Way-Vna-932

Caggiano, Thomas J.

doi:10.1358/dof.2002.027.03.659890

Cited by 18 publications

(19 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The different benzazepines were coupled to the aromatic acids as described before via acyl chloride intermediate (Scheme ). The V 2 receptor agonist VNA-932 ( 42 ) was prepared from benzodiazepine 31 . The coupling products 39a and 39b , obtained from ketone 26 , were further reduced by sodium borohydride to obtain the alcohols 40a and 40b .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism

et al. 2018

View full text Add to dashboard Cite

Oxytocin (OT) and its receptor (OT-R) are implicated in the etiology of autism spectrum disorders (ASD), and OT-R is a potential target for therapeutic intervention. Very few nonpeptide oxytocin agonists have currently been reported. Their molecular and in vivo pharmacology remain to be clarified, and none of them has been shown to be efficient in improving social interaction in animal models relevant to ASD. In an attempt to rationalize the design of centrally active nonpeptide full agonists, we studied in a systematic way the structural determinants of the affinity and efficacy of representative ligands of the V and V vasopressin receptor subtypes (V-R and V-R) and of the oxytocin receptor. Our results confirm the subtlety of the structure-affinity and structure-efficacy relationships around vasopressin/oxytocin receptor ligands and lead however to the first nonpeptide OT receptor agonist active in a mouse model of ASD after peripheral ip administration.

show abstract

Section: Resultsmentioning

confidence: 99%

“…The V 2 receptor agonist VNA-932 (42) was prepared from benzodiazepine 31. 70 The coupling products 39a and 39b, obtained from ketone 26, were further reduced by sodium borohydride to obtain the alcohols 40a and 40b. 64 Structures and yields are given in Scheme 4.…”

Section: ■ Resultsmentioning

confidence: 99%

LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism

et al. 2018

View full text Add to dashboard Cite

show abstract

“…It has a different profile of binding to dopamine receptors compared with the typical antipsychotic drugs . Arginine vasopressin (AVP) antagonists, such as VPA-985 and VNA-932, have a curative effect for the diseases associated with excess renal reabsorption of water (Figure ). Thus, the development of convenient methods for the construction of this skeleton is desirable.…”

mentioning

confidence: 99%

Photoredox-Catalyzed Radical Cascade Reaction To Synthesize Fluorinated Pyrrolo[1,2-d]benzodiazepine Derivatives

Lian

Liu

et al. 2019

J. Org. Chem.

View full text Add to dashboard Cite

A new photoredox-catalyzed cascade reaction is described to access fluorinated pyrrolo[1,2-d]benzodiazepine derivatives under mild conditions. In this process, single electron transfer (SET) between the excited state photocatalyst fac-Ir(ppy) 3 and ethyl bromodifluoroacetate initiated the regioselective radical addition to a wide range of 2-(1H-pyrrol-1-yl) anilines or indol-substituted anilines, followed by another SET process and intramolecular amidation.

show abstract

“…We have already reported on the genesis of the potent, orally active V 2 selective antagonist VPA-985 3 and the first V 2 selective agonist VNA-932. 4 In connection with the isosteric replacement of the amide bond of VPA-985 with small heterocyclic rings leading to the discovery of VNA-932 ( Fig. 1), we have investigated a number of tricyclic benzodiazepines as potential Ôprivileged structureÕ variations.…”

mentioning

confidence: 99%

Pyridobenzodiazepines: A novel class of orally active, vasopressin V2 receptor selective agonists

Failli

Shumsky

Steffan

et al. 2006

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

Way-Vna-932

Cited by 18 publications

References 0 publications

LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism

LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism

Photoredox-Catalyzed Radical Cascade Reaction To Synthesize Fluorinated Pyrrolo[1,2-d]benzodiazepine Derivatives

Pyridobenzodiazepines: A novel class of orally active, vasopressin V2 receptor selective agonists

Contact Info

Product

Resources

About