Pyrimidine Derivatives. V. Structure-Activity Studies of Antihypertensive Quinazoline Derivatives Using the Adaptive Least-Squares Method
The structure-activity relationships of thirty 2-(4-cinnamoyl-1-piperazinyl)-6, 7-dimethoxy-4-quinazolinamine derivatives for antihypertensive activity were analyzed by the adaptive least-squares (ALS) method. When the retention index (ΔRI) obtained from a C-18 reversed-phase column high-pressure li...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1983/08/25, Vol.31(8), pp.2779-2785 |
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| container_end_page | 2785 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | SEKIYA, TETSUO IMADA, SATOSHI HATA, SHUNSUKE YAMADA, SHUNICHI |
| description | The structure-activity relationships of thirty 2-(4-cinnamoyl-1-piperazinyl)-6, 7-dimethoxy-4-quinazolinamine derivatives for antihypertensive activity were analyzed by the adaptive least-squares (ALS) method. When the retention index (ΔRI) obtained from a C-18 reversed-phase column high-pressure liquid chromatography system was used as a lipophilic parameter, the discriminant equation L=-1.022ΔRI-2.560ΣσPh-1.966IPh(2-OR)+0.799 gave the best prediction, where L is the discriminant score, Σσph is the sum of the Hammett substituent constants of the substituents on the phenyl group and Iph(2-OR) is an indicator variable assigned a value of 1 for the presence of 2-alkoxy groups on the phenyl group. The effects of the lipophilicity and electronic character of substituents on the activity are discussed. |
| doi_str_mv | 10.1248/cpb.31.2779 |
| format | Article |
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When the retention index (ΔRI) obtained from a C-18 reversed-phase column high-pressure liquid chromatography system was used as a lipophilic parameter, the discriminant equation L=-1.022ΔRI-2.560ΣσPh-1.966IPh(2-OR)+0.799 gave the best prediction, where L is the discriminant score, Σσph is the sum of the Hammett substituent constants of the substituents on the phenyl group and Iph(2-OR) is an indicator variable assigned a value of 1 for the presence of 2-alkoxy groups on the phenyl group. The effects of the lipophilicity and electronic character of substituents on the activity are discussed.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.31.2779</identifier><identifier>PMID: 6652822</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Antihypertensive Agents ; Biological and medical sciences ; General pharmacology ; hydrophobic parameter ; Medical sciences ; Pharmacology. Drug treatments ; Physicochemical properties. 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V. Structure-Activity Studies of Antihypertensive Quinazoline Derivatives Using the Adaptive Least-Squares Method</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The structure-activity relationships of thirty 2-(4-cinnamoyl-1-piperazinyl)-6, 7-dimethoxy-4-quinazolinamine derivatives for antihypertensive activity were analyzed by the adaptive least-squares (ALS) method. When the retention index (ΔRI) obtained from a C-18 reversed-phase column high-pressure liquid chromatography system was used as a lipophilic parameter, the discriminant equation L=-1.022ΔRI-2.560ΣσPh-1.966IPh(2-OR)+0.799 gave the best prediction, where L is the discriminant score, Σσph is the sum of the Hammett substituent constants of the substituents on the phenyl group and Iph(2-OR) is an indicator variable assigned a value of 1 for the presence of 2-alkoxy groups on the phenyl group. The effects of the lipophilicity and electronic character of substituents on the activity are discussed.