Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions

Džambaski, Zdravko; Toljić, Đorđe; Bondžić, Bojan P.; Marković, Rade; Baranac‐Stojanović, Marija

doi:10.1016/j.tet.2013.09.004

Cited by 5 publications

(12 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 41, which corresponds to one of the most promising inhibitors reported in this series, showed dominant hydrogen bond interactions with two catalytic histidines, His 134 and His 252 ( Figure 4F). Furthermore, identical interactions with His 134 or His 252 were also observed for compounds 4,13,18,27,31, Supporting Information Table S2). In addition, compounds 4 and 27 showed H-donor interactions with residues Asp 168 and Glu 39 (Supporting Information Table S2), which are also implicated in the cleavage of scissile phosphate.…”

Section: Dnase I Inhibitionmentioning

confidence: 53%

“…26,27 Desired N,N-dimethyl enamines 36 and 37 were prepared by the regioselective C-5 functionalization of 2-alkylidene-4-oxothiazolidines in a reaction with Bredereck's reagent. 5-Hydroxy thiazolidine derivatives 31 and 32 were prepared from corresponding vinyl-chlorides 31 by dimethyl sulfoxide (DMSO) initiated chloride transfer from the exocyclic C=C bond to the C(5) position of the ring and subsequent formation and hydrolysis of alkoxydimethylsulfonium salt. 32 Compound 35 was prepared by regioselective Michael addition of thiazolidinone substrate to acrolein, according to the published procedure.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives

Kolarević

Ilić

Kocić

et al. 2018

J of Cellular Biochemistry

Self Cite

View full text Add to dashboard Cite

Twelve new thiazolidinones were synthesized and, together with 41 previously synthesized thiazolidinones, evaluated for inhibitory activity against deoxyribonuclease I (DNase I) in vitro. Ten compounds inhibited commercial bovine pancreatic DNase I with an IC below 200 μM and showed to be more potent DNase I inhibitors than crystal violet (IC = 365.90 ± 47.33 μM), used as a positive control. Moreover, three compounds were active against DNase I in rat liver homogenate, having an IC below 200 μM. (3-Methyl-1,4-dioxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide (41) exhibited the most potent DNase I inhibition against both commercial and rat liver DNase I with IC values of 115.96 ± 11.70 and 151.36 ± 15.85 μM, respectively. Site Finder and molecular docking defined the thiazolidinones interactions with the most important catalytic residues of DNase I, including the H-acceptor interaction with residues His 134 and His 252 and/or H-donor interaction with residues Glu 39 and Asp 168. The three most active compounds against both commercial and rat liver DNase I (31, 38, and 41) exhibited favorable physico-chemical, pharmacokinetic, and toxicological properties. These observations could be utilized to guide the rational design and optimization of novel thiazolidinone inhibitors. Thiazolidinones as novel DNase I inhibitors could have potential therapeutic applications due to the significant involvement of DNase I in the pathophysiology of many disease conditions.

show abstract

Section: Dnase I Inhibitionmentioning

confidence: 53%

Section: Methodsmentioning

confidence: 99%

Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives

Kolarević

Ilić

Kocić

et al. 2018

J of Cellular Biochemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…further optimized by varying the amounts of PIDA between 0.5-1.3 equiv and NiCl 2 ·6H 2 O between 1.0-2.5 equiv (Table 1, entries [14][15][16][17][18][19][20]. The optimized reaction conditions were 1.0 equiv of enamine, 1.2 equiv of PIDA and 2.0 equiv of NiCl 2 ·6H 2 O in acetonitrile which produce a yield of 64% (Table 1, entry 19).…”

Section: (11-diacetoxyiodo)benzene and A Halide Sourcementioning

confidence: 99%

“…Enamides − and enamines , have proved to be useful building blocks for complex nitrogen-containing compounds and substrates of various synthetic reactions such as the Porarov reaction, the Diels–Alder reaction, the Mannich reaction, metal-catalyzed regioselective functionalization, and halogenation. Among these products, halogenated enamides and enamines are important intermediates for the synthesis of heterocycles, α-halo-β-amino acid derivatives, − and α-aryl-β-amino acid derivatives, − some of which are bioactive. , However, only a few procedures have been used in preparing α-chloroenamides. − In the NBS/DABCO procedure, only succinimide substituted α-chloroenamide products were prepared. In the Pummerer reactions of sulfoxides, the products were limited to tetrasubstituted α-chloroenamides.…”

Section: Introductionmentioning

confidence: 99%

“…Among these products, halogenated enamides and enamines are important intermediates for the synthesis of heterocycles, α-halo-β-amino acid derivatives, − and α-aryl-β-amino acid derivatives, − some of which are bioactive. , However, only a few procedures have been used in preparing α-chloroenamides. − In the NBS/DABCO procedure, only succinimide substituted α-chloroenamide products were prepared. In the Pummerer reactions of sulfoxides, the products were limited to tetrasubstituted α-chloroenamides. Currently enamides are available through the Wittig reaction and Pd-catalyzed cross-coupling reaction of an amide and an acrylic ester .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Stereoselective Chlorination and Bromination of Enamides and Enamines via an Electrostatic Attraction Effect Using (1,1-Diacetoxyiodo)benzene and a Halide Source

Xing

2015

J. Org. Chem.

View full text Add to dashboard Cite

The direct chlorination and bromination of (E)-enamines and (Z)-enamides to the corresponding (Z)-configurated α-chloroenamines, α-bromoenamines, and α-chloroenamides have been realized using NiCl2·6H2O or tetrabutyl ammonium bromide as a halide source and (1,1-diacetoxyiodo)benzene as an oxidant. The high stereoselective reactions which produce products with only (Z)-configurations can be attributed to the structure of the intermediates, the conformations of which are controlled by the electrostatic attractions between the positively charged nitrogen atoms and the oxygen atoms of the carbonyl group. This type of electrostatic effect has never been reported in olefin halogenations. For this reason, the three-membered bromonium ion is only a minor intermediate in the enamine bromination pathway. These methods open pathways to prepare α-chloroenamines and α-chloroenamides, which are not accessible via the currently used methods.

show abstract

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Biesen,

Müller

2023

Chemistry A European J

View full text Add to dashboard Cite

Aroyl‐S,N‐ketene acetals represent a peculiar class of heterocyclic merocyanines, compounds bearing pronounced and rather short dipoles with great push‐pull characteristics that define their rich properties. They are accessible via a wide array of synthetic concepts and procedures, ranging from addition‐elimination and condensation procedures up to rearrangement and metal‐mediated reactions. With our work from 2020, aroyl‐S,N‐ketene acetals have been identified as powerful and promising dyes with pronounced and vastly tunable solid‐state emission and aggregation‐induced emission properties. One characteristic trademark of this class of dye molecules is the level of control that could be exerted, and which was thoroughly explored. Based on these results, the field was opened to extend the system to bi‐ and multichromophoric systems by the full toolkit of synthetic organic chemistry thus giving access to even more exciting properties and manifolded substance libraries capitalizing on the AIE properties. This review aims at outlining the reaction‐based principles that allow for a swift and facile access to aroyl‐S,N‐ketene acetals, their methodical and structural evolution and the plethora of fluorescence and aggregation properties.

show abstract

Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions

Cited by 5 publications

References 29 publications

Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives

Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives

Stereoselective Chlorination and Bromination of Enamides and Enamines via an Electrostatic Attraction Effect Using (1,1-Diacetoxyiodo)benzene and a Halide Source

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Contact Info

Product

Resources

About