5,6-二羟基-7-甲氧基-2H-苯并吡喃-2-酮 | 50656-75-2

• 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
• 中文名称: 5,6-二羟基-7-甲氧基-2H-苯并吡喃-2-酮
• 英文名称: 5,6-dihydroxy-7-methoxycoumarin
• 英文别名: isofraxetin；5,6-dihydroxy-7-methoxy-chromen-2-one；5,6-dihydroxy-7-methoxychromen-2-one
• CAS: 50656-75-2
• 化学式: C₁₀H₈O₅
• 分子量: 208.171
• InChiKey: ICFLIFNKWPXOAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-二羟基-7-甲氧基-2H-苯并吡喃-2-酮 、 二碘甲烷 在 sodium hydride 作用下， 生成 4-Methoxy-[1,3]dioxolo[4,5-f]chromen-7-one
  参考文献：
  名称：

  A High-Yield Method for the Methylenation ofo-Dihydroxyaromatic Compounds: Synthesis of Methylenedioxycoumarins

  摘要：

  在六甲基膦酰胺和二氟甲烷中，o-二羟基香豆素和儿茶酚与氢化钠反应，可以在温和条件下以优异的产率生成相应的亚甲基二氧化合物。

  DOI：

  10.1055/s-1986-31796
• 作为产物：
  描述：

  isofraxetin 6-O-β-D-glucopyranoside 在 Angelica sinensis (Oliv_.) Diels callus 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以1.1 mg的产率得到8'-dehydroxymethyl cleomiscosin A
  参考文献：
  名称：

  Biotransformation of isofraxetin-6- O - β - d -glucopyranoside by Angelica sinensis (Oliv.) Diels callus

  摘要：

  Isofraxetin-6-O-beta-D-glucopyranoside, identified from traditional medicinal herbal Xanthoceras sorbifolia Bunge, has been demonstrated to be a natural neuroinflammatory inhibitor. In order to obtain more derivatives with potential anti-neuroinflammatory effects, biotransformation was carried out. According to the characteristics of coumarin skeleton, suspension cultures of Angelica sinensis (Oliv.) Diels callus (A. sinensis callus) were employed because of the presence of diverse phenylpropanoids biosynthetic enzymes. As a result, 15 products were yielded from the suspension cultures, including a new coumarin: 8'-dehydroxymethyl cleomiscosin A (1), together with 14 known compounds. Their structures were elucidated by extensive spectroscopic analysis. Furthermore, the biotransformed pathways were discussed. Among them, compound 13 was transformed from isofraxetin-6-O-beta-D-glucopyranoside, while compounds 1-6, 10-12, 14-15 were derived from the culture medium stimulated by the substrate. The biotransformation processes include hydroxylation, oxidation and esterification. Furthermore, their inhibitory effects on lipopolysaccharide (LPS)-activated nitric oxide (NO) production were evaluated in BV2 microglial cells. It is worth noting that, 1,1'-methanediylbis(4-methoxybenzene) (3), obtucarbamates A (5), 2-nonyl-4-hydroxyquinoline N-oxide (10) and 1H-indole-3-carbaldehyde (11) exhibited significant inhibitory effect against neuroinflammation with IC50 values at 1.22, 10.57, 1.02 and 0.76 mu M respectively, much stronger than that of the positive control minocycline (IC50 35.82 mu M). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.11.069

文献信息

• REISCH, JOHANNES;WICKRAMASINGHE, ANURA;KUMAR, VIJAYA, J. NATUR. PROD., 52,(1989) N, C. 1379-1382
  作者：REISCH, JOHANNES、WICKRAMASINGHE, ANURA、KUMAR, VIJAYA

  DOI：——

  日期：——
• CASTILLO P.; RODRIGUEZ-UBIS J. C.; ROODRIGUEZ F., SYNTHESIS,(1986) N 10, 839-840
  作者：CASTILLO P.、 RODRIGUEZ-UBIS J. C.、 ROODRIGUEZ F.

  DOI：——

  日期：——
• A High-Yield Method for the Methylenation of<i>o</i>-Dihydroxyaromatic Compounds: Synthesis of Methylenedioxycoumarins
  作者：P. Castillo、J. C. Rodriguez-Ubis、F. Rodriguez

  DOI：10.1055/s-1986-31796

  日期：——

  Reaction of o-dihydroxycoumarins and catechols with sodium hydride in hexamethylphosphoric triamide and dihalomethane provides the corresponding methylenedioxy compounds under mild conditions and in excellent yields.

  在六甲基膦酰胺和二氟甲烷中，o-二羟基香豆素和儿茶酚与氢化钠反应，可以在温和条件下以优异的产率生成相应的亚甲基二氧化合物。
• Biotransformation of isofraxetin-6- O - β - d -glucopyranoside by Angelica sinensis (Oliv.) Diels callus
  作者：Di Zhou、Yuhua Zhang、Zhe Jiang、Yue Hou、Kun Jiao、Chunyan Yan、Ning Li

  DOI：10.1016/j.bmcl.2016.11.069

  日期：2017.1

  Isofraxetin-6-O-beta-D-glucopyranoside, identified from traditional medicinal herbal Xanthoceras sorbifolia Bunge, has been demonstrated to be a natural neuroinflammatory inhibitor. In order to obtain more derivatives with potential anti-neuroinflammatory effects, biotransformation was carried out. According to the characteristics of coumarin skeleton, suspension cultures of Angelica sinensis (Oliv.) Diels callus (A. sinensis callus) were employed because of the presence of diverse phenylpropanoids biosynthetic enzymes. As a result, 15 products were yielded from the suspension cultures, including a new coumarin: 8'-dehydroxymethyl cleomiscosin A (1), together with 14 known compounds. Their structures were elucidated by extensive spectroscopic analysis. Furthermore, the biotransformed pathways were discussed. Among them, compound 13 was transformed from isofraxetin-6-O-beta-D-glucopyranoside, while compounds 1-6, 10-12, 14-15 were derived from the culture medium stimulated by the substrate. The biotransformation processes include hydroxylation, oxidation and esterification. Furthermore, their inhibitory effects on lipopolysaccharide (LPS)-activated nitric oxide (NO) production were evaluated in BV2 microglial cells. It is worth noting that, 1,1'-methanediylbis(4-methoxybenzene) (3), obtucarbamates A (5), 2-nonyl-4-hydroxyquinoline N-oxide (10) and 1H-indole-3-carbaldehyde (11) exhibited significant inhibitory effect against neuroinflammation with IC50 values at 1.22, 10.57, 1.02 and 0.76 mu M respectively, much stronger than that of the positive control minocycline (IC50 35.82 mu M). (C) 2016 Elsevier Ltd. All rights reserved.