methyl (5,7-dihydroxy-4-methyl-2-oxochromen-3-yl)acetate | 892559-73-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: methyl (5,7-dihydroxy-4-methyl-2-oxochromen-3-yl)acetate
• 英文别名: methyl (5,7-dihydroxy-4-methyl-2-oxo-2H-chromen-3-yl)acetate；methyl 2-(5,7-dihydroxy-4-methyl-2-oxochromen-3-yl)acetate
• CAS: 892559-73-8
• 化学式: C₁₃H₁₂O₆
• mdl: MFCD08741832
• 分子量: 264.235
• InChiKey: MLXZZQOKSOVMSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (5,7-dihydroxy-4-methyl-2-oxochromen-3-yl)acetate 在 sodium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 1.0h， 以78%的产率得到(5,7-dihydroxy-4-methyl-2-oxochromen-3-yl)acetic acid
  参考文献：
  名称：

  Modified coumarins. 27. Ssynthesis and antioxidant activity of 3-substituted 5,7-dihydroxy-4-methylcoumarins

  摘要：

  通过活化酯法，使用 N-羟基琥珀酰亚胺和二异丙基碳二亚胺或与 N,N-羰基咪唑反应，合成了 5,7-二羟基-4-甲基香豆素-3-基乙酸的酰胺。分析了 3-取代的 5,7-二羟基-4-甲基香豆素对 2,2-二苯基-1-苦基肼和超氧自由基的反应性。研究了合成化合物对黄嘌呤氧化酶活性的影响。

  DOI：

  10.1007/s10600-007-0055-8
• 作为产物：
  描述：

  间苯三酚 、 乙酰丁二酸二甲酯 在 盐酸 作用下， 以 甲醇 为溶剂， 以86%的产率得到methyl (5,7-dihydroxy-4-methyl-2-oxochromen-3-yl)acetate
  参考文献：
  名称：

  改性香豆素。25.含有香豆素片段的N-酰基胞嘧啶衍生物

  摘要：

  通过用香豆素-3-乙酸酰化制备新的修饰的胞嘧啶衍生物。

  DOI：

  10.1007/s10600-007-0053-x

文献信息

• Coumarin derivatives protect against ischemic brain injury in rats
  作者：Mingna Sun、Jinfeng Hu、Xiuyun Song、Donghui Wu、Linglei Kong、Yupeng Sun、Dongmei Wang、Yan Wang、Naihong Chen、Gang Liu

  DOI：10.1016/j.ejmech.2013.04.015

  日期：2013.9

  Neuroprotection strategies are of great importance in the treatment of ischemic brain injury. Screening of our in-stock coumarin derivatives identified compound 1 as exhibiting neuroprotective activity. Subsequently, a structural optimization was carried out, which led to the discovery of the potent compound 20. This compound significantly attenuated the damage in a cell line derived from a pheochromocytoma of the rat adrenal medulla induced by oxygen glucose deprivation in vitro. Furthermore, compound 20 exhibited clear neuroprotection in middle cerebral artery occlusion rats by reducing infarct size and brain-water content, improving neurological function, and suppressing neuronal loss and neuropathological changes in the cortex and hippocampus. Pharmacokinetic evaluation indicated that compound 20 could penetrate the blood brain barrier of rats. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Biocatalytic C-Glucosylation of Coumarins Using an Engineered C-Glycosyltransferase
  作者：Dawei Chen、Ridao Chen、Kebo Xie、Tian Yue、Xiaolin Zhang、Fei Ye、Jungui Dai

  DOI：10.1021/acs.orglett.8b00378

  日期：2018.3.16

  The enzymatic synthesis of coumarin C-glucosides by an engineered C-glycosyltransferase, MiCGTb-GAGM, was explored in vitro and in vivo. MiCGTb-GAGM exhibited a robust C-glucosylation capability toward structurally diverse coumarin derivatives. The whole-cell bioconversion of MiCGTb-GAGM was exploited for large-scale production of coumarin C-glucosides. Two C-glucosides exhibited potent SGLT2 inhibitory activities with IC50 values at 10(-6) M. These findings provide cost-effective and practical synthetic strategies to generate structurally diverse and novel bioactive coumarin C-glycosides for drug discovery.
• Modified coumarins. 25. N-acyl cytisine derivatives containing a coumarin fragment
  作者：I. V. Nagorichna、A. S. Ogorodniichuk、M. M. Garazd、V. I. Vinogradova、V. P. Khilya

  DOI：10.1007/s10600-007-0053-x

  日期：2007.1

  New modified cytisine derivatives were prepared by acylation with coumarin-3-acetic acids.

  通过用香豆素-3-乙酸酰化制备新的修饰的胞嘧啶衍生物。
• Modified coumarins. 27. Ssynthesis and antioxidant activity of 3-substituted 5,7-dihydroxy-4-methylcoumarins
  作者：M. M. Garazd、O. V. Muzychka、A. I. Vovk、I. V. Nagorichna、A. S. Ogorodniichuk

  DOI：10.1007/s10600-007-0055-8

  日期：2007.1

  Amides of 5,7-dihydroxy-4-methylcoumaryl-3-ylacetic acid were synthesized by the activated ester method using N-hydroxysuccinimide and diisopropylcarbodiimide or by reaction with N,N-carbonylimidazole. The reactivity of 3-substituted 5,7-dihydroxy-4-methylcoumarins toward 2,2-diphenyl-1-picrylhydrazyl and superoxide radical was analyzed. The effect of the synthesized compounds on xanthineoxidase activity was studied.

  通过活化酯法，使用 N-羟基琥珀酰亚胺和二异丙基碳二亚胺或与 N,N-羰基咪唑反应，合成了 5,7-二羟基-4-甲基香豆素-3-基乙酸的酰胺。分析了 3-取代的 5,7-二羟基-4-甲基香豆素对 2,2-二苯基-1-苦基肼和超氧自由基的反应性。研究了合成化合物对黄嘌呤氧化酶活性的影响。