2-苯基-4-吡啶甲酰肼 | 58481-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-苯基-4-吡啶甲酰肼
• 英文名称: 2-phenylisonicotinohydrazide
• 英文别名: 2-phenyl-isonicotinic acid hydrazide；2-Phenyl-isonicotinsaeure-hydrazid；2-Phenylpyridine-4-carbohydrazide
• CAS: 58481-06-4
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: RPXUGIXOYDOMAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-苯基-4-吡啶甲酰肼 在 碘 、 potassium carbonate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 2-(4-methoxyphenyl)-5-(2-phenylpyridin-4-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Discovery of PIM-1 kinase inhibitors based on the 2,5-disubstituted 1,3,4-oxadiazole scaffold against prostate cancer: Design, synthesis, in vitro and in vivo cytotoxicity investigation

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115220
• 作为产物：
  描述：

  2-苯基-吡啶-4-甲酸 在 hydrazine hydrate 、 硫酸 作用下， 以 乙醇 为溶剂， 生成 2-苯基-4-吡啶甲酰肼
  参考文献：
  名称：

  Discovery of PIM-1 kinase inhibitors based on the 2,5-disubstituted 1,3,4-oxadiazole scaffold against prostate cancer: Design, synthesis, in vitro and in vivo cytotoxicity investigation

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115220

文献信息

• Chemotherapie der experimentellen Tuberkulose III. Derivate des 2-Methyl-isonicotinsäurehydrazids
  作者：O. Isler、H. Gutmann、O. Straub、B. Fust、E. Böhni、A. Studer

  DOI：10.1002/hlca.19550380425

  日期：——

  Some fifty-two derivatives of 2-methylisonicotinic acid hydrazide were synthesized and tested for their antitubercular action. The derivatives were prepared by reaction of 2-methylisonicotinic acid hydrazide with aldehydes, ketones, and carboxylic acid chlorides, by condensation of 2-methylisonicotinic acid chloride with dialkylated hydrazines, and by hydrogenation of 2-methylisonicotinyl hydrazones

  合成了约52个2-甲基异烟酸酰肼衍生物，并测试了它们的抗结核作用。通过2-甲基异烟酰胺酰肼与醛，酮和羧酸氯化物的反应，通过2-甲基异烟酰胺酰氯与二烷基化肼的缩合，以及2-甲基异烟碱酰肼的氢化来制备衍生物。
• Synthesis, Characterization, and Biological Activity of Transition Metal Complexes of Oxadiazole
  作者：D Harikishore Kumar Reddy、Y Harinath、Y Suneetha、K Seshaiah、A V.R. Reddy

  DOI：10.1080/15533174.2011.555862

  日期：2011.4.11

  and its metal complexes have been synthesized and characterized. The ligand potassium 2-(2-phenylisonicotinoyl)hydrazinecarbodithioate [K+(H2L)−] (1) on reaction with transition metals in EtOH-H2O medium undergoes cyclization and converted to 5-(2-phenyl-4-pyridyl)-1,3,4-oxadiazole-2-thione (ppot), which yielded a series of mononuclear transition metal complexes. Four transition metal complexes of ligand

  一种新的恶二唑及其金属配合物已经合成并表征。在EtOH-H 2 O介质中与过渡金属反应的配体2-（2-苯基异烟酰酰基）肼碳二硫代钾盐[K +（H 2 L）- ]（1）环化并转化为5-（2-苯基-4-吡啶基）-1,3,4-恶二唑-2-硫酮（ppot），可产生一系列单核过渡金属配合物。根据元素分析，IR，1 H NMR，UV-vis光谱和热重分析-差热分析（​​TG-DTA），制备并表征了四种配体的过渡金属配合物。根据获得的数据，配合物的结构具有通式[M（ppot）2 Cl 2（H2 O）2 ]，其中M Cu（II），Co（II），Ni（II），Zn（II）。这些配合物的热行为表明，该配合物在第一步中失去了配位的水分子，随后在随后的步骤中分解了配体分子。该配体及其过渡金属配合物进行了真菌和细菌的体外筛选。获得的数据表明，配体本身表现出中等的生物学活性，而金属络合物对细菌和真菌均表现出更高的抑制作用。
• Process for producing 1,2,4-triazole compound and intermediate therefor
  申请人：Nakamura Hiroshi

