acetoxysinapinoyl chloride | 39657-48-2

• 分子结构分类: 有机化合物
• 英文名称: acetoxysinapinoyl chloride
• 英文别名: acetyl sinapic chloride；3-(4-acetoxy-3,5-dimethoxyphenyl)prop-2-enoyl chloride；sinapinic acid acetate chloride；4-O-acetylsinapic acid chloride；3-(4-acetoxy-3,5-dimethoxy-phenyl)-acryloyl chloride；4-acetoxy-3,5-dimethoxy-cinnamoyl chloride；Acetylsinapinsaeure-chlorid；4-Acetoxy-3,5-dimethoxycinnamic acid chloride；[4-(3-chloro-3-oxoprop-1-enyl)-2,6-dimethoxyphenyl] acetate
• CAS: 39657-48-2
• 化学式: C₁₃H₁₃ClO₅
• 分子量: 284.696
• InChiKey: NIWUDNDULAYEIK-UHFFFAOYSA-N

物化性质

• 沸点：
  367.9±37.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  acetoxysinapinoyl chloride 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 水 为溶剂， 70.0 ℃ 、200.0 kPa 条件下， 反应 2.0h， 生成 4-({4-[3-(4-hydroxy-3,5-dimethoxy-phenyl)-propionyl]-piperazin-1-yl}-acetyl)-morpholine
  参考文献：
  名称：

  Fauran; Turin; Raynaud, European Journal of Medicinal Chemistry, 1975, vol. 10, # 4, p. 373 - 377

  摘要：

  DOI：
• 作为产物：
  描述：

  芥子酸 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 acetoxysinapinoyl chloride
  参考文献：
  名称：

  Synthesis of Quercetin‐Acid Esters and Its Reduction of H ₂ O ₂ ‐Triggered PC12 Cells Damage by Down‐Regulating ROS

  摘要：

  AbstractQuercetin is a kind of polyphenolic flavonoid compounds which has perfect antioxidant properties. However, quercetin is not available in many situations due to its poor bioavailability. In this work, the QAEs with better solubility and even stronger antioxidant properties were synthesized, through the esterification between quercetin and the chlorinated cinnamic acid or its derivatives, whose chlorination were achieved by using SOCl2. The protective effects of the QAEs were evaluated by the H2O2‐induced apoptosis experiment in rat adrenal pheochromocytoma cells (PC12 cells) and its ability to remove ROS generated by oxidative stress. Compared with the original quercetin group, the QAEs groups showed much improved cell viability and capability of removing ROS, which means their higher bioavailability than the parent.

  DOI：

  10.1002/cbdv.202200897

文献信息

• DERIVATIVES OF THE SINAPINIC ACID
  申请人：PHARMASYNTHESE

  公开号：US20150353469A1

  公开（公告）日：2015-12-10

  The object of the present invention is a compound of general formula (I) as well as to its pharmaceutically acceptable salt, and to the use of this compound for cosmetic and pharmaceutical applications.

  本发明的对象是一种具有通式（I）的化合物，以及其药用可接受的盐，以及该化合物在化妆品和药物应用中的使用。
• Synthesis of hydroxyethyl starch derivatives with phenylpropanoid fragments attached through ester or sulfide bonds
  作者：M. A. Torlopov、E. V. Udoratina、V. Yu. Belyaev

  DOI：10.1007/s11172-014-0710-8

  日期：2014.9

  Approaches to the synthesis of hydroxyethyl starch derivatives containing phenylpropanoic acid fragments with various degree of substitution were suggested. Esterification of hydroxyethyl starch in heterogeneous aqueous organic medium gave rise to the corresponding esters of ferulic, p-coumaric, and sinapinic acids. A reaction of hydroxyethyl starch mercaptodeoxy derivative with acetoxy derivatives of these hydroxycinnamic acids led to the mixed polysaccharides with the oxyphenyl-3-mercaptopropanoic acid fragments.

  提出了合成含有不同取代度的苯丙酸片段的羟乙基淀粉衍生物的方法。羟乙基淀粉在异相水性有机介质中发生酯化反应，生成相应的阿魏酸、对香豆酸和山奈酸酯。羟乙基淀粉巯基脱氧衍生物与这些羟基肉桂酸的乙酰氧基衍生物反应后，产生了带有氧苯基-3-巯基丙酸片段的混合多糖。
• A Newly Synthesized Sinapic Acid Derivative Inhibits Endothelial Activation In Vitro and In Vivo
  作者：Xiaoyun Zeng、Jinhong Zheng、Chenglai Fu、Hang Su、Xiaoli Sun、Xuesi Zhang、Yingjian Hou、Yi Zhu

