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1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity
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| Zeitschriftentitel: | Antiviral Chemistry and Chemotherapy |
|---|---|
| Personen und Körperschaften: | , , , , , , , |
| In: | Antiviral Chemistry and Chemotherapy, 9, 1998, 2, S. 127-137 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
SAGE Publications
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| Schlagwörter: |
| author_facet |
Di Santo, R Costi, R Artico, M Massa, S Marongiu, ME Loi, AG De Montis, A La Colla, P Di Santo, R Costi, R Artico, M Massa, S Marongiu, ME Loi, AG De Montis, A La Colla, P |
|---|---|
| author |
Di Santo, R Costi, R Artico, M Massa, S Marongiu, ME Loi, AG De Montis, A La Colla, P |
| spellingShingle |
Di Santo, R Costi, R Artico, M Massa, S Marongiu, ME Loi, AG De Montis, A La Colla, P Antiviral Chemistry and Chemotherapy 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity Psychiatry and Mental health Neuropsychology and Physiological Psychology |
| author_sort |
di santo, r |
| spelling |
Di Santo, R Costi, R Artico, M Massa, S Marongiu, ME Loi, AG De Montis, A La Colla, P 2040-2066 2040-2066 SAGE Publications Psychiatry and Mental health Neuropsychology and Physiological Psychology http://dx.doi.org/10.1177/095632029800900204 <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> 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity Antiviral Chemistry and Chemotherapy |
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| title |
1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_unstemmed |
1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_full |
1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_fullStr |
1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_full_unstemmed |
1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_short |
1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_sort |
1,2,5-benzothiadiazepine and pyrrolo[2,1-d]-[1,2,5]benzothiadiazepine derivatives with specific anti-human immunodeficiency virus type 1 activity |
| topic |
Psychiatry and Mental health Neuropsychology and Physiological Psychology |
| url |
http://dx.doi.org/10.1177/095632029800900204 |
| publishDate |
1998 |
| physical |
127-137 |
| description |
<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> |
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| author | Di Santo, R, Costi, R, Artico, M, Massa, S, Marongiu, ME, Loi, AG, De Montis, A, La Colla, P |
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| description | <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> |
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| imprint | SAGE Publications, 1998 |
| imprint_str_mv | SAGE Publications, 1998 |
| institution | DE-Rs1, DE-Pl11, DE-105, DE-14, DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1, DE-Zwi2, DE-D161, DE-Gla1, DE-Zi4, DE-15 |
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| physical | 127-137 |
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| series | Antiviral Chemistry and Chemotherapy |
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| spelling | Di Santo, R Costi, R Artico, M Massa, S Marongiu, ME Loi, AG De Montis, A La Colla, P 2040-2066 2040-2066 SAGE Publications Psychiatry and Mental health Neuropsychology and Physiological Psychology http://dx.doi.org/10.1177/095632029800900204 <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> 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity Antiviral Chemistry and Chemotherapy |
| spellingShingle | Di Santo, R, Costi, R, Artico, M, Massa, S, Marongiu, ME, Loi, AG, De Montis, A, La Colla, P, Antiviral Chemistry and Chemotherapy, 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity, Psychiatry and Mental health, Neuropsychology and Physiological Psychology |
| title | 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_full | 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_fullStr | 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_full_unstemmed | 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_short | 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| title_sort | 1,2,5-benzothiadiazepine and pyrrolo[2,1-d]-[1,2,5]benzothiadiazepine derivatives with specific anti-human immunodeficiency virus type 1 activity |
| title_unstemmed | 1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity |
| topic | Psychiatry and Mental health, Neuropsychology and Physiological Psychology |
| url | http://dx.doi.org/10.1177/095632029800900204 |