(4,6-dichloro-[1,3,5]triazin-2-yl)-(2,6-dimethylphenyl)amine | 27315-07-7

• 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-[1,3,5]triazin-2-yl)-(2,6-dimethylphenyl)amine
• 英文别名: 4,6-dichloro-N-(2,6-dimethylphenyl)-1,3,5-triazin-2-amine；2,4-dichloro-6-(2,6-dimethylphenylamino)-1,3,5-triazine；(4,6-dichloro-[1,3,5]triazin-2-yl)-(2,6-dimethyl-phenyl)-amine；N-(2,6-dichlorophenyl)-4,6-dichloro-1,3,5-triazin-2-amine；2-(2.6-Dimethylphenyl)-amino-4.6-dichlor-s-triazin
• CAS: 27315-07-7
• 化学式: C₁₁H₁₀Cl₂N₄
• 分子量: 269.133
• InChiKey: FRRLRHHQUHGSNK-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C
• 沸点：
  440.7±55.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-[1,3,5]triazin-2-yl)-(2,6-dimethylphenyl)amine 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (3-{4-[(4-chloro-6-(2,6-dimethylphenylamino)-[1,3,5]triazin-2-yl)oxymethyl]-[1,2,3]triazol-1-yl}propyl)-(7-chloroquinolin-4-yl)amine
  参考文献：
  名称：

  Synthesis of 4-aminoquinoline-1,2,3-triazole and 4-aminoquinoline-1,2,3-triazole-1,3,5-triazine Hybrids as Potential Antimalarial Agents

  摘要：

  We report herein synthesis of a series of 4‐aminoquinoline‐1,2,3‐triazole and 4‐aminoquinoline‐1,2,3‐triazole‐1,3,5‐triazine hybrids and evaluate their antimalarial activity against D6 and W2 strains of Plasmodium falciparum. To study the structure–activity relationship of substituted 4‐aminoquinoline–based hybrids, 34 structurally diverse compounds were synthesized and tested against D6 and W2 strains of P. falciparum. Some of the compounds have shown promising antimalarial activity without toxicity against Vero cells.

  DOI：

  10.1111/j.1747-0285.2011.01115.x
• 作为产物：
  描述：

  三聚氯氰 、 2,6-二甲基苯胺 生成 (4,6-dichloro-[1,3,5]triazin-2-yl)-(2,6-dimethylphenyl)amine
  参考文献：
  名称：

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

  摘要：

  本发明涉及新型化合物（I），其中包含两个二取代三嗪环通过有机连接剂共价连接形成二聚体。这些化合物对非洲锥虫病、恙虫病、利什曼病、疟疾和艾滋病等感染性疾病的致病微生物具有活性。本发明还涉及这些疾病的预防和/或治疗。

  公开号：

  US20140323488A1

文献信息

• Trisubstituted 1,3,5,-triazine derivatives
  申请人：Janssen Pharmaceutica N.V.

  公开号：US06372729B1

  公开（公告）日：2002-04-16

  This invention concerns the use of the compounds of formula the N-oxides, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein A is CH, CR4 or N; n is 0, 1, 2, 3 or 4; R1 and R2 are each independently selected from hydrogen, hydroxy, C1-12alkyl, C1-12alkyloxy, C1-12alkylcarbonyl, C1-12alkyloxycarbonyl, aryl, amino, mono- or di(C1-12alkyl)amino, mono- or di(C1-12alkyl)aminocarbonyl wherein each of the aforementioned C1-12alkyl groups may optionally and each individually be substituted; or R1 and R2 taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-12alkyl)aminoC1-4alkylidene; R3 is hydrogen, aryl, C1-6alkylcarbonyl, optionally substituted C1-6alkyl; and each R4 independently is hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy; L is —X—R5 or —X-Alk-R6; wherein R5 and R6 each independently are indanyl, indolyl or phenyl; each of said indanyl, indolyl or phenyl may be substituted; and X is —NR3—, —NH—NH—, —N═N—, —O—, —S—, —S(═O)— or —S(═O)2—; aryl is optionally substituted phenyl; Het is an optionally substituted aliphatic or aromatic heterocyclic radical; for the manufacture of a medicine for the treatment of subjects suffering from HIV (Human Immunodeficiency Virus) infection. It further relates to new compounds being a subgroup of the compounds of formula (I), their preparation and pharmaceutical compositions comprising them.

  这项发明涉及使用公式中的化合物N-氧化物、药用可接受的加合盐和立体化学异构体，其中A为CH、CR4或N；n为0、1、2、3或4；R1和R2分别独立地选自氢、羟基、C1-12烷基、C1-12烷氧基、C1-12烷基羰基、C1-12烷氧羰基、芳基、氨基、单烷基或双烷基氨基、单烷基或双烷基氨基羰基，其中上述每个C1-12烷基基团可能选择性地且各自被取代；或者R1和R2联合形成吡咯烷基、哌啶基、吗啉基、叠氮基或单烷基或双烷基氨基C1-4烷基亚甲基；R3为氢、芳基、C1-6烷基羰基、可选择地取代的C1-6烷基；且每个R4独立地为羟基、卤素、C1-6烷基、C1-6烷氧基、氰基、氨基羰基、硝基、氨基、三卤甲基或三卤甲氧基；L为—X—R5或—X-烷基-R6；其中R5和R6各自独立地为茚基、吲哚基或苯基；每个所述的茚基、吲哚基或苯基可能被取代；X为—NR3—、—NH—NH—、—N=N—、—O—、—S—、—S(O)—或—S(O)2—；芳基为可选择取代的苯基；Het为可选择取代的脂肪族或芳香族杂环基；用于制造用于治疗患有HIV（人类免疫缺陷病毒）感染的受试者的药物。它还涉及新化合物，它们是公式（I）化合物的一个子组，其制备和包含它们的药物组合物。
• [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。
• Synthesis, structure, and dynamic behavior in solution of arylamino-1,3,5-triazines
  作者：P. A. Belyakov、A. V. Shastin、Yu. A. Strelenko

  DOI：10.1007/s11172-006-0135-0

  日期：2005.10

  3,5-triazines were synthesized and studied by dynamic NMR spectroscopy. The free energies of the hindered rotation ΔG≠?are in 59–77 kJ mol− 1 range. Using difference-mode NOE NMR experiments, the structures of the major and minor rotation isomers were proved. The DFT B3LYP/6-31G* calculations were performed. The difference between the calculated rotation barriers and the experimental values obtained

  十个不对称取代的芳基氨基-1,3,5-三嗪合成并通过动态核磁共振光谱研究。受阻旋转的自由能 ΔG≠? 在 59–77 kJ mol− 1 范围内。使用差模 NOE NMR 实验，证明了主要和次要旋转异构体的结构。进行了 DFT B3LYP/6-31G* 计算。计算出的旋转障碍与通过线形分析获得的实验值之间的差异小于 7.6 kJ mol-1。旋转势垒的高度在 18 kJ mol-1 范围内变化，具体取决于三嗪环中的取代基。
• 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.
• PATEL, J. M.;DAVE, M. P.;THAKER, K. A., J. INST. CHEM., INDIA, 1984, 56, N 4, 165-166
  作者：PATEL, J. M.、DAVE, M. P.、THAKER, K. A.

  DOI：——

  日期：——