1-甲基-4-氧代-1,4-二氢-3-吡啶磺酰胺 | 182556-18-9

• 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
• 中文名称: 1-甲基-4-氧代-1,4-二氢-3-吡啶磺酰胺
• 英文名称: 1,4-dihydro-1-methyl-4-oxo-3-pyridinesulfonamide
• 英文别名: 1-methyl-1,4-dihydro-4-oxo-3-pyridinesulfonamide；1-methyl-3-aminosulfonyl-4(1H)-pyridone；1-methyl-4-oxopyridine-3-sulfonamide
• CAS: 182556-18-9
• 化学式: C₆H₈N₂O₃S
• 分子量: 188.207
• InChiKey: HTPSIFNKXNIAJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-甲基-4-氧代-1,4-二氢-3-吡啶磺酰胺 、 4,6-二甲氧基-2-(苯氧基羰基)氨基嘧啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 生成 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-[1-methyl-4(1H)-pyridone]-3-sulfonamide
  参考文献：
  名称：

  Pyridonesulfonylurea compounds, process for their production and

  摘要：

  一种吡啶烷磺酰脲化合物或其盐，其化学式为(I)：##STR1## 其中Q为##STR2## 用作除草剂，其中变量如下所定义。

  公开号：

  US05869428A1
• 作为产物：
  描述：

  1-methyl-3-tert-butylaminosulfonyl-4(1H)-pyridone 在 三氟乙酸 作用下， 生成 1-甲基-4-氧代-1,4-二氢-3-吡啶磺酰胺
  参考文献：
  名称：

  Pyridonesulfonylurea compounds, process for their production and

  摘要：

  一种吡啶烷磺酰脲化合物或其盐，其化学式为(I)：##STR1## 其中Q为##STR2## 用作除草剂，其中变量如下所定义。

  公开号：

  US05869428A1

文献信息

• 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。
• Pyridonesulfonylurea compounds, process for their production and herbicides containing them
  申请人：ISHIHARA SANGYO KAISHA, LTD.

  公开号：EP0733629A1

  公开（公告）日：1996-09-25

  A pyridonesulfonylurea compound of the formula (I) or its salt: wherein Q is R1 is a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group which may be substituted, an alkylcarbonyl group which may be substituted, an alkoxycarbonyl group which may be substituted, an alkylsulfinyl group which may be substituted, an alkylsulfonyl group which may be substituted, G is a halogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group which may be substituted, an alkylcarbonyl group which may be substituted, an alkoxycarbonyl group which may be substituted, an alkylsulfinyl group which may be substituted, an alkylsulfonyl group which may be substituted, each of R2 and R3 which are independent of each other, is a hydrogen atom, an alkyl group, an alkylcarbonyl group, an alkylsulfinyl group or an alkylsulfonyl group, each of R4, R5 and R8 which are independent of one another, is a hydrogen atom or an alkyl group, each of R6 and R7 which are independent of each other, is a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group, n is an integer of from 0 to 3, each of X and Y which are independent of each other, is a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkoxy group, a haloalkoxy group, a monoalkylamino group or a dialkylamino group, and A is CH or N. This compound or its salt shows a wide herbicidal spectrum at a low dose and thus is useful as an active ingredient for a herbicide.

  式 (I) 的吡啶酮磺酰脲化合物或其盐： 其中 Q 是 R1是氢原子、可被取代的烷基、可被取代的烯基、可被取代的炔基、可被取代的烷氧基、可被取代的烷硫基、可被取代的烷基羰基、可被取代的烷氧羰基、可被取代的烷基亚磺酰基、可被取代的烷基磺酰基、 G是卤素原子、可被取代的烷基、可被取代的烯基、可被取代的炔基、可被取代的烷氧基、可被取代的烷硫基、可被取代的烷羰基、可被取代的烷氧羰基、可被取代的烷基亚磺酰基、可被取代的烷基磺酰基、 相互独立的 R2 和 R3 各为氢原子、烷基、烷基羰基、烷基亚磺酰基或烷基磺酰基； 相互独立的 R4、R5 和 R8 各为氢原子或烷基； 相互独立的 R6 和 R7 各为氢原子、n为 0 至 3 的整数，X 和 Y 互不相关，各自为卤素原子、烷基、卤代烷基、烷氧基、烷氧基、卤代烷氧基、单烷基氨基或二烷基氨基，A 为 CH 或 N。这种化合物或其盐在低剂量下具有广阔的除草谱，因此可用作除草剂的活性成分。
• 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.
• US5869428A
  申请人：——

  公开号：US5869428A

  公开（公告）日：1999-02-09