Novel Ag(I)‐based 1,2,4‐Oxadiazole Complexes: Synthesis, X‐Ray Crystal Structure, and Biological Evaluation as Anticancer Candidates
Mohammed Salah AyoupRabia E. AlashhabSaied M. SolimanHamida Abdel‐HamidDavid B. CordesAidan P. McKayDoaa A. GhareebAliaa A. MasoudAsmaa E. KassabMohamed N. Abd Al Moaty
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ABSTRACT The 3,5‐diaryl‐1,2,4‐oxadiazole scaffolds 2 and 3 were synthesized and used as ligands to obtain three novel Ag(I) complexes 4–6 . The structure of the Ag(I) complexes 4–6 has been confirmed by single crystal X‐ray diffraction. Complex 4 has the dinuclear formula [Ag(2)(NO 3 )] 2 . 5 and 6 are monomeric complexes having the formula [Ag(3) 2 (NO 3 )] and [Ag(3) 2 ]ClO 4 , respectively. In vitro, trypsin, ALDH2, and iNOS inhibition activities were assessed for the free ligands and their Ag(I) complexes. Interestingly, Ag(I) complexes 4–6 revealed more prominent trypsin inhibitory activity than the ligands 2 and 3 . The oxadiazole derivative 3 and its Ag(I) complex ( 6 ) showed significant ALDH2 inhibition (45% and 55%, respectively). Complex 6 (IC 50 = 35.61 μM) surpassed its 1,2,4‐oxadiazole ligand 3 (IC 50 = 88 μM) and evidenced the most prominent ALDH2 inhibitory activity. The oxadiazole derivative 3 and its corresponding Ag(I) complexes 5 and 6 showed significant iNOS inhibition (77.77%, 84.12%, and 84.15%, respectively). With IC 50 values of 18.13, 18.15, and 13.96 μM, respectively, complex 6 is the most potent against iNOS, surpassing the reference standard.Keywords:
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An efficient and one-pot method for synthesis of 2-alkylthio-1,3,4-oxadiazole derivatives in mild conditions is described.Some novel derivatives such as bis-1,3,4-oxadiazole analogs are also synthesized.
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1,3,4-Oxadiazole derivatives have been widely applied as organic electron transport and emmiting materials because of their thermo and chemical stabilities and highly electron affinity.In this paper the recently progreess on the liquid crystals containing 1,3,4-oxadiazole units has been reviewed.Including the linear and star shaped LC containing 1,3,4-oxadiazole unit as well as oxadiazole unit contained polymers.Fucosed on the releationship among the strcutre and mesophase behavior and the elctrooptical properties of such LC.All the studies have shown that by combining the LC property with the electrooptical properties of 1,3,4-oxadiazole derivatives would be benefit to the much more widely application of such new materials.
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Abstract Summary: Two types of bis(2,5‐diphenyl‐1,3,4‐oxadiazole)s, macrocyclic and acyclic, were prepared and evaluated as electron‐transporting and hole‐blocking materials in phosphorescent EL devices. Maximum efficiencies of η ext = 10.4% at J = 0.11 mA · cm −2 for the macrocycle and η ext = 14.1% at J = 3.01 mA · cm −2 for the acycle were observed. X‐ray crystallographic analysis and DSC measurements revealed a strong intermolecular interaction between the macrocycles and weaker intermolecular interactions between the acycles. The EL characteristics depend on the intermolecular interactions. The two types of bis(2,5‐diphenyl‐1,3,4‐oxadiazole)s used in the study. magnified image The two types of bis(2,5‐diphenyl‐1,3,4‐oxadiazole)s used in the study.
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3-Amino-1,2,4-oxadiazole (3a) has been prepared from t-butoxycarbonylamino-1,2,4-oxadiazole (3h), and also from hydroxyguanidine and formyl fluoride. The amine is unexpectedly stable; on acid hydrolysis it gives hydroxyguanidine. 3-Cyano-1,2,4-oxadiazole (3m), prepared by dehydration of 1,2,4-oxadiazole-3-carboxamide (3l), is highly reactive but thermally stable. Some reactions of the amine (3a) and the nitrile (3m) are described.
