Synthesis of 2,4-Dioxoimidazolidines from 2-Arylimino-1,3-thiazines and Their Antifungal Activity

Ichinari, Mitsuhiro; Nakayama, Kuniyoshi; Hayase, Yoshio

doi:10.3987/com-88-4699

Cited by 12 publications

(16 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In its 1 H-NMR spectrum, the peaks at δ 7.92 (2H, J = 7.5 Hz), δ 7.90 (2H, s), δ 7.79 (2H, J = 7.7 Hz) and δ 7.48 (2H, J = 7.6 Hz) corresponded to eight aromatic protons and were due to the presence of two 3-chlorobenzoyl groups. By complete analysis of the IR and 1 H-NMR spectra, the structure of the compound was ascertained as 5'-O-N-acetylsulfanilyl-2',3'-di-O-(3-chlorobenzoyl)uridine (12). After similar solvent removal and chromatographic techniques, the 4-chlorobenzoyl derivative (13) was isolated in good yield.…”

Section: Compound No Rt (H) Rf Yield (%) Physical Statementioning

confidence: 99%

“…Treatment of compound 2 with 3-chlorobenzoyl chloride and silica gel chromatographic purification, furnished the 2',3'-substitution product (12). In its 1 H-NMR spectrum, the peaks at δ 7.92 (2H, J = 7.5 Hz), δ 7.90 (2H, s), δ 7.79 (2H, J = 7.7 Hz) and δ 7.48 (2H, J = 7.6 Hz) corresponded to eight aromatic protons and were due to the presence of two 3-chlorobenzoyl groups.…”

Section: Compound No Rt (H) Rf Yield (%) Physical Statementioning

confidence: 99%

“…Table 2. Physicochemical properties of the synthesized of uridine derivatives (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14).…”

Section: Scheme 1 Synthesis Of 5'-o-n-acetylsulfanilyluridine (2)mentioning

confidence: 99%

“…Synthesis of 2',3'-di-O-acylated uridine derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14).…”

Section: Scheme 1 Synthesis Of 5'-o-n-acetylsulfanilyluridine (2)mentioning

confidence: 99%

“…From literature survey revealed that a large number of biologically active compounds possess aromatic and heteroaromatic nucleus and acyl substituents [12] [13]. It is also known that, if an active nucleus is linked to another nucleus, the resulting molecule may possess greater potential for biological activity [14].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities

Kawsar¹,

Ara²,

Uddin³

et al. 2015

IJOC

View full text Add to dashboard Cite

A new N-acetylsulfanilylation series of uridine have been synthesized in good yield using direct acylation method and afforded the 5'-O-N-acetylsulfanilyluridine. In order to obtain newer products, the 5'-O-N-acetylsulfanilyluridine derivative was further transformed to a series of 2',3'-di-Oacyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were confirmed on the basis of their FTIR, 1 H-NMR spectroscopy, physicochemical properties and elemental analysis. All the synthesized uridine derivatives were tested for their in vitro antibacterial activity against six human pathogenic bacterial strains and for comparison standard antibiotic Ampicillin was also determined. The study revealed that the selectively acylated derivatives 5'-O-N-acetylsulfanilyl-2',3'-di-O-lauroyluridine and 5'-O-N-acetylsulfanilyl-2',3'-di-O-pivaloyluridine showed highest inhibition against Staphylococcus aureus and Bacillus cereus, respectively. We also observed that the introduction of hexanoyl, decanoyl, lauroyl, myristoyl and pivaloyl groups, the antibacterial functionality of the compound uridine increases. Another noteworthy observation was that the uridine derivatives * Corresponding author. S. M. A. Kawsar et al. 233were found comparatively more effective against Gram-positive microorganisms than those of Gram-negative microorganisms. In addition, the test chemicals were also tested for cytotoxicity by brine shrimp lethality bioassay and compounds showed different rate mortality with different concentrations.

show abstract

Section: Compound No Rt (H) Rf Yield (%) Physical Statementioning

confidence: 99%

Section: Compound No Rt (H) Rf Yield (%) Physical Statementioning

confidence: 99%