ferulic acid | 132980-20-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ferulic acid
• 英文别名: (E)-3-(3-methoxy-4-methylphenyl)acrylic acid；3-(3-Methoxy-4-methylphenyl)-2-propenoic acid；3-(3-Methoxy-4-methylphenyl)acrylic acid；(E)-3-(3-methoxy-4-methylphenyl)prop-2-enoic acid
• CAS: 132980-20-2
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: VAQDMGWYJCJJIE-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ferulic acid 在 palladium on activated charcoal 盐酸 、 草酰氯 、 氢气 、 四氯化锡 、 N,N-二甲基甲酰胺 、 亚硝酸异戊酯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 25.0~45.0 ℃ 、413.69 kPa 条件下， 反应 11.75h， 生成 2-(hydroxyimino)-5-methoxy-6-methyl-1-indanone
  参考文献：
  名称：

  Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)

  摘要：

  The racemate and the enantiomers of 1-(3-methoxy-4-methylphenyl)-2-aminopropane (6) and racemic 5-methoxy-6-methyl-2-aminoindan (11) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Both 6 and 11 were found to substitute with high potency in 3,4-(methylenedioxy)methamphetamine (1) and (S)-1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (2) trained rats. In the latter assay, both enantiomers of 6 had identical potencies, but their dose-response curves were not parallel. Racemic 6, but not 11, partially substituted for LSD. Racemic 6 and 11 did not substitute in (S)-amphetamine-trained rats. All of the test compounds were potent inhibitors of [H-3]-5-HT uptake into synaptosomes in vitro, with the S enantiomer of 6 being most active. Rat brain monoamine levels were unaltered 1 week following a single high dose (10 or 20 mg/kg, sc) of 6 or 11, or two weeks following a subacute dosing regimen (20 mg/kg, sc, twice a day for 4 days). In addition, radioligand-binding parameters in rat brain homogenate with the 5-HT uptake inhibitor [H-3]proxetine were unchanged after subacute dosing with either racemic 6 or 11. The results indicate that compounds 6 and 11 have animal behavioral pharmacology similar to the methylenedioxy compounds 1 and 2, but that they do not induce the serotonin neurotoxicity that has been observed for the latter two drugs.

  DOI：

  10.1021/jm00109a020
• 作为产物：
  描述：

  3-甲氧基-4-甲基苯甲醛 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 生成 ferulic acid
  参考文献：
  名称：

  Benzylideneacetone Derivatives Inhibit Osteoclastogenesis and Activate Osteoblastogenesis Independently Based on Specific Structure–Activity Relationship

  摘要：

  （E）-3,4-羟基苯基羰基乙酮（化合物1）通过竞争性抑制RANKL诱导的C57BL/6骨髓间充质和巨噬细胞的骨质疏松化，其IC50为7.8 μM（与阿仑地平的IC50 3.7 μM相对），同时刺激MC3T3-E1骨生成细胞的分化，并诱导Runt相关转录因子2、碱性磷酸酶和 osteocalcin的表达。（E）-4-（2-羟基-3-甲氧基苯基）-3-酮（化合物2c）显示出显著增强的骨质疏松阻断活性，其IC50为0.11 μM，同时保持骨生成刺激活性。化合物2g（E）-4（3-羟基-4-甲氧基苯基）-3-酮（化合物2g）在50 μM浓度下抑制碱性磷酸酶的分泌2倍，而不改变骨质疏松阻断活性，与化合物1相比。口服阿帕拉西坦0.5 g/kg（1）、1 g/kg（2c）和2.5 g/kg（2g）预防了ddY小鼠因子宫切除引起的骨质疏松，其预防效果与其骨质疏松阻断活性成正比。与10 g/kg的阿仑地平相当的是，1 mg/kg-day的2c干预骨质疏松 rodent model的骨量,histomorphometry));而在 ozial Salvation 管理和研究药物治疗骨质疏松方面，此结论为骨质疏松关节病的潜在治疗提供了依据。本研究表明，几类苯基迪酮衍生物的在 vitro 能力不仅能抑制骨质疏松的骨生成活化，还能增强骨质疏松修复的obiology.这暗示了治疗骨质疏松小鼠模型的小鼠模型的 dadidiotherapeutic 效应。综上所述，这些苯基迪酮衍生物在 vivo 中抑制骨质疏松的能力与骨生成活化相互独立，证实了在 vivo 管理骨质疏松疾病中具有潜在的治疗意义。这些化合物的可能为骨质疏松性骨病的新型治疗提供了一种途径。

