2-甲基-4-硝基苯磺酰胺 | 22952-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲基-4-硝基苯磺酰胺
• 英文名称: 2-methyl-4-nitrobenzenesulfonamide
• 英文别名: 2-methyl-4-nitro-benzenesulfonamide；5-nitro-toluene-2-sulfonic acid amide；5-Nitro-toluol-2-sulfonsaeure-amid；2-Methyl-4-nitro-benzolsulfonsaeure-amid；5-Nitro-toluol-sulfonsaeure-(2)-amid；2-Methyl-4-nitrobenzolsulfonylamid；2-Methyl-4-nitrobenzene-1-sulfonamide
• CAS: 22952-19-8
• 化学式: C₇H₈N₂O₄S
• mdl: MFCD00828709
• 分子量: 216.218
• InChiKey: KVRWKUUAOATUGG-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  432.7±55.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲基-4-硝基苯磺酰胺 在 chromium(VI) oxide 、 ammonium hydroxide 、 sodium dithionite 、 五氯化磷 、 硫酸 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 80.0h， 生成 3-N-(4-methylphenyl)-1,1-dioxo-1,2-benzothiazole-3,5-diamine
  参考文献：
  名称：

  Structure-based design and synthesis of novel pseudosaccharine derivatives as antiproliferative agents and kinase inhibitors

  摘要：

  This study is concerned with the implementation of structure-based techniques for the design of new heterocyclic compounds based on pseudosaccharine scaffold with protein kinase inhibition activity. This nucleus was exploited based on the well-known quinazoline core and its interactions with several protein kinases. Two series of compounds employing this new scaffold were synthesized and evaluated at enzymatic and cellular levels. Compound 9b displayed broad spectrum antiproliferative activity on NCI 60-cell lines panel with mean GI(50) of 5.4 mu M. Investigation of the molecular mechanism showed probable inhibitory activity against Src kinase. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.039
• 作为产物：
  描述：

  4-硝基-2-甲苯胺 在 盐酸 、 碳酸氢铵 、 sodium nitrite 作用下， 反应 2.0h， 生成 2-甲基-4-硝基苯磺酰胺
  参考文献：
  名称：

  Structure-based design and synthesis of novel pseudosaccharine derivatives as antiproliferative agents and kinase inhibitors

  摘要：

  This study is concerned with the implementation of structure-based techniques for the design of new heterocyclic compounds based on pseudosaccharine scaffold with protein kinase inhibition activity. This nucleus was exploited based on the well-known quinazoline core and its interactions with several protein kinases. Two series of compounds employing this new scaffold were synthesized and evaluated at enzymatic and cellular levels. Compound 9b displayed broad spectrum antiproliferative activity on NCI 60-cell lines panel with mean GI(50) of 5.4 mu M. Investigation of the molecular mechanism showed probable inhibitory activity against Src kinase. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.039

文献信息

• BIARYL AMIDE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
  申请人：Katayama Seiji

  公开号：US20130116227A1

  公开（公告）日：2013-05-09

  Disclosed is a novel biaryl amide derivative represented by formula (1) and having an affinity for the aldosterone receptor; also disclosed is a pharmaceutically acceptable salt thereof. (In the formula, A is any of the groups represented by formula (a); L is —CONH—, etc.; R 1 is a substitutable aminosulfonyl group, etc.; R 2 is a hydrogen atom, etc.; R 3 is a hydrogen atom, etc.; R 4 is a hydrogen atom, a halogen atom, hydroxy group, a substitutable amino group, a substitutable C 1-6 alkoxy group, a substitutable 4- to 7-membered cyclic amino group, etc.; R 5a , R 5b and R 5c are each independently hydrogen atoms, etc.; R 6 is a halogen atom, a cyano group, etc.; R 7 and R 8 are each independently a hydrogen atom, etc.; and m is an integer such as 0.)

