methanesulfonic acid 2-formyl-5-methoxyphenyl ester | 1447351-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methanesulfonic acid 2-formyl-5-methoxyphenyl ester
• 英文别名: (2-Formyl-5-methoxyphenyl) methanesulfonate；(2-formyl-5-methoxyphenyl) methanesulfonate
• CAS: 1447351-60-1
• 化学式: C₉H₁₀O₅S
• 分子量: 230.241
• InChiKey: QCKGNFKNHKIYIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 2-formyl-5-methoxyphenyl ester 在 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  7-Substituted-sulfocoumarins are isoform-selective, potent carbonic anhydrase II inhibitors

  摘要：

  A series of 7-substituted sulfocoumarins and 3,4-dihydrosulfocoumarins was obtained by cyclization of the methanesulfonate of 2,4-dihydroxy- or 2-hydroxy-4-methoxybenzaldehyde, followed by derivatization reactions. The new compounds incorporate a range of substituents in position 7 of the heterocyclic ring (hydroxyl, methoxy, carboxylic and alkylsulfonate ester). The compounds were tested for the inhibition of the zinc enzyme human (h) carbonic anhydrase (hCA, EC 4.2.1.1). Unlike the 6-substituted sulfocoumarins which were potent hCA IX and XII inhibitors and ineffective hCA I and II inhibitors, compounds from this series showed low nanomolar hCA II inhibitory properties, and inhibited the mitochondrial isoform hCA VA with K(I)s in the range of 91-9960 nM, but were ineffective as hCA I, IX and XII inhibitors. The structure activity relationship for this class of inhibitors was rather clear, with the nature of the 7-substituent strongly influencing hCA VA inhibition, whereas the nature of these groups were less relevant for hCA II inhibition (all reported compounds were highly effective hCA II inhibitors, with K(I)s in the range of 1.5-8.4 nM). Since both hCA II and hCA VA are important drug targets (hCA II for antiglaucoma agents; hCA VA for antiobesity drugs), these isoform-selective inhibitors reported here may be considered of interest for various biomedical applications. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.032
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到methanesulfonic acid 2-formyl-5-methoxyphenyl ester
  参考文献：
  名称：

  7-Substituted-sulfocoumarins are isoform-selective, potent carbonic anhydrase II inhibitors

  摘要：

  A series of 7-substituted sulfocoumarins and 3,4-dihydrosulfocoumarins was obtained by cyclization of the methanesulfonate of 2,4-dihydroxy- or 2-hydroxy-4-methoxybenzaldehyde, followed by derivatization reactions. The new compounds incorporate a range of substituents in position 7 of the heterocyclic ring (hydroxyl, methoxy, carboxylic and alkylsulfonate ester). The compounds were tested for the inhibition of the zinc enzyme human (h) carbonic anhydrase (hCA, EC 4.2.1.1). Unlike the 6-substituted sulfocoumarins which were potent hCA IX and XII inhibitors and ineffective hCA I and II inhibitors, compounds from this series showed low nanomolar hCA II inhibitory properties, and inhibited the mitochondrial isoform hCA VA with K(I)s in the range of 91-9960 nM, but were ineffective as hCA I, IX and XII inhibitors. The structure activity relationship for this class of inhibitors was rather clear, with the nature of the 7-substituent strongly influencing hCA VA inhibition, whereas the nature of these groups were less relevant for hCA II inhibition (all reported compounds were highly effective hCA II inhibitors, with K(I)s in the range of 1.5-8.4 nM). Since both hCA II and hCA VA are important drug targets (hCA II for antiglaucoma agents; hCA VA for antiobesity drugs), these isoform-selective inhibitors reported here may be considered of interest for various biomedical applications. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.032

文献信息

• Chalcone derivatives and their use to treat diseases
  申请人：Ni Liming

  公开号：US20060189549A1

  公开（公告）日：2006-08-24

  The invention relates to compounds, pharmaceutical compositions and methods of using compounds of the general formula or its pharmaceutically acceptable salt or ester, wherein the substituents are defined in the application.

  本发明涉及一般式化合物、药物组合物及使用该一般式化合物或其药学上可接受的盐或酯的方法，其中取代基在申请中定义。
• CHALCONE DERIVATIVES AND THEIR USE TO TREAT DISEASES
  申请人：Atherogenics, Inc.

  公开号：EP1465854A2

  公开（公告）日：2004-10-13
• EP1465854A4
  申请人：——

  公开号：EP1465854A4

  公开（公告）日：2005-06-08
• [EN] CHALCONE DERIVATIVES AND THEIR USE TO TREAT DISEASES<br/>[FR] DERIVES DE CHALCONE ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES
  申请人：ATHEROGENICS INC

  公开号：WO2003053368A2

  公开（公告）日：2003-07-03

  The invention relates to compounds, pharmaceutical compositions and use of compounds of the general formula (I), or its pharmaceutically acceptable salt or ester, wherein the substituents are defined in the application.