Molecular modeling and docking studies of new antimicrobial antipyrine-thiazole hybrids was written by Abu-Melha, Sraa. And the article was included in Arabian Journal of Chemistry in 2022.Recommanded Product: Ethyl 4-chloro-3-oxobutanoate The following contents are mentioned in the article:
A series of new antipyrine incorporated thiazole derivatives I (R = CHO, {2-[(5Z)-5-[(4-chlorophenyl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]hydrazin-1-ylidene}methyl, [2-(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl, [2-(5-acetyl-4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl, etc.) having phenoxyacetamide moiety as a link bridge was synthesized. The synthetic strategy involves condensation of the precursor N-(4-antipyrinyl)-2-(4-formylphenoxy)acetamide with thiosemicarbazide followed by heterocyclization of the produced thiosemicarbazone with various α-halogenated carbonyl compounds (namely; 4-chlorophenacyl bromide, Et bromoacetate, 3-chloroacetylacetone and Et 4-chloroacetoacetate). Moreover, the quantum chem. calculations at DFT/B3LYP level were used to determine the HOMO-LUMO energies and Fukui’s indexes toward nucleophilic, electrophilic and radical attacks. The investigated compounds were arranged due to HOMO-LUMO energy gap as following I ((2-[(5Z)-5-[(4-chlorophenyl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]hydrazin-1-ylidene)methyl[2-(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl[2-(5-acetyl-4-methyl-4,5-dihydro-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl[(carbamothioylamino)imino]methyl(CHO){2-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]hydrazin-1-ylidene}methyl({2-[4-(2-ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]hydrazin-1-ylidene}methyl). The synthesized antipyrinyl-thiazole hybrids were screened to evaluate their antibacterial and antifungal efficacies. Using Chloramphenicol as reference material, the synthesized antipyrinyl-thiazole hybrids were revealed a remarkable activity against S. aureus than B. subtilis, as example for Gram’s pos. strains. The antipyrine-thiazole compounds I (R = [2-(5-acetyl-4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]methy, 4-(4-chlorophenyl)-1,3-thiazol-2-yl, (5Z)-5-[(4-chlorophenyl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl and Et 2-(4-methyl-1,3-thiazol-5-yl)acetate) exhibited significant MIC values. However, the antipyrine-thiazole hybrid displayed reputable activities against Gram’s neg. strains S. typhimurium and E. coli, resp., in comparison with Cephalothin. Likewise, the compounds I (R = {[2-(5-acetyl-4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl, 2-[4-(2-ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]hydrazin-1-ylidene}methyl) were demonstrated respectable antifungal efficacy toward C. albicans in contrast to cycloheximide grade. The theor. mol. docking studies were applied to simulate reactivity of the synthesized antipyrine-thiazole hybrids against contrasting binding sites for both of Staphylococcus aureus ”Homo sapiens” (pdb: 3HUN) protein and E.coli ”Homo sapiens” (PDB: 2EXB) protein. The theor. and practical antibacterial and antifungal activities result in this work designated a proper agreement. This study involved multiple reactions and reactants, such as Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3Recommanded Product: Ethyl 4-chloro-3-oxobutanoate).
Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Recommanded Product: Ethyl 4-chloro-3-oxobutanoate
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics