4-chloro-N-(3-nitrophenyl)butanamide | 304684-54-6

• 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: 4-chloro-N-(3-nitrophenyl)butanamide
• CAS: 304684-54-6
• 化学式: C₁₀H₁₁ClN₂O₃
• mdl: MFCD01918226
• 分子量: 242.662
• InChiKey: KNMIIQANYVGPTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  65-67 °C
• 沸点：
  442.3±30.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(3-nitrophenyl)butanamide 在 四氢吡咯 、 盐酸 、 亚硝酸特丁酯 、 copper(ll) sulfate pentahydrate 、 10% palladium on activated carbon 、 氢气 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 15.75h， 生成 N,N',N''-((benzene-1,3,5-triyltris(1H-1,2,3-triazole-4,1-diyl))tris(benzene-3,1-diyl))tris(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
• 作为产物：
  描述：

  间硝基苯胺 、 4-氯丁酰氯 以86%的产率得到4-chloro-N-(3-nitrophenyl)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。
• Copper-Catalyzed Synthesis of Benzoxazoles via a Regioselective C−H Functionalization/C−O Bond Formation under an Air Atmosphere
  作者：Satoshi Ueda、Hideko Nagasawa

  DOI：10.1021/jo900513z

  日期：2009.6.5

  An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160 degrees C allows the use of air as the tern-final oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.
• Exploring DOXP-reductoisomerase binding limits using phosphonated N-aryl and N-heteroarylcarboxamides as DXR inhibitors
  作者：Taryn Bodill、Anne C. Conibear、Marius K.M. Mutorwa、Jessica L. Goble、Gregory L. Blatch、Kevin A. Lobb、Rosalyn Klein、Perry T. Kaye

  DOI：10.1016/j.bmc.2013.04.076

  日期：2013.7

  DOXP-reductoisomerase (DXR) is a validated target for the development of antimalarial drugs to address the increase in resistant strains of Plasmodium falciparum. Series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts have been prepared as analogues of the potent DXR inhibitor fosmidomycin. The effects of the carboxamide N-substituents and the length of the methylene linker have been explored using in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays using both EcDXR and PfDXR. These studies indicate an optimal linker length of two methylene units and have confirmed the importance of an additional binding pocket in the PfDXR active site. Insights into the constraints of the PfDXR binding site provide additional scope for the rational design of DXR inhibitors with increased ligand-receptor interactions. (C) 2013 Elsevier Ltd. All rights reserved.
• WO2008/122667
  申请人：——

  公开号：——

  公开（公告）日：——
• 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,