  公开号：US20060189811A1

  公开（公告）日：2006-08-24

  Provided is a process for producing 1,2,4-triazole compound (5), or a salt or hydrate thereof which comprises reacting compound (1) with Rc-X (2) to give compound (3), reacting compound (3) with a nitrilization agent to give compound (4), and then removing the group Rc, as shown by the reaction scheme: (Wherein Ra, Rb and Rd represent a group, Rc represents a group which can be removed by an acid) A 1,2,4-triazole compound (5) having an optionally substituted 2-cyanopyridin-4-yl group at 3-position and an optionally substituted aromatic group at 5-position which inhibits a xanthine oxidase and is useful for treatment of gout and hyperuricemia can be obtained from compound (1) in a high yield without requiring isolation of reaction products in the course of reactions.

  提供一种生产1,2,4-三唑化合物(5)或其盐或水合物的方法，该方法包括将化合物(1)与Rc-X(2)反应得到化合物(3)，将化合物(3)与腈化试剂反应得到化合物(4)，然后去除Rc基团，如下反应方程所示:(其中，Ra、Rb和Rd代表一个基团，Rc代表可以通过酸去除的基团)从化合物(1)中可以高产得到一种1,2,4-三唑化合物(5)，其在3位具有可选取代的2-氰基吡啶-4-基基团，在5位具有可选取代的芳香基团，可以抑制黄嘌呤氧化酶，并且对于痛风和高尿酸血症的治疗有用，而不需要在反应过程中分离反应产物。
• PROCESS FOR PRODUCING 1,2,4-TRIAZOLE COMPOUND AND INTERMEDIATE THEREFOR
  申请人：Fujiyakuhin Co., Ltd.

  公开号：EP1650204A1

  公开（公告）日：2006-04-26

  Provided is a process for producing 1,2,4-triazole compound (5), or a salt or hydrate thereof which comprises reacting compound (1) with Rc-X (2) to give compound (3), reacting compound (3) with a nitrilization agent to give compound (4), and then removing the group Rc, as shown by the reaction scheme: (Wherein Ra, Rb and Rd represent a group, Rc represents a group which can be removed by an acid) A 1,2,4-triazole compound (5) having an optionally substituted 2-cyanopyridin-4-yl group at 3-position and an optionally substituted aromatic group at 5-position which inhibits a xanthine oxidase and is useful for treatment of gout and hyperuricemia can be obtained from compound (1) in a high yield without requiring isolation of reaction products in the course of reactions.

  本发明提供了一种生产 1，2，4-三唑化合物（5）或其盐或水合物的工艺，如反应方案所示，该工艺包括将化合物（1）与 Rc-X (2) 反应得到化合物（3），将化合物（3）与硝化剂反应得到化合物（4），然后除去基团 Rc： (其中 Ra、Rb 和 Rd 代表基团，Rc 代表可被酸去除的基团） 一种 1,2,4-三唑化合物(5)，在 3-位上有一个任选取代的 2-氰基吡啶-4-基团，在 5-位上有一个任选取代的芳香基团，可抑制黄嘌呤氧化酶，可用于治疗痛风和高尿酸血症，可以从化合物(1)高产率地得到，而不需要在反应过程中分离反应产物。
• Discovery of 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole, FYX-051-a xanthine oxidoreductase inhibitor for the treatment of hyperuricemia
  作者：Takahiro Sato、Naoki Ashizawa、Koji Matsumoto、Takashi Iwanaga、Hiroshi Nakamura、Tsutomu Inoue、Osamu Nagata

  DOI：10.1016/j.bmcl.2009.08.091

  日期：2009.11

  Our previous study identified 2-[2-(2-methoxy-ethoxy)-ethoxy]-5-[5-(2-methyl-4-pyridyl)-1H-[1,2,4]-triazol-3-yl]-benzonitrile (2) as a safe and potent xanthine oxidoreductase (XOR) inhibitor for the treatment of hyperuricemia. Here, we synthesized a series of 3,5-dipyridyl-1,2,4-triazole derivatives and, in particular, examined their in vivo activity in lowering the serum uric acid levels in rats. As a result, we identified 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole (FYX-051, compound 39) to be one of the most potent XOR inhibitors; it exhibited an extremely potent in vivo activity, weak CYP3A4-inhibitory activity and a better pharmacokinetic pro. le than compound 2. Compound 39 is currently being evaluated in a phase 2 clinical trial. (C) 2009 Elsevier Ltd. All rights reserved.