2,2-difluoro-8-(4-{[2-(methanesulfonylsulfanyl)ethyl]amino}phenyl)-4,6,10,12-tetramethyl-1λ5,3-diaza-2-boratricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-1-ylium-2-uide

• ChemBase ID: 158804
• Molecular Formular: C22H26BF2N3O2S2
• Molecular Mass: 477.3985464
• Monoisotopic Mass: 477.15275593
• SMILES: c12c(cc(n1[B-]([N+]1=C(C=C(C1=C2c1ccc(cc1)NCCSS(=O)(=O)C)C)C)(F)F)C)C
• Canonical SMILES: CC1=CC(=[N+]2C1=C(c1ccc(cc1)NCCSS(=O)(=O)C)c1c(C)cc(n1[B-]2(F)F)C)C
• InChI: InChI=1S/C22H26BF2N3O2S2/c1-14-12-16(3)27-21(14)20(22-15(2)13-17(4)28(22)23(27,24)25)18-6-8-19(9-7-18)26-10-11-31-32(5,29)30/h6-9,12-13,26H,10-11H2,1-5H3
• InChIKey: KMZRIAVXLIWCSW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-difluoro-8-(4-{[2-(methanesulfonylsulfanyl)ethyl]amino}phenyl)-4,6,10,12-tetramethyl-1λ^5,3-diaza-2-boratricyclo[7.3.0.0^3,^7]dodeca-1(12),4,6,8,10-pentaen-1-ylium-2-uide
• IUPAC Traditional name: 2,2-difluoro-8-(4-{[2-(methanesulfonylsulfanyl)ethyl]amino}phenyl)-4,6,10,12-tetramethyl-1λ^5,3-diaza-2-boratricyclo[7.3.0.0^3,^7]dodeca-1(12),4,6,8,10-pentaen-1-ylium-2-uide
• Synonyms: 8-[4-(Aminoethyl Methanethiosulfonyl)phenyl] Bodipy; (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol Sulfate; Ziagen; Abacavir Sulfate

Database IDs

• CAS Number: 188062-50-2
• PubChem SID: 162252939
• PubChem CID: 45038128

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.5919269
• LogD (pH = 7.4): -1.5811138
• Log P: -1.5809742
• Molar Refractivity: 141.6517 cm^3
• Polarizability: 48.889866 Å^3
• Polar Surface Area: 54.11 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: Dark Orange Solid; Off-White Solid
• Melting Point: 180-182°C; 222-225°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A105000

A nucleoside reverse transcriptase inhibitor (NRTI).

Toronto Research Chemicals - A609160

Reacts specifically and rapidly with thiols to form mixed disulfides. Used to probe the structures of the ACh receptor channel of the GABA receptor channel and of lactose permease.

REFERENCES

• Daluge, S.M., et al.: Antimicrob. Ag. Chemother., 41, 1082 (1997)
• Foster, R.H., et al.: Drugs, 55, 729 (1997)
• Staszewski, S., et al.: J. Am. Med. Assoc., 285, 1155 (1997)