3,6-bis-(5-trifluoromethyl-2-pyridine)-1,2,4,5-tetrazine | 1208065-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 3,6-bis-(5-trifluoromethyl-2-pyridine)-1,2,4,5-tetrazine
• 英文别名: 3,6-Bis[5-(trifluoromethyl)-2-pyridyl]-1,2,4,5-tetrazine；3,6-bis[5-(trifluoromethyl)pyridin-2-yl]-1,2,4,5-tetrazine
• CAS: 1208065-78-4
• 化学式: C₁₄H₆F₆N₆
• 分子量: 372.232
• InChiKey: REJRSFKNPBHEAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2-氰基-5-三氟甲基吡啶 在 hydrazine hydrate 、 sulfur 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 22.0h， 以7.2%的产率得到3,6-bis-(5-trifluoromethyl-2-pyridine)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Bilability is Defined when One Electron is Used to Switch between Concerted and Stepwise Pathways in Cu(I)-Based Bistable [2/3]Pseudorotaxanes

  摘要：

  Supramolecular switches operate as simple machines by using a stimulus to turn stations off and on, generating thermodynamic differences that define bistability and enable motion. What has not been previously investigated, yet is required to gain further control over molecular movements for complex operations, is an understanding of how the same stimulus can also switch pathways off and on, thus, defining the kinetic property of bilability. To address this challenge, the mechanisms of the forward and return reactions of redox-switchable Cu(I)-based [2/3]pseudorotaxanes have been quantitatively characterized utilizing mechanistic cyclic voltammetry and employing a series of isosteric bis-bidentate ligands. First, the bistability of the switch is retained across the series of ligands: Reduction of the ligand drives the reaction forward where a [2]pseudorotaxane switches into a reduced [3]pseudorotaxane and reoxidation drives the switching cycle back to the beginning. Second, the switch is bilabile with the forward reaction following an association-activated interchange pathway (concerted), whereas the reverse reaction follows a different dissociation-based dethreading pathway (stepwise). The forward reaction is more sensitive to denticity (bidentate tetrazinyl ligand, k(2) = 12 000 M-1 s(-1), versus the monodentate pyrazinyl ligand, k(2) = 1500 M-1 s(-1)) than to electronics (k(2) = 12 000 M-1 s(-1) for methyl and trifluoromethyl substituents). The rate of return with the pyrazinyl ligand is k(1) = 50 s(-1). Consequently, both the mechanism and the thermodynamics of switching are stimuli dependent; they change with the oxidation state of the ligand. These findings have implications for the future design of molecular motors, which can be built from systems displaying allosterically coupled bistability and bilability.

  DOI：

  10.1021/ja908877d

文献信息

• BIO-ORTHOGONAL DRUG ACTIVATION
  申请人：KONINKLIJKE PHILIPS N.V.

  公开号：US20160106859A1

  公开（公告）日：2016-04-21

  The invention relates to a Prodrug activation method, for therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention also relates to a Prodrug kit comprising at least one Prodrug and at least one Activator, wherein the Prodrug comprises a Drug and a first Bio-orthogonal Reactive Group (the Trigger), and wherein the Activator comprises a second Bio-orthogonal Reactive Group. The invention also relates to targeted therapeutics used in the above-mentioned method and kit. The invention particularly pertains to antibody-drug conjugates and to bi- and trispecific antibody derivatives.

  该发明涉及一种用于治疗学的原药激活方法，其中使用了表现出彼此生物正交反应性的非生物活性化学基团。该发明还涉及一种包含至少一种原药和至少一种激活剂的试剂盒，其中原药包含药物和第一个生物正交反应基团（触发器），而激活剂包含第二个生物正交反应基团。该发明还涉及在上述方法和试剂盒中使用的靶向治疗剂。该发明特别适用于抗体药物偶联物和双特异性及三特异性抗体衍生物。
• Bio-orthogonal drug activation
  申请人：TAGWORKS PHARMACEUTICALS B.V.

  公开号：US10004810B2

  公开（公告）日：2018-06-26

  The invention relates to a Prodrug activation method, for therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention also relates to a Prodrug kit comprising at least one Prodrug and at least one Activator, wherein the Prodrug comprises a Drug and a first Bio-orthogonal Reactive Group (the Trigger), and wherein the Activator comprises a second Bio-orthogonal Reactive Group. The invention also relates to targeted therapeutics used in the above-mentioned method and kit. The invention particularly pertains to antibody-drug conjugates and to bi- and trispecific antibody derivatives.

  本发明涉及一种用于治疗的原药活化方法，其中使用了相互之间具有生物正交反应性的非生物活性化学基团。本发明还涉及一种原药试剂盒，包括至少一种原药和至少一种活化剂，其中原药包括药物和第一生物正交反应基团（触发器），活化剂包括第二生物正交反应基团。本发明还涉及上述方法和试剂盒中使用的靶向治疗药物。本发明尤其涉及抗体-药物共轭物以及双特异性和三特异性抗体衍生物。
• PRETARGETING KIT FOR IMAGING OR THERAPY COMPRISING A TRANS-CYCLOOCTENE DIENOPHILE AND A DIENE
  申请人：Tagworks Pharmaceuticals B.V.

  公开号：EP2707035B1

  公开（公告）日：2020-04-01
• US9421274B2
  申请人：——

  公开号：US9421274B2

  公开（公告）日：2016-08-23
• US9913921B2
  申请人：——

  公开号：US9913921B2

  公开（公告）日：2018-03-13