(3E)-N,5-bis(4-chlorophenyl)-3-{[(2H7)propan-2-yl]imino}-3,5-dihydrophenazin-2-amine

• ChemBase ID: 164049
• Molecular Formular: C27H22Cl2N4
• Molecular Mass: 473.39638
• Monoisotopic Mass: 472.12215208
• SMILES: c12c(nc3c(n1c1ccc(cc1)Cl)c/c(=N\C(C)C)/c(c3)Nc1ccc(cc1)Cl)cccc2
• Canonical SMILES: Clc1ccc(cc1)Nc1cc2nc3ccccc3n(c2c/c/1=N\C(C)C)c1ccc(cc1)Cl
• InChI: InChI=1S/C27H22Cl2N4/c1-17(2)30-24-16-27-25(15-23(24)31-20-11-7-18(28)8-12-20)32-22-5-3-4-6-26(22)33(27)21-13-9-19(29)10-14-21/h3-17,31H,1-2H3/b30-24+
• InChIKey: WDQPAMHFFCXSNU-BGABXYSRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-N,5-bis(4-chlorophenyl)-3-{[(^2H₇)propan-2-yl]imino}-3,5-dihydrophenazin-2-amine
• IUPAC Traditional name: (3E)-N,5-bis(4-chlorophenyl)-3-[(^2H₇)propan-2-ylimino]phenazin-2-amine
• Synonyms: N,5-Bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl-d7)imino]-2-phenazinamine; 3-(p-Chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino-d7)phenazine; 2-(4-Chloroanilino)-3-(isopropyl-d7)imino-5-(4-chlorophenyl)-3,5-dihydrophenazine; B 663-d7; Chlofazimine-d7; Hansepran-d7; Lampren-d7; Lamprene-d7; NSC 141046-d7; Clofazimine-d7

Database IDs

• PubChem SID: 162258184
• PubChem CID: 71314667

CALCULATED PROPERTIES

• Acid pKa: 16.154114
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.042732
• LogD (pH = 7.4): 5.4225707
• Log P: 7.304315
• Molar Refractivity: 142.5521 cm^3
• Polarizability: 51.55547 Å^3
• Polar Surface Area: 39.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C324302

Labelled Clofazimine (C324300). Antibacterial (tuberculostatic, leprostatic).

REFERENCES

• Doak, A., et al.: J. Med. Chem., 53, 4259 (2010)
• Rodgers, A., et al.: Chem. Res. Toxicol., 23, 724 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)