(E)-2-(4-fluorobenzylidene)hydrazine-1-carboxamide | 120445-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(4-fluorobenzylidene)hydrazine-1-carboxamide
• 英文别名: (E)-2-(p-fluorobenzylidene)hydrazinecarboxamide；4-fluoro-benzaldehyde-semicarbazone；4-Fluor-benzaldehyd-semicarbazon；(2E)-2-(4-Fluorobenzylidene)hydrazinecarboxamide；[(E)-(4-fluorophenyl)methylideneamino]urea
• CAS: 120445-38-7
• 化学式: C₈H₈FN₃O
• 分子量: 181.169
• InChiKey: PLPRLKYWNVWATE-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-fluorobenzylidene)hydrazine-1-carboxamide 在 吡啶 、 sodium acetate 、 溶剂黄146 作用下， 反应 19.0h， 生成 N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-(bromo)benzamide
  参考文献：
  名称：

  Optimization of a 1,3,4-oxadiazole series for inhibition of Ca2+/calmodulin-stimulated activity of adenylyl cyclases 1 and 8 for the treatment of chronic pain

  摘要：

  Adenylyl cyclases type 1 (AC1) and 8 (AC8) are group 1 transmembrane adenylyl cyclases (AC) that are stimulated by Ca2+/calmodulin. Studies have shown that mice depleted of AC1 have attenuated inflammatory pain response, while AC1 /AC8 double-knockout mice display both attenuated pain response and opioid dependence. Thus, AC1 has emerged as a promising new target for treating chronic pain and opioid abuse. We discovered that the 1,3,4-oxadiazole scaffold inhibits Ca2+/calmodulin-stimulated cyclic adenosine 3',5'-monophosphate (cAMP) production in cells stably expressing either AC1 or AC8. We then carried out structure-activity relationship studies, in which we designed and synthesized 65 analogs, to modulate potency and selectivity versus each AC isoform in cells. Furthermore, molecular docking of the analogs into an AC1 homology model suggests the molecules may bind at the ATP binding site. Finally, a prioritized analog was tested in a mouse model of inflammatory pain and exhibited modest analgesic properties. In summary, our data indicate the 1,3,4-oxadiazoles represent a novel scaffold for the cellular inhibition of Ca2+/calmodulin-stimulated AC1- and AC8 CAMP and warrant further exploration as potential lead compounds for the treatment of chronic inflammatory pain. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.036
• 作为产物：
  描述：

  对氟甲苯 在 乙醇 、 乌洛托品 作用下， 生成 (E)-2-(4-fluorobenzylidene)hydrazine-1-carboxamide
  参考文献：
  名称：

  232.芳香族侧链反应的机理，特别涉及取代基的极性效应。第十四部分。醛-氰醇与卤代苯甲醛的反应：卤素取代基的极性作用

  摘要：

  DOI：

  10.1039/jr9490001089

文献信息

• Pyrimidine-thiazolidinone derivatives
  申请人：UNITED ARAB EMIRATES UNIVERSITY

  公开号：US10689374B1

  公开（公告）日：2020-06-23

  Pyrimidine-thiazolidinone derivatives may be used for preventing or treating diseases in humans or animals, and have demonstrated efficacy specifically in treating type-2 diabetes. Methods of synthesizing the pyrimidine-thiazolidinone derivatives, described herein, can provide high yields in a short time and with high purity. The pyrimidine-thiazolidinone derivatives demonstrate improved hypoglycemic activity compared to most anti-diabetic drugs currently available.

  嘧啶噻唑烷酮衍生物可用于预防或治疗人类或动物的疾病，并已证明在治疗2型糖尿病方面具有特效。本文所述的嘧啶噻唑烷酮衍生物合成方法，能在短时间内提供高产率和高纯度。与目前大多数抗糖尿病药物相比，嘧啶噻唑烷酮衍生物显示出更强的降血糖活性。
• A general and stereoselective approach to 14-membered cyclic bis-semicarbazones involving BF₃-catalyzed amidoalkylation of 2-(trimethylsilyloxy)propene
  作者：Anastasia A. Fesenko、Anatoly D. Shutalev

  DOI：10.1039/d2ob00644h

  日期：——

  11-hexaazacyclotetradeca-7,14-diene-3,10-diones, starting from aldehyde semicarbazones has been developed. The key intermediates, 4-(3-oxobut-1-yl)semicarbazones, were prepared by BF3-catalyzed amidoalkylation of 2-(trimethylsilyloxy)propene with 4-[(aryl)(methoxy)methyl]- or 4-[(aryl)(tosyl)methyl]semicarbazones. Treatment of these intermediates with excess of hydrazine gave hydrazones of 4-(3-oxob

  14 元环状双氨基脲、5,12-二芳基-7,14-二甲基-1,2,4,8,9,11-六氮杂环十四烷-7,14-二烯-3 的通用立体选择性五步法,10-二酮，从醛缩氨基脲开始开发。关键中间体 4-(3-氧代丁-1-基)氨基脲是由 BF 3催化的 2-(三甲基甲硅烷氧基)丙烯与 4-[(芳基)(甲氧基)甲基]-或 4-[(芳基）（甲苯磺酰基）甲基]缩脲。用过量的肼处理这些中间体得到4-(3-氧代丁-1-基)氨基脲或4-(3-氧代丁-1-基)氨基脲的腙，它们在TsOH存在下转化为目标大环化合物。这种方法的所有步骤都可以轻松扩展到多克级别。
• Some aryl semicarbazones possessing anticonvulsant activitie
  作者：JR Dimmock、KK Sidhu、SD Tumber、SK Basran、M Chen、JW Quail、J Yang、I Rozas、DF Weaver

  DOI：10.1016/0223-5234(96)88237-7

  日期：——

  A number of aryl semicarbazones displayed anticonvulsant activity in the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens when administered intraperitoneally to mice. When given by the oral route to rats, protection was afforded in the MES but not scPTZ tests. Correlations were noted between the sigma and sigma* values of the aryl substituents, the interplanar angles made by the aryl rings with the adjacent carbimino groups and the shapes of certain semicarbazones determined by X-ray crystallography, and the activities in the rat oral MES screen. Molecular modeling studies revealed a number of statistically significant descriptors which contributed to anticonvulsant activity.
• Conversion of 2-amino-5-R-phenyl-1,3,4-oxadiazoles into 3-R-phenyl-5-alkoxy-1,2,4-triazoles
  作者：V. Ya. Alekseeva、Yu. A. Boitkov、I. V. Viktorovskii、K. A. V'yunov

  DOI：10.1007/bf00471813

  日期：1986.11
• Soni, R. P., Journal fur praktische Chemie (Leipzig 1954), 1981, vol. 323, # 5, p. 853 - 856
  作者：Soni, R. P.

  DOI：——

  日期：——