methyl E-(3-chloro-4-hydroxyphenyl)acrylate | 185527-66-6

• 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: methyl E-(3-chloro-4-hydroxyphenyl)acrylate
• 英文别名: (3-chloro-4-hydroxyphenyl)methyl acrylate；Methyl 3-(3-chloro-4-hydroxyphenyl)acrylate；methyl (E)-3-(3-chloro-4-hydroxyphenyl)prop-2-enoate
• CAS: 185527-66-6
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: BZHVHNVZOHIELV-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  methyl E-(3-chloro-4-hydroxyphenyl)acrylate 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 lithium hydroxide monohydrate 、 盐酸羟胺 、 potassium acetate 、 三乙胺 、 N,N-二异丙基乙胺 、 联硼酸频那醇酯 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 3-(3'-adamantan-1-yl-2-chloro-4'-hydroxybiphenyl-4-yl)-N-hydroxyacrylamide
  参考文献：
  名称：

  Influence of the adamantyl moiety on the activity of biphenylacrylohydroxamic acid-based HDAC inhibitors

  摘要：

  To investigate the influence of the adamantyl group on the biological properties of known HDAC inhibitors with a 4-phenylcinnamic skeleton, a series of compounds having the adamantyl moiety in the cap structure were synthesized and compared to the corresponding hydroxamic acids lacking this group. An unexpected finding was the substantial reduction of inhibitory activity toward the tested enzymes, in particular HDAC6, following the introduction of the adamantyl group. In spite of the reduced ability to function as HDAC inhibitors, the compounds containing the adamantyl moiety still retained a good efficacy as antiproliferative and proapoptotic agents. A selected compound (2c; ST3056) of this series exhibited an appreciable antitumor activity against the colon carcinoma xenograft HCT116. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.021
• 作为产物：
  描述：

  3-氯-4-羟基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 Dowex 50 W (8200 4) 作用下， 以 吡啶 为溶剂， 反应 3.0h， 生成 methyl E-(3-chloro-4-hydroxyphenyl)acrylate
  参考文献：
  名称：

  Bolzacchini, Ezio; Canevali, Carmen; Morazzoni, Franca, Journal of the Chemical Society, Dalton Transactions, 1997, # 24, p. 4695 - 4699

  摘要：

  DOI：

文献信息

• Synthesis and Structure−Activity Relationships of a New Series of Retinoid-Related Biphenyl-4-ylacrylic Acids Endowed with Antiproliferative and Proapoptotic Activity
  作者：Raffaella Cincinelli、Sabrina Dallavalle、Raffaella Nannei、Serena Carella、Daniele De Zani、Lucio Merlini、Sergio Penco、Enrico Garattini、Giuseppe Giannini、Claudio Pisano、Loredana Vesci、Paolo Carminati、Valentina Zuco、Chiara Zanchi、Franco Zunino

  DOI：10.1021/jm049440h

  日期：2005.7.1

  Atypical retinoids (AR) represent a class of proapoptotic agents with promising potential in the treatment of neoplastic diseases. In the present work 4'-hydroxybiphenyl-4-ylacrylic acids were studied as a novel series of AR. The synthesized compounds were evaluated for their antiproliferative activity in a human promyelocytic leukemia cell line (NB4) and in an ovarian carcinoma cell system including IGROV-1, carrying a functional wild-type p53, and a cisplatin-resistant subline, IGROV-1/Pt-1. The presence of a bulky lipophilic group at position 3' (adamantan-1-yl being the best) and the E configuration of the acrylic moiety appear essential for activity below 1 mu M. No substitution on the rings or on the double bond improved the activity. A qualitative correlation between the log P and molecular volume of the 3'-substituent and the antiproliferative activity was found. From the study of a few selected compounds, it appears that the presence of the carboxylic group is an essential requirement for apoptogenic properties but not for antiproliferative activity, this being maintained in amide derivatives. On the other hand, compounds able to induce apoptosis produced a detectable level of genotoxic damage. This observation supports the hypothesis that the genotoxic stress is a critical event mediating apoptosis induction by compounds of this class. Among the compounds investigated, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (2) was chosen for further investigation.
• TUCKER H., J. MED. CHEM., 1980, 23, NO 10, 1122-1126
  作者：TUCKER H.

  DOI：——

  日期：——
• Influence of the adamantyl moiety on the activity of biphenylacrylohydroxamic acid-based HDAC inhibitors
  作者：Raffaella Cincinelli、Loana Musso、Giuseppe Giannini、Valentina Zuco、Michelandrea De Cesare、Franco Zunino、Sabrina Dallavalle

  DOI：10.1016/j.ejmech.2014.04.021

  日期：2014.5

  To investigate the influence of the adamantyl group on the biological properties of known HDAC inhibitors with a 4-phenylcinnamic skeleton, a series of compounds having the adamantyl moiety in the cap structure were synthesized and compared to the corresponding hydroxamic acids lacking this group. An unexpected finding was the substantial reduction of inhibitory activity toward the tested enzymes, in particular HDAC6, following the introduction of the adamantyl group. In spite of the reduced ability to function as HDAC inhibitors, the compounds containing the adamantyl moiety still retained a good efficacy as antiproliferative and proapoptotic agents. A selected compound (2c; ST3056) of this series exhibited an appreciable antitumor activity against the colon carcinoma xenograft HCT116. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Bolzacchini, Ezio; Canevali, Carmen; Morazzoni, Franca, Journal of the Chemical Society, Dalton Transactions, 1997, # 24, p. 4695 - 4699
  作者：Bolzacchini, Ezio、Canevali, Carmen、Morazzoni, Franca、Orlandi, Marco、Rindone, Bruno、Scotti, Roberto

  DOI：——

  日期：——