title: Synthesis and evaluation of the pharmacological activity of rigid analogues of sympathomimetic catecholamines derived from bicyclo[2.2.1]heptane.
abstract: endo-3-Amino-exo-2-(3,4-dihydroxyphenyl)-2-hydroxybicyclo[2.2.1]he ptane (4a) and its N-isopropyl derivative (4b) were synthesized and assayed for their adrenergic activity on various isolated preparations. Compounds 4a and 4b, tested up to a dose of 10(-4) M, did not reveal any activity, either stimulant or blocking, on the alpha- and beta-adrenoceptors. Possible rationalizations of the results obtained, however, are suggested.
authors.affiliation: Istituto di Chimica Farmaceutica, Istituto Policattedra di Discipline Biologiche, Università di Pisa, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Balsamo
authors.forename: M C
authors.initials: MC
authors.lastname: Breschi
authors.forename: A
authors.initials: A
authors.lastname: Lapucci
authors.forename: B
authors.initials: B
authors.lastname: Macchia
authors.forename: F
authors.initials: F
authors.lastname: Macchia
authors.forename: E
authors.initials: E
authors.lastname: Martinotti
authors.forename: S
authors.initials: S
authors.lastname: Nencetti
authors.forename: P
authors.initials: P
authors.lastname: Nieri
authors.forename: E
authors.initials: E
authors.lastname: Orlandini
mesh_terms: D000818:Animals; D016275:Atrial Function; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D001952:Bridged-Ring Compounds / Q000494:pharmacology*; D002395:Catecholamines / Q000138:chemical synthesis / Q000494:pharmacology*; D055598:Chemical Phenomena; D002621:Chemistry; D006168:Guinea Pigs; D006325:Heart Atria / Q000187:drug effects; D008297:Male; D008968:Molecular Conformation; D051381:Rats; D011919:Rats, Inbred Strains; D011942:Receptors, Adrenergic, alpha / Q000187:drug effects* / Q000502:physiology; D011943:Receptors, Adrenergic, beta / Q000187:drug effects* / Q000502:physiology; D013329:Structure-Activity Relationship; D014132:Trachea / Q000187:drug effects / Q000502:physiology; D014649:Vas Deferens / Q000187:drug effects / Q000502:physiology
chemical_list: D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D002395:Catecholamines; D011942:Receptors, Adrenergic, alpha; D011943:Receptors, Adrenergic, beta; C059111:3-amino-2-(3,4-dihydroxyphenyl)-2-hydroxybicyclo(2.2.1)heptane; C059112:N-isopropyl-3-amino-2-(3,4-dihydroxyphenyl)-2-hydroxybicyclo(2.2.1)heptane