6-(4-chlorophenylamino)-1H-pyrimidine-2,4-dione | 21333-02-8

• 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: 6-(4-chlorophenylamino)-1H-pyrimidine-2,4-dione
• 英文别名: 6-(4-chloroanilino)uracil；6-(4-chloro-anilino)-1H-pyrimidine-2,4-dione；6-[(4-chlorophenyl)amino]pyrimidine-2,4(1H,3H)-dione；6-[(4-chlorophenyl)amino]pyrimidine-2,4(1H,4H)-dione；6-(4-Chlor-phenylamino)-uracil；6-(4-Chloro-phenylamino)-1H-pyrimidine-2,4-dione；6-(4-chloroanilino)-1H-pyrimidine-2,4-dione
• CAS: 21333-02-8
• 化学式: C₁₀H₈ClN₃O₂
• 分子量: 237.645
• InChiKey: POKMZWROIKHVLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-chlorophenylamino)-1H-pyrimidine-2,4-dione 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 10-(4-chlorophenyl)-3-methyl-9-(trifluoromethyl)-2H,3H,4H,10H-pyrimido[4,5-b]quinoline-2,4-dione
  参考文献：
  名称：

  5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2

  摘要：

  Based on previous reports of certain 5-deazaflavin derivatives being capable of activating the tumour suppressor p53 in cancer cells through inhibition of the p53-specific ubiquitin E3 ligase HDM2, we have conducted an structure-activity relationship (SAR) analysis through systematic modification of the 5-deazaflavin template. This analysis shows that HDM2-inhibitory activity depends on a combination of factors. The most active compounds (e. g., 15) contain a trifluoromethyl or chloro substituent at the deazaflavin C9 position and this activity depends to a large extent on the presence of at least one additional halogen or methyl substituent of the phenyl group at N10. Our SAR results, in combination with the HDM2 RING domain receptor recognition model we present, form the basis for the design of drug-like and potent activators of p53 for potential cancer therapy. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.038
• 作为产物：
  描述：

  对氯苯胺 、 4-氨基-2,6-二羟基嘧啶 在 溶剂黄146 作用下， 反应 3.0h， 以32%的产率得到6-(4-chlorophenylamino)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  黄素类化合物是潜在的抗疟药。1. 10-（卤代苯基）-3-甲基黄素。

  摘要：

  DOI：

  10.1021/jm00399a020

文献信息

• UV₃₆₅ light promoted catalyst-free synthesis of pyrimido[4,5-<i>b</i>]quinoline-2,4-diones in aqueous-glycerol medium
  作者：Geetmani Singh Nongthombam、George Kupar Kharmawlong、John Elisa Kumar、Rishanlang Nongkhlaw

  DOI：10.1039/c8nj01459k

  日期：——

  Herein, a highly efficient and environmentally benign protocol for the synthesis of biologically important pyrimido[4,5-b]quinolinone-2,4-diones from aromatic amines, barbituric acid and aryl aldehyde is reported. This process takes place at room temperature under direct irradiation from a UV365 light source in the absence of a photocatalyst. The reported approach has several advantages such as high

  在此，报道了一种由芳族胺，巴比妥酸和芳基醛合成生物上重要的嘧啶并[4,5 - b ]喹啉酮-2,4-二酮的高效，环保的方法。该过程在室温下在不存在光催化剂的情况下在来自UV 365光源的直接照射下进行。报道的方法具有许多优势，例如高收率，干净的反应条件，无色谱法合成以及使用便宜的水-甘油溶剂系统，它也是一种环境友好的溶剂。该协议适用于大规模合成嘧啶并[4,5 - b ]喹啉酮-2,4-二酮而不浪费任何昂贵的化学药品是一个附加的优势。
• Compounds inhibiting the aggregation of superoxide dismutase-1
  申请人：Lansbury Peter

  公开号：US20060194821A1

  公开（公告）日：2006-08-31

  The invention is directed to methods of inhibiting the rate at which superoxide dismutse-1 (SOD) aggregates using compounds that stabilize SOD dimers. The methods are useful in the study and therapy of amyotrophic lateral sclerosis. The invention also includes assays that can be used to identify compounds that stabilize dimers and SOD molecules that have been modified for use in these assays.

  本发明涉及使用稳定SOD二聚体的化合物来抑制超氧化物歧化酶-1（SOD）聚集的速率的方法。该方法在进行肌萎缩侧索硬化的研究和治疗中非常有用。本发明还包括可用于识别稳定二聚体化合物和已经改性用于这些测定的SOD分子的测定方法。
• Synthesis of 5-deazaflavin derivatives and their activation of p53 in cells
  作者：Jennifer M. Wilson、Graham Henderson、Fiona Black、Andrew Sutherland、Robert L. Ludwig、Karen H. Vousden、David J. Robins

  DOI：10.1016/j.bmc.2006.10.011

  日期：2007.1.1

  A family of 5-deazaflavin derivatives has been synthesised using a two-step convergent strategy. The biological activity of these compounds was evaluated in cells, by assessing their ability to stabilize and activate p53. These compounds may act as low molecular weight inhibitors of the E3 activity of HMD2 in tumours that retain wild-type p53. Importantly, we have demonstrated that the nitro group present in all three of the original lead compounds [1-3 (HL198C-E)] is not essential for observation of this biological activity. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, biological active molecular design, and molecular docking study of novel deazaflavin–cholestane hybrid compounds
  作者：Ajaya R. Shrestha、Takashi Shindo、Noriyuki Ashida、Tomohisa Nagamatsu

  DOI：10.1016/j.bmc.2008.07.089

  日期：2008.9

  Novel deazaflavin-cholestane hybrid compounds, 3',8'-disubstituted-5'-deazacholest-2,4-dieno[2,3g] pteridine-2',4'(3'H, 8'H)-diones, have been synthesized by condensation reaction between 6-(monosubstituted amino)-pyrimidin-2,4(1H,3H)-diones and 2-hydroxymethylenecholest-4-en-3-one in presence of p-toluenesulfonic acid monohydrate and diphenyl ether. The antitumor activities against human tumor cell lines (CCRF-HSB-2 and KB cells) have been investigated in vitro, and many of these compounds showed promising antitumor activities. Furthermore, molecular docking study using LigandFit within the software package Discovery Studio 1.7 was done for lead optimization of these compounds as potential PTK inhibitors. In general, all of the synthesized steroid-hybrid compounds showed good binding affinities into PTK (PDB code: 1t46). (C) 2008 Elsevier Ltd. All rights reserved.
• Nagamatsu, Tomohisa; Hashiguchi, Yuko; Yoneda, Fumio, Journal of the Chemical Society. Perkin transactions I, 1984, # 3, p. 561 - 565
  作者：Nagamatsu, Tomohisa、Hashiguchi, Yuko、Yoneda, Fumio

  DOI：——

  日期：——