Reactions of 1-Nitroso-1-phenyl-3-(4-pyridylmethyl)ureas
Treatment of 1-nitroso-1-phenyl- and 1-nitroso-1-(4-tolyl)-3-(4-pyridylmethyl)ureas (Ia, b) with methanol and ethanol at room temperature gave methyl and ethyl N-(4-pyridylmethyl)-carbamates (IIIa, b) in almost quantitative yields, together with benzene (IVa) and toluene (IVb), respectively. Treatme...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1986/01/25, Vol.34(1), pp.385-389 |
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| creator | KAMIYA, SHOZO MIYAHARA, MAKOTO MIYAHARA, MICHIKO |
| description | Treatment of 1-nitroso-1-phenyl- and 1-nitroso-1-(4-tolyl)-3-(4-pyridylmethyl)ureas (Ia, b) with methanol and ethanol at room temperature gave methyl and ethyl N-(4-pyridylmethyl)-carbamates (IIIa, b) in almost quantitative yields, together with benzene (IVa) and toluene (IVb), respectively. Treatment of Ia, b with benzene at 70°C gave 4-pyridylmethylamine (V) with biphenyl (VIa) and its 4-methyl derivative (VIb), respectively. Treatment of Ia, b with sodium azide in aqueous acetone at -5°C gave 1, 3-bis(4-pyridylmethyl)urea (VII) and phenylazides (VIIIa, b) in more than 90% yields.Compound Ia showed antitumor activity against rat ascites hepatoma AH13, but not against mouse lymphoid leukemia L1210. The mechanisms of these reactions and the mechanism of antitumor action of Ia are discussed |
| doi_str_mv | 10.1248/cpb.34.385 |
| format | Article |
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Treatment of Ia, b with benzene at 70°C gave 4-pyridylmethylamine (V) with biphenyl (VIa) and its 4-methyl derivative (VIb), respectively. Treatment of Ia, b with sodium azide in aqueous acetone at -5°C gave 1, 3-bis(4-pyridylmethyl)urea (VII) and phenylazides (VIIIa, b) in more than 90% yields.Compound Ia showed antitumor activity against rat ascites hepatoma AH13, but not against mouse lymphoid leukemia L1210. 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Pharm. Bull.</addtitle><description>Treatment of 1-nitroso-1-phenyl- and 1-nitroso-1-(4-tolyl)-3-(4-pyridylmethyl)ureas (Ia, b) with methanol and ethanol at room temperature gave methyl and ethyl N-(4-pyridylmethyl)-carbamates (IIIa, b) in almost quantitative yields, together with benzene (IVa) and toluene (IVb), respectively. Treatment of Ia, b with benzene at 70°C gave 4-pyridylmethylamine (V) with biphenyl (VIa) and its 4-methyl derivative (VIb), respectively. Treatment of Ia, b with sodium azide in aqueous acetone at -5°C gave 1, 3-bis(4-pyridylmethyl)urea (VII) and phenylazides (VIIIa, b) in more than 90% yields.Compound Ia showed antitumor activity against rat ascites hepatoma AH13, but not against mouse lymphoid leukemia L1210. The mechanisms of these reactions and the mechanism of antitumor action of Ia are discussed</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>mouse lymphoid leukemia L1210</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><recordid>eNpFkEtPwzAQhC0EEiVw4Rf0wAGQXPza2D6iipdUgYTgbDl-0FRpEtnhkH9PqlblsnuY2dF-g9A1JQvKhHpwfbXgYsEVnKAZ5UJiYIyfohkhRGPGS36OLnLeEMKASD5D6jNYN9Rdm-ddnFP8Xg-pyx2muF-Hdmwwx7cC92Oq_dhsw7Aem7vfFGy-RGfRNjlcHXaBvp-fvpavePXx8rZ8XGEnFBtwiKXWsZIQhPeRME8kxAjAQAIRSjLQnkZuoyspRIiVlR64BmdjCV5VvED3-1w3_ZVTiKZP9dam0VBidsxmYjZcmIl5Mt_szb3NzjYx2dbV-XihSq7V1EeBlnvbJg_2Jxx1m4baNWGXSDWoXSo9DAX_6tomE1r-B5xobZc</recordid><startdate>19860101</startdate><enddate>19860101</enddate><creator>KAMIYA, SHOZO</creator><creator>MIYAHARA, MAKOTO</creator><creator>MIYAHARA, MICHIKO</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19860101</creationdate><title>Reactions of 1-Nitroso-1-phenyl-3-(4-pyridylmethyl)ureas</title><author>KAMIYA, SHOZO ; MIYAHARA, MAKOTO ; MIYAHARA, MICHIKO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c482t-ef699fb75e4ddf02d075ff5525750487259d1f3afc615f5fba7d5395caf65d8b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>mouse lymphoid leukemia L1210</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KAMIYA, SHOZO</creatorcontrib><creatorcontrib>MIYAHARA, MAKOTO</creatorcontrib><creatorcontrib>MIYAHARA, MICHIKO</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KAMIYA, SHOZO</au><au>MIYAHARA, MAKOTO</au><au>MIYAHARA, MICHIKO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reactions of 1-Nitroso-1-phenyl-3-(4-pyridylmethyl)ureas</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1986-01-01</date><risdate>1986</risdate><volume>34</volume><issue>1</issue><spage>385</spage><epage>389</epage><pages>385-389</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Treatment of 1-nitroso-1-phenyl- and 1-nitroso-1-(4-tolyl)-3-(4-pyridylmethyl)ureas (Ia, b) with methanol and ethanol at room temperature gave methyl and ethyl N-(4-pyridylmethyl)-carbamates (IIIa, b) in almost quantitative yields, together with benzene (IVa) and toluene (IVb), respectively. Treatment of Ia, b with benzene at 70°C gave 4-pyridylmethylamine (V) with biphenyl (VIa) and its 4-methyl derivative (VIb), respectively. Treatment of Ia, b with sodium azide in aqueous acetone at -5°C gave 1, 3-bis(4-pyridylmethyl)urea (VII) and phenylazides (VIIIa, b) in more than 90% yields.Compound Ia showed antitumor activity against rat ascites hepatoma AH13, but not against mouse lymphoid leukemia L1210. The mechanisms of these reactions and the mechanism of antitumor action of Ia are discussed</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.34.385</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives mouse lymphoid leukemia L1210 Organic chemistry Preparations and properties |
| title | Reactions of 1-Nitroso-1-phenyl-3-(4-pyridylmethyl)ureas |
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