7-bromo-6-chloro-3-{3-[(3R)-3-hydroxypiperidin-2-yl]-2-oxopropyl}-3,4-dihydroquinazolin-4-one hydrochloride

• ChemBase ID: 169831
• Molecular Formular: C16H18BrCl2N3O3
• Molecular Mass: 451.14242
• Monoisotopic Mass: 448.99085881
• SMILES: Brc1c(cc2c(c1)ncn(c2=O)CC(=O)CC1[C@@H](CCCN1)O)Cl.Cl
• Canonical SMILES: O=C(Cn1cnc2c(c1=O)cc(c(c2)Br)Cl)CC1NCCC[C@H]1O.Cl
• InChI: InChI=1S/C16H17BrClN3O3.ClH/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14;/h5-6,8,14-15,19,23H,1-4,7H2;1H/t14?,15-;/m1./s1
• InChIKey: XFFYBQUXAJOKAL-NUNOUFIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-bromo-6-chloro-3-{3-[(3R)-3-hydroxypiperidin-2-yl]-2-oxopropyl}-3,4-dihydroquinazolin-4-one hydrochloride
• IUPAC Traditional name: halofuginone hydrochloride
• Synonyms: rel-7-Bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone Hydrochloride; 7-Bromo-6-chlorofebrifugine Hydrochloride; HAL; Halofuginone Hydrochloride

Database IDs

• CAS Number: 1217623-74-9
• PubChem SID: 162263963
• PubChem CID: 71317187

CALCULATED PROPERTIES

• Acid pKa: 14.481945
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.4232763
• LogD (pH = 7.4): -0.16228056
• Log P: 1.7095169
• Molar Refractivity: 95.8668 cm^3
• Polarizability: 36.06648 Å^3
• Polar Surface Area: 82.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 247-249°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H102500

Halofuginone is a halogenated derivative of Febrifugine (F228500). Halofuginone is used as an antiprotozoal.

REFERENCES

• Ryley, J.G., et al.: Parasitology, 70, 203 (1975)