2-cyano-N'-((4-oxo-4H-chromen-3-yl)methylene)acetohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-cyano-N'-((4-oxo-4H-chromen-3-yl)methylene)acetohydrazide
• 英文别名: 2-cyano-N-[(4-oxochromen-3-yl)methylideneamino]acetamide
• 化学式: C₁₃H₉N₃O₃
• 分子量: 255.233
• InChiKey: LFNUULBHKBKRLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-cyano-N'-((4-oxo-4H-chromen-3-yl)methylene)acetohydrazide 在 三乙胺 、 三氯氧磷 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 以44%的产率得到3-{[(4,6-dioxo-2-hydroxy-2-oxido-1,3,2-diazaphosphinan-1-yl)imino]methyl}-4H-chromen-4-one
  参考文献：
  名称：

  2-氰基[(4-oxo-4H-chromen-3-yl)methylidene] acetohydrazide 与磷试剂的反应：一些新型 1,2-氮杂磷、1,2,3-二氮杂磷和抗癌活性的合成和评价带有色酮环的 1,3,2-二氮杂膦

  摘要：

  摘要 通过处理多功能 2-氰基[(4)，合成了一系列带有色酮环的 1,2-氮杂磷、1,2,3-二氮杂磷、1,3,2-二氮磷和二烷基吡唑并嘧啶膦酸酯。 -oxo-4H-chromen-3-yl)methylidene]acetohydrazide (2)、一些磷试剂如膦酸及其酯、硫化磷以及干燥二恶烷中的卤化磷。评估了分离产物的抗癌活性和血管内皮生长因子 (VEGF) 抑制的表达。在分离的产物中，化合物3和10对乳腺癌细胞表现出比参比药物更高的作用，并且对VEGF的表达有抑制作用。图形概要

  DOI：

  10.1080/00397911.2017.1332224
• 作为产物：
  描述：

  氰乙酰肼 、 色酮-3-甲醛 以 乙醇 为溶剂， 反应 2.0h， 以85%的产率得到2-cyano-N'-((4-oxo-4H-chromen-3-yl)methylene)acetohydrazide
  参考文献：
  名称：

  三齿ONO ligand配体的新的二元和三元Cu（II），Ni（II）和Co（II）配合物的合成，光谱，磁性，DFT计算，抗菌研究和苯恶嗪酮合酶仿生催化活性

  摘要：

  合成了2-氰基-N'-（（4-氧代-4H-铬-3-基）亚甲基）乙酰肼的新型单核铜（II），镍（II）和钴（II）配合物。通过物理化学和光谱技术对制备的配合物进行结构鉴定，包括元素分析，红外，电子，质量和电子自旋共振光谱，热分析，电导率和磁化率测量，粉末X射线衍射和透射电子显微镜。分离的二元络合物是中性单核络合物（具有1：1和1：2； M：L化学计量比）和三元络合物（具有1：1：1； M：L：L'化学计量比）。分析和光谱技术说明了ligand配体与γ-吡喃酮氧的单阴离子三齿行为，烯醇氧和甲亚胺氮的配位位点。金属络合物显示方形平面，四面体和八面体几何形状。对螯合剂及其铜（II）螯合物进行了密度泛函理论计算。研究和讨论了二元铜（II）配合物的苯恶嗪酮合酶活性。评估了ligand配体及其配合物对某些革兰氏阳性菌，革兰氏阴性菌，酵母菌和真菌的抗菌活性。

  DOI：

  10.1080/24701556.2020.1770794

文献信息

• Novel Chromeno[2,3-b]pyridines from Basic Rearrangement of 4-Oxo-chromene-3-carbonitrile
  作者：Magdy A. Ibrahim

  DOI：10.1080/00397910902788141

  日期：2009.9.8

  Abstract A new series of 2,3-disubstituted-5-oxochromeno[2,3-b]pyridine derivatives has been obtained throughout a 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed reaction of 4-oxo-4H-chromene-3-carbonitrile with various active methyl and methylene compounds. The Friedländer reaction of 2-amino-4-oxo-4H-chromene-3-carboxaldehyde with the same active methyl and methylene compounds led to the identical

  摘要 通过 1,8-二氮杂双环[5.4.0]十一碳-7-烯 (DBU) 催化反应，获得了一系列新的 2,3-二取代-5-氧代色基[2,3-b]吡啶衍生物。 4-oxo-4H-chromene-3-carbonitrile 与各种活性甲基和亚甲基化合物。2-amino-4-oxo-4H-chromene-3-carboxaldehyde 与相同的活性甲基和亚甲基化合物的 Friedländer 反应产生相同的产物，表明在反应过程中发生了碱性催化的环重排。
• Novel electrospun fibers as carriers for delivering a biocompatible Sm(<scp>iii</scp>) nanodrug for cancer therapy: fabrication, characterization, cytotoxicity and toxicity
  作者：R. Fouad、Amira A. M. Ali

  DOI：10.1039/d2ra06052c

  日期：——

  The current study represents the successful fabrication and characterization of a Sm(iii) nano complex based on 2-cyano-N′-((4-oxo-4H-chromen-3-yl)methylene)acetohydrazide (CCMA).

