1-Methoxy-1H-[1,2,3]triazolo[4,5-b]pyridine | 291274-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: 1-Methoxy-1H-[1,2,3]triazolo[4,5-b]pyridine
• 英文别名: 1-Methoxytriazolo[4,5-b]pyridine
• CAS: 291274-20-9
• 化学式: C₆H₆N₄O
• 分子量: 150.14
• InChiKey: JZEBBQWPPHJCPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Methoxy-1H-[1,2,3]triazolo[4,5-b]pyridine 在 sodium thiophenolate 作用下， 以 氘代二甲亚砜 、 氘代氯仿 为溶剂， 生成 4-aza-1-hydroxybenzotriazole
  参考文献：
  名称：

  Comparison of the Effects of 5- and 6-HOAt on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers^,

  摘要：

  [GRAPHICS]Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.

  DOI：

  10.1021/ol006013z
• 作为产物：
  描述：

  4-aza-1-hydroxybenzotriazole 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以67%的产率得到1-Methoxy-1H-[1,2,3]triazolo[4,5-b]pyridine
  参考文献：
  名称：

  Comparison of the Effects of 5- and 6-HOAt on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers^,

  摘要：

  [GRAPHICS]Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.

  DOI：

  10.1021/ol006013z

文献信息

• [EN] A METHOD FOR MODIFICATION OF PEPTIDES IMMOBILIZED ON A SOLID SUPPORT BY TRACELESS REDUCTIVELY CLEAVABLE LINKER MOLECULES<br/>[FR] PROCÉDÉ DE MODIFICATION DE PEPTIDES IMMOBILISÉS SUR UN SUPPORT SOLIDE PAR DES MOLÉCULES DE LIAISON POUVANT ÊTRE CLIVÉES PAR RÉDUCTION SANS TRACE
  申请人：BELYNTIC GMBH

  公开号：WO2021023892A1

  公开（公告）日：2021-02-11

  The present invention relates to a method for modifying and purifying peptides comprising an immobilizing step, a modification step and a releasing step. In the immobilizing step, a crude linker-tagged peptide L-P is coupled to a solid support yielding an immobilized linker-tagged peptide S-L-P. Subsequently, the immobilized linker-tagged peptide S-L-P is modified with one or more organic molecules yielding an immobilized linker-tagged peptide S-L-mP. Finally, the modified peptide is released via a reduced intermediate RI. The linker molecule is a compound of formula 1, X-Tb-Va-U-Y-Z (1), which can be coupled to a purification resin via the moiety X and to a peptide via the moiety Y under the release of the leaving group Z. T is an optional spacer moiety and V is an optional electron withdrawing moiety. U is an aryl or 5- or 6-membered heteroaryl moiety bound to at least one electron withdrawing moiety V, W or E. The linker is stable under acidic conditions and releases the peptide upon addition of a reducing agent.

  本发明涉及一种修饰和纯化肽的方法，包括固定步骤、修饰步骤和释放步骤。在固定步骤中，将粗链联标记的肽L-P偶联到固体支持上，得到固定的链联标记的肽S-L-P。随后，用一个或多个有机分子修饰固定的链联标记的肽S-L-P，得到固定的链联标记的肽S-L-mP。最后，通过还原中间体RI释放修饰的肽。链联分子是化合物1的化学式，X-Tb-Va-U-Y-Z（1），可以通过基团X偶联到纯化树脂，通过基团Y偶联到肽，释放离去基团Z。T是可选的间隔基团，V是可选的电子吸引基团。U是芳基或与至少一个电子吸引基团V、W或E结合的芳基或5-或6-成员杂芳基基团。该链联在酸性条件下稳定，并在加入还原剂后释放肽。
• [EN] METHODS FOR THE PREPARATION OF LINKER PAYLOAD CONSTRUCTS<br/>[FR] PROCÉDÉS POUR LA PRÉPARATION DE CONSTRUCTIONS DE CHARGE UTILE DE LIEUR
  申请人：SYNAFFIX BV

  公开号：WO2021260232A1

  公开（公告）日：2021-12-30

  The present invention concerns a method for the preparation of an alkyne-linker-payload construct of structure Q-L-C (O)-NR3-D (1), comprising reacting (i) an alkyne compound of structure Q-L- C(O)-X (2), wherein Q is an alkyne moiety selected from the group consisting of terminal alkyne and (hetero)cycloalkyne; L is a linker, and X is a leaving group selected from halogen, SR1, O-succinimidyl, O-(hetero)aryl(R2)1-5, wherein R1 is selected from C1 - C6 alkyl and (hetero)aryl; and R2 is C1 - C6 alkyl, halogen or NO2; with (ii) a molecule of structure D-NHR3 (3), wherein D is a payload, and R3 is selected from hydrogen, optionally substituted C1 - C24 alkyl, optionally substituted aryl. The activated ester derivatives (2) are highly stable and provide for smooth and high-yielding attachment to a cytotoxic payload. The invention further concerns a method for preparing bioconjugates and alkyne compound of structure Q-L-C (O)-X (2).

  本发明涉及一种制备结构为Q-L-C（O）-NR3-D（1）的炔基-连接剂-药物构造物的方法，包括反应（i）结构为Q-L-C（O）-X（2）的炔基化合物，其中Q是从末端炔基和（杂）环烷基组成的炔基基团；L是连接剂，X是从卤素、SR1、O-琥珀酰亚胺基、O-（杂）芳基（R2）1-5中选择的离去基团，其中R1选择自C1-C6烷基和（杂）芳基；R2是C1-C6烷基、卤素或NO2；与（ii）结构为D-NHR3（3）的分子反应，其中D是药物，R3选择自氢、可选取代C1-C24烷基、可选取代芳基。活化酯衍生物（2）非常稳定，可实现对细胞毒性药物的平稳高产附着。本发明还涉及一种制备生物共轭物和结构为Q-L-C（O）-X（2）的炔基化合物的方法。
• Comparison of the Effects of 5- and 6-HOAt on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers^,
  作者：Louis A. Carpino、Hideko Imazumi、Bruce M. Foxman、Michael J. Vela、Peter Henklein、Ayman El-Faham、Jana Klose、Michael Bienert

  DOI：10.1021/ol006013z

  日期：2000.7.1

  [GRAPHICS]Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.