3-nitro-benzenesulfonic acid-[1]naphthylamide | 419559-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-nitro-benzenesulfonic acid-[1]naphthylamide
• 英文别名: 3-Nitro-N-(naphthyl-(1))-benzolsulfonamid-(1)；3-Nitro-benzolsulfonsaeure-[1]naphthylamid；1-m-Nitrobenzolsulfonylaminonaphthalin；N-(1-Naphthyl)-3-nitrobenzenesulfonamide；N-naphthalen-1-yl-3-nitrobenzenesulfonamide
• CAS: 419559-79-8
• 化学式: C₁₆H₁₂N₂O₄S
• 分子量: 328.348
• InChiKey: WIFWFLHGNPQTSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitro-benzenesulfonic acid-[1]naphthylamide 在 N-甲基吗啉 、 tin(ll) chloride 、 氯甲酸异丁酯 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 生成 Hexadecanoic acid {2-[3-(naphthalen-1-ylsulfamoyl)-phenylcarbamoyl]-ethyl}-amide
  参考文献：
  名称：

  Design, synthesis and early structure–activity relationship of farnesyltransferase inhibitors which mimic both the peptidic and the prenylic substrate

  摘要：

  Inhibition of the farnesylation of ras proteins has been identified as a promising target in tumor therapy. Only a few farnesyltransferase inhibitors are bisubstrate analogues displaying features of both substrates, the farnesylpyrophosphate and the C-terminal CAAX-tetrapeptide sequence of the res protein. These known bisubstrate analogues consist of an AAX-tripeptide and a farnesyl residue connected through various linkers. We have developed a class of novel compounds that mimic a bisubstrate inhibitor structure and that differ from the known ones by lacking peptidic or farnesylic substructures. Long chain fatty acids and aryl-substituted carboxylic acids were used as farnesyl surrogates. These structures were linked to isoleucine amide, benzoic acid amide, N-substituted aminobenzenesulfonamides and N-alpha-aryl-substituted methionine derivatives, respectively, which function as AA- or AAX-mimetics. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00138-3
• 作为产物：
  描述：

  1-萘胺 、 3-硝基苯磺酰氯 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 生成 3-nitro-benzenesulfonic acid-[1]naphthylamide
  参考文献：
  名称：

  Design, synthesis and early structure–activity relationship of farnesyltransferase inhibitors which mimic both the peptidic and the prenylic substrate

  摘要：

  Inhibition of the farnesylation of ras proteins has been identified as a promising target in tumor therapy. Only a few farnesyltransferase inhibitors are bisubstrate analogues displaying features of both substrates, the farnesylpyrophosphate and the C-terminal CAAX-tetrapeptide sequence of the res protein. These known bisubstrate analogues consist of an AAX-tripeptide and a farnesyl residue connected through various linkers. We have developed a class of novel compounds that mimic a bisubstrate inhibitor structure and that differ from the known ones by lacking peptidic or farnesylic substructures. Long chain fatty acids and aryl-substituted carboxylic acids were used as farnesyl surrogates. These structures were linked to isoleucine amide, benzoic acid amide, N-substituted aminobenzenesulfonamides and N-alpha-aryl-substituted methionine derivatives, respectively, which function as AA- or AAX-mimetics. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00138-3

文献信息

• 376. Substitution in arylsulphon-1- and -2-naphthalides
  作者：Raphael Consden、Joseph Kenyon

  DOI：10.1039/jr9350001591

  日期：——
• 411. The nitration of phthalonaphthylimides and the facile preparation of 8-nitro-1-naphthylamine
  作者：Herbert H. Hodgson、J. Harold Crook

  DOI：10.1039/jr9360001844

  日期：——
• Tarnowska, Societatis Scientiarum Lodziensis, Acta Chimica, 1957, vol. 2, p. 101,107
  作者：Tarnowska

  DOI：——

  日期：——
• Chrzaszczewska et al., Societatis Scientiarum Lodziensis, Acta Chimica, 1958, vol. 3, p. 63,65
  作者：Chrzaszczewska et al.

  DOI：——

  日期：——
• Tarnowska, Societatis Scientiarum Lodziensis, Acta Chimica, 1959, vol. 4, p. 143,144
  作者：Tarnowska

  DOI：——

  日期：——

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