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Folate antagonists. 12. Antimalarial and antibacterial effects of 2,4-diamino-6-[(aralkyl and alicyclid)thio-, sulfinyl-, and sulfonyl]quinazolines

A series of 2,4-diamino-6-[(aralkyl and alicyclic)thio-, sulfinyl-, and sulfonyl]quinazolines was prepared via condensation of 5-chloro-2-nitrobenzonitrile or 5,6-dichloro-2-nitrobenzonitrile with the appropriate aralkyl or alicyclic thiopseudourea, reduction of the resulting 2-nitro-5-[(aralkyl or...

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Published in:	Journal of medicinal chemistry 1978-07, Vol.21 (7), p.639-643
Main Authors:	Elslager, E F, Davoll, J, Jacob, P, Johnson, A M, Johnson, J, Werbel, L M
Format:	Article
Language:	English
Subjects:	Animals Anti-Bacterial Agents - chemical synthesis Antimalarials - chemical synthesis Antimalarials - therapeutic use Enterococcus faecalis - drug effects Folic Acid Antagonists - chemical synthesis Folic Acid Antagonists - pharmacology Folic Acid Antagonists - therapeutic use Malaria - drug therapy Mice Microbial Sensitivity Tests Plasmodium berghei Quinazolines - chemical synthesis Quinazolines - pharmacology Quinazolines - therapeutic use Staphylococcus aureus - drug effects
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container_end_page	643
container_issue	7
container_start_page	639
container_title	Journal of medicinal chemistry
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creator	Elslager, E F Davoll, J Jacob, P Johnson, A M Johnson, J Werbel, L M
description	A series of 2,4-diamino-6-[(aralkyl and alicyclic)thio-, sulfinyl-, and sulfonyl]quinazolines was prepared via condensation of 5-chloro-2-nitrobenzonitrile or 5,6-dichloro-2-nitrobenzonitrile with the appropriate aralkyl or alicyclic thiopseudourea, reduction of the resulting 2-nitro-5-[(aralkyl or alicyclic)thio]benzonitrile with stannous chloride to the amine, and cyclization with chloroformamidine hydrochloride. Oxidation was effected with hydrogen peroxide or the bromine complex of 1,4-diazabicyclo[2.2.2]octane. These analogues when examined for suppressive activity against drug-sensitive lines of Plasmodium berghei in mice were not as active as 2,4-diamino-6-[3,4-dichlorobenzyl)amino]quinazoline (Ia).
doi_str_mv	10.1021/jm00205a009
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Antimalarial and antibacterial effects of 2,4-diamino-6-[(aralkyl and alicyclid)thio-, sulfinyl-, and sulfonyl]quinazolines</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>A series of 2,4-diamino-6-[(aralkyl and alicyclic)thio-, sulfinyl-, and sulfonyl]quinazolines was prepared via condensation of 5-chloro-2-nitrobenzonitrile or 5,6-dichloro-2-nitrobenzonitrile with the appropriate aralkyl or alicyclic thiopseudourea, reduction of the resulting 2-nitro-5-[(aralkyl or alicyclic)thio]benzonitrile with stannous chloride to the amine, and cyclization with chloroformamidine hydrochloride. Oxidation was effected with hydrogen peroxide or the bromine complex of 1,4-diazabicyclo[2.2.2]octane. 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Antimalarial and antibacterial effects of 2,4-diamino-6-[(aralkyl and alicyclid)thio-, sulfinyl-, and sulfonyl]quinazolines</title><author>Elslager, E F ; Davoll, J ; Jacob, P ; Johnson, A M ; Johnson, J ; Werbel, L M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p119t-c7de46a4e33dd4cb35597249d6851d7dcb7773639862d0330d932f46f36b9eba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1978</creationdate><topic>Animals</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Antimalarials - chemical synthesis</topic><topic>Antimalarials - therapeutic use</topic><topic>Enterococcus faecalis - drug effects</topic><topic>Folic Acid Antagonists - chemical synthesis</topic><topic>Folic Acid Antagonists - pharmacology</topic><topic>Folic Acid Antagonists - therapeutic use</topic><topic>Malaria - drug therapy</topic><topic>Mice</topic><topic>Microbial Sensitivity Tests</topic><topic>Plasmodium berghei</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - pharmacology</topic><topic>Quinazolines - therapeutic use</topic><topic>Staphylococcus aureus - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Elslager, E F</creatorcontrib><creatorcontrib>Davoll, J</creatorcontrib><creatorcontrib>Jacob, P</creatorcontrib><creatorcontrib>Johnson, A M</creatorcontrib><creatorcontrib>Johnson, J</creatorcontrib><creatorcontrib>Werbel, L M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Elslager, E F</au><au>Davoll, J</au><au>Jacob, P</au><au>Johnson, A M</au><au>Johnson, J</au><au>Werbel, L M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Folate antagonists. 12. Antimalarial and antibacterial effects of 2,4-diamino-6-[(aralkyl and alicyclid)thio-, sulfinyl-, and sulfonyl]quinazolines</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>1978-07</date><risdate>1978</risdate><volume>21</volume><issue>7</issue><spage>639</spage><epage>643</epage><pages>639-643</pages><issn>0022-2623</issn><abstract>A series of 2,4-diamino-6-[(aralkyl and alicyclic)thio-, sulfinyl-, and sulfonyl]quinazolines was prepared via condensation of 5-chloro-2-nitrobenzonitrile or 5,6-dichloro-2-nitrobenzonitrile with the appropriate aralkyl or alicyclic thiopseudourea, reduction of the resulting 2-nitro-5-[(aralkyl or alicyclic)thio]benzonitrile with stannous chloride to the amine, and cyclization with chloroformamidine hydrochloride. Oxidation was effected with hydrogen peroxide or the bromine complex of 1,4-diazabicyclo[2.2.2]octane. These analogues when examined for suppressive activity against drug-sensitive lines of Plasmodium berghei in mice were not as active as 2,4-diamino-6-[3,4-dichlorobenzyl)amino]quinazoline (Ia).</abstract><cop>United States</cop><pmid>97382</pmid><doi>10.1021/jm00205a009</doi><tpages>5</tpages></addata></record>
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source	ACS CRKN Legacy Archives
subjects	Animals Anti-Bacterial Agents - chemical synthesis Antimalarials - chemical synthesis Antimalarials - therapeutic use Enterococcus faecalis - drug effects Folic Acid Antagonists - chemical synthesis Folic Acid Antagonists - pharmacology Folic Acid Antagonists - therapeutic use Malaria - drug therapy Mice Microbial Sensitivity Tests Plasmodium berghei Quinazolines - chemical synthesis Quinazolines - pharmacology Quinazolines - therapeutic use Staphylococcus aureus - drug effects
title	Folate antagonists. 12. Antimalarial and antibacterial effects of 2,4-diamino-6-[(aralkyl and alicyclid)thio-, sulfinyl-, and sulfonyl]quinazolines
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