3-benzyl-[1,2,4]triazolo[4,3-a]pyridine | 59696-86-5

• 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: 3-benzyl-[1,2,4]triazolo[4,3-a]pyridine
• CAS: 59696-86-5
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: JZFRXJXPFNYNLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-肼吡啶 在 copper(l) iodide 、 lithium tert-butoxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 12.5h， 生成 3-benzyl-[1,2,4]triazolo[4,3-a]pyridine
  参考文献：
  名称：

  铜（i）通过直接CH官能化催化三唑并吡啶的苄基化。

  摘要：

  开发了一种通用且有效的铜催化的三唑并吡啶与N-甲苯磺酰azo的苄基化反应。该反应通过交叉偶联形成C（sp2）-C（sp3）键，并且代表一种非常实用的方法，以中等至良好的产率提供3-苄基化的三唑并吡啶。概述了该反应基础的拟议的机理途径。这种催化转化应能在官能化化学中实现广泛的合成应用，从而可以合成新的药学上相关的三唑并吡啶衍生物。

  DOI：

  10.1039/c9ob01433k

文献信息

• Electrochemical synthesis of 1,2,4-triazole-fused heterocycles
  作者：Zenghui Ye、Mingruo Ding、Yanqi Wu、Yong Li、Wenkai Hua、Fengzhi Zhang

  DOI：10.1039/c7gc03739b

  日期：——

  cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free

  在温和的电解条件下已开发出无试剂的分子内脱氢C–N交叉偶联反应。在这种原子经济和一步经济的一锅法中，有价值的1,2,4-三唑并[4,3- a ]吡啶和相关的杂环化合物可以从可商购的脂族或（杂）芳族醛和2-肼基吡啶。各种官能团都与这种无金属和无氧化剂的方案兼容，可以轻松地以克为单位进行操作。这种新方法被应用于最畅销药物Xanax的合成和后期功能化，以在生物学相关的先导分子中产生化学多样性。
• A convenient one-pot synthesis of N-fused 1,2,4-triazoles via oxidative cyclization using chromium (VI) oxide
  作者：Ashish Bhatt、Rajesh K. Singh、Ravi Kant

  DOI：10.1080/00397911.2018.1529795

  日期：2019.1.2

  Abstract A facile one-pot synthesis of N-fused 1,2,4-triazoles from heterocyclic hydrazines and aldehydes is reported. The reaction is efficiently promoted by chromium (VI) oxide to afford the desired products mostly in high yields and in relatively short time. The high yield of the products and short reaction time are notable advantages of the developed protocol. This protocol is effective toward

  摘要 报道了一种从杂环肼和醛中简便地一锅法合成 N-稠合 1,2,4-三唑的方法。该反应通过氧化铬 (VI) 有效促进，以高产率和相对较短的时间提供所需的产物。产品的高产率和反应时间短是所开发协议的显着优势。该协议对具有不同功能的各种基板有效。图形概要
• Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
  作者：Nicolai A. Aksenov、Alexander V. Aksenov、Nikita K. Kirilov、Nikolai A. Arutiunov、Dmitrii A. Aksenov、Vladimir Maslivetc、Zhenze Zhao、Liqin Du、Michael Rubin、Alexander Kornienko

  DOI：10.1039/d0ob01007c

  日期：——

  2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4′,3′-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving phosphorylated nitronates, believed to be the electrophilic intermediates formed from nitroalkanes

  我们发现了硝基烷烃与 2-肼基喹啉、2-肼基吡啶和双 2,4-二肼基嘧啶在多磷酸 (PPA) 中的反应，得到 1,2,4-三唑并[4,3- a ]喹啉, 1,2,4 -三唑并[4,3- a ]吡啶和双[1,2,4]三唑并[4,3- a :4′,3′- c]嘧啶，分别。该反应扩大了涉及磷酸化硝酸盐的杂环环化的范围，被认为是由 PPA 中的硝基烷形成的亲电子中间体。几种合成的三唑类化合物通过诱导神经母细胞瘤癌细胞分化而显示出有希望的抗癌活性。由于迫切需要用于神经母细胞瘤治疗的新型分化剂，这一发现值得进一步评估这类化合物对神经母细胞瘤的治疗作用。
• [EN] TRIAZOLO-PYRIDINES AS ANTI-INFLAMMATORY COMPOUNDS<br/>[FR] TRIAZOLO-PYRIDINES UTILISEES COMME COMPOSES ANTI-INFLAMMATOIRES
  申请人：PFIZER PROD INC

  公开号：WO2004072072A1

  公开（公告）日：2004-08-26

  The present invention relates to novel triazolo-pyridines of the formula (I) wherein X is >CH2, >NH, sulfur, >S=O, >S02 or oxygen; wherein said >CH2 and >NH may optionally be substituted with a suitable substituent; R1 is selected from the group consisting of hydrogen, (C1-C6)alkyl and other suitable substituents; R2 is selected from the group consisting of hydrogen, (Cl-C6)alkyl and other suitable 10 substituents; s is an integer from 0-4; R3 is R4, R5-(NR6)-, R5-S-, R5-(S=O)-, R5-(S02)-, R5-S02-NR6-, R5-(NR6)-S02-, R5-O-,R5-(C=O)-, R5-(NR6)-(C=O)-, R5-(C=O)-NR6-, R5-O-(C=O)-, R5-(C=O)-O-, R5-CR7=CR8- or R5-C=-C-; such that the molecular weight of R3 is less than 500 AMU, preferably less than 250 15 AMU; R4, R5 and R6 are each selected from the group consisting of hydrogen, (C1-C6)alkyl and other suitable substituents; or a pharmaceutically acceptable salt thereof; to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

  本发明涉及具有以下式(I)的新型三唑吡啶，其中X为>CH2，>NH，硫，>S=O，>SO2或氧；其中所述的>CH2和>NH可以选择性地被适当的取代基取代；R1选自氢，(C1-C6)烷基和其他适当的取代基组成的群；R2选自氢，(Cl-C6)烷基和其他适当的取代基组成的群；s为0-4的整数；R3为R4，R5-(NR6)-，R5-S-，R5-(S=O)-，R5-(SO2)-，R5-SO2-NR6-，R5-(NR6)-SO2-，R5-O-，R5-(C=O)-，R5-(NR6)-(C=O)-，R5-(C=O)-NR6-，R5-O-(C=O)-，R5-(C=O)-O-，R5-CR7=CR8-或R5-C=-C-；使得R3的分子量小于500 AMU，最好小于250 AMU；R4，R5和R6分别选自氢，(C1-C6)烷基和其他适当的取代基组成的群；或其药学上可接受的盐；用于它们的制备的中间体，含有它们的药物组合物以及它们的药用。本发明的化合物是MAP激酶的有效抑制剂。它们在治疗炎症、骨关节炎、类风湿关节炎、癌症、中风或心脏病发作中的再灌注或缺血、自身免疫疾病和其他疾病中具有用途。
• Novel triazolo-pyridines as anti-inflammatory compounds
  申请人：Braganza Frederick John

  公开号：US20050075365A1

  公开（公告）日：2005-04-07

  The present invention relates to novel triazolo-pyridines of the formula wherein X is >CH 2 , >NH, sulfur, >S═O, >SO 2 or oxygen; wherein said >CH 2 and >NH may optionally be substituted with a suitable substituent; R 1 is selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl and other suitable substituents; R 2 is selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl and other suitable substituents; s is an integer from 0-4; R 3 is R 4 , R 5 —(NR 6 )—, R 5 —S—, R 5 —(S═O)—, R 5 —(SO 2 )—, R 5 —SO 2 —NR 6 —, R 5 —(NR 6 )—SO 2 —, R 5 —O—, R 5 —(C═O)—, R 5 —(NR 6 )—(C═O)—, R 5 —(C═O)—NR 6 —, R 5 —O—(C═O)—, R 5 —(C═O)—O—, R 5 —CR 7 ═CR 8 — or R 5 —C≡C_; such that the molecular weight of R 3 is less than 500 AMU, preferably less than 250 AMU; R 4 , R 5 and R 6 are each selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl and other suitable substituents; or a pharmaceutically acceptable salt thereof; to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

  本发明涉及一种新型的三唑吡啶，其化学式为其中X为> CH2，> NH，硫，> S = O，> SO2或氧，其中所述的> CH2和> NH可以选择性地用适当的取代基进行取代；R1选自氢，（C1-C6）烷基和其他适当的取代基组成的群；R2选自氢，（C1-C6）烷基和其他适当的取代基组成的群；s为0-4的整数；R3为R4，R5-（NR6）-，R5-S-，R5-（S = O）-，R5-（SO2）-，R5-SO2-NR6-，R5-（NR6）-SO2-，R5-O-，R5-（C = O）-，R5-（NR6）-（C = O）-，R5-（C = O）-NR6-，R5-O-（C = O）-，R5-（C = O）-O-，R5-CR7 = CR8-或R5-C≡C_；使得R3的分子量小于500 AMU，最好小于250 AMU；R4，R5和R6分别选自氢，（C1-C6）烷基和其他适当的取代基；或其药学上可接受的盐；以及制备它们的中间体，含有它们的药物组合物和它们的医药用途。本发明的化合物是MAP激酶的有效抑制剂。它们用于治疗炎症，骨关节炎，类风湿性关节炎，癌症，脑卒中或心脏病的再灌注或缺血，自身免疫性疾病和其他疾病。