Novel Synthesis of 4-Bromo-3-oxo-2-phenylhydrazonobutyronitrile and 4-Cyano-3-oxo-2-phenylhydrazonobutyronitrile: Synthesis of Pyridazine, Thiazole, 1,2,4-Triazine and Pyrido[2,3-e]-1,2,4-triazine Derivatives

1992 ◽  
Vol 57 (8) ◽  
pp. 1758-1769 ◽  
Author(s):  
Rafat Milad Mohareb ◽  
Nadia Iskander Abdel-Sayed
Keyword(s):  
Thiazole Derivatives ◽  
Chemical Reagents ◽  
Novel Synthesis ◽  
Triazine Derivatives ◽  
Nucleophilic Reagents

4-Bromo-3-oxo-2-phenylhydrazono-butyronitrile (II) reacted with thioamides to afford the thiazole derivatives III and VI. Compound II reacted with nucleophilic reagents to afford XIIIa and XIIIb. The reactivity of XIIIa with some chemical reagents was studied to afford pyridazine, thiazole, 1,2,4-triazine derivatives.

Heterocyclization of 2-(2-phenylhydrazono)cyclohexane-1,3-dione to Synthesis Thiophene, Pyrazole and 1,2,4-triazine Derivatives with Anti-Tumor and Tyrosine Kinase Inhibitions

2020 ◽  
Vol 20 (10) ◽  
pp. 1209-1220
Author(s):  
Rafat M. Mohareb ◽  
Ensaf S. Alwan
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Tyrosine Kinases ◽  
Proliferative Activity ◽  
Cancer Cell Lines ◽  
Thiazole Derivatives ◽  
Wide Range ◽  
Cytotoxic Compounds ◽  
Triazine Derivatives ◽  
Target Molecules

Background: Recently tetrahydrobenzo[b]thiazole derivatives acquired a special attention due to their wide range of pharmacological activities especially the therapeutic activities. Through the market it was found that many pharmacological drugs containing the thiazole nucleus were known. Objective: This work aimed to synthesize target molecules not only possess anti-tumor activities but also kinase inhibitors. The target molecules were obtained starting from the arylhydrazonocyclohexan-1,3-dione followed by their heterocyclization reactions to produce anticancer target molecules. Methods: The arylhydrazone derivatives 3a-c underwent different heterocyclization reactions to produce thiophene, thiazole, pyrazole and 1,2,4-triazine derivatives. The anti-proliferative activity of twenty six compounds among the synthesized compounds toward the six cancer cell lines namely A549, H460, HT-29, MKN-45, U87MG, and SMMC-7721 was studied. Results: Anti-proliferative evaluations, tyrosine and Pim-1 kinase inhibitions were perform for most of the synthesized compounds where the varieties of substituent through the aryl ring and the thiophene moiety afforded compounds with high activities. Conclusion: The compounds with high anti-proliferative activity towards the cancer cell lines showed that compounds 3b, 3c, 5e, 5f, 8c, 9c, 11c, 12c, 14e, 14f and 16c were the most cytotoxic compounds. Further tests of the latter compounds toward the five tyrosine kinases c-Kit, Flt-3, VEGFR-2, EGFR, and PDGFR and Pim-1 kinase showed that compounds 3c, 5e, 5f, 8c, 9c, 12c, 14e, 14f and 16c were the most potent of the tested compounds toward the five tyrosine kinases and compounds 6d, 11a, 20b and 21e were of the highest inhibitions towards Pim-1 kinase. Pan Assay Interference Compounds (PAINS) for the most cytotoxic compounds showed zero PAINS alert and can be used as lead compounds.

ChemInform Abstract: NOVEL SYNTHESIS OF 5-(5-NITRO-2-FURYL)THIAZOLE DERIVATIVES

1985 ◽  
Vol 16 (29) ◽  
Author(s):  
G. D. KRAPIVIN ◽  
E. B. USOVA ◽  
V. G. KUL'NEVICH
Keyword(s):  
Thiazole Derivatives ◽  
Novel Synthesis

scholarly journals Synthesis and Anticancer Evaluations of Novel Thiazole Derivatives Derived from 4-Phenylthiazol-2-amine

2021 ◽  
Vol 68 (3) ◽  
pp. 604-616
Author(s):  
Amira E. M. Abdallah ◽  
Rafat M. Mohareb ◽  
Maher H. E. Helal ◽  
Germeen J. Mofeed
Keyword(s):  
Anticancer Agents ◽  
Human Cancer ◽  
Human Cell Line ◽  
Breast Adenocarcinoma ◽  
Small Cell Lung ◽  
Thiazole Derivatives ◽  
Human Cancer Cell Lines ◽  
Chemical Reagents ◽  
Cns Cancer ◽  
Mcf 7

Many novel thiazole derivatives were designed and synthesized using 4-phenylthiazol-2-amine. The reactivity of the latter compound toward different chemical reagents was studied. The structure of the newly synthesized compounds was established based on elemental analysis and spectral data. Furthermore, twenty compounds of the synthesized systems were selected and evaluated in (μM) as significant anticancer agents towards three human cancer cell lines [MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer)] and normal fibroblasts human cell line (WI-38). The results showed that compounds 9 and 14a displayed higher effeciency than the reference doxorubicin.

scholarly journals Reactions with 5-Arylmethylene-2-phenylhydrazono-4-thiazolidinones A Novel Synthesis of Thiazolo[2,3-c]triazine Derivatives

1984 ◽  
Vol 39 (3) ◽  
pp. 390-392 ◽  
Author(s):  
Sanaa O. Abd Allah ◽  
Sherif M. Fahmy ◽  
Hamed A. Ead
Keyword(s):  
Alkaline Solution ◽  
Carbon Disulphide ◽  
Phenacyl Bromide ◽  
Ethyl Bromoacetate ◽  
Novel Synthesis ◽  
Triazine Derivatives ◽  
Derivatives Of

The 5-arylmethylene derivatives of 2-phenylhydrazono-4-thiazolidinone (1) reacted with phenacyl bromide and with ethyl bromoacetate to yield the thiazolo[2,3-c]triazine derivatives (3) and (4). The reaction of 1 with carbon disulphide in alkaline solution afforded the bis(N1- 2-phenylhydrazono-4-thiazolidinone)thiocarbonyl derivatives (6). Cyanoethylation of 1 afforded the N1-β-cyanoethylphenylhydrazono derivatives (7).

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