N-[2-(3-Hydroxy-propylamino)-ethyl]-2-nitro-benzenesulfonamide | 192379-55-8

• 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: N-[2-(3-Hydroxy-propylamino)-ethyl]-2-nitro-benzenesulfonamide
• 英文别名: Benzenesulfonamide, N-[2-[(3-hydroxypropyl)amino]ethyl]-2-nitro-；N-[2-(3-hydroxypropylamino)ethyl]-2-nitrobenzenesulfonamide
• CAS: 192379-55-8
• 化学式: C₁₁H₁₇N₃O₅S
• 分子量: 303.339
• InChiKey: DYWGUFPSMVGYML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[2-(3-Hydroxy-propylamino)-ethyl]-2-nitro-benzenesulfonamide 在 potassium carbonate 、 苯硫酚 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.33h， 生成 tert-butyl N-[2-[[6-(aminomethyl)pyridin-2-yl]methylamino]ethyl]-N-(3-hydroxypropyl)carbamate
  参考文献：
  名称：

  Solution Phase Combinatorial Chemistry. Synthesis of Novel Linear Pyridinopolyamine Libraries with Potent Antibacterial Activity

  摘要：

  Novel linear pyridinopolyamine derivatives 1-3, 7, and 8 have been synthesized as scaffolds for combinatorial drug discovery. The mono-t-Boc- and monotosyl-protected linear scaffolds 1 and 2 were obtained by a Schiff base type cyclization of 2,6-pyridinedicarboxaldehyde (24) with monoprotected triamines 22 and 23 using Ni2+ as a metal template, followed by reductive cleavage and decomplexation in a one-pot procedure. The unprotected linear scaffold 3 was obtained by treating 1 with TFA, Scaffold 1 was also synthesized from the orthogonally protected pyridinopolyamine 7 which was constructed from 2,6-bis(bromomethylipyridine (29) in four steps. Selective deprotection of the key intermediate 7 afforded 8, which was further selectively deprotected to give scaffold 1. A combinatorial chemistry strategy involving solution phase simultaneous addition of functionalities (SPSAF) is described. Thirteen high-purity tertiary amine libraries 19-21) (total 1638 compounds) were synthesized by the SPSAF and fix last methodologies from linear polyamine scaffolds 1 and 2. All libraries were examined by TLC, purified by chromatographic techniques, and characterized by H-1 NMR and ESI RIS spectral data. A fur last methodology was utilized to minimize chemical reactions and perform SAR studies directly on libraries. Several first-round sublibraries of scaffold 1 containing 126 compounds each, exhibited potent antibacterial activity with MICs of 1-12 mu M against Streptococcus pyogenes and Escherichia coli imp(-).

  DOI：

  10.1021/jo970535j
• 作为产物：
  描述：

  N-(3-羟丙基)乙二胺 、 邻硝基苯磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以57%的产率得到N-[2-(3-Hydroxy-propylamino)-ethyl]-2-nitro-benzenesulfonamide
  参考文献：
  名称：

  Solution Phase Combinatorial Chemistry. Synthesis of Novel Linear Pyridinopolyamine Libraries with Potent Antibacterial Activity

  摘要：

  Novel linear pyridinopolyamine derivatives 1-3, 7, and 8 have been synthesized as scaffolds for combinatorial drug discovery. The mono-t-Boc- and monotosyl-protected linear scaffolds 1 and 2 were obtained by a Schiff base type cyclization of 2,6-pyridinedicarboxaldehyde (24) with monoprotected triamines 22 and 23 using Ni2+ as a metal template, followed by reductive cleavage and decomplexation in a one-pot procedure. The unprotected linear scaffold 3 was obtained by treating 1 with TFA, Scaffold 1 was also synthesized from the orthogonally protected pyridinopolyamine 7 which was constructed from 2,6-bis(bromomethylipyridine (29) in four steps. Selective deprotection of the key intermediate 7 afforded 8, which was further selectively deprotected to give scaffold 1. A combinatorial chemistry strategy involving solution phase simultaneous addition of functionalities (SPSAF) is described. Thirteen high-purity tertiary amine libraries 19-21) (total 1638 compounds) were synthesized by the SPSAF and fix last methodologies from linear polyamine scaffolds 1 and 2. All libraries were examined by TLC, purified by chromatographic techniques, and characterized by H-1 NMR and ESI RIS spectral data. A fur last methodology was utilized to minimize chemical reactions and perform SAR studies directly on libraries. Several first-round sublibraries of scaffold 1 containing 126 compounds each, exhibited potent antibacterial activity with MICs of 1-12 mu M against Streptococcus pyogenes and Escherichia coli imp(-).

  DOI：

  10.1021/jo970535j

文献信息

• Solution Phase Combinatorial Chemistry. Synthesis of Novel Linear Pyridinopolyamine Libraries with Potent Antibacterial Activity
  作者：Haoyun An、Becky D. Haly、Allister S. Fraser、Charles J. Guinosso、P. Dan Cook

  DOI：10.1021/jo970535j

  日期：1997.7.1

  Novel linear pyridinopolyamine derivatives 1-3, 7, and 8 have been synthesized as scaffolds for combinatorial drug discovery. The mono-t-Boc- and monotosyl-protected linear scaffolds 1 and 2 were obtained by a Schiff base type cyclization of 2,6-pyridinedicarboxaldehyde (24) with monoprotected triamines 22 and 23 using Ni2+ as a metal template, followed by reductive cleavage and decomplexation in a one-pot procedure. The unprotected linear scaffold 3 was obtained by treating 1 with TFA, Scaffold 1 was also synthesized from the orthogonally protected pyridinopolyamine 7 which was constructed from 2,6-bis(bromomethylipyridine (29) in four steps. Selective deprotection of the key intermediate 7 afforded 8, which was further selectively deprotected to give scaffold 1. A combinatorial chemistry strategy involving solution phase simultaneous addition of functionalities (SPSAF) is described. Thirteen high-purity tertiary amine libraries 19-21) (total 1638 compounds) were synthesized by the SPSAF and fix last methodologies from linear polyamine scaffolds 1 and 2. All libraries were examined by TLC, purified by chromatographic techniques, and characterized by H-1 NMR and ESI RIS spectral data. A fur last methodology was utilized to minimize chemical reactions and perform SAR studies directly on libraries. Several first-round sublibraries of scaffold 1 containing 126 compounds each, exhibited potent antibacterial activity with MICs of 1-12 mu M against Streptococcus pyogenes and Escherichia coli imp(-).