Conformationally constrained butyrophenones with mixed dopaminergic (D2) and serotoninergic (5-HT2A, 5-HT2C) affinities: synthesis, pharmacology, 3D-QSAR, and molecular modeling of (aminoalkyl)benzo- and -thienocycloalkanones as putative atypical antipsychotics was written by Ravina, Enrique;Negreira, Jesus;Cid, Jose;Masaguer, Christian F.;Rosa, Elizabeth;Rivas, M. Emilia;Fontenla, Jose A.;Loza, M. Isabel;Tristan, Helena;Cadavid, M. Isabel;Sanz, Ferran;Lozoya, Estrella;Carotti, Angelo;Carrieri, Antonio. And the article was included in Journal of Medicinal Chemistry in 1999.Formula: C12H14ClFO2 This article mentions the following:
A series of novel conformationally restricted butyrophenones (2-(aminoethyl)- and 3-(aminomethyl)thieno- or benzocycloalkanones bearing (6-fluorobenzisoxazolyl)piperidine, (p-fluorobenzoyl)piperidine, (o-methoxyphenyl)piperazine, or linear butyrophenone fragments) were prepared and evaluated as atypical antipsychotic agents by in vitro assays of affinity for dopamine receptors (D1, D2) and serotonin receptors (5-HT2A, 5-HT2C) and by in vivo assays of antipsychotic potential and the risk of inducing extra pyramidal side effects. Potency and selectivity depended mainly on the amine fragment connected to the cycloalkanone structure. As a group, compounds with a benzisoxazolyl fragment had the highest 5-HT2A activities, followed by the benzoylpiperidine derivatives; in general, α-substituted cycloalkanone derivatives were more active than the corresponding β-substituted congeners. CoMFA (comparative mol. field anal.) and docking studies showed electrostatic, steric, and lipophilic determinants of 5-HT2A and D2 affinities and 5-HT2A/D2 selectivity. The in vitro and in vivo pharmacol. profiles of N-[(4-oxo-4H-5,6-dihydrocyclopenta[b]thiophene-5-yl)ethyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine (QF 0510B), N-[(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-yl)ethyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine (QF 0610B), and N-[(7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-6-yl)ethyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine (QF 0902B) suggest that they may be effective antipsychotic drugs with low propensity to induce extra pyramidal side effects. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Formula: C12H14ClFO2).
2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Formula: C12H14ClFO2
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem