2-Amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine | 107412-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-Amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine
• 英文别名: 4-Amino-6-anilino-2-pyridyl-(2)-1,3,5-triazin；N-phenyl-6-pyridin-2-yl-[1,3,5]triazine-2,4-diamine；2-N-phenyl-6-pyridin-2-yl-1,3,5-triazine-2,4-diamine
• CAS: 107412-68-0
• 化学式: C₁₄H₁₂N₆
• 分子量: 264.289
• InChiKey: SNJKHBIYYOBZOB-UHFFFAOYSA-N

物化性质

• 熔点：
  232-233 °C(Solv: ethanol (64-17-5))
• 沸点：
  553.3±42.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 2-Amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine 以 甲醇 为溶剂， 以84%的产率得到[Re(CO)3(2-amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine)Cl]
  参考文献：
  名称：

  DNA Binding and Cytotoxicity of Ruthenium(II) and Rhenium(I) Complexes of 2-Amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine

  摘要：

  [Ru((t)Bu(2)bpy)(2)(2-appt)](PF6)(2) [1 center dot(PF6)(2), (t)Bu(2)bpy = 4,4'-di-tert-butyl-2,2'-bipyridine, 2-appt = 2-amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine] and [Re(CO)(3)(2-appt)Cl] (2) were prepared and characterized by X-ray crystal analysis. The binding of 1 center dot(PF6)(2) and 2 to calf thymus DNA (ct DNA) led to increases in the DNA melting temperature (Delta T-m = +12 degrees C), modest hypochromism (29% and 5% of the absorption bands at lambda(max) = 450 and 376 nm, respectively), and insignificant shifts in the absorption maxima. The binding constants of 1 center dot(PF6)(2) and 2 with ct DNA, as determined by absorption titration, are (8.9 +/- 0.5) x 10(4) and (3.6 +/- 0.1) x 10(4) dm(3) mol(-1), respectively. UV-vis absorption titration, DNA melting studies, and competition dialysis using synthetic oligonucleotides [poly(dA-dT)(2) and poly(dG-dC)(2)] revealed that 1 center dot(PF6)(2) and 2 exhibit a binding preference for AT sequences. A modeling study on the interaction between 1 or 2 and B-DNA revealed that the minor groove is the most favored binding site and an extensive hydrogen-bonding network is formed. As determined by MTT assays, 1 center dot(PF6)(2) and 2 exhibited moderate cytotoxicities toward several human cancer cell lines (KB-3-1, HepG2, and HeLa), as well as a multi-drug-resistant cancer cell line (KB-V-1). According to confocal microscopic and flow cytometric studies, 1 center dot(PF6)(2) and 2 induced apoptosis (50-60%) in cancer cells with <5% necrosis detected.

  DOI：

  10.1021/ic061518s
• 作为产物：
  描述：

  2-吡啶甲酸乙酯 、 1-苯基双胍 盐酸盐 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以69%的产率得到2-Amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine
  参考文献：
  名称：

  Synthesis and properties of sym-triazine derivatives. 7. Synthesis of pyridyl-substituted 2-amino- and 2,4-diamino-sym-triazines

  摘要：

  DOI：

  10.1007/bf00755698

文献信息

• [EN] HERBICIDAL AZINES<br/>[FR] AZINES HERBICIDES
  申请人：BASF SE

  公开号：WO2015007711A1

  公开（公告）日：2015-01-22

  The present invention relates to diaminotriazine compounds of the formula (I) and to their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation. Formula (I), wherein A is 5- or 6-membered monocyclic heteroaryl, which comprises 1, 2 or 3 heteroatoms as ring members, which are selected from O, S and N, where heteroaryl is substituted by 1, 2, 3, 4, or 4 substituents RA, R1, R5 are inter alia H, OH, S(O)2NH2, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C1-C6-alkoxy, (C1-C6-alkoxy)-C1-C6-alkyl, (C1-C6-alkyl)-carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)sulfonyl, (C1-C6- alkylamino)carbonyl, di(C1-C6-alkyl)aminocarbonyl, (C1-C6-alkylamino)sulfonyl, di(C1-C6-alkyl)aminosulfonyl and (C1-C6-alkoxy)sulfonyl, etc. R2 is H, halogen, OH, CN, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, (C1-C6-alkoxy)- C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkoxy or (C3-C6- cycloalkyl)-C1-C4-alkoxy, where the aliphatic and cycloaliphatic parts of the 9 aforementioned radicals are unsubstituted, partly or completely halogenated; R3 is selected from the group consisting of H, halogen, CN, C1-C6-alkyl, C1-C6- haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; R4 is selected from the group consisting of H, halogen, CN, C1-C6-alkyl, C2-C6- alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C3-C6- cycloalkenyl and C1-C6-alkoxy-C1-C6-alkyl, where the aliphatic and cycloaliphatic parts of the 7 aforementioned radicals are unsubstituted, partly or completely halogenated; or R3 and R4 together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl and three- to six-membered heterocyclyl, including their agriculturally acceptable salts.

