Synthesis, reactions and conformational analysis of 5-arylidene-2-thiohydantoins as potential antiviral agents

Article abstract of DOI:10.1080/10426500108040603

(Z)-5-Arylidene-1-(4-methylphenylsulfonyl)-2-thiohydantoins 5a,b were synthesized from the direct condensation of the aromatic aldehydes 4a,b with 1-(4-methylphenylsulfonyl)-2-thiohydantoins 3a,b. Compounds 5a,b were coupled with 2′-deoxy-3′,5′-di(4-methylbenzoyl)-α-D-erythro-pentofura nosyl chloride 6 under alkaline conditions to afford N₃-protected nucleosides 7a,b. Reaction of 5a,b with chloromethyl methyl sulfide and/or 2-bromoacetaldehyde diethyl acetal in alkaline medium afforded N₃-alkyl derivatives 8a-c. Reaction of 5a with 1,2-dichloroethane in alkaline conditions afforded bis-thiohydantoinylethane 9a,b. Compounds 5a,b were condensed with formaldehyde and secondary amines to afford 3-aminomethyl-2-thiohydantoins derivatives 10a-d. On the other hand, reaction of unsubstituted 2-thiohydantoins derivatives 11b,c with chloromethyl methyl sulfide afforded the mono- and bis-methylthio derivatives 12a,b and 13a,b, respectively. Reaction of 11b,c with secondary amines and formaldehyde gave 3-aminomethyl-2-thiohydantoins 14a-e. Reaction of 11a-C with bromoacetaldehyde diethyl acetal yielded the S-alkyl derivatives 15a-c which can be hydrolysed with ethanolic hydrochloric acid to afford 5-arylidenehydantoins 16a-c. The compounds do not display any antiviral activity.

Full text of DOI:10.1080/10426500108040603

This article was downloaded by: [Laurentian University]
On: 29 October 2013, At: 07:44
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Phosphorus, Sulfur, and Silicon
and the Related Elements
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/gpss20
SYNTHESIS, REACTIONS
AND CONFORMATIONAL
ANALYSIS OF 5-ARYLIDENE-2-
THIOHYDANTOINS AS
POTENTIAL ANTIVIRAL AGENTS
A. I. Khodair a , A. A. El-barbary b , Y. A. Abbas a &
D. R. Imam a
a Chemistry Department, Faculty of Education ,
Tanta University , Kafr El-Sheikh Branch, Kafr El-
Sheikh, Egypt
b Chemistry Department, Faculty of science , Tanta
University , Tanta, Egypt
Published online: 27 Oct 2006.
To cite this article: A. I. Khodair , A. A. El-barbary , Y. A. Abbas & D. R. Imam
(2001) SYNTHESIS, REACTIONS AND CONFORMATIONAL ANALYSIS OF 5-ARYLIDENE-2-
THIOHYDANTOINS AS POTENTIAL ANTIVIRAL AGENTS, Phosphorus, Sulfur, and Silicon
and the Related Elements, 170:1, 261-278, DOI: 10.1080/10426500108040603
To link to this article: http://dx.doi.org/10.1080/10426500108040603
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and

are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions