- Synthesis and biological investigations of 3β-aminotropane arylamide derivatives with atypical antipsychotic profile
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This work is a continuation of our previous research, concentrating this time on lead structure modification to increase the 5-HT1A receptor affinity and water solubility of designed compounds. Therefore, the compounds synthesised within the present project included structural analogues of 3β-acylamine derivatives of tropane with the introduction of a methyl substituent in the benzyl ring and a 2-quinoline, 3-quinoline, or 6-quinoline moiety. A series of novel 3β-aminotropane derivatives was evaluated for their affinity for 5-HT1A, 5-HT2A, and D2 receptors, which allowed for the identification of compounds 12e, 12i, and 19a as ligands with highest affinity for the tested receptors; they were then subjected to further evaluation in preliminary in vivo studies. Selected compounds 12i and 19a displayed antipsychotic properties in the d-amphetamine-induced and MK-801-induced hyperlocomotor activity test in mice. Moreover, compound 19a showed significant antidepressant-like activity in the forced swim test in mice.
- Stefanowicz, Jacek,S?owiński, Tomasz,Wróbel, Martyna Z.,?lifirski, Grzegorz,Dawidowski, Maciej,Stefanowicz, Zdzis?awa,Jastrz?bska-Wi?sek, Magdalena,Partyka, Anna,Weso?owska, Anna,Tur?o, Jadwiga
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p. 1906 - 1928
(2018/06/26)
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- Discovery of novel (S)-α-phenyl-γ-amino butanamide containing CCR5 antagonists via functionality inversion approach
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By using functionality inversion approach, we identified a new scaffold containing (S)-α-phenyl-γ-amino butanamide as CCR5 antagonists derived from the 1,3-propanediamine carboxamide pharmacophore protocol. The (2S)-2-phenyl-4-(8-aza-bicyclo[3.2.1]octan-8
- Zhang, Hu-Shan,Feng, Dong-Zhi,Chen, Li,Long, Ya-Qiu
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body text
p. 2219 - 2223
(2010/07/05)
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- METHOD FOR PRODUCING N-SUBSTITUTED 3β-AMINONORTROPANES
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The invention relates to a method for producing, on the basis of the corresponding 3-oxonortropane or the corresponding 3α-aminonortropane, N-substituted 3β-aminonortropanes of formula (I), wherein R1 is defined as in the claim. According to the inventive method, the starting compounds are converted to the corresponding imines by means of an arylmethylamine or an arylaldehyde, said imines are tautomerized or isomerized and then hydrolyzed. The invention also relates to the novel compounds of formula (V), wherein R1 and Ar are defined as in the claims.
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Page/Page column 9-10
(2008/06/13)
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- A practical synthesis of 7-azaindolylcarboxy-endo-tropanamide (DF 1012)
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An optimised cost-effective synthesis of the new antitussive drug, DF1012, is herewith reported. The new synthetic route to the key intermediate DF1005 is based on the unusual deprotection step of the 1-tert-butyl-3-cyano-7-azaindole intermediate, which can also be regarded as a convenient way for the industrial production of the expensive 7-azaindole 1. The second key intermediate, endo-tropanamine 6, was obtained in high yield by a novel one-pot stereoselective process using a Pd-catalysed reductive amination procedure.
- Allegretti, Marcello,Anacardio, Roberto,Cesta, M. Candida,Curti, Roberto,Mantovanini, Marco,Nano, Giuseppe,Topai, Alessandra,Zampella, Giuseppe
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p. 209 - 213
(2013/09/05)
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- Molecular features associated with polyamine modulation of NMDA receptors
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The effect of 1,3-diamines on basal and spermine-stimulated [3H]MK-801 binding was investigated. Systematic variations in the molecular parameters revealed that, in general, lipophilic 1,3-diamines inhibited and hydrophilic 1,3-diamines enhance
- Lewin, Anita H.,Fudala, Louise,Navarro, Hernan,Zhou, Li-Ming,Popik, Piotr,Faynsteyn, Alexander,Skolnick, Phil
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p. 988 - 995
(2007/10/03)
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- Synthesis and binding affinities of a series of 1,2-benzisoxazole-3-carboxamides to dopamine and serotonin receptors
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A series of 1,2-benzisoxazole-3-carboxamides derived from tertiary cycloalkylamines was synthesized and evaluated for affinity for serotonergic (5-HT3 and 5-HT4) and dopaminergic (D2) receptors using radioligand binding as
- Nuhrich,Varache-Lembege,Vercauteren,Dokhan,Renard,Devaux
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p. 957 - 964
(2007/10/03)
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- SUBSTITUTED THIENOBENZODIAZEPINONES AND SALTS THEREOF
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Compounds of the formula STR1 wherein R is 1-methyl-4-piperididinyl, 4-methyl-1-piperazinyl, or 3-or 3-tropanyl, each of which may optionally have another methyl substituent attached to the heterocyclic ring;R 1 is hydrogen or alkyl of 1 to 4 carbon atoms;R 2 is hydrogen, halogen or alkyl of 1 to 4 carbon atoms; andX is oxygen,--NH--or--N(CH. sub.3)--;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as anti-ulcerogenics.
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