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Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3' allyl end and at the phenyl ring of the cinnamyl chain on µ-receptor affinity and opioid antinociception

Pinna, Gérard Aimé and Cignarella, Giorgio and Ruiu, Stefania and Loriga, Giovanni and Murineddu, Gabriele and Villa, Stefania and Grella, Giuseppe Enrico and Fratta, Walter (2003) Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3' allyl end and at the phenyl ring of the cinnamyl chain on µ-receptor affinity and opioid antinociception. Bioorganic & Medicinal Chemistry, Vol. 11 (18), p. 4015-4026. ISSN 0968-0896. Article.

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DOI: 10.1016/S0968-0896(03)00373-0

Abstract

Two series of analogues of 9-propionyl-10-cinnamyl-9,10-diazatricyclo[4.2.1.12,5]decane (1a) and 2-propionyl-7-cinnamyl-2,7-diazatricyclo[4.4.0.03,8]decane (2a), in which the cinnamyl moiety was replaced by various aralkenyl chains, 1b-l and 2-l, respectively, have been synthesized and evaluated for their ability to bind to the opioid µ-, δ-and k-receptors. The binding data indicated that compounds 1b,d,e,h and 2b,d,e,f,h,i showed a µ-affinity in the low nanomolar range with moderate or negligible affinity towards δ- and k-receptors. Selected DTDs, the pairs 1,2b, 1,2e and 1,2h, were also evaluated for analgesic effect. In the hot plate test, only 1b given ip was found to have similar opioid antinociception and chronic tolerance as morphine.

Item Type:Article
ID Code:404
Status:Published
Refereed:Yes
Uncontrolled Keywords:Ethylenic compound, carboxamide, tricyclic compound, nitrogen heterocycle, chemical synthesis, naloxone, μ opioid receptor, biological fixation
Subjects:Area 03 - Scienze chimiche > CHIM/08 Chimica farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Pergamon-Elsevier Science
ISSN:0968-0896
Copyright Holders:© 2003 Elsevier Science
Deposited On:18 Aug 2009 10:02

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