{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T06:03:41Z","timestamp":1760853821026},"reference-count":17,"publisher":"SAGE Publications","issue":"2","license":[{"start":{"date-parts":[[1998,4,1]],"date-time":"1998-04-01T00:00:00Z","timestamp":891388800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.sagepub.com\/page\/policies\/text-and-data-mining-license"},{"start":{"date-parts":[[1998,4,1]],"date-time":"1998-04-01T00:00:00Z","timestamp":891388800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.sagepub.com\/page\/policies\/text-and-data-mining-license"}],"content-domain":{"domain":["journals.sagepub.com"],"crossmark-restriction":true},"short-container-title":["Antivir Chem Chemother"],"published-print":{"date-parts":[[1998,4]]},"abstract":"<jats:p> We synthesized and tested as novel inhibitors of human immunodeficiency virus type 1 (HIV-1) bi- and tricyclic thiadiazine ring homologues of 7-chloro-2-ethyl-2 H-1,2,4-benzothiadiazin-3-(4 H)-one 1,1-dioxide, which is a compound endowed with anti-HIV-1 activity at low micromolar concentrations. Benzothiadiazepine derivatives were obtained by alkylation of 8-chloro-2,3-dihydro-3-methyl-1,2,5-benzothiadiazepin-4(5 H)-one 1,1-dioxide, which was obtained by intramolecular cyclization of 2-(2-amino-5-chloro-benzenesulphonamido) propanoic acid. Pyrrolobenzothiadiazepines were synthesized from N-substituted 5-chloro-2-(1 H-pyrrol-1-yl)benzenesulphonamides by treating with triphosgene. N<jats:sub>6<\/jats:sub>-substituted pyrrolo[2,1-d][1,2,5]benzothiadiazepin-7(6 H)-one 5,5-dioxides were active, thoughnot very potent. Both a chlorine atom and an unsaturated alkyl chain were found to be determinants of anti-HIV-1 activity. The highest potency was shown by a derivative with a TIBO-related 3,3-dimethylallyl chain. 2,3-Dihydro-1,2,5-benzothiadiazepin-4(5 H)-one 1,1-dioxides were scarcely active in HIV-1-infected MT-4 cell assays; however, the introduction of the dimethylallyl chain into 7-chloro-1,2,5-benzothiadiazepine moiety led to a bicyclic derivative which was more potent and less cytotoxic than the tricyclic pyrrole-containing counterpart. <\/jats:p>","DOI":"10.1177\/095632029800900204","type":"journal-article","created":{"date-parts":[[2015,5,8]],"date-time":"2015-05-08T22:10:56Z","timestamp":1431123056000},"page":"127-137","update-policy":"http:\/\/dx.doi.org\/10.1177\/sage-journals-update-policy","source":"Crossref","is-referenced-by-count":33,"title":["1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity"],"prefix":"10.1177","volume":"9","author":[{"given":"R","family":"Di 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Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"ME","family":"Marongiu","sequence":"additional","affiliation":[{"name":"Dipartimento di Biologia Sperimentale, Universit\u00e0 di Cagliari, Viale Regina Margherita 45, 09137 Cagliari, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"AG","family":"Loi","sequence":"additional","affiliation":[{"name":"Dipartimento di Biologia Sperimentale, Universit\u00e0 di Cagliari, Viale Regina Margherita 45, 09137 Cagliari, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"A","family":"De Montis","sequence":"additional","affiliation":[{"name":"Dipartimento di Biologia Sperimentale, Universit\u00e0 di Cagliari, Viale Regina Margherita 45, 09137 Cagliari, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"P","family":"La Colla","sequence":"additional","affiliation":[{"name":"Dipartimento di Biologia Sperimentale, Universit\u00e0 di Cagliari, Viale Regina Margherita 45, 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