Benzocycloheptenes and heterocyclic analogues as potential drugs. II. Amines of 8-chloro-2,3,4,5-tetrahydro-1-benzoxepin series

Protiva, M.; Seidlová, V.; Svátek, E.; Hradil, F.

doi:10.1135/cccc19720868

Cited by 14 publications

(14 citation statements)

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“…The reaction between m -chloro-phenol ( 2 ) and gamma-butyrrolactone gave the acid 3 , which upon cyclization with polyphosphoric acid (PPA) afforded the ketone 4 [11]. The readily available ketone was converted to the hydroxyketoester 5 using a Claisen reaction with diethyl oxalate in the presence of sodium ethylate.…”

Section: Resultsmentioning

confidence: 99%

“…R f = 0.15 (petroleum ether/EtOAc 8:2); m.p. : 47 °C (51–53 °C) [11]. IR (ν/cm −1 ): 3223 (OH), 1709 (CO).…”

Section: Methodsmentioning

confidence: 99%

“…Yield: 2.46 g (45.53%); b.p. : 46–47 °C/27 mm Hg (107 °C/0.4 Torr) [11]. 1 H-NMR (200 MHz, CDCl 3 ): δ 2.22 (qu, 2H, J = 6.4 Hz), 2.89 (t, 2H, J = 6.8 Hz), 4.25 (t, 2H, J = 6.6 Hz), 7.05–7.16 (m, 2H), 7.71 (d, 1H, J = 7.0 Hz).…”

Section: Methodsmentioning

confidence: 99%

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Development of Oxygen-Bridged Pyrazole-Based Structures as Cannabinoid Receptor 1 Ligands

et al. 2019

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In this work, the synthesis of the cannabinoid receptor 1 neutral antagonists 8-chloro-1-(2,4-dichlorophenyl)-N-piperidin-1-yl-4,5-dihydrobenzo-1H-6-oxa-cyclohepta[1,2-c]pyrazole-3-carboxamide 1a and its deaza N-cyclohexyl analogue 1b has led to a deepening of the structure-activity studies of this class of compounds. A series of novel 4,5-dihydrobenzo-oxa-cycloheptapyrazoles analogues of 1a,b, derivatives 1c–j, was synthesized, and their affinity towards cannabinoid receptors was determined. Representative terms were evaluated using in vitro tests and isolated organ assays. Among the derivatives, 1d and 1e resulted in the most potent CB1 receptor ligands (KiCB1 = 35 nM and 21.70 nM, respectively). Interestingly, both in vitro tests and isolated organ assays evidenced CB1 antagonist activity for the majority of the new compounds, excluding compound 1e, which showed a CB1 partial agonist behaviour. CB1 antagonist activity of 1b was further confirmed by a mouse gastrointestinal transit assay. Significant activity of the new CB1 antagonists towards food intake was showed by preliminary acute assays, evidencing the potentiality of these new derivatives in the treatment of obesity.

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Section: Resultsmentioning

confidence: 99%

“…R f = 0.15 (petroleum ether/EtOAc 8:2); m.p. : 47 °C (51–53 °C) [11]. IR (ν/cm −1 ): 3223 (OH), 1709 (CO).…”

Section: Methodsmentioning

confidence: 99%

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Development of Oxygen-Bridged Pyrazole-Based Structures as Cannabinoid Receptor 1 Ligands

et al. 2019

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“…In recent periods, seven membered ring oxacycles 1 have received increasing attention due to their existence in natural products, biological activities, 2a-d and their use as natural herbicides 3 . The benzo[c]oxepine scaffold is found in a great number of scaffolds distributed in number of biologically active natural products isolated predominantly from plant resources pertaining to their interesting properties [4][5][6][7][8][9] . Some of the natural products such as cassialactone, 10 psorolactone, 11 secofuranoeremophilane 12 also contains this structural framework.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of benzoxepinopyrrolidines/spiropyrrolidines via oxa-Pictet–Spengler and [3+2] cycloaddition reactions

Bakthadoss

Sivakumar

Devaraj

2015

Tetrahedron Letters

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“…3 and 4, Figure 1). [17][18][19][20] We now report an efficient synthesis of 5-amino-2,5-dihydrobenzoxepines from commercially available salicylaldehydes using a one-pot multibond forming process for introduction of the amine functionality and consecutive formation of the oxepine ring. As well as demonstrating the general scope of this strategy, we also explore the synthetic utility of 5-amino-2,5-dihydro-1-benzoxepines for the preparation of 2,3,4,5tetrahydro-1-benzoxepine targets.…”

mentioning

confidence: 99%

One-Pot Synthesis of 5-Amino-2,5-dihydro-1-benzoxepines: Access to Pharmacologically Active Heterocyclic Scaffolds

et al. 2015

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A one-pot multibond-forming process involving a thermally mediated Overman rearrangement and a ring closing metathesis reaction of allylic trichloroacetimidates bearing a 2-allyloxyaryl group has been developed for the synthesis of 5-amino-substituted 2,5-dihydro-1-benzoxepines. Chemoselective reduction and functionalization of these compounds allowed access to a range of pharmacologically active 5-amino-2,3,4,5-tetrahydro-1-benzoxepine scaffolds.

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Benzocycloheptenes and heterocyclic analogues as potential drugs. II. Amines of 8-chloro-2,3,4,5-tetrahydro-1-benzoxepin series

Cited by 14 publications

References 0 publications

Development of Oxygen-Bridged Pyrazole-Based Structures as Cannabinoid Receptor 1 Ligands

Development of Oxygen-Bridged Pyrazole-Based Structures as Cannabinoid Receptor 1 Ligands

Synthesis of benzoxepinopyrrolidines/spiropyrrolidines via oxa-Pictet–Spengler and [3+2] cycloaddition reactions

One-Pot Synthesis of 5-Amino-2,5-dihydro-1-benzoxepines: Access to Pharmacologically Active Heterocyclic Scaffolds

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