artepillin C methyl ester | 72944-04-8

• 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: artepillin C methyl ester
• 英文别名: 3-(4-hydroxy-3,5-bis(3-methyl-2-butenyl)phenyl)acrylic acid methyl ester；methyl (E)-3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoate
• CAS: 72944-04-8
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: DKDGLQSOIBOYQO-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  artepillin C methyl ester 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 18.0h， 以92%的产率得到蒿素C
  参考文献：
  名称：

  钯催化的苯酚的定向对C H官能化

  摘要：

  已经开发了各种实用的方法来对邻位进行选择性C-H官能化，最近还对芳烃的间位进行了官能化。继我们对甲苯衍生物的直接基团辅助对羟基官能化的最新发展之后，我们在此报告了通过使用可回收的含硅联苯基模板进行的苯酚衍生物的首次远程对羟基官能化。通过不同的合成工艺以及各种基于苯酚的天然产物的合成，说明了该策略的有效性。

  DOI：

  10.1002/anie.201601999
• 作为产物：
  描述：

  重氮甲烷 生成 artepillin C methyl ester
  参考文献：
  名称：

  ZDERO, C.;BOHLMANN, F.;SOLOMON, J. C.;KING, R. M.;ROBINSON, H., PHYTOCHEMISTRY, 28,(1989) N, C. 531-542

  摘要：

  DOI：

文献信息

• PHENOL DERIVATIVES, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF
  申请人：Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo

  公开号：EP1184362A1

  公开（公告）日：2002-03-06

  Disclosed are an efficient, safe process for producing artepillin C and derivatives thereof by an organic synthesis. The process comprises a step of reacting a phenol derivative with an acrylate or acrylic acid.

  本发明揭示了一种通过有机合成生产artepillin C及其衍生物的高效、安全的方法。该方法包括将苯酚衍生物与丙烯酸酯或丙烯酸反应的步骤。
• Capillartemisin A and B, two new choleretic principles from Artemisiae Capillaris Herba.
  作者：Isao Kitagawa、Yoichi Fukuda、Minoru Yoshihara、Johji Yamahara、Masayuki Yoshikawa

  DOI：10.1248/cpb.31.352

  日期：——

  By monitoring with a choleretic activity test for rat-duodenum, two new choleretic principles named capillartemisin A (1) and B (2) were isolated from Artemisiae Capillaris Herba ("Inchinko" in Japanese, the aerial part of Artemisia capillaris Thunb.), and their structures were determined on the basis of spectral evidence and by a synthesis of the methyl ester of 1 (1a). Capillartemisin A (1) and B (2) showed more potent and lasting choleretic activity than sodium dehydrocholate and the other hitherto identified choleretic principles of "Inchinko". A new flavonoid isoarcapillin (6) was also chemically elucidated.

  通过对大鼠十二指肠的胆汁活性试验进行监测，从茵陈蒿（日语中的 "Inchinko"，即茵陈蒿的气生部分）中分离出了两种新的利胆物质，分别命名为茵陈蒿素 A（1）和 B（2），并根据光谱证据和 1（1a）的甲酯合成确定了它们的结构。茵陈蒿素 A（1）和 B（2）比脱氢胆酸钠和其他迄今已确定的 "茵陈蒿 "利胆成分显示出更强效、更持久的利胆活性。此外，还从化学角度阐明了一种新的黄酮类物质异水芹素（6）。
• First Total Synthesis of Artepillin C Established by <i>o</i><i>,</i><i>o</i><i>‘</i>-Diprenylation of <i>p</i>-Halophenols in Water
  作者：Yoshihiro Uto、Akihiko Hirata、Tomoya Fujita、Syunsuke Takubo、Hideko Nagasawa、Hitoshi Hori

  DOI：10.1021/jo0056904

  日期：2002.4.1

  We have demonstrated that prenylation of p-halophenols was dependent on the solvent effect and succeeded in o,o'-diprenylation of p-halophenols in water. Following the Mizoroki-Heck coupling of the diprenyl-p-iodophenol 3c with methyl acrylate and then hydrolysis, we first synthesized artepillin C [3-4-hydroxy-3,5-di(3-methyl-2-butenyl)phenyl}-2(E)-propenoic acid] (1), which is a biologically active constituent of propolis. These reactions may be applicable to the synthesis of various useful natural products such as 2,4,6-trisubstituted phenol derivatives.
• In vitro Evaluation of the Antileishmanial and Antischistosomal Activities of p‐Coumaric Acid Prenylated Derivatives
  作者：Tatiana M. Vieira、Júlia G. Barco、Lucas A. L. Paula、Paulo C. A. Felix、Jairo K. Bastos、Lizandra G. Magalhães、Antônio E. M. Crotti

  DOI：10.1002/cbdv.202400491

  日期：2024.5

  We have evaluated eight p‐coumaric acid prenylated derivatives in vitro for their antileishmanial activity against Leishmania amazonensis promastigotes and their antischistosomal activity against Schistosoma mansoni adult worms. Compound 7 ((E)‐3,4‐diprenyl‐4‐isoprenyloxycinnamic alcohol) was the most active against L. amazonensis (IC50=45.92 μM) and S. mansoni (IC50=64.25 μM). Data indicated that the number of prenyl groups, the presence of hydroxyl at C9, and a single bond between C7 and C8 are important structural features for the antileishmanial activity of p‐coumaric acid prenylated derivatives.