(羟基-3-甲氧基-7-苯并呋喃基-2)-羧酸甲酯 | 104796-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: (羟基-3-甲氧基-7-苯并呋喃基-2)-羧酸甲酯
• 英文名称: (hydroxy-3 methoxy-7 benzofuryl-2)-carboxylate de methyle
• 英文别名: methyl 3-hydroxy-7-methoxybenzofuran-2-carboxylate；Methyl 3-hydroxy-7-methoxy-1-benzofuran-2-carboxylate
• CAS: 104796-34-1
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: WBQPMEBCGKYSPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (羟基-3-甲氧基-7-苯并呋喃基-2)-羧酸甲酯 在 喹啉 、 水 、 铜 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 dimethoxy-3,7 benzofuranne
  参考文献：
  名称：

  Synthetic Models Related to Methoxalen – CYP2A6 Interactions. Dimethoxybenzofuran Derivatives as Potent and Selective Inhibitors of CYP2A6

  摘要：

  The human CYP2A6 enzyme metabolizes several xenobiotics including nicotine, the addictive component in tobacco. Reduced activity of CYP2A6, either for genetic reasons or by administering inhibitors of CYP2A6, reduces tobacco smoking. The reported compound methoxalen had a potent inhibitory effect on activity of CYP2A6 with an IC50 value of 1.27 mu M. We selected methoxalen as a lead compound and prepared various dimethoxybenzofuran derivatives that have inhibitory effects on activity of human cytochrome P450 (CYP) 2A6. Synthetic benzofuran derivatives (3,6-dimethoxybenzofuran: IC50=1.92 mu M and 3,7-dimethoxybenzofuran: IC50=2.00 mu M) also exhibited comparable activities against CYP2A6 and were selective inhibitors of CYP2A6. These compounds can be used as lead compounds in the development of drugs for smoking reduction therapy.

  DOI：

  10.3987/com-13-12744
• 作为产物：
  描述：

  3-甲氧基水杨酸甲酯 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 4.0h， 生成 (羟基-3-甲氧基-7-苯并呋喃基-2)-羧酸甲酯
  参考文献：
  名称：

  Synthetic Models Related to Methoxalen – CYP2A6 Interactions. Dimethoxybenzofuran Derivatives as Potent and Selective Inhibitors of CYP2A6

  摘要：

  The human CYP2A6 enzyme metabolizes several xenobiotics including nicotine, the addictive component in tobacco. Reduced activity of CYP2A6, either for genetic reasons or by administering inhibitors of CYP2A6, reduces tobacco smoking. The reported compound methoxalen had a potent inhibitory effect on activity of CYP2A6 with an IC50 value of 1.27 mu M. We selected methoxalen as a lead compound and prepared various dimethoxybenzofuran derivatives that have inhibitory effects on activity of human cytochrome P450 (CYP) 2A6. Synthetic benzofuran derivatives (3,6-dimethoxybenzofuran: IC50=1.92 mu M and 3,7-dimethoxybenzofuran: IC50=2.00 mu M) also exhibited comparable activities against CYP2A6 and were selective inhibitors of CYP2A6. These compounds can be used as lead compounds in the development of drugs for smoking reduction therapy.

  DOI：

  10.3987/com-13-12744

文献信息

• Transition Metal‐Catalyzed Synthesis of 3‐Coumaranone‐Containing NH‐Aziridines from 2 <i>H</i> ‐Azirines: Nickel(II) versus Gold(I)
  作者：Pavel A. Sakharov、Nikolai V. Rostovskii、Alexander F. Khlebnikov、Olesya V. Khoroshilova、Mikhail S. Novikov

  DOI：10.1002/adsc.201900366

  日期：2019.7.11

  catalytic nucleophilic addition reaction of 3‐hydroxybenzofuran‐2‐carboxylic acid derivatives to 2H‐azirines for the high‐yield synthesis of NH‐aziridines with a 3‐coumaranone substituent has been developed. The Ph3PAuNTf2‐catalyzed reaction is diastereoselective to give predominantly (RS,SR)‐isomer of aziridine in good yield. The Ni(hfacac)2‐catalyzed reaction affords aziridines in up to 98% yield and low

  已开发出3-羟基苯并呋喃-2-羧酸衍生物与2 H-叠氮基的亲核催化加成反应，可高产合成带有3-coumaranone取代基的NH-氮丙啶。Ph 3 PAuNTf 2催化的反应是非对映选择性的，主要以高收率得到氮丙啶的（RS，SR）-异构体。Ni（hfacac）2催化反应可提供氮丙啶，产率高达98％，低或中等非对映选择性，在某些情况下与金（I）催化反应相反。Ph 3 PAuNTf 2对于受位阻的叠氮基以及带有吸电子基团的苯并呋喃，其效果很好，而Ni（hfacac）2是制备具有重氮乙酰基取代基的氮丙啶的首选催化剂。后一种化合物可以用作通过布氏环扩环反应合成稠合氮丙啶的底物。
• BENZENE-FUSED HETEROCYCLIC DERIVATIVE AND USE OF THE SAME
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0751126A1

  公开（公告）日：1997-01-02

  Novel compounds having strong TXA2 receptor antagonist activities and PGI2 receptor agonist activities, which are effective for therapy and prevention of diseases related to TXA2, are disclosed. The compound of the present invention is represented by the following formula (I). (wherein the meanings of the symbols in the formula are as described in the specification)

  本发明公开了具有很强的TXA2受体拮抗剂活性和PGI2受体激动剂活性的新型化合物，可有效治疗和预防与TXA2有关的疾病。本发明的化合物由下式（I）表示。 (其中式中符号的含义如说明书所述）
• CONNOR, DAVID T.;CETENKO, WIACZESLAW A.;UNANGST, PAUL C.;JOHNSON, ELIZABE+
  作者：CONNOR, DAVID T.、CETENKO, WIACZESLAW A.、UNANGST, PAUL C.、JOHNSON, ELIZABE+

  DOI：——

  日期：——
• LAMOTTE G.; DEMERSEMAN P.; ROYER R.; GAYRAL PH.; FOURNIAT J., EUR. J. MED. CHEM., 21,(1986) N 5, 379-383
  作者：LAMOTTE G.、 DEMERSEMAN P.、 ROYER R.、 GAYRAL PH.、 FOURNIAT J.

  DOI：——

  日期：——
• Lamotte; Demerseman; Royer, European Journal of Medicinal Chemistry, 1986, vol. 21, # 5, p. 379 - 383
  作者：Lamotte、Demerseman、Royer、et al.

  DOI：——

  日期：——