benzomalvin C

• CAT Number: I011857
• CAS Number: 157047-98-8
• Molecular Formula: C24H17N3O3
• Molecular Weight: 395.418
• Purity: 95%
• Synonyms: benzomalvin C
• Appearance: White to off-white solid
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: 6'-methyl-3-phenylspiro[oxirane-2,7'-quinazolino[3,2-a][1,4]benzodiazepine]-5',13'-dione
• InChI: InChI=1S/C24H17N3O3/c1-26-21(28)17-12-6-8-14-19(17)27-22(29)16-11-5-7-13-18(16)25-23(27)24(26)20(30-24)15-9-3-2-4-10-15/h2-14,20H,1H3
• InChIKey: TWDKBDSVUUKABK-UHFFFAOYSA-N
• SMILES: CN1C(=O)C2=CC=CC=C2N3C(=O)C4=CC=CC=C4N=C3C15C(O5)C6=CC=CC=C6

Benzomalvin C(cas#  157047-98-8) is a weak antagonist of the neurokinin-1 (NK1) receptor inhibiting binding of substance P by 46% when used at 100 μg/ml in vitro. It is also a weak inhibitor of indolamine 2,3-dioxygenase (IDO) with an IC50 value of 130 μM for recombinant IDO. It was isolated from Penicillium and contains an epoxide group at C-19 and C-20, which is not present in benzomalvins A, B, or E.

Reference

1. Benzomalvins, new substance P inhibitors from a Penicillium sp. Sun H.H. et al., J. Antibiot. 1994, 47, 515.
2. The first total synthesis of (-)-benzomalvin A and benzomalvin B via the intramolecular aza-Wittig reactions.
Sugimori T. et al., Tetrahedron 1998, 54, 7997.
3. Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus: fermentation, isolation
and biological properties. Goetz M.A. et al., J. Antibiot. 1985, 38, 1633.
4. Benzomalvin E, an indoleamine 2,3-dioxygenase inhibitor isolated from Penicillium sp. FN070315. Jang J-P. et
al., J. Antibiot. 2012, 65, 215.