Quinazolines and 1,4-Benzodiazepines. VI.<sup>1a</sup> Halo-, Methyl-, and Methoxy-substituted 1,3-Dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones<sup>1b,c</sup>

Sternbach, L. H.; Fryer, R. Ian; Metlesics, W.; Reeder, E.; Sach, G. S.; Saucy, G.; Stempel, Arthur

doi:10.1021/jo01058a010

Cited by 160 publications

(74 citation statements)

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“…The acid 11, obtained from the ester 10 , which was available from the literature, 3, 50 was stirred with CDI in DMF, followed by stirring with the required diol and DBU to provide bromide dimers 12 or 13 , respectively. They were converted into the trimethylsilylacetylenyl 14 or 15 , respectively under standard conditions (Pd-mediated, Heck-type coupling).…”

Section: Methodsmentioning

confidence: 99%

A study of the structure–activity relationship of GABAA–benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis

Han

Försterling

et al. 2008

Bioorganic & Medicinal Chemistry

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The stable conformations of GABAA-benzodiazepine receptor bivalent ligands were determined by low temperature NMR spectroscopy and confirmed by single crystal X-ray analysis. The stable conformations in solution correlated well with those in the solid state. The linear conformation was important for these dimers to access the binding site and exhibit potent in vitro affinity and was illustrated for α5 subtype selective ligands. Bivalent ligands with an oxygen-containing linker folded back upon themselves both in solution and the solid state. Dimers which are folded do not bind to Bz receptors.

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Section: Methodsmentioning

confidence: 99%

A study of the structure–activity relationship of GABAA–benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis

Han

Försterling

et al. 2008

Bioorganic & Medicinal Chemistry

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“…However, as illustrated, Table 2. Table 2 (compounds 6, 8, 9, and 10) were prepared by base-mediated cyclization of a-aminoamides using published methods (25). The a-aminoamides were obtained either by acylation ofthe appropriate 2-aminobenzophenone with D-or L-tryptophan acid chloride, or by coupling with BOC-D-or -L-tryptophan followed by acid-catalyzed N-deprotection.…”

mentioning

confidence: 99%

Design of potent, orally effective, nonpeptidal antagonists of the peptide hormone cholecystokinin.

Evans¹,

Bock²,

Rittle³

et al. 1986

Proc. Natl. Acad. Sci. U.S.A.

285

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We describe the design and synthesis of nonpeptidal antagonists of the peptide hormone cholecystokinin. Several of these compounds have high specificity and nanomolar binding affinity and are active after oral administration. To our knowledge, the design of such agents has not previously been accomplished for any peptide hormone. The structural similarities between these synthetic compounds and the anxiolytic 1,4-benzodiazepines are noted, and the potential of this structural feature for future design of ligands for other peptide hormone receptors is discussed.selective nonpeptidal antagonist of CCK in vitro and in vivo (7). However, asperlicin has liabilities as a pharmacological or potential therapeutic agent, including lack of oral bioavailability, modest potency, and poor water solubility (7, 42).Many important drugs such as ivermectin (18)

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“…A progression of 1600 f 80 cm-I is observed (Fig. 4) which corresponds to carbon-nitrogen double bond stretching [28]. The only system so far unassigned in the PE spectrum of benzophenonmethylimine is located at 9.6 eV.…”

Section: 4-benzodiazepin-2-onesmentioning

confidence: 94%

Application of photoelectron spectroscopy to biologically active molecules and their constituent parts. IX. 1,4‐Benzodiazepin‐2‐ones

Klasinc̆¹,

Ruščić²,

Sabljić³

et al. 1983

Int J of Quantum Chemistry

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The He1 photoelectron (PE) spectra of desmethyldiazepam, diazepam, oxazepam, temazepam, 3 4 s ) -methyldesmethyldiazepam, 3-(S);methyldiazepam, 5-methyl-2H-1,4-benzodiazepin-2-one, and benzophenonmethylimine have been measured and analyzed. Their low-energy regions (up to 12.0 eV) have been completely assigned by the composite molecule method using the PE spectra of diphenylmethane, benzophenonmethylimine, acetamide, chlorobenzene, and acetophenonmethylimine to compare the electronic structure of equivalent parts.

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Quinazolines and 1,4-Benzodiazepines. VI.^1a Halo-, Methyl-, and Methoxy-substituted 1,3-Dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones^1b,c

Cited by 160 publications

References 0 publications

A study of the structure–activity relationship of GABAA–benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis

A study of the structure–activity relationship of GABAA–benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis

Design of potent, orally effective, nonpeptidal antagonists of the peptide hormone cholecystokinin.

Application of photoelectron spectroscopy to biologically active molecules and their constituent parts. IX. 1,4‐Benzodiazepin‐2‐ones

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Quinazolines and 1,4-Benzodiazepines. VI.1a Halo-, Methyl-, and Methoxy-substituted 1,3-Dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones1b,c

Cited by 160 publications

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A study of the structure–activity relationship of GABAA–benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis

A study of the structure–activity relationship of GABAA–benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis

Design of potent, orally effective, nonpeptidal antagonists of the peptide hormone cholecystokinin.

Application of photoelectron spectroscopy to biologically active molecules and their constituent parts. IX. 1,4‐Benzodiazepin‐2‐ones

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Quinazolines and 1,4-Benzodiazepines. VI.^1a Halo-, Methyl-, and Methoxy-substituted 1,3-Dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones^1b,c