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At least 19 recordsLinked to original sources
PubMed2002

Palladium-catalyzed sequential alkylation-alkenylation reactions. Application to the synthesis of 2-substituted-4-benzoxepines and 2,5-disubstituted-4-benzoxepines.

The synthesis of 2-substituted-4-benzoxepines and 2,5-disubstituted-4-benzoxepines from aryl iodides and bromoenoates is described. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the reaction conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20 mol %), norbornene (2 equiv), Cs(2)CO(3) (2 equiv), CH(3)CN, 85 degrees C), moderate to excellent yields of benzoxepines bearing numerous substituents (Me, F, Cl, etc.) are obtained.

Journal Article↗
PubMed2004

Chemo- and stereoselective synthesis of benzocycloheptene and 1-benzoxepin derivatives as alpha-sympathomimetic and anorexigenic agents.

The synthesis and pharmacological evaluation of cis- and trans-6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ols 4a-c and 5a-c and cis- and trans-4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ols 4d-f and 5d-f were carried out. Chemo- and stereoselective synthesis of 5a-f was achieved by reduction of corresponding alpha-amino ketones 3a-f with LiAl(t-BuO)3H. cis-4-Amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ol 4d and trans-4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ol 5d exhibited marked anorexigenic activity in mice at a dose of LD50 800 and 500 mg/kg and ED50 75 and 55 mg/kg, respectively, while the analog cis-2,3-dihydroxy-6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol 8 showed typical alpha-sympathomimetic activity.

Amphetamines↗
PubMed1980

1-[Ethoxyamino)methyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepins: a new class of antianaphylactic agents.

The synthesis and biological activity in the rat passive cutaneous anaphylaxis (PCA) test of a new class of compounds, 1-[(ethoxyamino)methyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepins, are reported. These compounds are synthesized from the adduct of 1-(bromomethyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepins, are reported. These compounds are synthesized from the adduct of 1-(bromomethyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin and ethylene glycol or chloroethanol. The influence of the amine function on activity in the rat PCA is discussed. Aryl- or heteroarylpiperazines favor activity with this class of compounds.

Animals↗
PubMed2000

Two new prenylated 3-benzoxepin derivatives as cyclooxygenase inhibitors from Perilla frutescens var. acuta.

Two novel prenyl 3-benzoxepin derivatives, perilloxin (1) and dehydroperilloxin (2), were isolated from the dichloromethane extract of the stems of Perilla frutescens var. acuta. Their structures were elucidated as (-)-(R)-5-methoxy-2,3-dihydrofuro[2, 3-g][3]benzoxepin and 5-methoxyfuro[2,3-g][3]benzoxepin, respectively, based on UV, MS, (1)H and (13)C NMR, NOE, (1)H-(13)C COSY, and HMBC spectral data. They were isolated following bioassay-guided fractionation, using an in vitro cyclooxygenase-1 test. Compounds 1 and 2 possess inhibitory activities, with IC(50) values of 23.2 microM and 30.4 microM, respectively.

Animals↗
PubMed1981

Tetrahydro-2-benzoxepins: a novel family of hypotensives.

A novel series of 1-(alkylamino)-1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepins shows hypotensive activity. A typical example is 1-[2-(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)ethyl]-4-(4-fluorophenyl)piperazine. This compound is an alpha blocker with peripheral and central activities.

Anesthesia↗
PubMed1977

Dibenz[b,e]oxepinalkanoic acids as nonsteroidal antiinflammatory agents. 2. Dihydro-10-oxofuro-and -thieno[3,2-c][1]benzoxepin-8-acetic acids.

4,10-Dihydro-10-oxofuro[3,2-c][1]benzoxepin-8-acetic acid and 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetic acid were evaluated in the carrageenan paw edema assay with the thieno analogue being ten times more active than the furano compound and 1.3. times more active than indomethacin. The therapeutic ratio (antiinflammatory activity/gastric irritation liability) of the thieno analogue was 25 times that of indomethacin.

Animals↗
PubMed1984

Dibenz[b,e]oxepinalkanoic acids as nonsteroidal antiinflammatory agents. 4. Synthesis and evaluation of 4-(4,10-dihydro-10-oxothieno[3,2-c] [1]benzoxepin-8-yl)butanol and -butyric acid and related derivatives.

4,10-Dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetic acid (6) was previously reported as a potent antiinflammatory-analgesic agent characterized by an impressive therapeutic ratio in comparison with indomethacin. With the goal of finding compounds that might display even more favorable therapeutic ratios and/or enhanced antiinflammatory/analgesic properties in comparison to 6, we synthesized 4-(4,10-dihydro-10-oxothieno [3,2-c][1]-benzoxepin-8-yl) butanol (4b) and -butyric acid (5a) and a series of related derivatives. All compounds were evaluated for potential analgesic activity in the phenylquinone-induced writhing (PQW) assay, for antiinflammatory activity in the carrageenan-induced paw edema (CPE) model and, where warranted, for gastric irritation (GI) liability. Of the compounds investigated, 4b (HP 573) displays moderate analgesic-like activity in PQW, is approximately half as potent as indomethacin or 6 as an antiinflammatory agent in the CPE, and is characterized by an extremely low propensity to induce GI as reflected by comparison of the therapeutic ratios (GI ED50/CPE ED50: 4b greater than 46, 6 = 9.9, indomethacin = 0.4). Compound 4b was selected for clinical evaluation.