</description><subject>Antihypertensive Agents</subject><subject>Biological and medical sciences</subject><subject>General pharmacology</subject><subject>hydrophobic parameter</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Physicochemical properties. Structure-activity relationships</subject><subject>Quinazolines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkU9v1DAQxS0EKtvCiTOSJSouKMH_ktjHVUsBaRGgUq6W40y6XmWT1HYqLd-Ab42jjRapF1ua9_O88TyE3lCSUybkRzvWOac5qyr1DK0oF1VWMMafoxUhRGWMl_wlOg9hRwgrSMXP0FlZFkwytkJ_fxy827vG9YCvwbtHE90jhBz_zvFt9JONk4dsbVPVxUMqTY2DgIcWr_votocRfIQ-pDf45-R682fonrTCd8H19zhuAa8bM841vAETYnb7MBmfgG8Qt0PzCr1oTRfg9XJfoLubT7-uvmSb75-_Xq03mRWSqcwYwRpoRW1ZKy0vjBUtFWXNJDfAG2ZUo3gNnNSskIUkQsmiTB-XtCVt2TB-gd4f-45-eJggRL13wULXmR6GKWhJZFpTVSXw3RNwN0y-T7NpKgqlhBClTNSHI2X9EIKHVo9pocYfNCV6jkeneDSneo4n0W-XnlO9h-bELnkk_XLRTbCma73prQsnTPHkWJQJuz5iuxDNPZx046OzHcyWVBVytl2O2f2_vDVeQ8__AX46sXQ</recordid><startdate>1983</startdate><enddate>1983</enddate><creator>SEKIYA, TETSUO</creator><creator>IMADA, SATOSHI</creator><creator>HATA, SHUNSUKE</creator><creator>YAMADA, SHUNICHI</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>1983</creationdate><title>Pyrimidine Derivatives. V. Structure-Activity Studies of Antihypertensive Quinazoline Derivatives Using the Adaptive Least-Squares Method</title><author>SEKIYA, TETSUO ; IMADA, SATOSHI ; HATA, SHUNSUKE ; YAMADA, SHUNICHI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4829-aa42def4bc2f8c35ac4f146b283ae3d2a9d93be30b2585804985600281f0f6d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>Antihypertensive Agents</topic><topic>Biological and medical sciences</topic><topic>General pharmacology</topic><topic>hydrophobic parameter</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Physicochemical properties. Structure-activity relationships</topic><topic>Quinazolines - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SEKIYA, TETSUO</creatorcontrib><creatorcontrib>IMADA, SATOSHI</creatorcontrib><creatorcontrib>HATA, SHUNSUKE</creatorcontrib><creatorcontrib>YAMADA, SHUNICHI</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SEKIYA, TETSUO</au><au>IMADA, SATOSHI</au><au>HATA, SHUNSUKE</au><au>YAMADA, SHUNICHI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pyrimidine Derivatives. V. Structure-Activity Studies of Antihypertensive Quinazoline Derivatives Using the Adaptive Least-Squares Method</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1983</date><risdate>1983</risdate><volume>31</volume><issue>8</issue><spage>2779</spage><epage>2785</epage><pages>2779-2785</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>The structure-activity relationships of thirty 2-(4-cinnamoyl-1-piperazinyl)-6, 7-dimethoxy-4-quinazolinamine derivatives for antihypertensive activity were analyzed by the adaptive least-squares (ALS) method. When the retention index (ΔRI) obtained from a C-18 reversed-phase column high-pressure liquid chromatography system was used as a lipophilic parameter, the discriminant equation L=-1.022ΔRI-2.560ΣσPh-1.966IPh(2-OR)+0.799 gave the best prediction, where L is the discriminant score, Σσph is the sum of the Hammett substituent constants of the substituents on the phenyl group and Iph(2-OR) is an indicator variable assigned a value of 1 for the presence of 2-alkoxy groups on the phenyl group. The effects of the lipophilicity and electronic character of substituents on the activity are discussed.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>6652822</pmid><doi>10.1248/cpb.31.2779</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1983/08/25, Vol.31(8), pp.2779-2785 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Antihypertensive Agents Biological and medical sciences General pharmacology hydrophobic parameter Medical sciences Pharmacology. Drug treatments Physicochemical properties. Structure-activity relationships Quinazolines - pharmacology Structure-Activity Relationship |
| title | Pyrimidine Derivatives. V. Structure-Activity Studies of Antihypertensive Quinazoline Derivatives Using the Adaptive Least-Squares Method |
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