Tricyclics with analgesic and antidepressant activity. 1. [[(Alkylamino)ethyl]thio]dibenz[b,f]oxepins and 10,11-dihydro derivatives

Abstract

A series of [[(alkylamino)ethyl]thio]dibenz[b,f]oxepins (I) and their 10,11-dihydro derivatives (II) was synthesized and subjected to broad analgesic/CNS screening. Several analogues of both types, carrying small N-substituents and frequently a nuclear fluorine function, have been found to possess potent analgesic activity in the phenylquinone writhing assay (PQW) and the tail-flick test in mice. Many of these compounds also exhibited significant activity in antagonizing tetrabenazine-induced ptosis, as exemplified by 10b, 16b, and 18b. Results from the mouse jumping test indicated low physical dependence potential for these compounds, and further evidence for a nonnarcotic profile was provided by the absence of significant naloxone interactions with the tail-flick response. Compound 10b did not produce tolerance in mice following chronic administration in the PQW screen.

Retracted: Design, Synthesis and Molecular Modeling of Nonsteroidal Anti‐inflammatory Drugs Tagged Substituted 1,2,3‐Triazole Derivatives and Evaluation of Their Biological Activities

“…Over the years, efforts have been devoted towards the evaluation of pharmacological properties of various benzoxepine derivatives. As a result, a wide range of biological activities has been reported for this class of compounds that include sedative‐hypnotic , antibacterial, hypertensive , antiviral , anticancer , anti‐implantation , anti‐allergic , analgesic , and anti‐inflammatory activities . The view focuses on the medicinal chemistry applications of heterocyclic compounds containing the 1,2,3‐triazole moiety, either as a component fused in a polycyclic structure or as a functionalized moiety, and on the synthetic procedures based on exploiting 1,3‐DCRs to yield such heterocyclic derivatives.…”

Synteza Pochodnych Dibenzo[b,f]oksepiny Podstawionych W Pierścieniu Aromatycznym

“…4), który, jak dowiedziono, silnie hamuje uwalnianie β-glukoronidazy i histaminy pochodzących z degranulacji komórek tucznych [7]. Podstawione dibenzo[b,f]oksepiny charakteryzują się tym, że wykazują silne właściwości antypsychotyczne [5,8,9], przeciwzapalne [5,10], przeciwdepresyjne [5,11], owadobójcze [5,12], przeciwpadaczkowe [5,13] czy też antyhipertensyjne [5].…”

An Efficient Synthesis of Dibenzo[b,f]oxepins by Ring‐Closing Metathesis

“…Tournefolic acid B (9) and isosalvianolic acid C (10) were isolated from Tournefortia sarmentosa, and are more potent than the hypocholesterolemic drug probucol. [5] Notably, natural products that contain the dibenzoA C H T U N G T R E N N U N G [b,f]oxepin moiety have received considerable attention from the medicinal community because of their potent biological properties, such as antipsychotic, [6] antidepressant, [7] antihypertensive, [8] antiestrogenic, [9] antiinflamatory, [10] and insecticidal activities. [11] Relatively very few syntheses of dibenzoA C H T U N G T R E N N U N G [b,f]oxepins have been reported.…”