N-(furan-2-ylmethyl)-4-nitrobenzenesulfonamide

• 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: N-(furan-2-ylmethyl)-4-nitrobenzenesulfonamide
• 英文别名: N-[(furan-2-yl)methyl]-4-nitrobenzene-1-sulfonamide
• 化学式: C₁₁H₁₀N₂O₅S
• mdl: MFCD00425515
• 分子量: 282.277
• InChiKey: ZVUFLKFUSZRKAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(furan-2-ylmethyl)-4-nitrobenzenesulfonamide 在 盐酸 、 tin 作用下， 以 乙醇 、 水 为溶剂， 以100%的产率得到4-氨基-N-呋喃-2-甲基苯磺酰胺
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050
• 作为产物：
  描述：

  2-呋喃甲胺 、 对硝基苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以72%的产率得到N-(furan-2-ylmethyl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050

文献信息

• Lewis base catalyzed asymmetric substitution/Diels–Alder cascade reaction: a rapid and efficient construction of enantioenriched diverse tricyclic heterocycles
  作者：Gong-Feng Zou、Feng Pan、Wei-Wei Liao

  DOI：10.1039/c3ob41454j

  日期：——

  The first tertiary amine catalyzed asymmetric allylic amination/cycloaddition cascade sequence has been developed, which provided a novel protocol to construct enantioenriched azapolyheterocycles under mild reaction conditions efficiently (up to 95% ee, endo/exo >20 : 1).

  开发了第一个叔胺催化的不对称烯丙胺化/环加成级联序列，它提供了一种在温和反应条件下高效构建对映体富集的氮杂多杂环的新方案（高达 95% ee，endo/exo >20–:–1） 。
• Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene
  作者：Mikail E. Abbasov、Brandi M. Hudson、Weixu Kong、Dean J. Tantillo、Daniel Romo

  DOI：10.1039/c6ob02738e

  日期：——

  acylammonium salts are useful dienophiles enabling highly enantioselective and stereodivergent Diels-Alder-initiated organocascades with furan-based dienes. Complex polycyclic systems can thus be obtained from readily prepared dienes, commodity acid chlorides, and a chiral isothiourea organocatalyst under mild conditions. We describe the use of furan-based dienes bearing pendant sulfonamides leading to the generation

  α，β-不饱和酰基铵盐是有用的二烯亲和体，能够与呋喃基二烯高度对映选择性和立体发散的Diels-Alder引发的有机级联反应。因此，可以在温和的条件下由容易制备的二烯，商品酰氯和手性异硫脲有机催化剂制得复杂的多环系统。我们描述了使用含呋喃基二烯的磺酰胺侧基导致氧代桥连，反式的产生稠合的三环γ-内酰胺。由于它们的可逆性，该方法与这些通常有问题的二烯构成了第一个高度对映体和非对映体选择性的有机催化Diels-Alder环加成反应。计算研究表明，这些呋喃二烯具有较高的非对映选择性，可能是由于内加合物可逆的Diels-Alder环加成反应所致。此外，该方法的实用性通过对核心结构的简洁方法得到了证明，该结构与天然产物板蓝素A和非肽基生长素释放肽受体反向激动剂相似。