3'-O-ethylluteolin | 1201807-91-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3'-O-ethylluteolin
• 英文别名: 2-(3-ethoxy-4-hydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one；2-(3-ethoxy-4-hydroxyphenyl)-5,7-dihydro-xy-4H-chromen-4-one；2-(3-ethoxy-4-hydroxyphenyl)-5,7-dihydroxychromen-4-one
• CAS: 1201807-91-1
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: CAIHJQODXVKKJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-benzyloxy-2-(4-benzyloxy-3-ethoxyphenyl)-5-hydroxy-4H-chromen-4-one 在 20% palladium hydroxide on carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 3'-O-ethylluteolin
  参考文献：
  名称：

  Discovery and synthesis of novel luteolin derivatives as DAT agonists

  摘要：

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.049

文献信息

• Directed Evolution of a Halide Methyltransferase Enables Biocatalytic Synthesis of Diverse SAM Analogs
  作者：Qingyun Tang、Christoph W. Grathwol、Aşkın S. Aslan‐Üzel、Shuke Wu、Andreas Link、Ioannis V. Pavlidis、Christoffel P. S. Badenhorst、Uwe T. Bornscheuer

  DOI：10.1002/anie.202013871

  日期：2021.1.18

  Biocatalytic alkylations are important reactions to obtain chemo‐, regio‐ and stereoselectively alkylated compounds. This can be achieved using S‐adenosyl‐l‐methionine (SAM)‐dependent methyltransferases and SAM analogs. It was recently shown that a halide methyltransferase (HMT) from Chloracidobacterium thermophilum can synthesize SAM from SAH and methyl iodide. We developed an iodide‐based assay for

  生物催化烷基化是获得化学、区域和立体选择性烷基化化合物的重要反应。这可以通过使用 S-腺苷-L-甲硫氨酸 (SAM) 依赖性甲基转移酶和 SAM 类似物来实现。最近的研究表明，来自嗜热氯酸杆菌的卤化物甲基转移酶（HMT）可以从 SAH 和碘甲烷合成 SAM。我们开发了一种基于碘化物的测定方法，用于拟南芥HMT 的定向进化，并用它来鉴定 V140T 变体，该变体也可以接受乙基、丙基和烯丙基碘，产生相应的 SAM 类似物（90、50 和15 毫克 SAH 的 70% 转化率）。 V140T AtHMT 与O-甲基转移酶（IeOMT 或 COMT）进行一锅级联，以实现木犀草素的区域选择性乙基化和 3,4-二羟基苯甲醛的烯丙基化。虽然 3,4-二羟基苯甲醛的丙基化级联反应转化率较低，但丙基-SAH 中间体可以通过 NMR 光谱得到证实。
• Discovery and synthesis of novel luteolin derivatives as DAT agonists
  作者：Jiange Zhang、Xianbo Liu、Xinsheng Lei、Lei Wang、Lihe Guo、Gang Zhao、Guoqiang Lin

  DOI：10.1016/j.bmc.2010.09.049

  日期：2010.11.15

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.