Platelet Aggregation Inhibitors. X. S-Substituted 2-Thioadenosines and Their Derivatives
A series of S-substituted 2-thioadenosines (IV) were prepared by treatment of 2-thioadenosine (III) with a requisite halide in NaOH-H2O, NaOH-H2O-EtOH, Na/dimeth-ylformamide, NaOMe/dimethylformamide or NaH/dimethylformamide. N-Substituted 2-aminoadenosines (V) were obtained by treatment of 2-chloroa...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1977/10/25, Vol.25(10), pp.2624-2637 |
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| container_issue | 10 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | KIKUGAWA, KIYOMI SUEHIRO, HIDEO AOKI, AKIJI |
| description | A series of S-substituted 2-thioadenosines (IV) were prepared by treatment of 2-thioadenosine (III) with a requisite halide in NaOH-H2O, NaOH-H2O-EtOH, Na/dimeth-ylformamide, NaOMe/dimethylformamide or NaH/dimethylformamide. N-Substituted 2-aminoadenosines (V) were obtained by treatment of 2-chloroadenosine (II) with a requisite amine. Compounds (IV and V) and N-oxide derivatives of them were tested as inhibitors of adenosine 5'-diphosphate- and collagen-induced rabbit platelet aggregation. 2-Cycloalkyl- or 2-polycycloalkylthioadenosines (IV7-9), water-soluble 2-piperazino-ethylthioadenosines (IV16-19) and 2-thioadenosine N-oxide (X2) were found effective. Most of them showed long lasting activity during the incubation with rabbit plasma. Compounds (IV7-9) were also inhibitory against human platelet aggregation. |
| doi_str_mv | 10.1248/cpb.25.2624 |
| format | Article |
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Compounds (IV and V) and N-oxide derivatives of them were tested as inhibitors of adenosine 5'-diphosphate- and collagen-induced rabbit platelet aggregation. 2-Cycloalkyl- or 2-polycycloalkylthioadenosines (IV7-9), water-soluble 2-piperazino-ethylthioadenosines (IV16-19) and 2-thioadenosine N-oxide (X2) were found effective. Most of them showed long lasting activity during the incubation with rabbit plasma. Compounds (IV7-9) were also inhibitory against human platelet aggregation.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.25.2624</identifier><identifier>PMID: 589709</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Adenosine - pharmacology ; Animals ; Depression, Chemical ; Humans ; In Vitro Techniques ; Platelet Aggregation - drug effects ; platelet aggregometer ; Rabbits ; Thionucleosides - pharmacology</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1977/10/25, Vol.25(10), pp.2624-2637</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 1977</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3244-a1bc7485dd975d66db9faf8d06258001282cd1cfe4c2502cc1f5a4dafee260433</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/589709$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>KIKUGAWA, KIYOMI</creatorcontrib><creatorcontrib>SUEHIRO, HIDEO</creatorcontrib><creatorcontrib>AOKI, AKIJI</creatorcontrib><title>Platelet Aggregation Inhibitors. X. S-Substituted 2-Thioadenosines and Their Derivatives</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of S-substituted 2-thioadenosines (IV) were prepared by treatment of 2-thioadenosine (III) with a requisite halide in NaOH-H2O, NaOH-H2O-EtOH, Na/dimeth-ylformamide, NaOMe/dimethylformamide or NaH/dimethylformamide. N-Substituted 2-aminoadenosines (V) were obtained by treatment of 2-chloroadenosine (II) with a requisite amine. Compounds (IV and V) and N-oxide derivatives of them were tested as inhibitors of adenosine 5'-diphosphate- and collagen-induced rabbit platelet aggregation. 2-Cycloalkyl- or 2-polycycloalkylthioadenosines (IV7-9), water-soluble 2-piperazino-ethylthioadenosines (IV16-19) and 2-thioadenosine N-oxide (X2) were found effective. Most of them showed long lasting activity during the incubation with rabbit plasma. Compounds (IV7-9) were also inhibitory against human platelet aggregation.