  本发明涉及公式（I）的二氨基三嗪化合物及其作为除草剂的用途。本发明还涉及用于作物保护的农药组合物以及控制不良植被的方法。 公式（I）中，A是5-或6-成员的单环杂芳基，其中包括1、2或3个杂原子作为环成员，所述杂原子选自O、S和N，其中所述杂芳基被1、2、3、4或4个取代基RA、R1、R5等取代，其中RA、R1、R5等取代基包括H、OH、S（O）2NH2、CN、C1-C6烷基、C2-C6烯基、C2-C6炔基、（C3-C6环烷基）-C1-C4烷基、C1-C6烷氧基、（C1-C6烷氧基）-C1-C6烷基、（C1-C6烷基）-羰基、（C1-C6烷氧基）羰基、（C1-C6烷基）磺酰基、（C1-C6烷基氨基）羰基、二（C1-C6烷基）氨基羰基、（C1-C6烷基氨基）磺酰基、二（C1-C6烷基）氨基磺酰基和（C1-C6烷氧基）磺酰基等。 R2是H、卤素、OH、CN、C1-C6烷基、C2-C6烯基、C3-C6炔基、（C1-C6烷氧基）-C1-C6烷基、C3-C6环烷基、C3-C6环烯基、（C3-C6环烷基）-C1-C4烷基、C1-C6烷氧基、C2-C6烯氧基、C2-C6炔氧基、C3-C6环烷氧基或（C3-C6环烷基）-C1-C4烷氧基，其中上述基中的脂肪族和环脂族部分未取代、部分或完全卤代；R3选择自H、卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基和C1-C6卤代烷氧基的群；R4选择自H、卤素、CN、C1-C6烷基、C2-C6烯基、C3-C6炔基、C3-C6环烷基、（C3-C6环烷基）-C1-C4烷基、C3-C6环烯基和C1-C6烷氧基-C1-C6烷基的群，其中上述基中的脂肪族和环脂族部分未取代、部分或完全卤代；或R3和R4与它们连接的碳原子一起形成从羰基、C2-C6烯基、C3-C6环烷基、C3-C6环烯基和三到六元杂环基中选择的一个基团，包括其在农业上可接受的盐。
• Herbicidal Azines
  申请人：BASF SE

  公开号：US20160159770A1

  公开（公告）日：2016-06-09

  The present invention relates to diaminotriazine compounds of the formula (I) wherein A and R 1 -R 5 are as defined herein, and their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation.

  本发明涉及公式（I）中A和R1-R5如定义的二氨基三嗪化合物，以及它们作为除草剂的用途。本发明还涉及用于农作物保护的农药组合物，以及控制不良杂草的方法。
• Herbicidal azines
  申请人：BASF SE

  公开号：US10479777B2

  公开（公告）日：2019-11-19

  The present invention relates to diaminotriazine compounds of the formula (I) wherein A and R1-R5 are as defined herein, and their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation.

  本发明涉及式 (I) 的二氨基三嗪化合物 其中 A 和 R1-R5 如本文所定义，以及它们作为除草剂的用途。本发明还涉及用于作物保护的农用化学品组合物和控制不需要的植被的方法。
• Structure of a C,N,N-cyclometallated palladium(<scp>II</scp>) complex of 2-amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine, and α-diimine ligand with donor–acceptor–donor hydrogen-bonding capability
  作者：Chin-Wing Chan、D. Michael P. Mingos、Andrew J. P. White、David J. Williams

  DOI：10.1039/dt9950002469

  日期：——

  A new class of (2,4-diamino-1,3,5-triazinyl)pyridine ligand has been made and its cyclopalladation reaction with palladium(ii) studied; the crystal structure of the C,N,N-cyclometallated complex reveals a rigid planar structure with a donor-acceptor-donor hydrogen-bonding function on its surface.
• XIMIYA GETEROTSIKL. SOED.,(1988) N 5, 674-680
  作者：

  DOI：——

  日期：——