methyl (2Z)-2-hydroxy-3-(4-hydroxyphenyl)acrylate | 214534-53-9

• 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 (2Z)-2-hydroxy-3-(4-hydroxyphenyl)acrylate
• 英文别名: methyl (Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 214534-53-9
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: QCZFQWATVFWNJO-TWGQIWQCSA-N

物化性质

• 沸点：
  376.0±42.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二苄氧基苯甲醛 、 methyl (2Z)-2-hydroxy-3-(4-hydroxyphenyl)acrylate 在 1,5-diazabicyclo[5.4.0]undecene 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以29%的产率得到2-[3,4-bis(phenylmethoxy)phenyl]-4-hydroxy-3-(4-hydroxyphenyl)-2H-furan-5-one
  参考文献：
  名称：

  Synthesis and biological activities of a series of 4,5-diaryl-3-hydroxy-2(5H)-furanones

  摘要：

  A series of thirteen 4,5-diaryl-3-hydroxy-2(5H)-furanones were synthesized. They were evaluated for their antioxidant potencies and inhibitory properties of 5-lipoxygenase, cyclooxygenases, HIV-1 integrase and PC3 cell proliferation. New hits were discovered either in the anti-proliferation test or in the HIV anti-integrase test. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.08.005
• 作为产物：
  描述：

  2-hydroxy-3-(4-hydroxyphenyl)acrylic acid 、 碘甲烷 在 1,5-diazabicyclo[5.4.0]undecene 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到methyl (2Z)-2-hydroxy-3-(4-hydroxyphenyl)acrylate
  参考文献：
  名称：

  Synthesis and biological activities of a series of 4,5-diaryl-3-hydroxy-2(5H)-furanones

  摘要：

  A series of thirteen 4,5-diaryl-3-hydroxy-2(5H)-furanones were synthesized. They were evaluated for their antioxidant potencies and inhibitory properties of 5-lipoxygenase, cyclooxygenases, HIV-1 integrase and PC3 cell proliferation. New hits were discovered either in the anti-proliferation test or in the HIV anti-integrase test. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.08.005

文献信息

• Synthesis and Biological Evaluation of Analogues of Butyrolactone I as PTP1B Inhibitors
  作者：Bihong Hong、Jianlin He、Chaochun Fan、Chao Tang、Qingqing Le、Kaikai Bai、Siwen Niu、Meitian Xiao

  DOI：10.3390/md18110526

  日期：——

  metabolites of marine microorganisms. Butyrolactone I was found to be produced by Aspergillus terreus isolated from several marine-derived samples. The hypoglycemic activity of butyrolactone I has aroused our great interest. In this study, we synthesized six racemic butenolide derivatives (namely BL-1–BL-6) by modifying the C-4 side chain of butyrolactone I. Among them, BL-3 and BL-5 improved the insulin

  近年来，已经从海洋微生物的次生代谢物中分离出了许多含有丁烯内酯官能团的药理活性化合物。发现丁内酯由土曲霉产生从几个海洋样本中分离出来。丁内酯I的降血糖活性引起了我们的极大兴趣。在这项研究中，我们通过修饰丁内酯I的C-4侧链合成了六种外消旋丁烯内酯衍生物（即BL-1–BL-6）。其中BL-3和BL-5改善了HepG2细胞的胰岛素抵抗，并不影响RIN-m5f细胞系的增殖，这表明BL-3和BL-5的功效和安全性。此外，BL-3，BL-4，BL-5和BL-6表现出显着的蛋白质酪氨酸磷酸酶1B（PTP1B）抑制作用，而BL-3的对映异构体表现出不同的50％百分比抑制浓度（IC 50）针对PTP1B的值。BLs和PTP1B分子对接模拟的结果解释了BL-3对映异构体之间观察到的生物学结果的差异，该对映异构体支持BLs作为PTP1B抑制剂，并且还表明C-4的手性可能会影响Cb-1的抑制作用BL。我们的发现
• New 3- and 4-hydroxyfuranones as anti-oxidants and anti-inflammatory agents
  作者：Valérie Weber、Catherine Rubat、Eliane Duroux、Claire Lartigue、Michel Madesclaire、Pascal Coudert