  DOI：

  10.1021/acs.jmedchem.9b00270

文献信息

• [EN] 3-ARYLOXY AND 3-HETEROARYLOXY SUBSTITUTED BENZO(B) THIOPHENES AS THERAPEUTIC AGENTS WITH PI3K ACTIVITY<br/>[FR] BENZO[B]THIOPHENES A SUBSTITUTION 3-ARYLOXY ET 3-HETEROARYLOXY EN TANT QU'AGENTS THERAPEUTIQUES A ACTIVITE PI3K
  申请人：WARNER LAMBERT CO

  公开号：WO2004108715A1

  公开（公告）日：2004-12-16

  The present invention provides benzo[b]thiophenes of Formula (I), wherein R1, R2, R3, R4, R5, and L have any of the values defined therefor in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including inflammatory diseases, cardiovascular diseases, and cancers. Also provided are pharmaceutical compositions comprising one or more compounds of Formula (I).

  本发明提供了式(I)的苯并[b]噻吩，其中R1、R2、R3、R4、R5和L具有规范中为其定义的任何值，以及药用可接受的盐，这些盐作为治疗疾病和状况的药剂是有用的，包括炎性疾病、心血管疾病和癌症。另外还提供了包含一个或多个式(I)化合物的药物组合物。
• 1,2,3-triazolo&lsqb;4,5-d&rsqb;pyrimidines as P2T receptor antagonists
  申请人：AstraZeneca UK Limited

  公开号：US06251910B1

  公开（公告）日：2001-06-26

  Compounds of formula having the following stereochemistry wherein R, R1, R2, R3 and R4 are as defined in the specification. The compounds are useful as P2T receptor antagonists.

  具有以下立体化学的式化合物 其中R、R1、R2、R3和R4如规范中所定义。这些化合物可用作P2T受体拮抗剂。
• [EN] FUSED RING ANALOGUES OF ANTI-FIBROTIC AGENTS<br/>[FR] ANALOGUES À CYCLES CONDENSÉS D'AGENTS ANTI-FIBROTIQUES
  申请人：FIBROTECH THERAPEUTICS PTY LTD

  公开号：WO2011047432A1

  公开（公告）日：2011-04-28

  The present invention relates to arylcarbonyl and heteroarylcarbonyl anthranilate compounds that may be useful as anti-fibrotic agents. The present invention also relates to methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment disorders.

  本发明涉及可能用作抗纤维化剂的芳基羰基和杂芳基羰基蒽酰胺化合物。本发明还涉及它们的制备方法、含有这些化合物的药物组合物以及这些化合物在治疗疾病中的用途。
• 3-Arylsulfanyl and 3-heteroarylsulfanyl substituted benzo[b]thiophenes as therapeutic agents
  申请人：——

  公开号：US20040248953A1

  公开（公告）日：2004-12-09

  The present invention provides benzo[b]thiophenes of Formula I: 1 wherein R 1 , R 2 , R 3 , and L have any of the values defined therefor in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including inflammatory diseases, cardiovascular diseases, and cancers. Also provided are pharmaceutical compositions comprising one or more compounds of Formula I.

  本发明提供了公式I:1中的苯并[b]噻吩，其中R1、R2、R3和L具有规范中定义的任何值，以及其药用可接受的盐，可用作治疗疾病和症状的药物，包括炎症性疾病、心血管疾病和癌症。还提供了包含一个或多个公式I化合物的药物组合物。
• Cycloalkylsulfanyl substituted benzo[b]thiophenes as therapeutic agents
  申请人：——

  公开号：US20040248954A1

  公开（公告）日：2004-12-09

  The present invention provides benzo[b]thiophenes of Formula I: 1 wherein R 1 , R 2 , R 3 , and L have any of the values defined therefor in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including inflammatory diseases, cardiovascular diseases, and cancers. Also provided are pharmaceutical compositions comprising one or more compounds of Formula I.

  本发明提供了公式I中的苯并[b]噻吩：其中R1、R2、R3和L具有规范中定义的任何值，以及其药用盐，这些化合物可用作治疗疾病和症状的药剂，包括炎症性疾病、心血管疾病和癌症的药剂。还提供了包括一个或多个公式I化合物的药物组合物。