6-(2-chlorophenylamino)-1H-pyrimidine-2,4-dione | 21416-58-0

• 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-(2-chlorophenylamino)-1H-pyrimidine-2,4-dione
• 英文别名: 6-(2-chloro-anilino)-1H-pyrimidine-2,4-dione；6-[(2-chlorophenyl)amino]pyrimidine-2,4(1H,3H)-dione；6-(2-Chlor-phenylamino)-uracil；6-(2-chloroanilino)-1H-pyrimidine-2,4-dione
• CAS: 21416-58-0
• 化学式: C₁₀H₈ClN₃O₂
• mdl: MFCD01077482
• 分子量: 237.645
• InChiKey: XPZKTMYYBVDAFQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.488±0.06 g/cm3(Predicted)

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-(2-chlorophenylamino)-1H-pyrimidine-2,4-dione 、 2,3-二甲氧基苯甲醛 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以48%的产率得到10-(2-chlorophenyl)-9-methoxypyrimido[4,5-b]quinoline-2,4(3H,10H)-dione
  参考文献：
  名称：

  Annulation of 6-aminouracils with 2,3-dimethoxy- and 2-fluorobenzaldehydes and 2-chloro-7-methoxyquinoline-3-carbaldehyde

  摘要：

  6-R-Aminouracils reacted with 2,3-dimethoxybenzaldehyde to give 10-R-substituted 9-methoxy-5-deazaflavins. No expected 5-deazaflavins were obtained in analogous reactions of 2,3-dimethoxybenzaldehyde with 6-aminouracil hydrochlorides. On the other hand, the corresponding 5-deazaflavin and naphthyridine hydrochlorides were formed in the reactions of 6-aminouracil hydrochlorides with 2-fluorobenzaldehyde and 2-chloro-7-methoxyquinoline-3-carbaldehyde. The newly synthesized 9,10-substituted 5-deazaflavins and benzo[b]pyrimido[5,4-g][1,8]naphthyridines attract interest as potential biologically active substances and substrates for further structural modifications.

  DOI：

  10.1134/s1070428015100152
• 作为产物：
  描述：

  6-氯尿嘧啶 、 邻氯苯胺 反应 0.33h， 以60%的产率得到6-(2-chlorophenylamino)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 5-deazaflavin derivatives and their activation of p53 in cells

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.10.011

文献信息

• 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。
• 5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2
  作者：Michael P. Dickens、Patricia Roxburgh、Andreas Hock、Mokdad Mezna、Barrie Kellam、Karen H. Vousden、Peter M. Fischer

  DOI：10.1016/j.bmc.2013.09.038

  日期：2013.11

  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.
• Synthesis of new tetrahydrobenzo[b]pyrimido- [5,4-g][1,8]naphthyridine-2,4-diones from 6-aminouracils
  作者：G. S. Karakhanyan

  DOI：10.1134/s1070428017100232

  日期：2017.10

  Cyclocondensation of N-substituted 6-aminouracils with 3- and 7-methyl-2-iodoquinoline-3-carbaldehydes gave the corresponding 12- or 9,12-substituted benzo[b]pyrimido[5,4-g][1,8]naphthyridine-2,4-dioncs.
• COMPOUNDS INHIBITING THE AGGREGATION OF SUPEROXIDE DISMUTASE-1
  申请人：The Brighamn and Women's Hospital, Inc.

  公开号：EP1853276A2

  公开（公告）日：2007-11-14
• [EN] COMPOUNDS INHIBITING THE AGGREGATION OF SUPEROXIDE DISMUTASE-1<br/>[FR] COMPOSES INHIBANT L'AGREGATION DE LA SUPEROXYDE DISMUTASE-1
  申请人：BRIGHAM & WOMENS HOSPITAL

  公开号：WO2006089221A2

  公开（公告）日：2006-08-24

  [EN] 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.
  [FR] L'invention concerne des méthodes permettant d'inhiber la vitesse à laquelle la superoxyde dismutase-1 (SOD) s'agrège à l'aide de composés qui stabilisent des dimères SOD. On utilise ces méthodes pour l'étude et la thérapie de la sclérose latérale amyotrophique. L'invention concerne également des dosages qui peuvent être utilisés pour identifier des composés qui stabilisent des dimères et des molécules SOD modifiés pour être utilisés dans lesdits dosages.