N-{2-[(1S)-5-bromo-6-hydroxy-7-(prop-2-en-1-yl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide

• ChemBase ID: 159678
• Molecular Formular: C17H22BrNO2
• Molecular Mass: 352.26608
• Monoisotopic Mass: 351.08339095
• SMILES: c1(c(c(c2c(c1)CC[C@H]2CCNC(=O)CC)CC=C)O)Br
• Canonical SMILES: C=CCc1c2[C@H](CCNC(=O)CC)CCc2cc(c1O)Br
• InChI: InChI=1S/C17H22BrNO2/c1-3-5-13-16-11(8-9-19-15(20)4-2)6-7-12(16)10-14(18)17(13)21/h3,10-11,21H,1,4-9H2,2H3,(H,19,20)/t11-/m0/s1
• InChIKey: SOKCOMOZGLSICY-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{2-[(1S)-5-bromo-6-hydroxy-7-(prop-2-en-1-yl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide
• IUPAC Traditional name: N-{2-[(1S)-5-bromo-6-hydroxy-7-(prop-2-en-1-yl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide
• Synonyms: N-[4-[[3-Butyl-2,3,6,9-tetrahydro-2,6-dioxo-1-(2-propen-1-yl)-1H-purin-8-yl]methyl]phenyl]acetamide; N-[4-(1-Allyl-3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)phenyl]acetamide

Database IDs

• CAS Number: 628279-02-7
• PubChem SID: 162253813
• PubChem CID: 10861106

CALCULATED PROPERTIES

• Acid pKa: 8.192975
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 4.2512245
• LogD (pH = 7.4): 4.187701
• Log P: 4.252099
• Molar Refractivity: 89.6367 cm^3
• Polarizability: 34.082283 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A549670

It is used for the preparation of amide-substituted xanthine derivatives as phosphoenolpyruvate carboxykinase inhibitors with gluconeogenesis modulating activity for treating type 2 diabetes.

REFERENCES

• Kawashima, Y., et al.: Chem. Pharm. Bull., 43, 1132 (1995)
• Sun, Y., et al.: J. Biol. Chem., 277, 23301 (1995)
• Foley, L., et al.: Bioorg. Med. Chem. Lett., 13, 3871 (1995)