Synthesis and biological evaluation of some new thioether-ester crown ethers

Article abstract of DOI:10.1080/10426500600917060

New thioether-ester crown ethers have been synthesized starting from oxalyl chloride and different β,β′-dihydroxydithioethers. The synthesized compounds are screened for their antibacterial activity. Among the macrocyclic thioether-esters (5a-j), only 5,12-di[(allyloxy)methyl]-1,4-dioxa-7, 10-dithiacyclododecane-2,3-dione (5e) and 5,12-di(isopropoxymethyl)-1,4-dioxa-7, 10-dithiacyclododecane-2,3-dione (5f) were effective inhibitors against Staphilococcus aureus methicillin resistance and Pseudomanas aeruginosa with an MIC value of 525 and 265 μM. Structures of the synthesized compounds have been confirmed by ¹H NMR, ¹³C NMR, and MS spectral studies. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500600917060

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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Synthesis and Biological
Evaluation of Some New
Thioether-Ester Crown Ethers
Seyed Mohammad Seyedi a , Ali Sadeghian b , Hamid
Sadeghian a , Ayla Hazrathoseyni a & Mohammad
Sadeghian c
a Department of Chemistry , Ferdowsi University of
Mashhad , Mashhad, I. R. Iran
b Department of Microbiology , Ghaem Hospital ,
Mashhad, I. R. Iran
c Faculty of Medicine , Medical University of
Mashhad , Mashhad, I. R. Iran
Published online: 18 Feb 2007.
To cite this article: Seyed Mohammad Seyedi , Ali Sadeghian , Hamid Sadeghian ,
Ayla Hazrathoseyni & Mohammad Sadeghian (2007) Synthesis and Biological Evaluation
of Some New Thioether-Ester Crown Ethers, Phosphorus, Sulfur, and Silicon and the
Related Elements, 182:2, 265-272, DOI: 10.1080/10426500600917060
To link to this article: http://dx.doi.org/10.1080/10426500600917060
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Phosphorus, Sulfur, and Silicon, 182:265–272, 2007
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500600917060
Synthesis and Biological Evaluation of Some New
Thioether-Ester Crown Ethers
Seyed Mohammad Seyedi
Department of Chemistry, Ferdowsi University of Mashhad,
Mashhad, I. R. Iran
Ali Sadeghian
Department of Microbiology, Ghaem Hospital, Mashhad, I. R. Iran
Hamid Sadeghian
Ayla Hazrathoseyni
Department of Chemistry, Ferdowsi University of Mashhad,
Mashhad, I. R. Iran
Mohammad Sadeghian
Faculty of Medicine, Medical University of Mashhad, Mashhad,
I. R. Iran
New thioether-ester crown ethers have been synthesized starting from oxalyl
chloride and different β,βꢀ-dihydroxydithioethers. The synthesized compounds
are screened for their antibacterial activity. Among the macrocyclic thioether-
esters (5a–j), only 5,12-di[(allyloxy)methyl]-1,4-dioxa-7,10-dithiacyclododecane-
2,3-dione (5e) and 5,12-di(isopropoxymethyl)-1,4-dioxa-7,10-dithiacyclododecane-
2,3-dione (5f) were effective inhibitors against Staphilococcus aureus methicillin
resistance and Pseudomanas aeruginosa with an MIC value of 525 and 265
1
μM. Structures of the synthesized compounds have been confirmed by H NMR,
13
C NMR, and MS spectral studies.
Keywords Dihydroxydithioethers; Pseudomanas aeruginosa; Staphilococcus aureus;
thioether-ester crown ethers
Received May 15, 2006; accepted June 26, 2006.
Address correspondence to Seyed Mohammad Seyedi, Ferdowsi University of
Mashhad, Department of Chemistry, Faculty of Sciences, Mashhad, 91775 I. R. Iran.
E-mail: smseyedi@yahoo.com
265

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266
S. M. Seyedi et al.
INTRODUCTION
β,βꢀ-dihydroxydithioethers with two α,αꢀ-substations have been re-
cently synthesized.1 The two secondary β,βꢀ-dihydroxy groups make
these compounds susceptible reagents to synthesize new thiocrown
ethers possessing various sidearms.2,3 Biological activities of such
sidearmed crownethers have been studied3 but no biological evalua-
tions have been reported on β,βꢀ-dihydroxydithioethers and their cor-
responding thiocrown ethers. In this article, we describe the synthesis
of β,βꢀ-dihydroxydithioether (3a–j) and their corresponding thioether-
ester crown ethers (5a–j). The antibacterial activity of these compounds
is also investigated.
RESULTS
Synthesis
β,βꢀ-dihydroxydithioether (3a) and the mixture of two diastreomrers1
of its derivatives (3b–j) were prepared by the action of two
mole equivalents of oxiranes (1a–j) with dimercaptoehane (2) us-
ing benzyltrimethylammonium hydroxide (Triton B) as a catalyst1
(Scheme 1). All dihydroxy compounds showed one spot on TLC except
the (3d), which was a mixture and was purified by column chromatogra-
phy (silica gel 60, 0.04–0.067 mm, hexane-ethylacetate 1:1). Treatment
of dihydroxy compounds (3a–i) and (3j) with oxalyl chloride (4) under a
basic condition of triehtylamine in dried dichloromethane afforded 5,12-
disubstituted 1,4-dioxa-7,10-dithiacyclododecane-2,3-diones (5a–i) and
perhydrodibenzo[e,k][1,4,7,10]dioxadithiacyclododecine-6,7-dione (5j),
respectively4 (Scheme 1).
Biological Evaluations
Antibacterial activities of β,βꢀ-dihydroxydithioethers (3a–j) and their
corresponding thioether-ester crown ether (5a–j) were evaluated. MIC
values, i.e., the lowest concentration of a drug that prevents growth of a
particular pathogen,5 of (3a–j) and (5a–j) against two strains of bacteria
S. aureus methicilin resistance and P. aeruginosa were measured. Ten
isolated strains of S. aureus and P. aeruginosa from different organs of
patients at the Microbiological Laboratory of Ghaem Hospital of Med-
ical University of Mashhad–Iran were tested. Oxacillin (for S. aureus)
and Gentamycin (for P. aeruginosa) were used as a positive control in all
tests, and their MIC values were expressed in μM. Among the synthe-
sized compounds (3a–j) and (5a–j), only (5e) and (5f) showed significant