7-benzyl-6-methyl-7H-quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione
benzomalvin A · Quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione, 6,7-dihydro-6-methyl-7-(phenylmethyl)-, (6S,7S)-
![7-benzyl-6-methyl-7H-quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione molecular structure](/img/chemical/190863.png)
Identifiers & Physical Properties
| CAS No. | 157047-96-6 |
|---|---|
| Molecular formula | C24H19N3O2 |
| Average molar mass | 381.4 g/mol |
| Monoisotopic mass | 381.14772686 g/mol |
| SMILES | CN1C(=O)c2ccccc2-n2c(nc3ccccc3c2=O)C1Cc1ccccc1 |
| InChIKey | YYWUABJYAOCACI-UHFFFAOYSA-N |
| PubChem CID | 190863 |
| DTXSID | DTXSID90935599 |
Chemical & Physical Properties
| XLogP | 3.7 |
|---|---|
| Topological polar surface area | 53 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 2 |
| Heavy atoms | 29 |
| Formal charge | 0 |
| Complexity | 684 |
| Boiling point | 599.3±60.0 °C(Predicted) |
| Density | 1.28±0.1 g/cm3(Predicted) |
| Storage conditions | Store at -20°C |
| Solubility | DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble |
| Physical state | A solid |
| pKa (acidity coefficient) | -0.46±0.40(Predicted) |
Applications & Uses
Description
Benzomalvin A is a fungal metabolite produced by Penicillium. It inhibits yeast α-glucosidase in vitro (IC50 = 383.2 μM). In vivo, benzomalvin A (3.1-31.6 mg/kg) decreases plasma glucose levels in mice following administration of sucrose. It also decreases the plasma glucose postprandial peak in nicotinamide-streptozotocin-induced hyperglycemic mice when administered at a dose of 10 mg/kg. Benzomalvin A also acts as an antagonist of neurokinin-1 (NK1) receptors, inhibiting binding of substance P to guinea pig, rat, and human NK1 (Kis = 12, 42, and 43 μM, respectively).
Uses
Benzomalvin A is a potent antagonist of neurokinin receptor isolated from Penicillium sp. Benzomalvin A shows inhibitory activity against substance P with Ki values of 12, 42 and 43 μM at the guinea pig, rat and human neurokinin NK1 receptors, respectively[1].