li-Jiau Huang、Shiow-Lin Pan、Jih-Hwa Guh、Che-Ming Teng、Sheng-Chu Kuo

  DOI：10.1021/jm020070b

  日期：2002.11.1

  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.