Animals↗
PubMed2004

Benzoxepin-derived estrogen receptor modulators: a novel molecular scaffold for the estrogen receptor.

We present and examine the efficacy of a novel benzoxepin-based scaffold for modulation of the human estrogen receptor. Receptor tolerance of this new molecular scaffold is examined through presentation of experimentally determined antiproliferative effects on human MCF-7 breast tumor cells and measured binding affinities. The effect of functional group substitution on the benzoxepin scaffold is explored through a brief computational structure-activity relationship investigation with molecular simulation.

Antineoplastic Agents↗
PubMed2006

An efficient synthesis of 2-benzoxepines from Morita-Baylis-Hillman adducts using heterogeneous recyclable catalysts.

2-Benzoxepines have efficiently been synthesized from Morita-Baylis-Hillman adducts, alkyl 3-aryl-3-hydroxy-2-methylenepropanoates by treatment with HCHO catalyzed by silica supported perchloric acid (HClO4.SiO2) or Amberlyst-15 in CH2Cl2 under reflux for a short period of time (1.5-2.5 h). The catalyst can be recovered and recycled. The antibacterial properties of the new 2-benzoxepines were studied but no activity was found.

Anti-Bacterial Agents↗
PubMed1991

2H-pyrano[3,2-d]-1-benzoxepin derivatives with platelet antiaggregating and other activities.

The synthesis of some N,N-disubstituted 4-amino-5,6-dihydro-3-phenyl-2H-pyrano[3,2-d]-1-benzoxepin-2 -ones by reaction of phenylchloroketene with a series of N,N-disubstituted (E)-4-aminomethylene-3,4-dihydro-1-benzoxepin-5(2H)-ones, followed by dehydrochlorination of the primary adducts with DBN, is described. Some of these compounds showed a platelet antiaggregating activity in vitro slightly superior to that of acetylsalicylic acid, as well as weak local anesthetic and antiinflammatory activities in mice and rats, respectively.

Anesthetics, Local↗
PubMed2004

Synthesis and anti-implantation activity of novel non-steroidal 4,5-disubstituted 2,3,4,5-tetrahydro-1-benzoxepines.

The synthesis and anti-implantation activity of some novel 4,5-disubstiuted 2,3,4,5-tetrahydro-1-benzoxepins are presented. The synthesized compounds were evaluated for their anti-implantation activity in mature female Sprague-Dawley rats. The antifertility activity, as assessed by post coital anti-implantation test, was of weak potency for most of the compounds. Compounds 9d and 10d exhibited the highest anti-implantation activity among the tested compounds.

Animals↗
PubMed1980

[Pseudotumoral uterine reaction in the rat treated with a benzofuro-benzoxepin].

When orally administered, 5-(3-diméthylamino propyliden)-benzofuro [2,3-c] benzoxepin-1, which antagonizes several biogenic amines, is slightly sedative and has also endocrinological properties in the Rat, induces the appearance of localized lesions of uterine stroma in 2 to 16% of the animals. The cytological picture could suggest a tumorogenesis. In fact, these lesions represent a non-tumoral reactional hyperplasia with nuclear abnormalities due to a hormonal stimulation.

Animals↗
PubMed1996

Role of nitric oxide in gastrokinetic effects of the new benzoxepine derivative exepanol hydrochloride.

The gastrokinetic effects of exepanol hydrochloride (rac. 3,5-cis-2,3,4,5-tetrahydro-3-methyl-amino-1-benzoxepine-5-ol hydrochloride, CAS 77416-65-0, KC 2450) on gastrointestinal motility were studied both in vivo and in vitro. Exepanol-HCl accelerated the gastrointestinal (GI) transit in vivo in mice. This effect of exepanol-HCl was reduced by atropine, hemicholinium-3, morphine and MCN-A-343 (4-(m-chlorophenylcarbamoyloxy)-2-butynyl trimethyl ammonium chloride). In guinea pig (GP) ileum, exepanol-HCl facilitated the peristaltic reflex to threshold pressures and restored the reflex in fatigued preparations. These effects of exepanol-HCl were compared with metoclopramide (MCP) which was used as reference compound in both in vivo and in vitro experiments. Exepanol-HCl also partially reversed the L-arginine induced tonic "hump' responses of GP ileum to transmural stimulation. These findings suggest a cholinergic involvement and a partial role of nitric oxide in the mechanism of action of exepantol-HCl on GI motility.

Animals↗
PubMed1998

Inhibitors of farnesyl protein transferase. Synthesis and biological activity of amide and cyanoguanidine derivatives containing a 5,11-dihydro[1]benzthiepin, benzoxepin, and benzazepin [4,3-b]pyridine ring system.

Bioisosteric replacement of the C-6 carbon atom in piperidine I and piperazine II with S, O, and N heteroatoms is described. Amide and cyanoguanidine derivatives of these compounds were evaluated in vitro and found to be good inhibitors of farnesyl-protein transferase. An improved method of preparing the 5,11-dihydro-[1]-benzthiepin nucleus 6 was accomplished in high yield and with excellent regioselectivity using an AlCl3 melt protocol.

Alkyl and Aryl Transferases↗