volume 21 issue 23 pages 4801-4809

Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity

Liban Saney 1
Tharindi Panduwawala 1
Xiang Li 1, 2
Kirsten E. Christensen 1
Miroslav Genov 3
Alexander Pretsch 3
Dagmar Pretsch 3
Mark G Moloney 1, 4
3
 
Oxford Antibiotic Group, The Oxford Science Park, Magdalen Centre, Oxford OX4 4GA, UK
4
 
Oxford Suzhou Centre for Advanced Research, Suzhou Industrial Park, Building A, 388 Ruo Shui Road, Jiangsu, 215123, P. R. China
Publication typeJournal Article
Publication date2023-05-26
scimago Q2
wos Q2
SJR0.600
CiteScore5.2
Impact factor2.7
ISSN14770520, 14770539
PubMed ID:  37232452
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A chemoselective route which provides direct access to bicyclic tetramates, making use of Dieckmann cyclisation of functionalised oxazolidines and imidazolidines derived from an aminomalonate, is reported; calculations suggest that the observed chemoselectivity is kinetically controlled and leads to the thermodynamically most stable product. Some compounds in the library showed modest antibacterial activity against Gram-positive bacteria, and this activity is maximal in a well-defined region of chemical space (554 < Mw < 722 g mol−1; 5.78 < cLogP < 7.16; 788 < MSA < 972 Å2; 10.3 < rel. PSA < 19.08).
Found 
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Saney L. et al. Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity // Organic and Biomolecular Chemistry. 2023. Vol. 21. No. 23. pp. 4801-4809.
GOST all authors (up to 50) Copy
Saney L., Panduwawala T., Li X., Christensen K. E., Genov M., Pretsch A., Pretsch D., G Moloney M. Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity // Organic and Biomolecular Chemistry. 2023. Vol. 21. No. 23. pp. 4801-4809.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1039/d3ob00594a
UR - https://xlink.rsc.org/?DOI=D3OB00594A
TI - Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity
T2 - Organic and Biomolecular Chemistry
AU - Saney, Liban
AU - Panduwawala, Tharindi
AU - Li, Xiang
AU - Christensen, Kirsten E.
AU - Genov, Miroslav
AU - Pretsch, Alexander
AU - Pretsch, Dagmar
AU - G Moloney, Mark
PY - 2023
DA - 2023/05/26
PB - Royal Society of Chemistry (RSC)
SP - 4801-4809
IS - 23
VL - 21
PMID - 37232452
SN - 1477-0520
SN - 1477-0539
ER -
BibTex |
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BibTex (up to 50 authors) Copy
@article{2023_Saney,
author = {Liban Saney and Tharindi Panduwawala and Xiang Li and Kirsten E. Christensen and Miroslav Genov and Alexander Pretsch and Dagmar Pretsch and Mark G Moloney},
title = {Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity},
journal = {Organic and Biomolecular Chemistry},
year = {2023},
volume = {21},
publisher = {Royal Society of Chemistry (RSC)},
month = {may},
url = {https://xlink.rsc.org/?DOI=D3OB00594A},
number = {23},
pages = {4801--4809},
doi = {10.1039/d3ob00594a}
}
MLA
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MLA Copy
Saney, Liban, et al. “Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity.” Organic and Biomolecular Chemistry, vol. 21, no. 23, May. 2023, pp. 4801-4809. https://xlink.rsc.org/?DOI=D3OB00594A.