3-acetoxy cinnamyl chloride | 906639-27-8

• 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: 3-acetoxy cinnamyl chloride
• 英文别名: 3-acetoxycinnamoyl chloride；(2E)-3-[3-(acetoxy)phenyl]-2-acryloyl chloride；(2E)-3-[3-(acetoxy)phenyl]acryloyl chloride；3-acetyloxycinnamoyl chloride；trans-3-(3-acetoxy-phenyl)-acryloyl chloride；3-acetoxycinnamic acid chloride；[3-[(E)-3-chloro-3-oxoprop-1-enyl]phenyl] acetate
• CAS: 906639-27-8
• 化学式: C₁₁H₉ClO₃
• 分子量: 224.644
• InChiKey: GQDFAJQQJAEMFR-AATRIKPKSA-N

物化性质

• 沸点：
  349.0±25.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetoxy cinnamyl chloride 在 吡啶 、 四亚甲基二胺 作用下， 以 氯仿 为溶剂， 生成 octadecyl (E)-m-coumarate
  参考文献：
  名称：

  Characterization and quantitation of hexadecyl, octadecyl, and eicosyl esters of p-coumaric acid in the vine and root latex of sweetpotato [Ipomoea batatas (L.) Lam.]

  摘要：

  Methanol extracts of vine latex of four cultivars of sweetpotato [Ipomoea batatas (L.) Lam.] were analyzed for their chemical phenolic composition by reversed-phase HPLC. Major components were identified as hexadecyl, octadecyl, and eicosyl p-coumarates by an evaluation of data from UV spectra, hydrolysis, synthesis, and GC/MS of their trimethylsilyl derivatives. Both Z- and E-isomers of the phenolic acid were found, with the latter predominating. Trace quantities of hexadecyl (Z)- and (E)-ferulates were also identified in ester concentrates. Levels of octadecyl (E)-p-coumarate ranged from 0.7% fresh weight in cv. Resisto to almost 2% in cv. Jewel, while the hexadecyl ester levels were only 1/4 to 1/3 these values. Levels of the Z-esters were 1/10 to 1/20 of the levels of the corresponding E-isomers. Levels of the esters in cv. Jewel sweetpotato root latex were 2-10-fold the levels in the vine latex, while the ratio of E-esters to Z-esters was found to be 7-14-fold. The concentration of Z-esters among the sweetpotato cultivars tested correlated closely with the leaf feeding index for the sweetpotato weevil (Cylas formicarius) (R(2): C-20 = 0.96; C-18 = 0.98; C-16 = 0.71). The results indicate a possible relationship between latex chemistry and insect resistance that might be exploited via plant breeding.

  DOI：

  10.1021/jf00047a041
• 作为产物：
  描述：

  间-香豆酸 在 吡啶 、 草酰氯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-acetoxy cinnamyl chloride
  参考文献：
  名称：

  一种含苯胺基丙烯酮类衍生物及制备方法和医药用途

  摘要：

  一种含苯胺基丙烯酮类衍生物及制备方法和医药用途，属于药物化学技术领域。为具有如通式(I)结构所示的化合物：其中，R1为或中的任意一种。可用于制备抗肿瘤药物。

  公开号：

  CN113402415B

文献信息

• A New Nonpeptide Tachykinin NK1 Receptor Antagonist Isolated from the Plants of Compositae.
  作者：Atsushi Yamamoto、Ko Nakamura、Kazuhito Furukawa、Yukari Konishi、Takashi Ogino、Kunihiko Higashiura、Hisashi Yago、Kaoru Okamoto、Masanori Otsuka