</description><subject>Adenosine - pharmacology</subject><subject>Animals</subject><subject>Depression, Chemical</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>Platelet Aggregation - drug effects</subject><subject>platelet aggregometer</subject><subject>Rabbits</subject><subject>Thionucleosides - pharmacology</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1977</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkEtr3DAUhUXpa5p21W0XhkA3xa509bC1DGnTBgItZArZCVm6ntHgsaeSHOi_r4YZUujm3sX5-DgcQt4z2jAQ3Wd36BuQDSgQz8iKcdHWEoA_JytKqa6BK_6avElpRylI2vJX5KXsdEv1ijz8HG3GEXN1tdlE3Ngc5qm6nbahD3mOqakemuq-vl_6lENeMvoK6vU2zNbjNKcwYars5Kv1FkOsvmAMj0XxiOkteTHYMeG7878gv26-rq-_13c_vt1eX93VjoMQtWW9a0Unvdet9Er5Xg926DxVIDtKGXTgPHMDCleqg3NskFZ4OyCCooLzC_Lx5D3E-feCKZt9SA7H0U44L8m0vFWUqbaAl_-Bu3mJU-lmmJC6A61AF-rTiXJxTiniYA4x7G38Yxg1x7FNGduANMexC_3h7Fz6Pfon9rRuiW9O8S5lu8Gn2MYc3IhHFdOyO-qK_XyL9x-wtdHgxP8CJSyR8Q</recordid><startdate>197710</startdate><enddate>197710</enddate><creator>KIKUGAWA, KIYOMI</creator><creator>SUEHIRO, HIDEO</creator><creator>AOKI, AKIJI</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>197710</creationdate><title>Platelet Aggregation Inhibitors. X. S-Substituted 2-Thioadenosines and Their Derivatives</title><author>KIKUGAWA, KIYOMI ; SUEHIRO, HIDEO ; AOKI, AKIJI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3244-a1bc7485dd975d66db9faf8d06258001282cd1cfe4c2502cc1f5a4dafee260433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1977</creationdate><topic>Adenosine - pharmacology</topic><topic>Animals</topic><topic>Depression, Chemical</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>Platelet Aggregation - drug effects</topic><topic>platelet aggregometer</topic><topic>Rabbits</topic><topic>Thionucleosides - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KIKUGAWA, KIYOMI</creatorcontrib><creatorcontrib>SUEHIRO, HIDEO</creatorcontrib><creatorcontrib>AOKI, AKIJI</creatorcontrib><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>KIKUGAWA, KIYOMI</au><au>SUEHIRO, HIDEO</au><au>AOKI, AKIJI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Platelet Aggregation Inhibitors. X. S-Substituted 2-Thioadenosines and Their Derivatives</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1977-10</date><risdate>1977</risdate><volume>25</volume><issue>10</issue><spage>2624</spage><epage>2637</epage><pages>2624-2637</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A series of S-substituted 2-thioadenosines (IV) were prepared by treatment of 2-thioadenosine (III) with a requisite halide in NaOH-H2O, NaOH-H2O-EtOH, Na/dimeth-ylformamide, NaOMe/dimethylformamide or NaH/dimethylformamide. N-Substituted 2-aminoadenosines (V) were obtained by treatment of 2-chloroadenosine (II) with a requisite amine. Compounds (IV and V) and N-oxide derivatives of them were tested as inhibitors of adenosine 5'-diphosphate- and collagen-induced rabbit platelet aggregation. 2-Cycloalkyl- or 2-polycycloalkylthioadenosines (IV7-9), water-soluble 2-piperazino-ethylthioadenosines (IV16-19) and 2-thioadenosine N-oxide (X2) were found effective. Most of them showed long lasting activity during the incubation with rabbit plasma. Compounds (IV7-9) were also inhibitory against human platelet aggregation.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>589709</pmid><doi>10.1248/cpb.25.2624</doi><tpages>14</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1977/10/25, Vol.25(10), pp.2624-2637 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Adenosine - pharmacology Animals Depression, Chemical Humans In Vitro Techniques Platelet Aggregation - drug effects platelet aggregometer Rabbits Thionucleosides - pharmacology |
| title | Platelet Aggregation Inhibitors. X. S-Substituted 2-Thioadenosines and Their Derivatives |
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