3-{[(3aR,7aR)-2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl]methyl}-7-bromo-6-chloro-3,4-dihydroquinazolin-4-one

• ChemBase ID: 169832
• Molecular Formular: C16H17BrClN3O3
• Molecular Mass: 414.68148
• Monoisotopic Mass: 413.0141811
• SMILES: Brc1c(cc2c(c1)ncn(c2=O)CC1(C[C@@H]2[C@H](O1)CCCN2)O)Cl
• Canonical SMILES: Brc1cc2ncn(c(=O)c2cc1Cl)CC1(O)C[C@@H]2[C@H](O1)CCCN2
• InChI: InChI=1S/C16H17BrClN3O3/c17-10-5-12-9(4-11(10)18)15(22)21(8-20-12)7-16(23)6-13-14(24-16)2-1-3-19-13/h4-5,8,13-14,19,23H,1-3,6-7H2/t13-,14-,16?/m1/s1
• InChIKey: BNXGPVDFDDSICC-UIDSBSESSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(3aR,7aR)-2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl]methyl}-7-bromo-6-chloro-3,4-dihydroquinazolin-4-one
• IUPAC Traditional name: 3-{[(3aR,7aR)-2-hydroxy-hexahydro-3H-furo[3,2-b]pyridin-2-yl]methyl}-7-bromo-6-chloroquinazolin-4-one
• Synonyms: rel-7-Bromo-6-chloro-3-[[(3aS,7aS)-octahydro-2-hydroxyfuro[3,2-b]pyridin-2-yl]methyl]-4(3H)-quinazolinone; cis-Halofuginone

Database IDs

• CAS Number: 1273594-72-1
• PubChem SID: 162263964
• PubChem CID: 71317188

CALCULATED PROPERTIES

• Acid pKa: 11.606973
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.70031387
• LogD (pH = 7.4): 0.64137775
• Log P: 2.4040291
• Molar Refractivity: 94.4933 cm^3
• Polarizability: 35.967106 Å^3
• Polar Surface Area: 74.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H102505

cis-Isomer of Halofuginone (H102500); a halogenated derivative of Febrifugine. Used as an antiprotozoal.

REFERENCES

• McIntosh, L., et al.: Biochem. Cell Biol., 73, 181 (1995)
• Leshem, Y., et al.: Exp. Cell Res., 274, 288 (1995)