Pyrid-2-yl-carboxomid-N-p-toluolsulfonyl | 83728-52-3

• 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: Pyrid-2-yl-carboxomid-N-p-toluolsulfonyl
• 英文别名: 2-pyridine-N-tosylbenzamide；N-tosylpicolinamide；pyridine-2-carboxylic acid toluene-4-sulfonylamide；N-(4-methylphenyl)sulfonylpyridine-2-carboxamide
• CAS: 83728-52-3
• 化学式: C₁₃H₁₂N₂O₃S
• 分子量: 276.316
• InChiKey: AYRBSPDGGWQHTI-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C
• 密度：
  1.322±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Pyrid-2-yl-carboxomid-N-p-toluolsulfonyl 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 N-(4-甲基苯基)吡啶-2-甲酰胺
  参考文献：
  名称：

  Morkved, Eva H.; Cronyn, Marshall W., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 6, p. 381 - 388

  摘要：

  DOI：
• 作为产物：
  描述：

  2-吡啶甲酸乙酯 、 对甲苯磺酰胺 在 四氯化钛 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 24.0h， 以45%的产率得到Pyrid-2-yl-carboxomid-N-p-toluolsulfonyl
  参考文献：
  名称：

  TiCl4-promoted direct N-acylation of sulfonamide with carboxylic ester

  摘要：

  Several Lewis acids were investigated as promoters in the intermolecular or intramolecular direct N-acylation reaction of sulfonamides using carboxylic ester as an acylating agent. TiCl4 was found to possess the highest activity and enhanced efficiently sulfonamide to form N-acylsulfonamides under optimized conditions. This method provides a novel approach to make N-acylsulfonamides from ester via an easy work-up procedure. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.092

文献信息

• Palladium-catalyzed site-selective hydrogen isotope exchange (HIE) reaction of arylsulfonamides using amino acid auxiliary
  作者：Wei Liu、Xingyu Xu、Hongyan Zhao、Xiaoyu Yan

  DOI：10.1016/j.tet.2018.06.024

  日期：2018.7

  Hydrogen isotope exchange (HIE) is a versatile method for the introduction of deuterium to organic compounds. Herein, regioselective deuteration of sulfonamides is achieved by palladium-Catalyzed HIE reaction. By using amino acid as weakly coordination-directing auxiliary, a variety of sulfonamides are efficiently deuterated at the ortho-position. Placing competing directing groups on the aromatic

  氢同位素交换（HIE）是将氘引入有机化合物的一种通用方法。在本文中，磺酰胺的区域选择性氘化是通过钯催化的HIE反应实现的。通过使用氨基酸作为弱配位导向助剂，多种磺酰胺在邻位被有效地氘化。在芳族环上放置竞争性的导向基团不影响位点选择性。
• Design, synthesis and biological evaluation of pyridine acyl sulfonamide derivatives as novel COX-2 inhibitors
  作者：Xiang Lu、Hui Zhang、Xi Li、Guo Chen、Qing-Shan Li、Yin Luo、Ban-Feng Ruan、Xian-Wei Chen、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.09.034

  日期：2011.11

  A series of pyridine acyl sulfonamide derivatives (1–24) have been designed and synthesized and their biological activities were also evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. Among all the compounds, compound 23 displayed the most potent COX-2 inhibitory activity with an IC50 of 0.8 μM. Antitumor and anti-inflammatory assays indicated that compound 23 owned high antiproliferative

  一系列吡啶酰基磺酰胺衍生物（的1 - 24）已经被设计和合成和它们的生物活性也进行了评价作为潜在的环氧合酶-2（COX-2）抑制剂。在所有化合物中，化合物23表现出最强的COX-2抑制活性，IC 50为0.8μM。抗肿瘤和抗炎实验表明，化合物23对B16-F10，HepG2和MCF-7癌细胞系具有很高的抗增殖活性，并且对鼠巨噬细胞RAW 264.7细胞具有COX-2衍生的前列腺素E 2（PGE 2）抑制活性。符合IC 50分别为2.8、1.2、1.8和0.15μM。进行对接模拟以将化合物23定位在COX-2活性位点中以确定可能的结合模型。
• N-(PHENYLSULFONYL) PICOLINAMIDE DERIVATIVES, PROCESS FOR PRODUCING THE SAME, AND HERBICIDE
  申请人：KUREHA KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP1069112A1

  公开（公告）日：2001-01-17

  A herbicide comprising as the active ingredient an N-(phenylsulfonyl)picolinamide derivative represented by the following general formula. This ingredient is synthesized by condensing a substituted picolinic acid with a substituted benzenesulfonamide or reacting a substituted picolinic phenyl ester with a substituted benzenesulfonamide in the presence of a basic compound: wherein X represents halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, (C1-C4 alkoxy)carbonyl group, (di-C1-C4 alkylamino)sulfonyl group, [N-(C1-C4 alkyl)-N-(C1-C4 alkoxy)amino]sulfonyl group, (C1-C4 alkylamino)sulfonyl group, C1-C4 alkylthio group, C1-C4 alkylsulfinyl group, C1-C4 alkylsulfonyl group or nitro group, n is an integer of 0 - 5, Y represents halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group, C1-C4 haloalkylthio group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, (C1-C4 alkoxy) C1-C4 alkyl group, (C1-C4 alkylthio) C1-C4 alkyl group or nitro group, m is an integer of 0 - 4.

  一种除草剂，其活性成分为由下式通式表示的 N-(苯磺酰基)吡啶酰胺衍生物。这种成分是通过将取代的吡啶甲酸与取代的苯磺酰胺缩合或将取代的吡啶苯基酯与取代的苯磺酰胺在碱性化合物存在下反应而合成的： 其中 X 代表卤素原子、C1-C4 烷基、C1-C4 卤代烷基、C1-C4 烷氧基、C1-C4 卤代烷氧基、(C1-C4 烷氧基)羰基、(二-C1-C4 烷基氨基)磺酰基、[N-(C1-C4 烷基)-N-(C1-C4 烷氧基)氨基]磺酰基、(C1-C4 烷基氨基)磺酰基、C1-C4 烷硫基、C1-C4 烷基亚磺酰基、C1-C4 烷基磺酰基或硝基，n 为 0-5 的整数、 Y 代表卤素原子、C1-C4 烷基、C1-C4 卤代烷基、C1-C4 烷氧基、C1-C4 卤代烷氧基、C1-C4 烷硫基、C1-C4 卤代烷硫基、氨基、C1-C4 烷基氨基、二 C1-C4 烷基氨基、(C1-C4 烷氧基) C1-C4 烷基、(C1-C4 烷硫基) C1-C4 烷基或硝基、 m 是 0 - 4 的整数。
• MORKVED, E. H.;CRONYN, M. W., ACTA CHEM. SCAND., 1982, 36, N 6, 381-388
  作者：MORKVED, E. H.、CRONYN, M. W.

  DOI：——

  日期：——
• US6610853B1
  申请人：——

  公开号：US6610853B1

  公开（公告）日：2003-08-26