N-(3,4,5-trimethoxyphenethyl)sulfamide | 1436392-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(3,4,5-trimethoxyphenethyl)sulfamide
• 英文别名: 1,2,3-Trimethoxy-5-[2-(sulfamoylamino)ethyl]benzene；1,2,3-trimethoxy-5-[2-(sulfamoylamino)ethyl]benzene
• CAS: 1436392-12-9
• 化学式: C₁₁H₁₈N₂O₅S
• 分子量: 290.34
• InChiKey: XURRVLONLNFQSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(3,4,5-三甲氧基苯基)丙酸 在 叠氮磷酸二苯酯 、 palladium on activated charcoal 、 氢气 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 73.0h， 生成 N-(3,4,5-trimethoxyphenethyl)sulfamide
  参考文献：
  名称：

  Synthesis and carbonic anhydrase inhibitory properties of sulfamides structurally related to dopamine

  摘要：

  A series of novel sulfamides incorporating the dopamine scaffold were synthesized. Reaction of amines and tert-butyl-alcohol/benzyl alcohol in the presence of chlorosulfonyl isocyanate (CSI) afforded sulfamoyl carbamates, which were converted to the title compounds by treatment with trifluoroacetic acid or by palladium-catalyzed hydrogenolysis. Inhibition of six alpha-carbonic anhydrases (CAs, EC 4.2.1.1), that is, CA I, CA II, CA VA, CA IX, CA XII and CA XIV, and two beta-CAs from Candida glabrata (CgCA) and Mycobacterium tuberculosis (Rv3588) with these sulfamides was investigated. All CA isozymes were inhibited in the low micromolar to nanomolar range by the dopamine sulfamide analogues. Kis were in the range of 0.061-1.822 mu M for CA I, 1.47-2.94 nM for CA II, 2.25-3.34 mu M for CA VA, 0.041-0.37 mu M for CA IX, 0.021-1.52 mu M for CA XII, 0.007-0.219 mu M for CA XIV, 0.35-5.31 mu M for CgCA and 0.465-4.29 mu M for Rv3588. The synthesized sulfamides may lead to inhibitors targeting medicinally relevant CA isoforms with potential applications as antiepileptic, antiobesity antitumor agents or anti-infective. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.077
• 作为试剂：
  描述：

  二氧化碳 在 α-carbonic anhydrase CA-I 、 N-(3,4,5-trimethoxyphenethyl)sulfamide 、 水 作用下， 以 aq. buffer 为溶剂， 生成 羟基甲酸酯
  参考文献：
  名称：

  Synthesis and carbonic anhydrase inhibitory properties of sulfamides structurally related to dopamine

  摘要：

  A series of novel sulfamides incorporating the dopamine scaffold were synthesized. Reaction of amines and tert-butyl-alcohol/benzyl alcohol in the presence of chlorosulfonyl isocyanate (CSI) afforded sulfamoyl carbamates, which were converted to the title compounds by treatment with trifluoroacetic acid or by palladium-catalyzed hydrogenolysis. Inhibition of six alpha-carbonic anhydrases (CAs, EC 4.2.1.1), that is, CA I, CA II, CA VA, CA IX, CA XII and CA XIV, and two beta-CAs from Candida glabrata (CgCA) and Mycobacterium tuberculosis (Rv3588) with these sulfamides was investigated. All CA isozymes were inhibited in the low micromolar to nanomolar range by the dopamine sulfamide analogues. Kis were in the range of 0.061-1.822 mu M for CA I, 1.47-2.94 nM for CA II, 2.25-3.34 mu M for CA VA, 0.041-0.37 mu M for CA IX, 0.021-1.52 mu M for CA XII, 0.007-0.219 mu M for CA XIV, 0.35-5.31 mu M for CgCA and 0.465-4.29 mu M for Rv3588. The synthesized sulfamides may lead to inhibitors targeting medicinally relevant CA isoforms with potential applications as antiepileptic, antiobesity antitumor agents or anti-infective. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.077

文献信息

• Synthesis and carbonic anhydrase inhibitory properties of sulfamides structurally related to dopamine
  作者：Kadir Aksu、Meryem Nar、Muhammet Tanc、Daniela Vullo、İlhami Gülçin、Süleyman Göksu、Ferhan Tümer、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2013.03.077

  日期：2013.6

  A series of novel sulfamides incorporating the dopamine scaffold were synthesized. Reaction of amines and tert-butyl-alcohol/benzyl alcohol in the presence of chlorosulfonyl isocyanate (CSI) afforded sulfamoyl carbamates, which were converted to the title compounds by treatment with trifluoroacetic acid or by palladium-catalyzed hydrogenolysis. Inhibition of six alpha-carbonic anhydrases (CAs, EC 4.2.1.1), that is, CA I, CA II, CA VA, CA IX, CA XII and CA XIV, and two beta-CAs from Candida glabrata (CgCA) and Mycobacterium tuberculosis (Rv3588) with these sulfamides was investigated. All CA isozymes were inhibited in the low micromolar to nanomolar range by the dopamine sulfamide analogues. Kis were in the range of 0.061-1.822 mu M for CA I, 1.47-2.94 nM for CA II, 2.25-3.34 mu M for CA VA, 0.041-0.37 mu M for CA IX, 0.021-1.52 mu M for CA XII, 0.007-0.219 mu M for CA XIV, 0.35-5.31 mu M for CgCA and 0.465-4.29 mu M for Rv3588. The synthesized sulfamides may lead to inhibitors targeting medicinally relevant CA isoforms with potential applications as antiepileptic, antiobesity antitumor agents or anti-infective. (C) 2013 Elsevier Ltd. All rights reserved.