1-{1-[(4-{7-phenyl-1H-imidazo[4,5-g]quinoxalin-6-yl}phenyl)methyl]piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one trifluoroacetic acid hydrate

• ChemBase ID: 153848
• Molecular Formular: C36H32F3N7O4
• Molecular Mass: 683.6789896
• Monoisotopic Mass: 683.2467872
• SMILES: c1ccc(cc1)c1c(nc2cc3c(cc2n1)[nH]cn3)c1ccc(cc1)CN1CCC(CC1)n1c2ccccc2[nH]c1=O.C(=O)(C(F)(F)F)O.O
• Canonical SMILES: OC(=O)C(F)(F)F.O=c1[nH]c2c(n1C1CCN(CC1)Cc1ccc(cc1)c1nc3cc4nc[nH]c4cc3nc1c1ccccc1)cccc2.O
• InChI: InChI=1S/C34H29N7O.C2HF3O2.H2O/c42-34-39-26-8-4-5-9-31(26)41(34)25-14-16-40(17-15-25)20-22-10-12-24(13-11-22)33-32(23-6-2-1-3-7-23)37-29-18-27-28(36-21-35-27)19-30(29)38-33;3-2(4,5)1(6)7;/h1-13,18-19,21,25H,14-17,20H2,(H,35,36)(H,39,42);(H,6,7);1H2
• InChIKey: CRRPFKCJZALCLQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{1-[(4-{7-phenyl-1H-imidazo[4,5-g]quinoxalin-6-yl}phenyl)methyl]piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one trifluoroacetic acid hydrate
• IUPAC Traditional name: 1-{1-[(4-{7-phenyl-1H-imidazo[4,5-g]quinoxalin-6-yl}phenyl)methyl]piperidin-4-yl}-3H-1,3-benzodiazol-2-one trifluoroacetic acid hydrate
• Synonyms: 1,3-Dihydro-1-(1-((4-(6-phenyl-1H-imidazo[4,5-g]quinoxalin-7-yl)phenyl)methyl)-4-piperidinyl)-2H-benzimidazol-2-one trifluoroacetate salt hydrate; Akt Inhibitor VIII trifluoroacetate salt hydrate; Akti-1/2 trifluoroacetate salt hydrate; Akt1/2 kinase inhibitor

Database IDs

• MDL Number: MFCD08705407
• PubChem SID: 162247987; 24891133
• PubChem CID: 16218954

CALCULATED PROPERTIES

• Acid pKa: 11.815566
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.1382613
• LogD (pH = 7.4): 5.1158957
• Log P: 5.6199303
• Molar Refractivity: 163.0057 cm^3
• Polarizability: 67.3554 Å^3
• Polar Surface Area: 90.04 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C34H29N7O · xC2HF3O2 · yH2O

DETAILS

Sigma Aldrich - A6730

Application
Akt plays a role in signal transduction pathways of cell proliferation, apoptosis, angiogenesis, and diabetes. Akt1 and Akt2 dual kinase inhibitors are capable of sensitizing tumor cells to certain apoptotic stimuli, and inhibit Akt phosphorylation in vivo. Akt1 kinase activity and its regulation by extracellular signaling factors in vivo in hematopoietic cells suggests the activation of AKT1 involves intracellular translocation of the kinase from cytosol to membrane.
Biochem/physiol Actions
Isozyme selective Akt1/2 kinase inhibitor. In in vitro kinase assays, Akt1/2 kinase inhibitor shows IC50 = 58 nM, 210 nM, and 2.12 mM for Akt1, Akt2, and Akt3, respectively, The inhibition appears to be pleckstrin homology (PH) domain-dependent and the Akt1/2 kinase inhibitor has no inhibitory effect against PH domain-lacking Akts, or other closely related AGC family kinases, PKA, PKC, and SGK, even at concentrations as high as 50 μM.