20011-97-6Relevant academic research and scientific papers
Glycerine and CeClH: An efficient and recyclable reaction medium for ring opening of epoxides with thioamides and amines
Narsaiah, A. Venkat,Wadavrao, Sachin B.,Reddy, A. Ramesh,Yadav
experimental part, p. 485 - 489 (2011/04/16)
Oxiranes undergo rapid ring-opening reaction with a range of thioamides and amines to afford the corresponding -amino alcohol derivatives. The reactions were carried out using glycerine and cerium(III) chloride as a recyclable reaction medium. All the reactions were carried out at room temperature and the products were obtained in excellent yields. Georg Thieme Verlag Stuttgart New York.
(+/-)-(N-alkylamino)benzazepine analogs: novel dopamine D1 receptor antagonists.
Shah,Izenwasser,Geter-Douglass,Witkin,Newman
, p. 4284 - 4293 (2007/10/03)
(+/-)-(N-Alkylamino)benzazepine analogs were prepared as novel dopamine D1 receptor antagonists to further elucidate the role of these receptor subtypes in the pharmacology and toxicology of cocaine. In the first series of compounds, (+/-)-7-chloro-8-hydroxy-3- [6-(N,N-dimethylamino)-hexyl]-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepi ne (15) showed the highest affinity (Ki = 49.3 nM) and subtype-selectivity for dopamine D1 over dopamine D2, 5-HT2a, and 5-HT2c receptors. Compounds 7a [(+/-)-7-Chloro-8-hydroxy-3-[4-(N,N-dimethylamino)butyl]-1-phenyl- 2,3,4,5-tetrahydro-1H-3-benzazepine], 11 [(+/-)-7-chloro-8-hydroxy-3-[6-[(N,N-dimethylamino)hexyl]-1- phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-cyanoborane], and 15 were moderately potent dopamine D1 receptor antagonists as evidenced by their ability to block dopamine-stimulated adenylyl cyclase activity in rat caudate (predicted Ki values = 60, 34, and 21 nM, respectively). Compound 7a appears to be unique in that, despite its relatively potent inhibition of dopamine stimulated adenylyl cyclase, it demonstrated relatively weak binding affinity at the dopamine D1 receptors (Ki = 811 nM). Unlike previously reported N-alkylbenzazepines, where a significant loss in dopamine D1 receptor binding affinity was observed when successive increases in the alkyl side chain size at the benzazepine nitrogen were made, several of these novel N-alkylamino analogs demonstrated high-affinity binding with an optimal chain length of six carbons. This initial series of compounds appears to be identifying another binding domain on the dopamine D1 receptor protein that has not previously been characterized and that accepts an amino function. Further, these compounds may serve as templates for the design of peripherally active dopamine D1 receptor antagonists.
Tricarbonylchromium(0) Promoted Stereoselective Cyclisations of the N-3,4-Dimethoxyphenethyl Derivatives of the 1-Phenyl Ethanolamines Halostachine, Ephedrine and Pseudoephedrine to 1-Phenyl-N-Methyl-7,8-Dimethoxy-1,2,4,5-Tetrahydrobenzazepines
Coote, Steven J.,Davies, Stephen G.,Middlemiss, David,Naylor, Alan
, p. 33 - 56 (2007/10/02)
Acid promoted cyclisation of homochiral (R)-N-(3,4-dimethoxyphenethyl)-halostachine proceeds with almost total racemisation to yield 1-phenyl-N-methyl-1,2,4,5-tetrahydrobenzazepine (e.e, 6percent).Coordination of the cyclisation precursor to the tricarbonylchromium(0) moiety renders the cyclisation completely stereospecific to afford, after decomplexation, homochiral (+)-(R)-1-phenyl-N-methyl-1,2,4,5-tetrahydrobenzazepine. (-)-(1R,2S)-N-(3,4-Dimethoxyphenethyl)ephedrine undergoes acid mediated cyclisation to furnish trans-(-)-(1R,2S)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine as a single diastereoisomer.In contrast, the epimeric cyclisation precursor (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudoephedrine cyclises to give a mixture (ratio 91:9) of trans- and cis-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine.However, cyclisation of the tricarbonylchromium(0) complex of (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudo-ephedrine is completely stereoselective to yield trans-(+)-(1S,2R)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine after decomplexation.
