5344-88-7Relevant academic research and scientific papers
Synthesis, molecular structure and computational study of (Z)-2-((E)-4-nitrobenzylidene)hydrazone)-1,2-diphenylethan-1-one
Elmaci, G?khan,Aktan, Ebru,Sefero?lu, Nurgül,H?kelek, Tuncer,Sefero?lu, Zeynel
, p. 83 - 91 (2015)
A new benzilmonohydrazone, (Z)-2-((E)-4-nitrobenzylidene)hydrazone)-1,2-diphenylethan-1-one (BMH) has been synthesized for the first time. It was characterized by UV-vis, FT-IR, FT-Raman, 1H/13C NMR and mass spectrometry techniques. Molecular structure of the title compound was determined by single crystal X-ray diffraction study. In addition, molecular structure of BMH was determined by single crystal X-ray diffraction technique and found that the compound crystallizes in triclinic, space group P-1. Furthermore, chemical calculations employing density functional theory (DFT) method were performed to study the structural and spectroscopic properties of BMH, and the results were compared with the experimental findings.
Theoretical insight into the disordered structure of (Z)-2-[(E)-(4-methoxybenzylidene)hydrazinylidene]-1,2-diphenylethanone: The role of noncovalent interactions
Tan, Xue-Jie,Wang, Di,Lei, Xu-Gang,Chen, Jun-Peng
, p. 1058 - 1067 (2018)
A global glide disorder has been discovered during an X-ray investigation of the crystal structure of (Z)-2-[(E)-(4-methoxybenzylidene)hydrazinylidene]-1,2-di-phenylethanone (MHDE, C22H18 N2O2) at room temperature. In another crystal, however, such disorder disappears (still at room temperature). Even though the disorder may be partly due to the poor quality of the harvested crystal, the structure can shed light on the nature of disorder. With the help of quantum chemical calculations, it is found that the global disorder seems to be connected with the need for stabilization of the somewhat rigid but mobile and unstable molecular structure. The most relevant feature driving the packing of the disordered structure concerns the slight perturbations (such as glide) of two or more disorder components (fractional occupancies) distributed throughout the crystal.
Synthesis, in-vitro evaluation, molecular docking, and kinetic studies of pyridazine-triazole hybrid system as novel α-glucosidase inhibitors
Moghimi, Setareh,Salarinejad, Somayeh,Toolabi, Mahsa,Firoozpour, Loghman,Esmaeil Sadat Ebrahimi, Seyed,Safari, Fatemeh,Madani-Qamsari, Fatemeh,Mojtabavi, Somayeh,Faramarzi, Mohammad Ali,Karima, Saeed,Pakrad, Roya,Foroumadi, Alireza
, (2021/02/16)
In this study, we reported the discovery of pyridazine based 1,2,3-triazole derivatives as inhibitors of α-glucosidase. All target compounds exhibited significant inhibitory activities against yeast and rat α-glucosidase enzymes compared to positive control, acarbose. The most potent compound 6j, ethyl 3-(2-(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)ethyl)-5,6-diphenylpyridazine-4-carboxylate exhibited IC50 values of 58, and 73 μM. Docking studies indicated the responsibility of hydrophobic and hydrogen bonding interactions in the ligand-enzyme complex stability. The in-vitro safety against the normal cell line was observed by toxicity evaluation of the selected compounds.
Synthesis, crystal structures, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil
Hei, Xiao-Ming,Ma, Jian-Ping,Tan, Xue-Jie,Wang, Di,Xing, Dian-Xiang,Yang, Feng-Cun,Zhu, Ya-Ling
, p. 44 - 63 (2020/01/23)
Eight novel Schiff bases derived from benzil dihydrazone (BDH) or benzil monohydrazone (BMH) and four fused-ring carbonyl compounds (3-formylindole, FI; 3-acetylindole, AI; 3-formyl-1-methylindole, MFI; 1-formylnaphthalene, FN) were synthesized and characterized by elemental analysis, ESI-QTOF-MS, 1H and 13C NMR spectroscopy, as well as single-crystal X-ray diffraction. They are (1Z,2Z)-1,2-bis{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BDHFI), C32H24N6, (1Z,2Z)-1,2-bis{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethane (BDHAI), C34H28N6, (1Z,2Z)-1,2-bis{(E)-[(1-methyl-1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BMHMFI) acetonitrile hemisolvate, C34H28N6·0.5CH3CN, (1Z,2Z)-1,2-bis{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BDHFN), C36H26N4, (Z)-2-{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHFI), C23H17N3O, (Z)-2-{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethanone (BMHAI), C24H19N3O, (Z)-2-{(E)-[(1-methyl-1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHMFI), C24H19N3O, and (Z)-2-{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHFN) C25H18N2O. Moreover, the in vitro cytotoxicity of the eight title compounds was evaluated against two tumour cell lines (A549 human lung cancer and 4T1 mouse breast cancer) and two normal cell lines (MRC-5 normal lung cells and NIH 3T3 fibroblasts) by MTT assay. The results indicate that four (BDHMFI, BDHFN, BMHMFI and BMHFN) are inactive and the other four (BDHFI, BDHAI, BMHFI and BMHAI) show severe toxicities against human A549 and mouse 4T1 cells, similar to the standard cisplatin. All the compounds exhibited weaker cytotoxicity against normal cells than cancer cells. The Swiss Target Prediction web server was applied for the prediction of protein targets. After analyzing the differences in frequency hits between these active and inactive Schiff bases, 18 probable targets were selected for reverse docking with the Surflex-dock function in SYBYL-X 2.0 software. Three target proteins, i.e. human ether-á-go-go-related (hERG) potassium channel, the inhibitor of apoptosis protein 3 and serine/threonine-protein kinase PIM1, were chosen as the targets. Finally, the ligand-based structure-activity relationships were analyzed based on the putative protein target (hERG) docking results, which will be used to design and synthesize novel hERG ion channel inhibitors.