  DOI：10.1016/j.bmc.2005.04.055

  日期：2005.7

  Two series of new furationes substituted by methylsulfonylphenyl or methylsulfamidophenyl moieties were found to protect against oxidation damage by inhibiting or quenching free radicals and reactive oxygen species in in vitro experiments. The effect on lipid peroxidation was also examined. In addition, we investigated the activity of products in two models of inflammation: phorbol ester-induced ear edema in mice and carrageenan-induced paw edema in rat. The most powerful compounds and with reducing activity against DPPH (IC50 = 1779 and 57 mu M, respectively), superoxide anion quenching capacity (IC50 = 511 and 49 mu M, respectively), lipid peroxidation inhibitory effect and anti-inflammatory properties (about 50-65% inhibition of edema at 200 mg/kg ip in both tests used) were selected for further pharmacological and toxicological tests because of their attractive profile for the treatment of inflammatory diseases. (c) 2005 Elsevier Ltd. All rights reserved.
• Polar Metabolites of the Tropical Green SeaweedCaulerpa taxifolia Which Is Spreading in the Mediterranean Sea: Glycoglycerolipids and Stable Enols (α\=Keto Esters)
  作者：Ines Mancini、Graziano Guella、Andrea Defant、M. Luz Candenas、Cristina P. Armesto、Daniela Depentori、Francesco Pietra

  DOI：10.1002/(sici)1522-2675(19980909)81:9<1681::aid-hlca1681>3.0.co;2-4

  日期：1998.9.9

  Examination of the polar components of the green seaweed Caulerpa taxifolia (VAHL) C. AGARDH, which is heavily spreading in the northeastern Mediterranean, led to two families of compounds. The new (2R)-3-O-beta-D-galactopyranosyl-1 -O-[(7Z,10Z,13Z)-hexadeca-7,10,13-trienoyl]-2-O-[(9Z,12Z,15Z)-octadeca-1,12,15-trienoyl]-sn-glycerol (2) was isolated in low abundance, like the analogues 1 and 3 already known from freshwater cyanobacteria. The acyl positions in 1 - 3 were determined by enzymatic methods and the absolute configuration from the O-galactosylglycerol obtained upon alcaline methanolysis. More abundant were the (4-hydroxyphenyl)- and (3,4-dihydroxyphenyl)pyruvic acid methyl esters, occurring in the enol (Z) forms 13a and 14a accompanied by very minor (E) forms 13b and 14b. The latter became predominant on UV irradiation of 13a or 14a, allowing the determination of the C=C configuration of these isolatable, stable enols from H-1,C-13 NMR couplings (larger H-C(3)/C(1) coupling constant in the (E) than in the (Z) isomer). Contrary to literature implications, the O-galactosylglycerolipids 1-3 lack any cholinergic or histaminegic activity; similarly, enols (= alpha-keto esters) 13 and 14 or terpenoids of this seaweed were also devoid of such biological activities (see Table).
• Synthesis and biological activities of a series of 4,5-diaryl-3-hydroxy-2(5H)-furanones
  作者：Fabrice Bailly、Clémence Queffélec、Gladys Mbemba、Jean-François Mouscadet、Nicole Pommery、Jean Pommery、Jean-Pierre Hénichart、Philippe Cotelle

  DOI：10.1016/j.ejmech.2007.08.005

  日期：2008.6

  A series of thirteen 4,5-diaryl-3-hydroxy-2(5H)-furanones were synthesized. They were evaluated for their antioxidant potencies and inhibitory properties of 5-lipoxygenase, cyclooxygenases, HIV-1 integrase and PC3 cell proliferation. New hits were discovered either in the anti-proliferation test or in the HIV anti-integrase test. (c) 2007 Elsevier Masson SAS. All rights reserved.