4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 171927
• Molecular Formular: C34H36Cl2N8O4
• Molecular Mass: 691.60684
• Monoisotopic Mass: 690.22365703
• SMILES: c1(ccc(cc1Cl)Cl)[C@]1(OC[C@@H](O1)COc1ccc(cc1)N1CCN(CC1)c1ccc(cc1)n1cnn(c1=O)C(C)C)Cn1cncn1
• Canonical SMILES: Clc1ccc(c(c1)Cl)[C@]1(OC[C@@H](O1)COc1ccc(cc1)N1CCN(CC1)c1ccc(cc1)n1cnn(c1=O)C(C)C)Cn1cncn1
• InChI: InChI=1S/C34H36Cl2N8O4/c1-24(2)44-33(45)43(23-39-44)28-6-4-26(5-7-28)40-13-15-41(16-14-40)27-8-10-29(11-9-27)46-18-30-19-47-34(48-30,20-42-22-37-21-38-42)31-12-3-25(35)17-32(31)36/h3-12,17,21-24,30H,13-16,18-20H2,1-2H3/t30-,34-/m0/s1
• InChIKey: YPJNBOZLRNFTJN-NHZFLZHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2-isopropyl-1,2,4-triazol-3-one
• Synonyms: cis-4-[4-[4-[4-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylethyl)-3H-1,2,4-triazol-3-one; Isopropyl Itraconazole

Database IDs

• CAS Number: 89848-49-7
• PubChem SID: 164227837
• PubChem CID: 71749617

CALCULATED PROPERTIES

• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): 6.777633
• LogD (pH = 7.4): 6.788706
• Log P: 6.788849
• Molar Refractivity: 195.876 cm^3
• Polarizability: 69.76246 Å^3
• Polar Surface Area: 100.79 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I872150

A novel Itraconazole (I937500) derivative, an antimycotic azole.

REFERENCES

• Heeres, J., et al.: J. Med. Chem., 27, 894 (1984)