7-methoxy-3,4-dihydro-benzo[e][1,2]oxathiine 2,2-dioxide | 55480-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 7-methoxy-3,4-dihydro-benzo[e][1,2]oxathiine 2,2-dioxide
• 英文别名: 7-Methoxy-3,4-dihydro-1,2lambda6-benzoxathiine 2,2-dioxide；7-methoxy-3,4-dihydro-1,2λ6-benzoxathiine 2,2-dioxide
• CAS: 55480-58-5
• 化学式: C₉H₁₀O₄S
• 分子量: 214.242
• InChiKey: XDDWGQLYYBIFHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methanesulfonic acid 2-formyl-5-methoxyphenyl ester 在 palladium 10% on activated carbon 、 氢气 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氯氧磷 作用下， 以 吡啶 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 5.0h， 生成 7-methoxy-3,4-dihydro-benzo[e][1,2]oxathiine 2,2-dioxide
  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

• 7-Substituted-sulfocoumarins are isoform-selective, potent carbonic anhydrase II inhibitors
  作者：Muhammet Tanc、Fabrizio Carta、Murat Bozdag、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2013.05.032

  日期：2013.8

  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.