4,6-dichloro-N-mesityl-1,3,5-triazin-2-amine

• 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: 4,6-dichloro-N-mesityl-1,3,5-triazin-2-amine
• 英文别名: 4,6-dichloro-N-(2,4,6-trimethylphenyl)-1,3,5-triazin-2-amine
• 化学式: C₁₂H₁₂Cl₂N₄
• 分子量: 283.16
• InChiKey: NDOFZIKYECXOHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-N-mesityl-1,3,5-triazin-2-amine 在 sodium 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 N2-mesityl-6-methoxy-N4-(1-Boc-piperidin-4-yl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  A novel series of piperidine-substituted triazine derivatives have been synthesized and evaluated for anti-HIV activities in MT-4 cells. Most compounds displayed extremely promising activity against wildtype HIV-1 with EC50 values in low nanomolar concentration, better than that of Nevirapine, Delavirdine, Zidovudine and Dideoxycitidine, and higher potency towards the resistant mutant strain K103N/Y181C than that of Nevirapine and Delavirdine. Selected compounds were also assayed against reverse transcriptase with lower IC50 values than that of Nevirapine. The structure-activity relationship (SAR) of these novel structural congeners was also discussed. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.019
• 作为产物：
  描述：

  三聚氯氰 、 2,4,6-三甲基苯胺 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 以95%的产率得到4,6-dichloro-N-mesityl-1,3,5-triazin-2-amine
  参考文献：
  名称：

  DISUBSTITUTED TRIAZINE DIMERS FOR TREATMENT AND/OR PREVENTION OF INFECTIOUS DISEASES

  摘要：

  本发明涉及包含两个二取代三嗪环的新化合物（I），通过有机连接物共价连接，从而形成二聚体。这些化合物对引起传染病如非洲锥虫病、克氏病、利什曼病、疟疾和艾滋病的致病性感染剂表现出活性。该发明还涉及这些疾病的预防和/或治疗。

  公开号：

  US20140323488A1

文献信息

• [EN] DISUBSTITUTED TRIAZINE DIMERS FOR TREATMENT AND/OR PREVENTION OF INFECTIOUS DISEASES<br/>[FR] DIMÈRES DE TRIAZINE DISUBSTITUÉE POUR LE TRAITEMENT E/OU LA PRÉVENTION DE MALADIES INFECTIEUSES
  申请人：UNIV ANTWERPEN

  公开号：WO2013068551A1

  公开（公告）日：2013-05-16

  The present invention relates to novel compounds (I) containing two disubstituted triazine rings covalently linked by an organic linker, thereby creating dimers. These compounds show activity against the causative infective agents of infectious diseases such as African trypanosomiasis, Chagas disease, Leishmaniasis, Malaria and HIV. The invention further relates to the prevention and/or treatment of these diseases.

  本发明涉及一种新型化合物（I），其中包含通过有机连接剂共价连接的两个二取代三嗪环，从而形成二聚体。这些化合物对致病的传染病如非洲锥虫病、克氏病、利什曼病、疟疾和艾滋病的感染性病原体表现出活性。该发明还涉及预防和/或治疗这些疾病。
• DISUBSTITUTED TRIAZINE DIMERS FOR TREATMENT AND/OR PREVENTION OF INFECTIOUS DISEASES
  申请人：LEWI Wim

  公开号：US20140323488A1

  公开（公告）日：2014-10-30

  The present invention relates to novel compounds (I) containing two disubstituted triazine rings covalently linked by an organic linker, thereby creating dimers. These compounds show activity against the causative infective agents of infectious diseases such as African trypanosomiasis, Chagas disease, Leishmaniasis, Malaria and HIV. The invention further relates to the prevention and/or treatment of these diseases.

  本发明涉及包含两个二取代三嗪环的新化合物（I），通过有机连接物共价连接，从而形成二聚体。这些化合物对引起传染病如非洲锥虫病、克氏病、利什曼病、疟疾和艾滋病的致病性感染剂表现出活性。该发明还涉及这些疾病的预防和/或治疗。
• Evolution of Anti-HIV Drug CandidatesPart 2: Diaryltriazine (DATA) Analogues
  作者：Donald W. Ludovici、Robert W. Kavash、Michael J. Kukla、Chih Y. Ho、Hong Ye、Bart L. De Corte、Koen Andries、Marie-Pierre de Béthune、Hilde Azijn、Rudi Pauwels、Henry E.L. Moereels、Jan Heeres、Lucien M.H. Koymans、Marc R. de Jonge、Koen J.A. Van Aken、Frederik F.D. Daeyaert、Paul J. Lewi、Kalyan Das、Edward Arnold、Paul A.J. Janssen

  DOI：10.1016/s0960-894x(01)00411-5

  日期：2001.9

  A synthesis program directed toward improving the stability of imidoyl thiourea based non-nucleoside reverse transcriptase inhibitors (NNRTIs) led to the discovery of diaryltriazines (DATAs), a new class of potent NNRTIs. The synthesis and anti-HIV structure-activity relationship (SAR) studies of a series of DATA derivatives are described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors
  作者：Xuwang Chen、Peng Zhan、Xin Liu、Ziheng Cheng、Caicai Meng、Siyuan Shao、Christophe Pannecouque、Erik De Clercq、Xinyong Liu

  DOI：10.1016/j.bmc.2012.04.030

  日期：2012.6

  A novel series of piperidine-linked amino-triazine derivatives were designed, synthesized and evaluated for in vitro anti-HIV activity as non-nucleoside reverse transcriptase inhibitors on the basis of our previous work. Screening results indicated that most compounds showed excellent activity against wild-type HIV-1 with EC50 values in low nanomolar concentration range (especially compound 6b3, EC50 = 4.61 nM, SI = 5945) and high activity against K103N/Y181C resistant mutant strain of HIV-1 with EC50 values in low micromolar concentration range. In addition, preliminary structure-activity relationship and molecular modeling of these new analogs were detailed in this manuscript. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• From human immunodeficiency virus non-nucleoside reverse transcriptase inhibitors to potent and selective antitrypanosomal compounds
  作者：Muthusamy Venkatraj、Kevin K. Ariën、Jan Heeres、Jurgen Joossens、Bertrand Dirié、Sophie Lyssens、Johan Michiels、Paul Cos、Paul J. Lewi、Guido Vanham、Louis Maes、Pieter Van der Veken、Koen Augustyns

  DOI：10.1016/j.bmc.2014.08.005

  日期：2014.10

  The presence of a structural recognition motif for the nucleoside P2 transporter in a library of pyrimidine and triazine non-nucleoside HIV-1 reverse transcriptase inhibitors, prompted for the evaluation of antitrypanosomal activity. It was demonstrated that the structure-activity relationship for anti-HIV and antitrypanosomal activity was different. Optimization in the diaryl triazine series led to 6-(mesityloxy)-N2-phenyl-1,3,5-triazine-2,4-diamine (69), a compound with potent in vitro and moderate in vivo antitrypanosomal activity.