Bioorganic and Medicinal Chemistry Letters, volume 19, issue 1, pages 136-141
One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1,2,3-dithiazoles and evaluation of their antimicrobial and antitumor activity
Rakitin Oleg A
,
Bolshakov Oleg I
1
,
Laborie Hélène
2
,
Tanga Annabelle
2
,
Sopéna Valérie
2
,
Lanneluc Isabelle
,
Picot Laurent
,
Sablé Sophie
2
,
Thiéry Valérie
,
Lanneluc I.
2
,
Picot Laurent
2
,
Thiéry Valérie
2
,
2
Université de La Rochelle, UMR CNRS 6250, LIENSs, Bât. Curie, Equipe ‘Molécules à Activités Biologiques’, Avenue Michel Crépeau, F-17042 La Rochelle, France
|
Publication type: Journal Article
Publication date: 2009-01-01
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.7
ISSN: 0960894X, 14643405
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
We here report the synthesis and biological evaluation of rare 4-substituted-5-phenylimino, 5-thieno- and 5-oxo-1,2,3-dithiazoles. Dithiazoles were selectively obtained in moderate to high yields (25-73%) via a one-pot reaction from various ethanoneoximes with sulfur monochloride, pyridine in acetonitrile followed by treatment by corresponding nucleophiles (aniline, thioacetamide and formic acid). All the synthesized compounds were screened for their antibacterial (against bacteria Escherichia coli, Salmonellaenterica serovar Typhimurium, Klebsiella pneumoniae, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Bacillus cereus and Listeria inocua), antifungal (against pathogenic strains Candida albicans, Candida glabrata, Candida tropicalis and Issatchenkia orientalis) and antitumor (on human cell lines MCF-7 and MDA-MB-231) activity. 4-(2-Pyridinyl)-5H-1,2,3-dithiazole-5-thione and 4-ethylcarboxyl-5H-1,2,3-dithiazole-5-thione (5d, 5h) that are active against Gram-positive bacteria are significantly active against fungi. 4-(2-Benzofuranyl)-5-phenylimino-5H-1,2,3-dithiazole (4e) exerts antiproliferative activity.
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Konstantinova L. S. et al. One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1,2,3-dithiazoles and evaluation of their antimicrobial and antitumor activity // Bioorganic and Medicinal Chemistry Letters. 2009. Vol. 19. No. 1. pp. 136-141.
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Konstantinova L. S., Bolshakov O. I., Obruchnikova N. V., Laborie H., Tanga A., Sopéna V., Lanneluc I., Picot L., Sablé S., Thiéry V., Rakitin O. A., Lanneluc I., Picot L., Thiéry V., Rakitin O. A. One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1,2,3-dithiazoles and evaluation of their antimicrobial and antitumor activity // Bioorganic and Medicinal Chemistry Letters. 2009. Vol. 19. No. 1. pp. 136-141.
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TY - JOUR
DO - 10.1016/J.BMCL.2008.11.010
UR - https://doi.org/10.1016%2FJ.BMCL.2008.11.010
TI - One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1,2,3-dithiazoles and evaluation of their antimicrobial and antitumor activity
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Konstantinova, Lidia S.
AU - Bolshakov, Oleg I
AU - Obruchnikova, Natalia V.
AU - Laborie, Hélène
AU - Tanga, Annabelle
AU - Sopéna, Valérie
AU - Lanneluc, Isabelle
AU - Picot, Laurent
AU - Sablé, Sophie
AU - Thiéry, Valérie
AU - Rakitin, Oleg A
AU - Lanneluc, I.
AU - Picot, Laurent
AU - Thiéry, Valérie
AU - Rakitin, Oleg A.
PY - 2009
DA - 2009/01/01 00:00:00
PB - Elsevier
SP - 136-141
IS - 1
VL - 19
SN - 0960-894X
SN - 1464-3405
ER -
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@article{2009_Konstantinova,
author = {Lidia S. Konstantinova and Oleg I Bolshakov and Natalia V. Obruchnikova and Hélène Laborie and Annabelle Tanga and Valérie Sopéna and Isabelle Lanneluc and Laurent Picot and Sophie Sablé and Valérie Thiéry and Oleg A Rakitin and I. Lanneluc and Laurent Picot and Valérie Thiéry and Oleg A. Rakitin},
title = {One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1,2,3-dithiazoles and evaluation of their antimicrobial and antitumor activity},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2009},
volume = {19},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016%2FJ.BMCL.2008.11.010},
number = {1},
pages = {136--141},
doi = {10.1016/J.BMCL.2008.11.010}
}
Cite this
MLA
Copy
Konstantinova, Lidia S., et al. “One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1,2,3-dithiazoles and evaluation of their antimicrobial and antitumor activity.” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 1, Jan. 2009, pp. 136-141. https://doi.org/10.1016%2FJ.BMCL.2008.11.010.