Several N'-substituted N~"-(dithiodi-2,l-ethanediyl)bis(l,w-alkanediamines)w ere prepared and evaluated for theirblocking activity on a-adrenoreceptors in the isolated rat vas deferens and human blood platelets. The results werecompared with those obtained for benextramine (N,N"-(dithiodi-2,l-ethanediyl)bis[N'-[(2-methoxyphenyl)-methyl] - 1 ,g-hexanediamine], 10). Bendotramine (N,"'- (dithiodi-2,1 -ethanediyl) bis [ N'- [ (2-methoxypheny1)-methyl]-1,12-dodecanediamine]1,6 ) proved to be as active as 10 on al-adrenoreceptors, showing that optimum activityis associated with two carbon chain lengths separating inner from outer nitrogens of tetraamine disulfides. On theother hand, 16 had no activity up to 20 pM at a2-adrenoreceptors. The optimum activity at this receptor subtypewas associated with a six to eight carbon chain (10-12). Furthermore, 10 proved to be more selective towarda,-adrenoreceptors whereas 16 was a selective al-antagonist. The tetraamine disulfides were shown also to be potentinhibitors of human platelet aggregation induced by ADP or epinephrine. The potency increased with the carbonchain length. However, the results on platelets did not parallel those found in the rat vas deferens, indicating thatdifferences exist between the a-adrenoreceptor subtypes investigated. In conclusion, 10 may be a useful tool incharacterizing a,-adrenoreceptors whereas 16 might help in investigating a,-adrenoreceptors.

Structure-Activity Relationships Among Benextramine Related Tetramine Disulfidxe. Chain Length Effect on alpha-adrenoreceptor Blocking Activity / Quaglia, W.; Brasili, Livio; Cristalli, G.; Giardin, D.; Picchio, M. T.; Melchiorre, C.. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - STAMPA. - 31:(1988), pp. 1861-1866.

Structure-Activity Relationships Among Benextramine Related Tetramine Disulfidxe. Chain Length Effect on alpha-adrenoreceptor Blocking Activity.

BRASILI, Livio;
1988

Abstract

Several N'-substituted N~"-(dithiodi-2,l-ethanediyl)bis(l,w-alkanediamines)w ere prepared and evaluated for theirblocking activity on a-adrenoreceptors in the isolated rat vas deferens and human blood platelets. The results werecompared with those obtained for benextramine (N,N"-(dithiodi-2,l-ethanediyl)bis[N'-[(2-methoxyphenyl)-methyl] - 1 ,g-hexanediamine], 10). Bendotramine (N,"'- (dithiodi-2,1 -ethanediyl) bis [ N'- [ (2-methoxypheny1)-methyl]-1,12-dodecanediamine]1,6 ) proved to be as active as 10 on al-adrenoreceptors, showing that optimum activityis associated with two carbon chain lengths separating inner from outer nitrogens of tetraamine disulfides. On theother hand, 16 had no activity up to 20 pM at a2-adrenoreceptors. The optimum activity at this receptor subtypewas associated with a six to eight carbon chain (10-12). Furthermore, 10 proved to be more selective towarda,-adrenoreceptors whereas 16 was a selective al-antagonist. The tetraamine disulfides were shown also to be potentinhibitors of human platelet aggregation induced by ADP or epinephrine. The potency increased with the carbonchain length. However, the results on platelets did not parallel those found in the rat vas deferens, indicating thatdifferences exist between the a-adrenoreceptor subtypes investigated. In conclusion, 10 may be a useful tool incharacterizing a,-adrenoreceptors whereas 16 might help in investigating a,-adrenoreceptors.
1988
31
1861
1866
Structure-Activity Relationships Among Benextramine Related Tetramine Disulfidxe. Chain Length Effect on alpha-adrenoreceptor Blocking Activity / Quaglia, W.; Brasili, Livio; Cristalli, G.; Giardin, D.; Picchio, M. T.; Melchiorre, C.. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - STAMPA. - 31:(1988), pp. 1861-1866.
Quaglia, W.; Brasili, Livio; Cristalli, G.; Giardin, D.; Picchio, M. T.; Melchiorre, C.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/449046
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