4-methoxy-3-pyridinesulfonamide | 1229666-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-methoxy-3-pyridinesulfonamide
• 英文别名: 4-Methoxypyridine-3-sulfonamide
• CAS: 1229666-20-9
• 化学式: C₆H₈N₂O₃S
• 分子量: 188.207
• InChiKey: YLDUTJXETDRGDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  163-165 °C
• 沸点：
  401.8±55.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-pyridinesulfonamide 、 3-硝基苯磺酰氯 以 乙腈 为溶剂， 以75%的产率得到3,8‐dimethoxy‐1,10‐bis-(3‐nitrobenzenesulfonylimino)deca‐2,4,6,8‐tetraene‐2,9‐disulfonamide
  参考文献：
  名称：

  关于4-取代的3-吡啶磺酰胺与一些苯磺酰氯衍生物的反应产物

  摘要：

  研究了4-取代的3-吡啶磺酰胺1a，1b，1c，1d，1e与苯磺酰氯2a，2b，2c，2d，2e，2f在乙腈中的反应。取决于芳基磺酰氯和以良好的收率得到了以下四种类型的产品的反应条件的结构：3-氨磺酰基- 4- [R -1- arylpyridinium氯化物3，4，5，6，7，8; 1,10-双（3- nitrobenzenesulfonylimino）癸-2,4,6,8-四烯-2,9- disulfonamides 9，10，11，12 ; 1-取代的1,4-二氢-4-氧代-3- pyridinesulfonamides 13，14 ; 和4-甲氧基-3- [ N-（2,5-二氯苯基）磺酰基]磺酰胺化物15和16。讨论了这些反应的机理。

  DOI：

  10.1002/jhet.1013
• 作为产物：
  描述：

  4-methoxy-3-pyridinesulfonamide hydrochloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以79%的产率得到4-methoxy-3-pyridinesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors: Synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides

  摘要：

  A series of novel 4-substituted-3-pyridinesulfonamides (2-27 and 31-33) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 42 11), that is, the cytosolic, ubiquitous isozymes CA I and II, and transmembrane isozymes CA IX, XII (cancer-associated) and XIV. Against the human isozymes hCA I, the new compounds showed inhibition constants in the range of 0.078-11.7 mu M, against hCA II in the range of 9.9-140 nM, against hCA IX in the range of 4.6-313 nM, against hCA XII in the range of 3.4-21.6 nM, and against hCA XIV in the range of 50.9-160 nM, respectively. Compounds 4, 6, 7, 9, 11-14, 19, 20, 22-24, 26, 27, 31 and 32 showed excellent hCA IX inhibitory efficacy, with inhibition constants of 4.6-12 0 nM, being much more effective as compared to the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND 4-[N'-(6-Chloro-7-cyano-1,1-dioxo-1,4,2-benzodithiazin-3-yl)hydrazino]-3-pyridinesulfonamide (31) is the prominent of the compounds due to its remarkable inhibitory activity toward hCA I (K(I)s = 0.078 mu M), hCA IX (K(I)s = 7.2 nM) and hCA XII (K(I)s = 3.4 nM).

  DOI：

  10.1016/j.ejmech.2010.02.020

文献信息

• Carbonic anhydrase inhibitors. Regioselective synthesis of novel series 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2012.08.006

  日期：2012.10

  A series of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides 4-6, 9-17 and 21-31 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and cancer-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed K(I)s in the range of 224-4830 nM, whereas toward hCA II, K(I)s = 318-873 nM. Isozyme hCA IX was inhibited with K(I)s = 11.8-93.4 nM, and hCA XII with 23.5 -82.3 nM. Compounds 12-14, 27 and 29-31 have an activity against hCA I (K(I)s = 224-889 nM) which is comparable to the clinically used sulfonamide DCP (K(I)s = 1200 nM). Several of new compounds, including 9, 10, 21, 24, 26-28 and 30 have an activity against hCA IX (K(I)s = 11.8-38.6 nM) which is comparable or more effective than the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). Compounds 9, 10, 13, 21-23, 26 and 27 were also very effective hCA XII inhibitors, with inhibition constants ranged from 23.5 to 47.2 nM comparable or more effective than sulfonamides EZA (K(I)s = 22 nM) or DCP (K(I)s = 50 nM), respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Carbonic anhydrase inhibitors. Regioselective synthesis of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2010.05.011

