“…The gastrin and CCK-peptides [Nle 15 ]-HG- [11][12][13][14][15][16][17] ([Nle]heptagastrin), 55 and [Thr,Nle]-CCK-9 ([Thr 28 ,Nle 31 ]-CCK- [25][26][27][28][29][30][31][32][33]), 56 were synthesized as described previously and used as reference compounds in the receptor binding assays. (1).…”
“…The gastrin and CCK-peptides [Nle 15 ]-HG- [11][12][13][14][15][16][17] ([Nle]heptagastrin), 55 and [Thr,Nle]-CCK-9 ([Thr 28 ,Nle 31 ]-CCK- [25][26][27][28][29][30][31][32][33]), 56 were synthesized as described previously and used as reference compounds in the receptor binding assays. (1).…”
“…Since the reaction outlined in Scheme is unlikely to cause racemization at C-3, it is clear that it would be possible to obtain the enantiomerically pure ureas after separation of the corresponding amines 5 , thus highlighting the strategic importance of such a key intermediate. The synthesis of the key intermediate 5 follows procedures disclosed in earlier reports. − Representative reaction conditions are provided in the Experimental Section describing the preparation of compounds represented in Schemes −3. 1 2 3 2 3-Amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1 H -1,5-benzodiazepine.…”
Section: Chemistrymentioning
confidence: 99%
“…Therefore, an alternative route was set up as reported in Scheme . The starting phenylenediamines 1 and 6 were generally prepared by reaction of 2-fluoronitrobenzene or substituted 2-fluoronitrobenzene with either aniline or 2-fluoroaniline in the presence of potassium fluoride and subsequent reduction of the nitro group . The resulting amines were alkylated generally by using an alkyl bromide in the presence of sodium hydride to obtain the intermediates 7 .…”
A series of 5-phenyl-3-ureidobenzodiazepine-2,4-diones was synthesized and evaluated as cholecystokinin-B (CCK-B) receptor antagonists. Structure-activity relationship (SAR) studies revealed the importance of the N-1 substituent for potent and selective CCK-B affinity. Addition of substituents at the urea side chain provided in some cases more potent compounds. Moreover the introduction of bulky substituents such as adamantylmethyl at N-1 and resolution of the racemic ureas resulted in our lead compound GV150013.
“…The synthesis of these compounds was accomplished using known procedures [12][13][14][17][18][19] , starting from phenylene diamine derivatives 3 (Scheme 1). As a general procedure, the starting diamines were reductively alkylated to give compounds 4.…”
Section: Chemistrymentioning
confidence: 99%
“…During these studies, we explored a variety of possible modifications on the benzodiazepine nucleus which could affect the potency and selectivity parameters [14,[17][18][19] . At first, the type of substitution at N-1 was widely explored and was found to be particularly significant in determining the molecule's overall activity.…”
The synthesis and biological evaluation of 3‐ureido and 3‐carbamate derivatives of 1,5‐benzodiazepines bearing bridged cycloalkyl substituents at N‐1 are reported. Their activity as CCK‐B receptor ligands is briefly discussed.
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