90754-75-9Relevant academic research and scientific papers
Synthesis, Characterization, Molecular Docking and Biological Activity Studies of Hydrazones with 3,4,5-Trimethoxyphenyl Moiety
Ayrim, Nabel B.,Balakit, Asim A.,Lafta, Souad J.
, p. 159 - 169 (2022/04/28)
In this work a series of hydrazone Schiff base compounds have been synthesized and characterized by FT-IR, 1H NMR, 13C NMR, and mass spectrometry. The structures of the target compounds designed to have 3,4,5-trimethoxy in acid hydrazide part and different substituents in the imine part. The antibacterial activity of the synthesized compounds has been studied against two gram positive bacteria (Staphylococcus aureus and Staphylococcus epidermidis) and two gram negative bacteria (Escherichia coli and Klebsiella sp.), while the antifungal activity was studied against candida albicans fungi. The results revealed that most of the synthesized hydrazone derivatives exhibit a moderate antimicrobial activity when compared with the standard drug ampicillin. Molecular docking studies were carried out on the bacteria strain Staphylococcus aureus with target protein DHFR and its complex with trimethoprim (PDB ID: 2W9H).
ACYL-HYDRAZONE AND OXADIAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND USES THEREOF
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Paragraph 0093, (2015/07/15)
The present invention relates to acyl-hydrazone compounds, in particular 3,4,5-trimethoxyphenyl-hydrazide derivatives, as well as the oxadiazole analogs thereof and other similar compounds, and to the pharmaceutical use of the same for the treatment of various diseases associated with cell proliferation, such as leukemias, including acute lymphoblastic leukemia (ALL), tumours and inflammation. Acyl-hydrazones have been obtained having activity similar to that of the compound used as a standard in experiments (colchicine). The greater selectivity of the compounds according to the invention is an important feature, associated with fewer side effects than the pharmaceuticals used at present in clinical treatments. The synthetised acyl-hydrazones, more particularly the compounds 02 and 07, exhibited important antileukemic activity, which suggests 02 and 07 as candidates to pharmaceutical prototypes, or to pharmaceuticals for the treatment of leukemias, in particular acute lymphoblastic leukemia (ALL), tumours and other proliferative diseases, such as inflammation. The action mechanism of the most active compounds was determined by using DNA microarrays and subsequent tests indicated by the chip, besides selectivity studies in healthy human lymphocytes.
ACYL-HYDRAZONE AND OXADIAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND USES THEREOF
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Paragraph 0068, (2014/10/15)
The present invention relates to acyl-hydrazone compounds, in particular 3,4,5-trimethoxyphenyl-hydrazide derivatives, as well as the oxadiazole analogs thereof and other similar compounds, and to the pharmaceutical use of the same for the treatment of various diseases associated with cell proliferation, such as leukemias, including acute lymphoblastic leukemia (ALL), tumours and inflammation. Acyl-hydrazones have been obtained having activity similar to that of the compound used as a standard in experiments (colchicine). The greater selectivity of the compounds according to the invention is an important feature, associated with fewer side effects than the pharmaceuticals used at present in clinical treatments. The synthetised acyl-hydrazones, more particularly the compounds 02 and 07, exhibited important anti-leukemic activity, which suggests 02 and 07 as candidates to pharmaceutical prototypes, or to pharmaceuticals for the treatment of leukemias, in particular acute lymphoblastic leukemia (ALL), tumours and other proliferative diseases, such as inflammation. The action mechanism of the most active compounds was determined by using DNA microarrays and subsequent tests indicated by the chip, besides selectivity studies in healthy human lymphocytes.
Design, synthesis, and biological evaluations of 2,5-diaryl-2,3-dihydro-1, 3,4-oxadiazoline analogs of combretastatin-A4
Lee, Lauren,Robb, Lyda M.,Lee, Megan,Davis, Ryan,Mackay, Hilary,Chavda, Sameer,Babu, Balaji,O'Brien, Erin L.,Risinger, April L.,Mooberry, Susan L.,Lee, Moses
experimental part, p. 325 - 334 (2010/05/02)
A total of 24 novel 2,5-diaryl-1,3,4-oxadiazoline analogs of combretastatin A-4 (CA-4, 1) were designed, synthesized, and evaluated for biological activities. The compounds represent two structural classes; the Type I class has three methoxy groups on the A ring and the Type II class has a single methoxy group on the A ring. Biological evaluations demonstrate that multiple structural features control the biological potency. Four of the compounds, 2-(3′-bromophenyl)-5-(3″,4″,5″-trimethoxyphenyl) -2-acetyl-2,3-dihydro-1,3, 4-oxadiazoline (91), 2-(2′,5′- dimethoxyphenyl)-5-(3″-methoxyphenyl)-2-acetyl-2,3-dihydro-1,3, 4-oxadiazoline (10h), 2-(3′,4′,5′-trimethoxyphenyl)-5- (3″-methoxyphenyl)-2-acetyl-2,3-dihydro-1,3,4-oxadiazoline (10i), and 2-(3′,5′-dimethoxyphenyl)-5-(3″-methoxyphenyl)-2-acetyl-2, 3-dihydro-1,3,4-oxadiazoline (10j), have potent antiproliferative activities against multiple cancer cell lines. Mechanistic studies indicate that they retain the microtubule disrupting effects of compound 1, including microtubule loss, the formation of aberrant mitotic spindles, and mitotic arrest. Compound 10i inhibits purified tubulin polymerization and circumvents drug resistance mediated by P-glycoprotein and βIII tubulin expression. The oxadiazoline analog 10i is a promising lead candidate worthy of further investigation.
