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3-{2-[Bis-(4-fluorophenyl)methoxy]ethyl}-6-substituted-3,6-diazabicyclo[3.1.1]heptanes as novel potent dopamine uptake inhibitors

Loriga, Giovanni and Ruiu, Stefania and Manca, Ilaria and Murineddu, Gabriele and Dessì, Christian and Pani, Luca and Pinna, Gérard Aimé (2007) 3-{2-[Bis-(4-fluorophenyl)methoxy]ethyl}-6-substituted-3,6-diazabicyclo[3.1.1]heptanes as novel potent dopamine uptake inhibitors. Bioorganic & Medicinal Chemistry, Vol. 15 (11), p. 3748-3755. eISSN 1464-3391. Article.

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DOI: 10.1016/j.bmc.2007.03.035


A series of analogues 2a–i related to 3-{2-[bis-(4-fluorophenyl)methoxy]ethyl}-8-(1H-indol-2-ylmethyl)-3,8-diazabicyclo[3.2.1]octane (1) in which the 3,8-diazabicyclo[3.2.1]octane core was replaced by 3,6-diazabicyclo[3.1.1]heptane ring system has been synthesized and evaluated for their ability to inhibit DA reuptake into striatal nerve endings (synaptosomes). Biological data showed that compound 2a, the closest analogue of lead 1, possessed an increased reuptake inhibition activity over 1 (2a, Ki = 5.5 nM). Replacement of the indole ring with bioisosteric aromatic rings—benzothiophene (2b), benzofurane (2c), or indene (2d)—resulted, with the exception of 2d, in a double digit nanomolar activity. Changing the indenyl moiety of 2d with simplified aryl groups led to compounds 2e–h which displayed a similar or slightly decreased activity with respect to the ground term. Naphthalene derivative (2i) demonstrated a weaker activity than aromatic analogues.

Item Type:Article
ID Code:7809
Uncontrolled Keywords:Cocaine abuse treatment, synthesis of 3,6-diazabicyclo[ 3.1.1]heptanes, DAT inhibitors
Subjects:Area 03 - Scienze chimiche > CHIM/08 Chimica farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Scienze del farmaco
Publisher:Pergamon / Elsevier
Deposited On:24 Jul 2012 09:47

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