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Synthesis and evaluation of acylguanidine FXa inhibitors
A series of acylguanidine derivatives were prepared and investigated as inhibitors of Factor Xa (FXa). These compounds were made by guanidine acylation with carboxylic acids using carbonyl diimidazole (CDI) as the coupling reagent. Conditions for the rapid synthesis and purification of these compoun...
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| Published in: | Bioorganic & medicinal chemistry 2008-08, Vol.18 (16), p.4696-4699 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c481t-1daed8cc98d9ad29d7aeb57bd6c0c3781623f8dd66f33136ecba94737ea11ff03 |
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| cites | cdi_FETCH-LOGICAL-c481t-1daed8cc98d9ad29d7aeb57bd6c0c3781623f8dd66f33136ecba94737ea11ff03 |
| container_end_page | 4699 |
| container_issue | 16 |
| container_start_page | 4696 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 18 |
| creator | O’Connor, Stephen P. Atwal, Karnail Li, Chi Liu, Eddie C.-K. Seiler, Steven M. Shi, Mengxiao Shi, Yan Stein, Philip D. Wang, Ying |
| description | A series of acylguanidine derivatives were prepared and investigated as inhibitors of Factor Xa (FXa). These compounds were made by guanidine acylation with carboxylic acids using carbonyl diimidazole (CDI) as the coupling reagent. Conditions for the rapid synthesis and purification of these compounds are described along with their ability to inhibit FXa. The best FXa inhibitor is
1 with a FXa IC
50 of 6
nM. |
| doi_str_mv | 10.1016/j.bmcl.2008.07.004 |
| format | article |
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1 with a FXa IC
50 of 6
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1 with a FXa IC
50 of 6
nM.</description><subject>Anticoagulants - chemical synthesis</subject><subject>Anticoagulants - pharmacology</subject><subject>Antithrombin III - chemical synthesis</subject><subject>Antithrombin III - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Blood Coagulation</subject><subject>Blood. Blood coagulation. Reticuloendothelial system</subject><subject>Carboxylic Acids - chemistry</subject><subject>Chemistry, Pharmaceutical - methods</subject><subject>Coagulation</subject><subject>Drug Design</subject><subject>Factor Xa</subject><subject>Factor Xa - chemistry</subject><subject>Guanidines - chemical synthesis</subject><subject>Guanidines - pharmacology</subject><subject>Guanine - chemistry</subject><subject>Humans</subject><subject>Imidazoles - chemistry</subject><subject>Inhibitory Concentration 50</subject><subject>Medical sciences</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Pharmacology. 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Blood coagulation. Reticuloendothelial system</topic><topic>Carboxylic Acids - chemistry</topic><topic>Chemistry, Pharmaceutical - methods</topic><topic>Coagulation</topic><topic>Drug Design</topic><topic>Factor Xa</topic><topic>Factor Xa - chemistry</topic><topic>Guanidines - chemical synthesis</topic><topic>Guanidines - pharmacology</topic><topic>Guanine - chemistry</topic><topic>Humans</topic><topic>Imidazoles - chemistry</topic><topic>Inhibitory Concentration 50</topic><topic>Medical sciences</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Serine protease</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>O’Connor, Stephen P.</creatorcontrib><creatorcontrib>Atwal, Karnail</creatorcontrib><creatorcontrib>Li, Chi</creatorcontrib><creatorcontrib>Liu, Eddie C.-K.</creatorcontrib><creatorcontrib>Seiler, Steven M.</creatorcontrib><creatorcontrib>Shi, Mengxiao</creatorcontrib><creatorcontrib>Shi, Yan</creatorcontrib><creatorcontrib>Stein, Philip D.</creatorcontrib><creatorcontrib>Wang, Ying</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>O’Connor, Stephen P.</au><au>Atwal, Karnail</au><au>Li, Chi</au><au>Liu, Eddie C.-K.</au><au>Seiler, Steven M.</au><au>Shi, Mengxiao</au><au>Shi, Yan</au><au>Stein, Philip D.</au><au>Wang, Ying</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of acylguanidine FXa inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2008-08-15</date><risdate>2008</risdate><volume>18</volume><issue>16</issue><spage>4696</spage><epage>4699</epage><pages>4696-4699</pages><issn>0960-894X</issn><issn>0968-0896</issn><eissn>1464-3405</eissn><eissn>1464-3391</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A series of acylguanidine derivatives were prepared and investigated as inhibitors of Factor Xa (FXa). These compounds were made by guanidine acylation with carboxylic acids using carbonyl diimidazole (CDI) as the coupling reagent. Conditions for the rapid synthesis and purification of these compounds are described along with their ability to inhibit FXa. The best FXa inhibitor is
1 with a FXa IC
50 of 6
nM.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>18644722</pmid><doi>10.1016/j.bmcl.2008.07.004</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2008-08, Vol.18 (16), p.4696-4699 |
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| language | eng |
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| source | ScienceDirect Journals |
| subjects | Anticoagulants - chemical synthesis Anticoagulants - pharmacology Antithrombin III - chemical synthesis Antithrombin III - pharmacology Biological and medical sciences Blood Coagulation Blood. Blood coagulation. Reticuloendothelial system Carboxylic Acids - chemistry Chemistry, Pharmaceutical - methods Coagulation Drug Design Factor Xa Factor Xa - chemistry Guanidines - chemical synthesis Guanidines - pharmacology Guanine - chemistry Humans Imidazoles - chemistry Inhibitory Concentration 50 Medical sciences Models, Chemical Molecular Structure Pharmacology. Drug treatments Serine protease |
| title | Synthesis and evaluation of acylguanidine FXa inhibitors |
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