  揭示了一种表示为公式（1）的新型联苯酰胺衍生物，具有与醛固酮受体的亲和力；还揭示了其药用可接受的盐。（在该公式中，A是由公式（a）表示的任何基团之一；L是—CONH—等；R1是可替代的氨基磺酰基等；R2是氢原子等；R3是氢原子等；R4是氢原子、卤原子、羟基、可替代的氨基基团、可替代的C1-6烷氧基、可替代的4-到7-成员环氨基基团等；R5a、R5b和R5c各自独立地是氢原子等；R6是卤原子、氰基等；R7和R8各自独立地是氢原子等；m是整数，例如0。）
• Preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl) -p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines
  申请人：——

  公开号：US20010051725A1

  公开（公告）日：2001-12-13

  The present invention provides a new process for the preparation of 2S, 3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride, wherein this compound is prepared directly from the chloromethylalcohol. Importantly, the process of the present invention results in higher yields of 2S, 3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride without sacrificing its purity. The processes of the present inventin can be used to prepare not only the 2S,3S-derivative, but also the 2R,3S-, 2S,2R- and the 2R,3R-derivatives.

  本发明提供了一种制备2S，3S-N-异丁基-N-(2-羟基-3-氨基-4-苯基丁基)-对硝基苯磺酰胺盐酸盐的新工艺，其中该化合物直接由氯甲基醇制备。重要的是，本发明的工艺不仅能够获得更高产率的2S，3S-N-异丁基-N-(2-羟基-3-氨基-4-苯基丁基)-对硝基苯磺酰胺盐酸盐，而且不会牺牲其纯度。本发明的工艺不仅可用于制备2S,3S衍生物，还可用于制备2R,3S-, 2S,2R-和2R,3R-衍生物。
• Saccharin Derivatives V. Synthesis of 5-Aminosaccharin and Related Compounds
  作者：Alton Warren、Glenn H. Hamor

  DOI：10.1002/jps.2600500723

  日期：1961.7

  The synthesis of the following compounds is reported: 5-nitrosaccharin, 5-aminosaccharin, 5-acetamidosaccharin, 2-methyl-5-nitrosaccharin, and 2-ethyl-5-nitrosaccharin. These substances lacked a sweet taste, being either bitter or tasteless.

  报告了以下化合物的合成：5-亚硝基糖精，5-氨基糖精，5-乙酰氨基糖精，2-甲基-5-亚精糖和2-乙基-5-亚精糖。这些物质缺乏苦味或无味的甜味。
• Improved preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-P-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines
  申请人：Ampac Fine Chemicals LLC

  公开号：EP2194038A2

  公开（公告）日：2010-06-09

  The present invention provides a new process for the preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenyl)-p-nitrobenzenesufonylamide hydrochloride, wherein this compound is prepared directly from the chloromethylalcohol. Importantly, the process of the present invention results in higher yields of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenyl)-p-nitrobenzenesufonylamide hydrochloride without sacrificing its purity.

  本发明提供了一种制备 2S,3S-N-异丁基-N-(2-羟基-3-氨基-4-苯基)-对硝基苯磺酰胺盐酸盐的新工艺，其中该化合物直接从氯甲醇中制备。重要的是，本发明的工艺可以在不影响纯度的情况下获得更高产率的 2S,3S-N-异丁基-N-（2-羟基-3-氨基-4-苯基）-对硝基苯磺酰胺盐酸盐。
• Improved preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)amine
  申请人：Ampac Fine Chemicals LLC

  公开号：EP2319824A2

  公开（公告）日：2011-05-11

  The present invention provides a new process for the preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonyl amide hydrochloride, wherein this compound is prepared directly from the chloromethyl alcohol. Importantly, the process of the present invention results in higher yields of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride without sacrificing its purity. The processes of the present invention can be used to prepare not only the 2S,3S-derivative, but also the 2R,3S-, 2S,2R- and the 2R,3R-derivatives.

  本发明提供了一种制备 2S,3S-N-异丁基-N-(2-羟基-3-氨基-4-苯基丁基)-对硝基苯磺酰胺盐酸盐的新工艺，其中该化合物直接从氯甲醇中制备。重要的是，本发明的工艺可以在不牺牲纯度的情况下获得更高产率的 2S,3S-N-异丁基-N-(2-羟基-3-氨基-4-苯基丁基)-对硝基苯磺酰胺盐酸盐。本发明的工艺不仅可用于制备 2S,3S-衍生物，还可用于制备 2R,3S-、2S,2R- 和 2R,3R-衍生物。