4-ethynylbenzamidoxime | 957470-94-9

• 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: 4-ethynylbenzamidoxime
• 英文别名: 4-ethynyl-N'-hydroxybenzenecarboximidamide
• CAS: 957470-94-9
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: XSRMCHVYPDYEIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-ethynylbenzamidoxime 在 copper(II) sulfate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 N-cyclohexyl-3-[4–1′-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-(2′-acetyl-3′-deoxy-sn-glyceryl-1H-1,2,3-triazol-4-ylmethoxy)phenyl]-1,2,4-oxadiazol-5-amine
  参考文献：
  名称：

  炔基化 1,2,4-恶二唑/1,2,3-1H-三唑糖缀合物的合成：发现用于肺癌和结核分枝杆菌化疗的新化合物

  摘要：

  共合成43种化合物，包括32种新化合物。在这些化合物中，选择了 17 种化合物并在人类肿瘤细胞系上进行测试：PC-3（前列腺腺癌）、HCT-116（结直肠肿瘤）、NCIH-460（肺癌）、SKMEL-103（黑色素瘤）和 AGP-01（胃肿瘤）。炔基化的 1,2,4-恶二唑2m、3g和3k在培养中表现出针对 NCIH-460 的抗增殖活性。炔基化Ñ -环己基-1,2,4-恶二唑3A-M和二-杂环glucoglycero-1,2,3-三唑ñ -环己基-1,2,4-恶二唑衍生物5A-K和6-11进行了评价对于他们的体外对结核分枝杆菌( Mtb ) H 37 Ra 和H 37 Rv 菌株的功效。通常，通过 1,2,3-三唑键（5a、5e、5j、5k和7）与 1,2,4-恶二唑缀合的甘油糖显示出对Mtb ( H 37 Rv) 的体外抑制活性。最大的分子双三唑10和11被证明对结核病无活性。可能是化合物8

  DOI：

  10.1016/j.ejmech.2021.113472
• 作为产物：
  描述：

  4-乙炔基苯甲腈 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 70.0h， 以93%的产率得到4-ethynylbenzamidoxime
  参考文献：
  名称：

  Synthesis, mechanism of formation, and molecular orbital calculations of arylamidoximes

  摘要：

  A simple and easy synthesis of ten arylamidoximes from arylnitriles and hydroxylamine is described. The formation of the arylamides has been observed to a much lesser extent in the present work. A new mechanism for the formation of arylamidoximes, as well as arylamides, from arylnitriles and hydroxylamine is suggested. Quantum mechanical calculations have been carried out to support this mechanism. The enthalpy of formation in conjunction with atomic charges of the reactants and intermediates helped to understand more about the generation of the products.

  DOI：

  10.1007/s00706-009-0186-7

文献信息

• Identification of New FLT3 Inhibitors That Potently Inhibit AML Cell Lines via an Azo Click-It/Staple-It Approach
  作者：Xiaochu Ma、Jie Zhou、Changhao Wang、Brandon Carter-Cooper、Fan Yang、Elizabeth Larocque、Jonathan Fine、Genichiro Tsuji、Gaurav Chopra、Rena G. Lapidus、Herman O. Sintim

  DOI：10.1021/acsmedchemlett.6b00468

  日期：2017.5.11

  Acute myeloid leukemia (AML) is an aggressive malignancy with only a handful of therapeutic options. About 30% of AML patients harbor mutated FLT3 kinase, and thus, this cancer-driver has become a hotly pursued AML target. Herein we report a new class of FLT3 inhibitors, which potently inhibit the proliferation of acute myeloid leukemia (AML) cells at nanomolar concentrations.
• Synthesis of glycosyl-triazole linked 1,2,4-oxadiazoles
  作者：Janaína V. dos Anjos、Denis Sinou、Sebastiao J. de Melo、Rajendra M. Srivastava

  DOI：10.1016/j.carres.2007.07.011

  日期：2007.11

  The synthesis of four different types of oxadiazoles containing a terminal acetylenic group is described. Reaction of these oxadiazoles with various azidoglycosides via a copper-catalyzed [3+2] cycloaddition ('click chemistry') afforded the corresponding glycosyl-triazole linked 1,2,4-oxadiazoles in good yields. (C) 2007 Elsevier Ltd. All rights reserved.
• Design and synthesis of 3,5-disubstituted boron-containing 1,2,4-oxadiazoles as potential combretastatin A-4 (CA-4) analogs
  作者：Bhaskar C. Das、Xiang-Ying Tang、Patrick Rogler、Todd Evans

  DOI：10.1016/j.tetlet.2012.02.110

  日期：2012.8

  We have designed and synthesized a small library of 3,5-disubstituted-1,2,4-oxadiazole containing combretastatin A-4 (CA-4) analogs. Our objective is to increase the efficacy of the CA-4 as an anti-tubulin and antimitotic agent by substituting the cis-alkene bond with one of its bioisosteres, the 1,2,4-oxadiazole ring. We also modified the substituents attached to both of the phenyl rings (ring A and B in Fig. 1) of CA-4 for the purpose of diversifying our analogs based on SAR. These compounds were synthesized via a coupling reaction between an amidoxime and a carboxylic acid in DMF solvent, with HOBt as a base, and utilizing EDCI as a coupling reagent. Using this protocol, we synthesized a small library of 10 compounds with moderate to good yields. A detailed biological study is currently undergoing in our laboratory to evaluate the activity of these compounds. (C) 2012 Elsevier Ltd. All rights reserved.
• Design and synthesis of 3,5-disubstituted 1,2,4-oxadiazole containing retinoids from a retinoic acid receptor agonist
  作者：Bhaskar C. Das、Xiang-Ying Tang、Swarnava Sanyal、Seetaram Mohapatra、Patrick Rogler、Sabita Nayak、Todd Evans

  DOI：10.1016/j.tetlet.2011.03.011

  日期：2011.5

  We previously synthesized novel retinoid libraries, and after screening for bioactivity found one compound BT10 that functions as a specific agonist for retinoic acid receptors. This lead compound was further derivatized using SAR and LRD to obtain 3,5-disubstituted-1,2,4-oxadiazole-containing retinoids. The new oxadiazole (amide bioisosters)-containing retinoids (compounds 1, 2, 3, 4, 5, and 6) were synthesized in 42-65% yield by reacting with (E)-4-((3-ethy1,2-4,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid and phenyl substituted amidoxime in DMF using CDI as the coupling reagent. The biological activities of the synthesized compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.
• Small Molecule Analogs Of The Protein E4ORF1 In The Treatment And Prevention Of Metabolic Disorders
  申请人：Texas Tech University System

  公开号：US20220071953A1

  公开（公告）日：2022-03-10

  In an embodiment, the present disclosure pertains to compositions and methods for modulating cellular glucose uptake. In general, the methods include associating cells with the compositions of the present disclosure. In another aspect, the present disclosure pertains to compositions and methods to treat or prevent a disorder in a subject. The methods generally include administering the compositions of the present disclosure to the subject.