N-(3-nitrophenyl)-4-(pyrrolidin-1-yl)butanamide | 851651-88-2

• 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-(3-nitrophenyl)-4-(pyrrolidin-1-yl)butanamide
• 英文别名: N-(3-nitrophenyl)-4-pyrrolidin-1-ylbutanamide
• CAS: 851651-88-2
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: ZCXDYYXKWGRAAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-nitrophenyl)-4-(pyrrolidin-1-yl)butanamide 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 甲酸铵 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 1,3-bis(3-(3-(4-(pyrrolidin-1-yl)butanamido)phenylcarbamoyl)phenyl)urea
  参考文献：
  名称：

  WO2008/122667

  摘要：

  公开号：
• 作为产物：
  描述：

  间硝基苯胺 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 N-(3-nitrophenyl)-4-(pyrrolidin-1-yl)butanamide
  参考文献：
  名称：

  Structure-based design of selective high-affinity telomeric quadruplex-binding ligands

  摘要：

  我们利用晶体结构数据作为计算机设计的起点，开发了一个基于三唑的端粒四链选择性配体库，该配体模仿了一个已建立的基于三取代吖啶的配体家族。通过电喷雾质谱法估算出的结合亲和力符合设计理念。

  DOI：

  10.1039/c0cc02917c

文献信息

• Click chemistry assembly of G-quadruplex ligands incorporating a diarylurea scaffold and triazole linkers
  作者：William C. Drewe、Stephen Neidle

  DOI：10.1039/b814576h

  日期：——

  A series of diarylurea ligands were designed to interact selectively with G-quadruplexes and were synthesised using copper(I) catalysed ‘click’ chemistry to incorporate the 1,4-substituted 1,2,3-triazole ring into the core of the ligands; the optimal ligands demonstrate a high degree of selective telomeric G-quadruplex stabilisation and are not cytotoxic in several cancer cell lines.

  设计了一系列二芳基脲配体，以选择性地与G-四重螺旋相互作用，并采用铜(I)催化的“点击”化学合成这些配体，将1,4-取代的1,2,3-三唑环引入配体的核心；最佳配体在稳定端粒G-四重螺旋方面表现出高度选择性，并且在多种癌细胞系中无细胞毒性。
• Rational Design of Substituted Diarylureas: A Scaffold for Binding to G-Quadruplex Motifs
  作者：William C. Drewe、Rupesh Nanjunda、Mekala Gunaratnam、Monica Beltran、Gary N. Parkinson、Anthony P. Reszka、W. David Wilson、Stephen Neidle

  DOI：10.1021/jm801245v

  日期：2008.12.25

  The design and synthesis of a series of urea-based nonpolycyclic aromatic ligands with alkylaminoanilino side chains as telomeric and genomic G-quadruplex DNA interacting agents are described. Their interactions with quadruplexes have been examined by means of fluorescent resonance energy transfer melting, circular dichroism, and surface plasmon resonance-based assays. These validate the design concept for such urea-based ligands and also show that they have significant selectivity over duplex DNA, as well as for particular G-quadruplexes. The ligand-quadruplex complexes were investigated by computational molecular modeling, providing further information on structure-activity relationships. Preliminary biological studies using shortterm cell growth inhibition assays show that some of the ligands have cancer cell selectivity, although they appear to have low potency for intracellular telomeric G-quadruplex structures, suggesting that their cellular targets may be other, possibly oncogene-related quadruplexes,
• [EN] UREYLENE DERIVATIVES<br/>[FR] DÉRIVÉS D'URÉYLÈNE
  申请人：UNIV LONDON PHARMACY

  公开号：WO2008122667A2

  公开（公告）日：2008-10-16

  [EN] The invention concerns compounds of Formula (I) or a salt, solvate or pro-drug thereof. The compounds may be used in therapy, particularly anti-cancer therapy.
  [FR] L'invention concerne des composés de la formule (I) ou un sel, un solvate ou un promédicament de ces derniers. Les composés précités peuvent être utilisés en thérapie, en particulier dans la thérapie anticancéreuse.
• WO2008/122667
  申请人：——

  公开号：——

  公开（公告）日：——
• Structure-based design of selective high-affinity telomeric quadruplex-binding ligands
  作者：Caterina Maria Lombardo、Iria Sánchez Martínez、Shozeb Haider、Valérie Gabelica、Edwin De Pauw、John E. Moses、Stephen Neidle

  DOI：10.1039/c0cc02917c

  日期：——

  A library of triazole-based telomeric quadruplex-selective ligands has been developed that mimic an established family of tri-substituted acridine-based ligands, using crystal structure data as a starting-point for computer-based design. Binding affinities, estimated by electrospray mass spectrometry, are in accord with the design concept.

  我们利用晶体结构数据作为计算机设计的起点，开发了一个基于三唑的端粒四链选择性配体库，该配体模仿了一个已建立的基于三取代吖啶的配体家族。通过电喷雾质谱法估算出的结合亲和力符合设计理念。