ENANTIOSPECIFIC SYNTHESIS OF (+)-(R)-1-PHENYL-3-METHYL-1,2,4,5-TETRAHYDROBENZAZEPINE FROM (+)-(S)-N-METHYL-1-PHENYL ETHANOLAMINE (HALOSTACHINE) via ARENE CHROMIUM TRICARBONYL METHODOLOGY
Coote, Steven J.,Davies, Stephen G.,Middlemiss, David,Naylor, Alan
, p. 3581 - 3584 (2007/10/02)
Acid promoted cyclisation of homochiral (R)-N-(3,4-dimethoxyphenethyl) halostachine chromium tricarbonyl is stereospecific, proceeding with retention of configuration, to afford, after decomplexation, homochiral (+)-(R)-1-phenyl-3-methyl-1,2,4,5-tatrahydr
Dopamine Agonists Related to 3-Allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol. 6-Position Modifications
Ross, Stephen T.,Franz, Robert G.,Gallagher, Gregory,Brenner, Martin,Wilson, James W.,et al.
, p. 35 - 40 (2007/10/02)
The N-allyl derivative (SK and F 85174) of 6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol (SK and F 82526) retains the DA-1 agonist potency of the latter compound but unlike the parent also shows substantial DA-2 agonist activity.In a previous study of N-substituted benzazepines these combined agonist effects were shown to be uniquely associated with the N-allyl group.A continuation of this research has examined dependency of combined DA-2/DA-1 agonist activities on 6=position modification with the specific objective of developing an agonist with maximum effectiveness and potency at the DA-2 receptor subtype.DA-2 agonist activity was measured in a rabbit ear artery assay, and DA-1 agonist activity was determined in an adenylate cyclase assay.Replacing chloro with bromo retains the activity pattern and the potency of the chloro compound: replacement with a hydrogen causes a decrease of both DA-1 and DA-2 receptor activating potency.Introduction of a 6-methyl group causes loss of DA-2 agonist activity and reduction in DA-1 agonist potency.Substitution with a 6-fluoro provides the best balance of DA-2 and DA-1 agonist activities; this compound was moderately in both assays.
Oxazolines. 2. 2-Substituted 2-Oxazolines as Synthons for N-(β-Hydroxyethyl)arylalkylamines, Intermediates in a Synthesis of 1,2,3,4-Tetrahydroisoquinolines and 2,3,4,5-Tetrahydro-1H-3-Benzazepines
Pridgen, Lendon N.,Killmer, Lewis B.,Webb, R. Lee
, p. 1985 - 1989 (2007/10/02)
2-(Arylalkyl)-2-oxazolines 4 (n = 1) and 2-aryl-2-oxazolines 4 (n = 0), the latter prepared in a novel reaction by cross-coupling aryl Grignard reagents with 2-(methylthio)-5-phenyl-2-oxazoline (10) and using palladium(II) chloride (14) as a catalyst, were reduced in a previously unreported reaction by diborane in refluxing THF to yield N-(β- hyroxyethyl)arylalkylamines 5 (n = 1,2).Amino alcohols 5 were cyclized to their respective heterocyclic derivatives 6 (n = 1,2) by treatment with H2SO4/TFA in refluxing methylene chloride.This paper disscuses how 2-substituted 2-oxazolines may be used to prepare1,2,3,4-tetrahydroisoquinolines 6 (n = 1) and 2,3,4,5-tetrahydro-1H-3-benzazepines 6 (n = 2) via amino alcohols 5.
6-HALO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINES
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, (2008/06/13)
7,8-Dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines having a halo substituent at the 6-position have potent dopaminergic activity. The 6-chloro congeners are most active.
Method for 6-bromination of 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds
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, (2008/06/13)
The preparation of 6-bromo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines is described by direct bromination of the nucleus.
PHARMACEUTICAL COMPOSITIONS AND METHODS INVOLVING BENZAZEPINE DERIVATIVES
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, (2008/06/13)
Pharmaceutical compositions and a method of stimulating peripheral dopamine receptors by administering internally a nontoxic effective quantity of a benzazepine derivative to an animal. Renal vasodilator and diuretic methods are also disclosed.
Pharmaceutical compositions and method of producing anti-Parkinsonism activity
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, (2008/06/13)
Pharmaceutical compositions and method of producing anti-Parkinsonism activity by administering internally a nontoxic effective quantity of a benzazepine derivative to an animal.
