N-(3-Cyano-4,5,6,7-tetrahydrobenzothiophen-2-yl)-2-[[5-[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)amino]-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide

Abstract

The small pyrazolone-bearing molecules attract attention and are widely explored in drug design as pharmacological agents. The new pyrazolone-thiadiazole hybrid molecule N-(3-cyano-4,5,6,7-tetrahydrobenzothiophen-2-yl)-2-[[5-[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)amino]-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide (3) has been synthesized following a two-stage protocol using simple, convenient transformations and cheap, commercially available reagents. The compound’s structure was confirmed using 1H, 13C nuclear magnetic resonance (NMR), and liquid chromatography–mass spectrometry (LC–MS) spectra. The anti-inflammatory potency of 3 was evaluated in silico using molecular docking. The docking studies results suggest that title compound 3 is of great interest for further structure optimization and in-depth studies as a possible 5-lipoxygenase (5-LOX) inhibitor.

2,2-Dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide

“…Starting compound 1 was prepared according to protocol described in [33]. The 2-chloro-1-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2yl]ethanone was accomplished by the reaction of 2-chloroacetyl chloride with appropriate 5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole according to the reported method described in [7].…”

“…The application of the hybridization concept allows the design and discovery of new small molecules as high-affinity ligands to potential anticancer targets, as well as fighting and overcoming the multidrug resistance problems [3][4][5]. The synthetic pathways applied for the obtaining of new anticancer agents in the molecular hybridization context require fast, easy, and cheap ("cost-effective") synthetic schemes to the target hybrid molecules with their high yield and purity [6][7][8].…”

Synthesis of Tetracyclic Spirooxindolepyrrolidine-Engrafted Hydantoin Scaffolds: Crystallographic Analysis, Molecular Docking Studies and Evaluation of Their Antimicrobial, Anti-Inflammatory and Analgesic Activities

“…In addition, the same compound established five hydrophobic interactions (π-alkyl interactions) with the following residues: ILE406 (A), ALA410 (A), LEU607 (A), VAL175 (A) and ALA672(A) (Table 9 and Figure 10a). In this regards, several studies [71][72][73] have revealed that that ASN554(A) and TYR558(A) play a central role in the inhibition of LOX-5 target. Moreover, we note clearly that the compound 4l establishes more binding interactions with active site residues of 5-LOX target compared to compound 4i.…”

rel-2-[4-Chloro-2-[(5R,6R,7S)-6-[5-(4-methoxyphenyl)-3-(2-naphthyl)-3,4-dihydropyrazole-2-carbonyl]-5-methyl-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-d]thiazol-7-yl]phenoxy]acetic Acid

“…Taking into account the abovementioned data, and due to our ongoing interest in pyrazoline-bearing molecules [7,12,13], we report the application of pyrazoline-containing dienophile to the construction of novel thiopyrano [2,3-d]thiazole via the hetero-Diels-Alder reaction. The structure characterization of the synthesized molecule, using NMR and LC-MS spectra and an in vitro anticancer activity evaluation, according to the "60 lines screening" algorithm (DTP NCI, USA), are also presented.…”