N-(4-methoxyphenethyl)sulfamide | 924307-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxyphenethyl)sulfamide
• 英文别名: 1-Methoxy-4-[2-(sulfamoylamino)ethyl]benzene；1-methoxy-4-[2-(sulfamoylamino)ethyl]benzene
• CAS: 924307-90-4
• 化学式: C₉H₁₄N₂O₃S
• 分子量: 230.288
• InChiKey: QOIDUIPJOJGEDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  benzyl N-(4-methoxyphenethyl)sulfamoylcarbamate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以74%的产率得到N-(4-methoxyphenethyl)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

文献信息

• 10.1021/acs.joc.4c00603
  作者：Jiang, Tuo、Coin, Guillaume、Bordi, Samuele、Nichols, Paula L.、Bode, Jeffrey W.、Wanner, Benedikt M.

  DOI：10.1021/acs.joc.4c00603

  日期：——

  conversion of primary amines to organic azides utilizing prepacked capsules containing all the required reagents, including imidazole-1-sulfonyl azide tetrafluoroborate. Apart from manually loading the primary amine into the reaction vessel, the entire reaction and product isolation process can be achieved automatically, with no further user involvement, and delivers the desired organic azide in high purity

  本文描述的是利用含有所有所需试剂（包括咪唑-1-磺酰叠氮化物四氟硼酸盐）的预包装胶囊开发一种自动化且可重复的方法，用于将伯胺转化为有机叠氮化物。除了手动将伯胺加载到反应容器中之外，整个反应和产物分离过程可以自动完成，无需用户进一步参与，并以高纯度提供所需的有机叠氮化物。这种实用且简单的基于胶囊的自动化方法提供了一种方便且安全的生成有机叠氮化物的方法，而无需处理或暴露潜在爆炸性试剂。
• 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.