  日期：2010.9

  A series of 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamide (2-16) have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is the cytosolic ubiquitous CA I and II, and cancer-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed inhibition constants in the range of 1.09-12.1 mu M, against hCA II in the range of 50.5-172 nM, against hCA IX in the range of 5.2-118 nM, and against hCA XII in the range of 8.7-381 nM, respectively. Compounds 2, 3, 5-9, 11, 13 and 14 showed excellent hCA IX inhibitory efficacy, with K(I)s = 5.2-11.0 nM, being much more effective as compared to the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). Compounds 2, 3, 5-9, 11 and 13 were also very effective hCA XII inhibitors (K(I)s = 8.7-45.2 nM) which are comparable or more effective than those clinically used EZA and DCP (K(I)s = 22 and 50 nM), respectively. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Carbonic anhydrase inhibitors. Synthesis, molecular structures, and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with novel 3-pyridinesulfonamide derivatives
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Maria Gdaniec、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2011.07.011

  日期：2011.9

  A series of novel 3-pyridinesulfonamide derivatives (2-5, 9-11 and 13-15) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is, the cytosolic ubiquitous CA I and II, and isozymes CA IX and XII (cancer-associated), and XIV. Against the human isozyme hCA I the new compounds showed K(I)s in the range of 0.089-251 mu M, whereas toward hCA II, K(I)s = 50.5-487 nM. Isozyme hCA IX was inhibited with K(I)s in the range of 5.2-18.3 nM, while hCA XII with K(I)s = 6.0-16.4 nM, and hCA XIV with K(I)s = 76.4-152.0 nM. All of the new compounds 2-5,9-11 and 13-15 showed excellent hCA IX inhibitory efficacy, with Kis = 5.2-18.3 nM, being much more effective as compared to the clinically used AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.
• Carbonic anhydrase inhibitors: Synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Franciszek Sączewski、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2010.02.020

  日期：2010.6

  A series of novel 4-substituted-3-pyridinesulfonamides (2-27 and 31-33) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 42 11), that is, the cytosolic, ubiquitous isozymes CA I and II, and transmembrane isozymes CA IX, XII (cancer-associated) and XIV. Against the human isozymes hCA I, the new compounds showed inhibition constants in the range of 0.078-11.7 mu M, against hCA II in the range of 9.9-140 nM, against hCA IX in the range of 4.6-313 nM, against hCA XII in the range of 3.4-21.6 nM, and against hCA XIV in the range of 50.9-160 nM, respectively. Compounds 4, 6, 7, 9, 11-14, 19, 20, 22-24, 26, 27, 31 and 32 showed excellent hCA IX inhibitory efficacy, with inhibition constants of 4.6-12 0 nM, being much more effective as compared to the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND 4-[N'-(6-Chloro-7-cyano-1,1-dioxo-1,4,2-benzodithiazin-3-yl)hydrazino]-3-pyridinesulfonamide (31) is the prominent of the compounds due to its remarkable inhibitory activity toward hCA I (K(I)s = 0.078 mu M), hCA IX (K(I)s = 7.2 nM) and hCA XII (K(I)s = 3.4 nM).
• On the Reaction Products of 4-Substituted 3-Pyridinesulfonamides with Some Benzenesulfonyl Chloride Derivatives
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Krzysztof Szafrański

  DOI：10.1002/jhet.1013

  日期：2014.1

  The reactions of 4‐substituted 3‐pyridinesulfonamides 1a, 1b, 1c, 1d, 1e with benzenesulfonyl chlorides 2a, 2b, 2c, 2d, 2e, 2f in acetonitrile were investigated. Depending on the structure of arylsulfonyl chlorides and the reaction conditions the following four types of products were obtained in good yields: 3‐sulfamoyl‐4‐R‐1‐arylpyridinium chlorides 3, 4, 5, 6, 7, 8; 1,10‐bis(3‐nitrobenzenesulfonylimino)deca‐2

  研究了4-取代的3-吡啶磺酰胺1a，1b，1c，1d，1e与苯磺酰氯2a，2b，2c，2d，2e，2f在乙腈中的反应。取决于芳基磺酰氯和以良好的收率得到了以下四种类型的产品的反应条件的结构：3-氨磺酰基- 4- [R -1- arylpyridinium氯化物3，4，5，6，7，8; 1,10-双（3- nitrobenzenesulfonylimino）癸-2,4,6,8-四烯-2,9- disulfonamides 9，10，11，12 ; 1-取代的1,4-二氢-4-氧代-3- pyridinesulfonamides 13，14 ; 和4-甲氧基-3- [ N-（2,5-二氯苯基）磺酰基]磺酰胺化物15和16。讨论了这些反应的机理。