{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T10:15:28Z","timestamp":1760782528033,"version":"3.28.0"},"reference-count":9,"publisher":"Oxford University Press (OUP)","issue":"1","license":[{"start":{"date-parts":[[2001,1,1]],"date-time":"2001-01-01T00:00:00Z","timestamp":978307200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2001,1,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Transition state phosphoramidate inhibitors of \u03b2-tubulin were designed as potential antifilarial agents.<\/jats:p>\n               <jats:p>The reactionof 2-aminobenzimidazole with diisopropyl phosphite and carbon tetrachloride at a low temperature gave the unexpected 1-diisopropoxyphosphoryl-2-aminobenzimidazole, which on heating gave the novel benzimidazole derivative, 2-(diisopropoxyphosphoryl)-aminobenzimidazole. Both products were fully characterized and the synthetic procedure to both compounds was optimized. The procedure was used to prepare the related 5-benzoyl-2-(diisopropoxyphosphoryl)aminobenzimidazole and 5-benzoyl-2-(diethoxyphosphoryl)amino-benzimidazole (1d). In a preliminary trial against Brugia pahangi compound 1d was found to have no antifilarial activity. This lack of activity may be attributed to its extreme insolubility and thus low bioavailability. The synthesis of analogous, more soluble, phosphorothioate-substituted benzimidazoles using the same methods may yield compounds with greater antifilarial activity.<\/jats:p>","DOI":"10.1211\/0022357011775055","type":"journal-article","created":{"date-parts":[[2003,7,18]],"date-time":"2003-07-18T23:43:52Z","timestamp":1058571832000},"page":"89-94","source":"Crossref","is-referenced-by-count":9,"title":["Potential transition state phosphoramidate inhibitors of \u03b2-tubulin as antifilarial agents"],"prefix":"10.1093","volume":"53","author":[{"given":"R J","family":"Anderson","sequence":"first","affiliation":[{"name":"Institute of Pharmacy and Chemistry, University of Sunderland , Sunderland SR1 3SD,","place":["UK"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D J","family":"Bendell","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy and Chemistry, University of Sunderland , Sunderland SR1 3SD,","place":["UK"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M","family":"Hooper","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy and Chemistry, University of Sunderland , Sunderland SR1 3SD,","place":["UK"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D","family":"Cairns","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy and Chemistry, University of Sunderland , Sunderland SR1 3SD,","place":["UK"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"S P","family":"Mackay","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy and Chemistry, University of Sunderland , Sunderland SR1 3SD,","place":["UK"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"S P","family":"Hiremath","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Gulbarga University , Gulbarga \u2014 585106, Karnataka,","place":["India"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"A S","family":"Jivanagi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Gulbarga University , Gulbarga \u2014 585106, Karnataka,","place":["India"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"S","family":"Badami","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Gulbarga University , Gulbarga \u2014 585106, Karnataka,","place":["India"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J S","family":"Biradar","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Gulbarga University , Gulbarga \u2014 585106, Karnataka,","place":["India"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"S","family":"Townson","sequence":"additional","affiliation":[{"name":"Tropical Parasitic Diseases Unit, Northwick Park Institute for Medical Research , Harrow, HA1 3UJ,","place":["UK"]}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"286","published-online":{"date-parts":[[2001,1,1]]},"reference":[{"key":"2024103110052702400_cit1","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1017\/S0022149X00005939","article-title":"A review of methods for testing compounds for filaricidal activity","volume":"53","author":"Denham","year":"1979","journal-title":"J. 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Parasitol."},{"key":"2024103110052702400_cit6","doi-asserted-by":"crossref","first-page":"655","DOI":"10.1002\/jhet.5570060511","article-title":"A study of some 1-alkyl-2,-3-dihydroimidazo[1,2-a] benzimidazoles","volume":"6","author":"North","year":"1969","journal-title":"J. Heterocycl. Chem."},{"key":"2024103110052702400_cit7","first-page":"567","volume-title":"Aldrich Library of NMR Spectra","author":"Pouchert","year":"1983","edition":"2nd"},{"key":"2024103110052702400_cit8","first-page":"67","volume-title":"Benzimidazoles and Congeneric Tricyclic Compounds","author":"Preston","year":"1981"},{"key":"2024103110052702400_cit9","doi-asserted-by":"crossref","first-page":"861","DOI":"10.1055\/s-1983-30546","article-title":"2-aminobenzimidazoles in organic synthesis","volume":"67","author":"Rastogi","year":"1983","journal-title":"Synthesis"}],"container-title":["Journal of Pharmacy and Pharmacology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1211%2F0022357011775055","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/academic.oup.com\/jpp\/article-pdf\/53\/1\/89\/60263498\/0022357011775055.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/jpp\/article-pdf\/53\/1\/89\/60263498\/0022357011775055.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,10,31]],"date-time":"2024-10-31T10:43:54Z","timestamp":1730371434000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/jpp\/article\/53\/1\/89\/6149663"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2001,1,1]]},"references-count":9,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2001,1,1]]},"published-print":{"date-parts":[[2001,1,1]]}},"URL":"https:\/\/doi.org\/10.1211\/0022357011775055","relation":{},"ISSN":["0022-3573","2042-7158"],"issn-type":[{"type":"print","value":"0022-3573"},{"type":"electronic","value":"2042-7158"}],"subject":[],"published-other":{"date-parts":[[2001,1]]},"published":{"date-parts":[[2001,1,1]]}}}