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This study aimed at investigating factors affecting the stability as well as structural properties of different Oxadiasole and Thiadiasole isomers based on theoretical level B3LYP/6-311+G**, Nuclear Magnetic Resonance (NMR), and Nucleus-independent Chemical Shift (NICS). Qualitative relationships between relative stabilities of 1,2,3-Oxadiazole, 1,2,4-Oxadiazole, 1,2,5-Oxadiazole and 1,3,4-Oxadiazole were obtained. Aromatic stabilization energy (ASE), aromatic ring current (NICS), HUMO-LUMO gaps, electro-negativity (X), hardness (η), softness (S), electro-philicity (ω) and structural parameters were also calculated in the same theoretical level. The results show that 1,3,4-Oxadiazole is more stable than 1,2,3-Oxadiazole, 1,2,4-Oxadiazole and 1,2,5-Oxadiazole. Unlike the trends observed in Oxadiazoles, 1,2,5-Thiadiazole isomer is more stable than other corresponding Isomers.
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In this minireview, the method of syntheses of mono, bis and tris-1,3,4-oxadiazole and N-substituted-2,5-disubstituted-1,3,4- oxadiazole is reviewed. To the best of my knowledge, reviews on the mono 1,3,4-oxadiazoles are extensive while now reviews are reported to cover the syntheses of the bis and tris counterparts. The bis and tris 1,3,4-oxadiazoles and N-substituted-2,5-disubstituted-1,3,4-oxadiazole and their precursors and derivatives are promising candidates for many different applications in industry notably the medicinal and pharmaceutical industries.
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包含 2 的新 cyclometalated 铂建筑群， 5 二度(naphthalene-1-yl )-1,3,4-oxadiazole ligand 被综合并且描绘。紫外力的吸收和相片 ligand 和它的铂建筑群的光性质被调查。在在紫外光谱的 439 nm 的一座典型 metal-ligand 费用转移吸收山峰和在在光致发光光谱的 625 nm 的一座强壮的排放山峰在 dichloromethane 为这建筑群被观察。周期的 voltammtry ( CV )分析表演E_(人)(精力水平最高占据了分子轨道)并且E_( LUMO )(精力水平最低没有住分子轨道)分别地，铂，建筑群关于 -5.69 和 -3.25 eV 显示 基于oxadiazole 的铂建筑群在发磷光的设备用作红射出的材料的电镀物品有潜在的应用。
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Abstract New electroluminescent materials of 1,3,4‐oxadiazole–1,2,3‐triazole and 1,3,4‐oxadiazole–1,2,3‐triazole–pyridine hybrid derivatives were synthesized and characterized. Following spectroscopic studies and characterization of their electronic properties, 1,3,4‐oxadiazole–1,2,3‐triazole hybrids and 1,3,4‐oxadiazole–1,2,3‐triazole–pyridine derivatives were found to be potentially efficient blue electroluminescent materials. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:322–328, 2006; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20210
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在现在的工作，包含 1,3,4-oxadiazole 单位的新热地稳定的聚合物通过芳香的 bis-tetrazole 的反应作为溶剂在 pyridine 与芳香 / 脂肪族的二度酸氯化物加重的 Huisgen 被综合了。获得的聚合物在象 DMSO 和 DMF 那样的极的 aprotic 溶剂不可溶解或稍微可溶。用 DSC 和 TGA 技术的聚合物的热分析证明聚合物改进了热稳定性。模型反应也被调查，产生 bis-1,3,4-oxadiazole 混合物被常规分光镜的方法描绘。关键词 1,3,4-Oxadiazole - 热地稳定的聚合物 - Bis-tetrazole - Huisgen 反应这个工作被 Mohaghegh Ardabili (伊朗) 的大学的毕业生委员会财政上支持。
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