2-amino-4-(3-nitrophenyl)-4H-benzo[h]chromene-3-carbonitrile

• ChemBase ID: 179864
• Molecular Formular: C20H13N3O3
• Molecular Mass: 343.33552
• Monoisotopic Mass: 343.09569129
• SMILES: C1(=C(Oc2c(C1c1cc([N+](=O)[O-])ccc1)ccc1c2cccc1)N)C#N
• Canonical SMILES: N#CC1=C(N)Oc2c(C1c1cccc(c1)[N+](=O)[O-])ccc1c2cccc1
• InChI: InChI=1S/C20H13N3O3/c21-11-17-18(13-5-3-6-14(10-13)23(24)25)16-9-8-12-4-1-2-7-15(12)19(16)26-20(17)22/h1-10,18H,22H2
• InChIKey: KLHQWXOILCCTOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(3-nitrophenyl)-4H-benzo[h]chromene-3-carbonitrile
• IUPAC Traditional name: 2-amino-4-(3-nitrophenyl)-4H-benzo[h]chromene-3-carbonitrile
• Synonyms: LY-290181

Database IDs

• CAS Number: 149550-36-7
• PubChem SID: 164235774
• PubChem CID: 3114320

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.9627988
• LogD (pH = 7.4): 3.962864
• Log P: 3.9628649
• Molar Refractivity: 106.8579 cm^3
• Polarizability: 37.320763 Å^3
• Polar Surface Area: 104.86 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Metalloproteinase inhibitor; Myocyte proliferation inhibitor; Protein kinase C inhibitor

Product Information

• Application(s): Antiarteriosclerotic; Antimitotic; Antiproliferative

REFERENCES

• 1. S. Chandrasekhar, A. K. Harvey, C. P. Dell, S. J. Ambler, C. W. Smith Identification of a Novel Chemical Series that Blocks Interleukin-1-Stimulated Metalloprotease Activity in Chondrocytes
• Journal of Pharmacology and Experimental Therapeutics 273(3): 1519-1528, 1995
• 2. D. L. Wood, D. Panda, T. R. Wiernicki, L. Wilson, M. A. Jordan, J. P.
• Singh nhibition of Mitosis and Microtubule Function through Direct Tubulin Binding by a Novel Antiproliferative Naphthopyran LY290181 Mol. Pharmacol. September 1, 1997 52:437-444
• 3. Birch K. A., Heath W. F., Hermling R. N., Johnston C. M., Stramm L., Dell C., Smith C., Williamson J. R., Miller A. R. (1996)
• LY290181, an inhibitor of diabetes-induced vascular dysfunction, blocks protein kinase C-stimulated transcription factor binding to phorbol response element. Diabetes 45:642?50.