Synthesis and antibacterial properties of hydrazonothiazolyl derivatives of saturated 2,4,4-substituted butanolides

Abstract

A method has been developed for the synthesis of new heterocyclic compounds containing g-butanolide fragments. The antibacterial properties of the obtained compounds have been investigated. The tested compounds exhibit moderate antibacterial activity.Ketolactones are known to be good synthons for preparing heterocyclic compounds of various classes. In particular, thiazolyl-and triazolyl-derivatives of lactones [1, 2], indolyllactones with cardiovascular properties [3,4], and thiosemicarbazones of ketolactones with antimutagenic activity [5] have been synthesized from them. Furthermore, the last can be used as starting materials for synthesizing a new class of lactone-containing heterocyclic compounds. We prepared thiosemicarbazones of ketolactones with various structures by reacting the latter with thiosemicarbazide in aqueous alcohol.The optimum conditions for obtaining high yields of IIa -j were developed. Next, we studied the reaction of thiosemicarbazones IIa -j with substituted bromoacetophenones. It was found that substitution and further heterocyclization formed a new class of lactone-containing heterocyclic compounds, hydrobromides of 2,4,4-trisubstituted 2-[2¢-(3¢-arylthiazol-2¢-yl)hydrazono]propyl(butyl)butanolides (IIIa -p), treatment of which with aqueous ammonia gave the corresponding free bases (IVa -p).The optimum conditions were developed to give high yields (78 -93%) of the target products.All synthesized compounds were characterized by physicochemical constants and IR and PMR spectra. The purity was verified by TLC and elemental analyses, which agreed with those calculated for each product. 144 0091-150X/09/4303-0144

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

“…For example, a synthetic α -amino- γ -lactone ketolide (Entry 19) showed excellent antibacterial activity against erythromycin-susceptible Streptococus pyogenes [ 45 ]. Additionally, hydrazonothiazolyl derivative (Entry 20) [ 46 ], β -cyclocitral derivative (Entry 21) [ 47 ], and α -methylene- γ -butyrolactone (Entry 22) [ 48 ] displayed potent antibacterial activities and a synthetic β -aryl- δ -iodo- γ -butyrolactone (Entry 23) exhibited bactericidal activity against Proteus mirabilis [ 49 , 50 ].…”

Synthesis of Alkynylated Dihydrofuran‐2(3H)‐ones as Potent and Selective Inhibitors of Tissue Non‐Specific Alkaline Phosphatase

“…Recently, Ghochikyan et al . reported the synthesis and antimicrobial activity of substituted dihydrofuran‐2(3 H )‐ones. In this study, we report our efforts to synthesize novel alkynylated dihydrofuran‐2(3 H )‐ones by Sonogashira reactions of a dihydrofuran‐2(3 H )‐one scaffold and their screening to identify and characterize selective and potent inhibitors of TNAP that might be useful for the treatment of vascular calcification.…”

Synthesis and transformations of 5,5-disubstituted 3-alkenyloxolan-2-ones

“…Previously we [12][13][14][15] developed new methods of preparation of mono-and dibutanolides fused with various heterocycles, among which compounds were discovered demonstrating antitumor, antioxidant, and antimutagenic properties. In continuation of research in the field of 4-butanolides aiming at widening the choice of compounds containing the butanolide ring, exploring the chemical and physical properties and developing new methods of synthesis of various compounds classes we selected as initial compounds in this study ethyl 5,5-disubstituted 2-oxooxolane-3carboxylate.…”