Design and synthesis of novel pyridazine N-aryl acetamides: In-vitro evaluation of α-glucosidase inhibition, docking, and kinetic studies
Faramarzi, Mohammad Ali,Firoozpour, Loghman,Foroumadi, Alireza,Moghimi, Setareh,Mojtabavi, Somayeh,Sadat Ebrahimi, Seyed Esmaeil,Safari, Fatemeh,Salarinejad, Somayeh,Toolabi, Mahsa
, (2020/07/21)
We herein applied the four step-synthetic route to prepare the pyridazine core attached to the various N-aryl acetamides. By this approach, a new series of pyridazine-based compounds were synthesized, characterized and evaluated for their activities against α-glucosidase enzyme. In-vitro α-glucosidase assay established that twelve compounds are more potent than acarbose. Compound 7a inhibited α-glucosidase with the IC50 value of 70.1 μM. The most potent compounds showed no cytotoxicity against HDF cell line. Molecular docking and kinetic studies were performed to determine the modes of interaction and inhibition, respectively.
Coumarin-based benzilmonohydrazone as a new proton-sensitive fluorescence dye: Synthesis and investigation of photophysical and acidochromic properties
Aydiner, Burcu
, p. 1086 - 1097 (2019/09/10)
Coumarin-based chromogenic and fluorogenic dye 4 was designed and synthesized. The photophysical properties of 4 were determined in solvents with different polarities. Protonation affinity was determined by adding trifluoroacetic acid (TFA) to a dichloromethane solution of dye 4 utilizing the UV-Vis and fluorescence titration methods. The protonation region was investigated by using the 1 H NMR method. Additionally, DFT and TDDFT studies were performed to support the structural and absorption spectral properties of 4.
Alkyl halide-free heteroatom alkylation and epoxidation facilitated by a recyclable polymer-supported oxidant for the in-flow preparation of diazo compounds
Nicolle, Simon M.,Hayes, Christopher J.,Moody, Christopher J.
supporting information, p. 4576 - 4579 (2015/03/18)
Highly reactive metal carbenes, generated from simple ketones via diazo compounds, including diazoamides and -phosphonates, using a recyclable reagent inflow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation. The method produces no organic waste, with the only byproducts being water, KI and nitrogen, without the attendant hazards of isolation of intermediate diazo compounds.
Evaluation of some classical hydrazones of ketones and 1,2-diketones as antileishmanial, antibacterial and antifungal agents
Al-Kahraman, Yasser M.S.A.,Yasinzai, Masoom,Singh, Girija S.
experimental part, p. 1009 - 1013 (2012/10/08)
The paper describes the synthesis and antimicrobial (antileishmanial, antibacterial and antifungal) activity of some classical hydrazones of benzophenones and of 1,2-diketones. N-(Diaryl) acyl derivatives of these hydrazones have also been synthesized and evaluated. 4,4,- Demthoxybenzil monohydrazone and 4,4'-dimethoxybenzophenone hydrazone showed significant antileishmanial activity. The effect of substituents on the bioactivity is discussed.
Influence of different aryl substitution on the crystal structures of benzil monohydrazone and dibenzil azine parent compounds
Wieland, Marcel,Seichter, Wilhelm,Schwarzer, Anke,Weber, Edwin
experimental part, p. 1267 - 1279 (2012/05/19)
A series of benzil monohydrazones (1a, 1d) and corresponding dibenzil azines (2a-2d) featuring different p-aryl substituents have been synthesized and studied in regard of their crystal structures. Configurational and conformational properties as well as non-covalent interaction and packing behaviour of the molecules connected with the different substitution are discussed. The dibenzil azine 2a was found as a polymorph with reference to a known crystal structure.
Pyridazine derivatives and related compounds, part 28.1 pyridazinesulfonamides: Synthesis and antimicrobial activity
El-Mariah, Fatma,Nassar, Ekhlass,Hosny, Mona,Deeb, Ali
body text, p. 92 - 102 (2009/04/16)
The reaction of 3-chloropyridazine 1 with N -(un)Substituted 4-aminosulfonamides 3 gave the 3-substituted aminopyridazines 4. Also In addition, pyridazine-3-sulfonamides 7 were prepared from the reaction of pyridazine-3-sulfonylchloride 6 with different amines. All of these derivatives have been characterized by analytical and spectroscopic studies, and also were tested for their in vitro antibacterial and antifungal activity against a variety of microorganisms.
