1-azido-2-fluoro-4-(methylsulfonyl)benzene | 1449785-86-7

• 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: 1-azido-2-fluoro-4-(methylsulfonyl)benzene
• 英文别名: 1-Azido-2-fluoro-4-methylsulfonylbenzene
• CAS: 1449785-86-7
• 化学式: C₇H₆FN₃O₂S
• 分子量: 215.208
• InChiKey: DHFJLOUEVQXKEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-propioloylpiperazine-1-carboxylate 、 1-azido-2-fluoro-4-(methylsulfonyl)benzene 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以85%的产率得到Tert-butyl 4-[1-(2-fluoro-4-methylsulfonylphenyl)triazole-4-carbonyl]piperazine-1-carboxylate
  参考文献：
  名称：

  一锅法合成新型叔丁基-4-取代苯基-1H-1,2,3-三唑哌嗪/哌啶羧酸盐，潜在的GPR119激动剂。

  摘要：

  我们使用简单的一锅点击化学合成了一系列新的 1,2,3-三唑并哌嗪和哌啶羧酸盐衍生物，显着缩短了反应时间（约 5 分钟）并提高了反应产率（约 95-98%）。测试了由此合成的十四种新化合物靶向 GPR119 的能力，GPR119 是一种 G 蛋白偶联靶受体，在调节 2 型糖尿病中起关键作用。四种类似物（3e、3g、5e 和 5g）表现出与先前报道的 AR231453 对 GPR119 的活性相似或更好的 EC50 值。

  DOI：

  10.1016/j.bmcl.2019.126707
• 作为产物：
  描述：

  2-氟-4-(甲基磺酰基)苯胺 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 以78%的产率得到1-azido-2-fluoro-4-(methylsulfonyl)benzene
  参考文献：
  名称：

  5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: Solution and X-ray crystallographic studies

  摘要：

  We report here a series of 2-thiophene-sulfonamides incorporating 1-substituted aryl-1,2,3-triazolyl moieties, prepared by click chemistry from 5-ethynylthiophene-2-sulfonamide and substituted aryl azides. The new sulfonamides were investigated as inhibitors of the zinc metalloenzyme CA (EC 4.2.1.1), and more specifically against the human (h) cytosolic isoforms hCA I and II and the transmembrane, tumor-associated ones hCA IX and XII: The new compounds were medium-weak hCA I inhibitors (K(I)s in the range of 224-7544 nM), but were compactly, highly effective, low nanomolar hCA II inhibitors (K(I)s of 2.2-7.7 nM). The tumor-associated hCA IX was inhibited with K(I)s ranging between 5.4 and 811 nM, whereas hCA XII with inhibition constants in the range of 3.4-239 nM. The X-ray crystal structure of the adducts of two such compounds bound to hCA II (one incorporating 1-naphthyl, the other one 3-cyanophenyl moieties) evidenced the reasons of the high affinity for hCA II. Highly favorable, predominantly hydrophobic interactions between the sulfonamide scaffold and the hCA II active site were responsible for the binding, in addition to the coordination of the sulfamoyl moiety to the zinc ion. The tails of the two inhibitors adopted very diverse orientations when bound to the active site, with the naphthyltriazolyl moiety orientated towards the hydrophobic half of the active site, and the 3-cyanophenyl one pointing towards the hydrophilic half. These data may be used for the structure-based drug design of even more effective hCA II inhibitors, with potential use as antiglaucoma agents or as diuretics. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.041