  DOI：10.1248/cpb.50.47

  日期：——

  To find new tachykinin NK1 receptor antagonists from natural sources, we examined the tachykinin antagonist activity in the extracts of approximately 200 species of plants by the use of isolated guinea pig ileum. As a result, we discovered a novel and potent NK1 receptor antagonist in the extract of dried flowers of Matricaria chamomilla L. (chamomile). The structure of the antagonist was established as N1, N5, N10, N14-tetrakis[3-(4-hydroxyphenyl)-2-propenoyl]-1, 5, 10, 14-tetraazatetradecane (tetracoumaroyl spermine, 1a). The Ki values of 1a, estimated from the inhibitory action on the substance P (SP)-induced contraction of the guinea pig ileum and the inhibition of the binding of [3H][Sar9, Met(O2)11]SP to human NK1 receptors, were 21.9 nM and 3.3 nM, respectively. 1a is the first potent NK1 receptor antagonist from natural sources and it has a unique structure of a polyacylated spermine. 1a was concentrated in pollen of Matricaria chamomilla L. and was also found in the extracts of flowers of other four species of Compositae. In addition, we found N1, N5, N10-tris[3-(4-hydroxyphenyl)-2-propenoyl]-1, 5, 10, 14-tetraazatetradecane (2) as a new compound in the extract of flowers of Matricaria chamomilla L., which did not exhibit any tachykinin antagonist activity. A number of related compounds were synthesized, and the structure–activity relationship was studied.

  为了从天然来源中发现新的速激肽NK1受体拮抗剂，我们利用离体豚鼠回肠检测了大约200种植物提取物的速激肽拮抗活性。结果，我们在母菊（Matricaria chamomilla L.）干花的提取物中发现了一种新型且强效的NK1受体拮抗剂。该拮抗剂的结构被确定为N1，N5，N10，N14-四[3-(4-羟基苯基)-2-丙烯酰基]-1，5，10，14-四氮杂十四烷（四香豆酰精胺，1a）。根据其对物质P（SP）诱导的豚鼠回肠收缩的抑制作用以及对[3H][Sar9，Met(O2)11]SP与人NK1受体结合的抑制作用，估算出1a的Ki值分别为21.9 nM和3.3 nM。1a是从天然来源中发现的首例强效NK1受体拮抗剂，它具有独特的多酰化精胺结构。1a主要集中在母菊的花粉中，并且在其他四种菊科植物的花提取物中也有发现。此外，我们在母菊花的提取物中发现了一种新化合物N1，N5，N10-三[3-(4-羟基苯基)-2-丙烯酰基]-1，5，10，14-四氮杂十四烷（2），该化合物不显示任何速激肽拮抗活性。我们还合成了许多相关化合物，并研究了结构-活性关系。
• Examination of α-exosite inhibitors against Botulinum neurotoxin A protease through structure-activity relationship studies of chicoric acid
  作者：Song Xue、Hajime Seki、Marek Remes、Peter Šilhár、Kim Janda

  DOI：10.1016/j.bmcl.2017.10.021

  日期：2017.11

  Chicoric acid (ChA) was previously reported as a BoNT/A inhibitor that binds to the enzyme’s α-exosite. Herein, we report the synthesis and structure-activity relationships (SARs) of a series of ChA derivatives, which revealed essential binding interactions between ChA and BoNT/A. Moreover, several ChA-based inhibitors with improved potency against the BoNT/A were discovered.

  肉毒杆菌神经毒素 (BoNT) 是已知毒性最强的物质之一，目前尚无针对神经元内 BoNT 中毒的有效治疗方法。菊苣酸 (ChA) 先前被报道为一种 BoNT/A 抑制剂，可与该酶的 α-外部位点结合。在此，我们报告了一系列 ChA 衍生物的合成和构效关系 (SAR)，揭示了 ChA 和 BoNT/A 之间的重要结合相互作用。此外，还发现了几种基于 ChA 的抑制剂，其对抗 BoNT/A 的效力有所提高。
• Design and synthesis novel di-carbonyl analogs of curcumin (DACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI)
  作者：Jianchang Qian、Xianxin Chen、Sheng Shu、Wenxin Zhang、Bo Fang、Xiaojing Chen、Yunjie Zhao、Zhiguo Liu、Guang Liang

