2028-74-2Relevant articles and documents
Design, synthesis, molecular docking and biological screening of N-ethyl-N-methylbenzenesulfonamide derivatives as effective antimicrobial and antiproliferative agents
Abd El-Gilil, Shimaa M.
, p. 144 - 156 (2019)
Sulfonamides are the most famous agents, which have been utilized for preparation of effective antiproliferated agents. Therefore, this article describes the synthesis of new series of N-ethyl-N-methylbenzenesulfonamide derivatives having various biologically active moieties such as, thiazoles 3, 4, 11, 12, 14, 15, 21, 1,3,4-thiadiazine 6, imidazo[2,1-b]thiazole 8, 2-oxo-2H-chromene 17, and 3-oxo-3H-benzo[f]chromene 19, starting with 4-(2-bromoacetyl)-N-ethyl-N-methylbenzenesulfonamide (2), that was synthesized from the interaction of 4-acetyl-N-ethyl-N-methylbenzenesulfonamide (1) with bromine under stirring in dioxane/diethylether mixture. The newly structures were be proved via their elemental analysis and spectral data. However, they were also screened for their cytotoxic activity against two different human cell lines, alveolar adenocarcinoma carcinoma (lung) (A-549) and liver carcinoma (HepG2) and antimicrobial. Compound 8 having imidazo[2,1-b]thiazole moiety exhibited the most potent cytotoxic activity against (A-549) cell line (SI; 30.77). While, compound 11 having 2-cyanomethyl thiazole moiety showed significant cytotoxic activity against (HepG2) cell line (SI; 67.11). On the other hand, compound 9 having 4-chlorophenyl moiety exerted significant antimicrobial activity more than the reference drugs. Molecular Operating Environment (MOE) was performed for the synthesized compounds to study their mode of action as inhibitors against DHFR enzyme active sites.
Acetylacetaldehyde Dimethyl Acetal as Versatile Precursors for the Synthesis of Arylazonicotinic Acid Derivatives: Green Multicomponent Syntheses of Bioactive Poly-Heteroaromatic Compounds
Hassaneen, Huwaida M. E.,Abdelhamid, Ismail A.
, p. 1048 - 1053 (2017)
A simple and efficient one-pot synthesis of interesting arylhydrazonals could be achieved via coupling of acetylacetaldehyde dimethyl acetal with aromatic diazonium salts. Dimroth type rearrangement was observed during the reaction of the arylhydrazonals with malononitrile or ethyl cyanoacetate leading to the formation of arylazonicotinic acid derivatives. The reaction of arylhydrazonals with malononitrile and aldehydes in the presence of DABCO afforded 4-styryl-1,2-dihydropyridine-3-carbonitrile whose structure was established by X-ray crystallography. Pyrazolyl-enaminone was accomplished and used as a scaffold to synthesize bioactive fused heterocyclic compounds such as 1,2,4-triazolo[1,5-a]pyrimidine 28, benzo[4,5]imidazo[1,2-a]pyrimidine 30 and pyrazole[1,5-a]pyrimidine derivatives 32.
Uses of ethyl benzoyl acetate for the synthesis of thiophene, pyran, and pyridine derivatives with antitumor activities
Ibrahim, Bishoy A.,Mohareb, Rafat M.
, p. 4023 - 4035 (2020/09/21)
The N-(arly)propanamide derivatives 3a,b were used for a series of heterocyclization reactions to give thiophene, pyran, and pyridine derivatives. Thus, these compounds underwent the Gewald's thiophene synthesis through their reactions with either malononitrile or ethyl cyanoacetate and elemental sulfur to afford compounds 6a-f, respectively. In addition, they were subjected through a series of multicomponent reactions (MCRs) to give pyran and fused derivatives. The reactions of 3a,b with either malononitrile or ethyl cyanoacetate gave pyridine derivatives 14a-d, respectively. The latter compounds afforded arylhydrazone derivatives 15a-m through their reactions with any of the aromatic diazonium salts 15a-c. The antitumor of the synthesized compounds against A549 (nonsmall cell lung cancer), H460 (human lung cancer), HT-29 (human colon cancer), and MKN-45 (human gastric cancer cancer) cancer cell lines together with foretinib as the positive control by a MTT assay was measured, and the results obtained showed that many compounds exhibited high potency against the six cancer cell lines.
Synthesis process of p-chlorophenylhydrazine hydrochloride
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Paragraph 0064-0092, (2019/10/29)
The invention relates to the technical field of organic synthesis, in particular to a synthesis process of p-chlorophenylhydrazine hydrochloride. The synthesis process comprises the following steps: (1) diazotization: mixing p-chloroaniline, strong acid and water, and adding a nitrite solution to obtain a substance A; and (2) catalytic hydrogenation: mixing the substance A with a catalyst under ahydrogen condition, and filtering the liquid to obtain the product. The process provided by the invention has the advantages of high yield and purity, environmental protection and simple operation.