  DOI：10.1124/mol.112.084368

  日期：2013.5

  Inhibition of oxidative stress and inflammation in vascular endothelial cells (ECs) may represent a new therapeutic strategy against endothelial activation. Sinapic acid (SA), a phenylpropanoid compound, is found in natural herbs and high-bran cereals and has moderate antioxidant activity. We aimed to develop new SA agents with the properties of antioxidation and blocking EC activation for possible therapy of cardiovascular disease. We designed and synthesized 10 SA derivatives according to their chemical structures. Preliminary screening of the compounds involved scavenging hydroxyl radicals and 2,2-diphenyl-1-picrylhydrazyl (DPPH⋅), croton oil-induced ear edema in mice, and analysis of the mRNA expression of adhesion molecules in ECs. 1-Acetyl-sinapic acyl-4-(3′-chlorine-)benzylpiperazine (SA9) had the strongest antioxidant and anti-inflammatory activities both in vitro and in vivo. Thus, the effect of SA9 was further studied. SA9 inhibited tumor necrosis factor α -induced upregulation of adhesion molecules in ECs at both mRNA and protein levels, as well as the consequent monocyte adhesion to ECs. In vivo, result of face-to-face immunostaining showed that SA9 reduced lipopolysaccharide-induced expression of intercellular adhesion molecule-1 in mouse aortic intima. To study the molecular mechanism, results from luciferase assay, nuclear translocation of NF- κ B, and Western blot indicated that the mechanism of the anti-inflammatory effects of SA9 might be suppression of intracellular generation of ROS and inhibition of NF- κ B activation in ECs. SA9 is a prototype of a novel class of antioxidant with anti-inflammatory effects in ECs. It may represent a new therapeutic approach for preventing endothelial activation in cardiovascular disorders.

  抑制血管内皮细胞（ECs）的氧化应激和炎症反应可能是防止内皮活化的一种新的治疗策略。西那吡酸（SA）是一种苯丙类化合物，存在于天然草药和高麸谷物中，具有中等程度的抗氧化活性。我们的目标是开发具有抗氧化和阻断心血管活化特性的新的西那皮酸制剂，以用于治疗心血管疾病。我们根据 SA 的化学结构设计并合成了 10 种 SA 衍生物。化合物的初步筛选包括清除羟自由基和 2,2-二苯基-1-苦基肼（DPPH⋅）、巴豆油诱导的小鼠耳水肿以及分析心血管细胞中粘附分子的 mRNA 表达。1-Acetyl-sinapic acyl-4-(3′-chlorine-)benzylpiperazine (SA9)在体外和体内都具有最强的抗氧化和抗炎活性。因此，我们进一步研究了 SA9 的作用。SA9 在 mRNA 和蛋白水平上抑制了肿瘤坏死因子 α 诱导的 EC 粘附分子的上调，并抑制了由此导致的单核细胞对 EC 的粘附。在体内，面对面免疫染色的结果显示，SA9能减少脂多糖诱导的小鼠主动脉内膜细胞间粘附分子-1的表达。为了研究其分子机制，荧光素酶实验、NF- κ B 核转位和 Western 印迹的结果表明，SA9 的抗炎作用机制可能是抑制细胞内 ROS 的产生和抑制 ECs 中 NF- κ B 的活化。SA9 是一类新型抗氧化剂的雏形，对心血管细胞具有抗炎作用。它可能是预防心血管疾病中内皮活化的一种新的治疗方法。
• Thienopyridine derivatives which are intermediates
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05256782A1

  公开（公告）日：1993-10-26

  Thienopyridine derivatives of the formula (I): ##STR1## wherein the ring A is an optionally substituted benzene ring; the ring B is an optionally substituted thiophene ring: X is a group of the formula: ##STR2## (wherein R.sup.1 is hydrogen, alkyl or alkoxy; and n is 0 or 1) or a group of the formula: ##STR3## (wherein R.sup.2 is hydrogen or alkyl); Y is a single bond, --NH--, alkylene having 1 or 2 carbon atoms or --CH.dbd.CH--; and R.sup.3 is an optionally substituted hydrocarbon group, or their salts are disclosed. They show strong ACAT inhibitory activities.

  公式（I）的噻吩并[3,2-c][1]苯并[2,4]噻二唑衍生物：其中，环A是可选取代的苯环；环B是可选取代的噻吩环；X是公式：其中，R1是氢、烷基或烷氧基；n为0或1；或者是公式：其中，R2为氢或烷基；Y是单键、--NH--、具有1或2个碳原子的烷基或--CH=CH--；R3是可选取代的碳氢基团，或它们的盐。它们表现出强烈的ACAT抑制活性。
• Thienopyridine derivatives and their pharmaceutical use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05143919A1

  公开（公告）日：1992-09-01

  Thienopyridine derivatives of the formula (I): ##STR1## wherein the ring A is an optionally substituted benzene ring; the ring B is an optionally substituted thiophene ring: X is a group of the formula: ##STR2## (wherein R.sup.1 is hydrogen, alkyl or alkoxy; and n is 0 or 1) or a group of the formula: ##STR3## (wherein R.sup.2 is hydrogen or alkyl); Y is a single bond, --NH--, alkylene having 1 or 2 carbon atoms or --CH.dbd.CH--; and R.sup.3 is an optionally substituted hydrocarbon group, or their salts are disclosed. They show strong ACAT inhibitory activities.

  公式（I）的噻吩并吡啶衍生物：##STR1## 其中，环A是可选取代的苯环；环B是可选取代的噻吩环；X是公式的一个基团：##STR2## （其中R1为氢、烷基或烷氧基；n为0或1），或公式的一个基团：##STR3## （其中R2为氢或烷基）；Y是单键，--NH--，具有1或2个碳原子的烷基或--CH=CH--；R3是可选取代的碳氢基团，或其盐。它们表现出强烈的ACAT抑制活性。