  本研究成功制备并表征了基于 2-氰基-N′-((4-氧代-4H-苯并吡喃-3-基)亚甲基)乙酰肼（CCMA）的 Sm(iii) 纳米配合物。
• Dual function of new Nd(III) and Gd(III) complexes for cytotoxic and optoelectronic fields: Synthesis, characterization, DFT calculations, and PVA composite films
  作者：Amira A. M. Ali、Akila A. Saleh、Hend A. M. Ali、Asmaa I. Nabeel、Rania Fouad

  DOI：10.1002/aoc.7192

  日期：2023.9

  New two lanthanide complexes of Neodymium (III) and Gadolinium (III) ions were prepared based on 2-Cyano-N′-([4-oxo-4H-chromen-3-yl]methylene) acetohydrazide as a chelating agent. The prepared Nd(III) and Gd(III) complexes were characterized via elemental analysis, molecular conductance, IR, and TGA. The obtained results showed the chelating agent behaves as tridentate via oxygen of γ pyrone and carbonyl

  以2-氰基-N'-([4-氧代-4H-苯并-3-基]亚甲基)乙酰肼为螯合剂，制备了两种新的钕(III)和钆(III)离子配合物。通过元素分析、分子电导、IR 和 TGA 对制备的 Nd(III) 和 Gd(III) 配合物进行了表征。结果表明，该螯合剂通过γ吡喃酮和羰基的氧以及偶氮甲碱基的氮形成三齿螯合剂。研究了分离的复合物针对艾利希腹水癌细胞系（EAC）的抗肿瘤活性。抗肿瘤活性结果表明，Gd(III)配合物的活性高于Nd(III)配合物，相对于顺式的活性中等铂和5-呋喃西林。此外，通过高斯程序对制备的 Nd(III) 和 Gd(III) 配合物进行了 DFT 计算。计算了理论参数。能隙值证实了 Gd(III) 络合物比其他 Nd(III) 络合物具有更高的活性。此外，采用流延技术制备了 Nd(III) 和 Gd(III) 配合物的复合薄膜。分析了这些聚合物复合材料的电学和光学吸收性能。
• Activity of some 3-formylchromone derivatives on the induction of chloroplast-free mutants in Euglena gracilis
  作者：Pavlı́na Foltı́nová、Margita Lácová、Dušan Loos

  DOI：10.1016/s0014-827x(99)00114-7

  日期：2000.1

  The hereditary bleaching test on Euglena gracilis was used for detecting extranuclear mutations. The highest bleaching activity (induction of the chloroplast-free mutants) was shown by the 6-R-3-formylchromones. On the other hand, bleaching-inactive 6-R-3-formylchromone acylhydrazones (derived from gallic and salicylic acids), added at sufficient concentrations in the case of chloroplast mutagenesis in E. gracilis, act as a potent antimutagen. This effect appeared to be a unique feature of chromone derivatives, but was dependent on the type of mutagen. These substances were very effective against the bleaching activity of acridine orange, and were less effective against N-methyl-N'-nitro-N-nitrosoguanidine. The genotoxic effects of these mutagens was reduced, especially during the first stages of induction of this specific cytoplasmic mutation. The experimental study of mutagenicity and antimutagenicty of 3-formylchromone hydrazones was reinforced by data obtained by the semi-empirical AM1 method and lipophilicity values. (C) 2000 Elsevier Science S.A. All rights reserved.
• Synthesis, antimicrobial activity and bleaching effect of some reaction products of 4-oxo-4H-benzopyran-3-carboxaldehydes with aminobenzothiazoles and hydrazides
  作者：Hafez M. El-Shaaer、Pavlína Foltínová、Margita Lácová、Jarmila Chovancová、Henrieta Stankovičová

  DOI：10.1016/s0014-827x(98)00015-9

  日期：1998.3

  The synthesis of the biologically active novel systems derived from reaction of 3-formylchromones with three types of amino derivatives, 6-R-2-2-aminobenzothiazoles, 6-amino-2-R-3-thiobenzothiazoles and hydrazide derivatives (derived from cyanoacetic, isonicotine, salicylic and gallic acids) was carried out. The structures of the prepared compounds have been proved by elemental analysis, H-1 NMR and IR spectra. Antimicrobial activity was studied against the following microorganisms-bacteria G(+) (Staphylococcus aureus 29/58, Bacillus subtilis 18/66), G(-) (Escherichia coli 326/71, Pseudomonas aeruginosa); yeasts: Candida albicans, Saccharomyces cerevisiae; moulds: Microsporum gypseum, Aspergillus niger, Scopulariopsis brevicaulis; and against typical and atypical mycobacteria: Mycobacterium tuberculosis (H37Rv), Mycobacterium kansasii (PFG8), Mycobacterium avium (My 80/72), Mycobacterium fortuitum (1021). The hereditary bleaching effect on the plastid system of Euglena gracilis, a unique phenomenon of the biological activity of chromone derivatives, is reported. The bleaching test on E. gracilis is used for detecting extranuclear mutations. (C) 1998 Elsevier Science S.A. All rights reserved.