Formation and antimicrobial activity of 2-azetidinones from selective ester cleavage in 1,3,3-trisubstituted4-[2′-(O-diarylacyl)hydroxyphenyl]-2- azetidinones

G. S. Singh, T. Pheko

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Treatment of the 1,3,3-trisubstituted 4-[2′-(O-diarylacyl)- hydroxyphenyl]-2-azetidinones with sodium hydroxide in ethanol at room temperature lead to selective cleavage of the ester linkage in the substrates forming new 1,3,3-trisubstituted 4-(2′-hydroxyphenyl)-2-azetidinones, which have been characterized on the basis of analytical and spectral (IR, 1H and 13C NMR, MS) data. The structure elucidation also involves application of the HMQC and HMBC studies using 2-D NMR ( 1H-13C COSY) spectra. The antibacterial and antifungal activities of the products are reported.

Original languageEnglish
Pages (from-to)159-162
Number of pages4
JournalIndian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Volume47
Issue number1
Publication statusPublished - Jan 1 2008

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Esters
Nuclear magnetic resonance
Sodium Hydroxide
Ethanol
Temperature
Substrates
2-azetidinone
Carbon-13 Magnetic Resonance Spectroscopy
Proton Magnetic Resonance Spectroscopy
vitamin B 12 factor III

All Science Journal Classification (ASJC) codes

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

Cite this

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abstract = "Treatment of the 1,3,3-trisubstituted 4-[2′-(O-diarylacyl)- hydroxyphenyl]-2-azetidinones with sodium hydroxide in ethanol at room temperature lead to selective cleavage of the ester linkage in the substrates forming new 1,3,3-trisubstituted 4-(2′-hydroxyphenyl)-2-azetidinones, which have been characterized on the basis of analytical and spectral (IR, 1H and 13C NMR, MS) data. The structure elucidation also involves application of the HMQC and HMBC studies using 2-D NMR ( 1H-13C COSY) spectra. The antibacterial and antifungal activities of the products are reported.",
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AU - Pheko, T.

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AB - Treatment of the 1,3,3-trisubstituted 4-[2′-(O-diarylacyl)- hydroxyphenyl]-2-azetidinones with sodium hydroxide in ethanol at room temperature lead to selective cleavage of the ester linkage in the substrates forming new 1,3,3-trisubstituted 4-(2′-hydroxyphenyl)-2-azetidinones, which have been characterized on the basis of analytical and spectral (IR, 1H and 13C NMR, MS) data. The structure elucidation also involves application of the HMQC and HMBC studies using 2-D NMR ( 1H-13C COSY) spectra. The antibacterial and antifungal activities of the products are reported.

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