  DOI：10.1016/j.ejmech.2019.02.042

  日期：2019.4

  A novel series of di-carbonyl analogs of curcumin (DACs) were prepared and evaluated for their anti-inflammatory properties. Preliminary results showed that a vast majority of compounds tested in this study could effectively suppress LPS-induced production of tumor necrosis factor (TNF)-α and interleukin (IL)-6. Structure-activity relationships of the compounds were discussed. Compounds 5a27 and 5a28

  制备了一系列新的姜黄素二羰基类似物（DACs），并评估了它们的抗炎特性。初步结果表明，本研究中测试的绝大多数化合物都可以有效抑制LPS诱导的肿瘤坏死因子（TNF）-α和白介素（IL）-6的产生。讨论了化合物的构效关系。化合物5a27和5a28显示出最有效的抗炎活性和具有比姜黄素更高的结构稳定性和生物利用度口服体外。从机制上讲，它们通过抑制有丝分裂原激活的蛋白激酶（MAPK）信号传导和NF-κB的核易位来抑制巨噬细胞的激活。在体内，5a275a28和5a28可以显着减轻脂多糖（LPS）诱导的急性肺损伤（ALI）。活性化合物使肺的干/湿比显着标准化，这与中性粒细胞浸润的抑制和促炎性细胞因子的产生是一致的。总的来说，这些结果提出了一系列新的姜黄素类似物，作为有望用于治疗ALI的抗炎药。
• 肉桂酸酰胺衍生物、制备方法及其在制备止血 化瘀药物中的应用
  申请人：广西大学

  公开号：CN103288752B

  公开（公告）日：2016-06-22

  本发明公开了肉桂酸酰胺衍生物、制备方法及其在制备止血化瘀药物中的应用。发明人以羟基肉桂酸与磺胺类药物为原料，将羟基肉桂酸溶于乙酸酐中，然后依次加入吡啶、四氢呋喃并与磺胺类药物反应得到酰胺化合物粗品，经过滤、洗涤、重结晶等工序得到一类新型的肉桂酸酰胺衍生物。研究发现，此类化合物能通过内外源凝血途径激活凝血因子，加强子宫活动，可以较好的与人血清结合，在体内很好的运输，发挥促凝活性和镇痛作用，同时有化瘀的双向调节效果。凝血四项指标、血浆复钙实验以及小鼠离体子宫实验证实，此类化合物分别存在促凝、抗凝以及双向调节的活性，具有止血化瘀药物用途，可应用在制备血液疾病药物方面。
• Synthesis and biological evaluation of a new series of cinnamic acid amide derivatives as potent haemostatic agents containing a 2-aminothiazole substructure
  作者：Wenqian Nong、Anran Zhao、Jinrui Wei、Xiao Lin、Lisheng Wang、Cuiwu Lin

  DOI：10.1016/j.bmcl.2017.07.058

  日期：2017.9

  Ten new cinnamic acid derivatives containing a 2-aminothiazole substructure were designed and synthesized. This series of compounds exhibited good thermostabilities as demonstrated by thermogravimetric analysis. In coagulation assays (prothrombin time, activated partial thromboplastin time and thrombin time) in vitro, most compounds demonstrated excellent activities to promote blood coagulation. Among

  设计并合成了十个含有2-氨基噻唑亚结构的肉桂酸衍生物。该系列化合物表现出良好的热稳定性，如通过热重分析所证明的。在体外凝血测定中（凝血酶原时间，活化的部分凝血活酶时间和凝血酶时间），大多数化合物表现出出色的促进血液凝固的活性。在所研究的系列中，化合物N1，N4，N5和W5表现出显着的凝结活性。进一步的研究表明，化合物N5（IC 50 = 1.87μmol/ L）表现出比临床使用的止血药依他木酸酯（IC 50  = 46.22μmol/ L）最合适的促进血小板凝集的功效。此外，在这项研究中探索了化合物的官能团与相应的凝血活性之间的关系。