| Identification | Back Directory | [Name]
KRIBB11 | [CAS]
342639-96-7 | [Synonyms]
KRIBB11
CS-2403
KRIBB 11;KRIBB-11
N2-1H-Indazol-5-yl-N6-methyl-3-nitro-2,6-pyridinediamine
2,6-Pyridinediamine, N2-1H-indazol-5-yl-N6-methyl-3-nitro- | [Molecular Formula]
C13H12N6O2 | [MDL Number]
MFCD30182306 | [MOL File]
342639-96-7.mol | [Molecular Weight]
284.27 |
| Chemical Properties | Back Directory | [Boiling point ]
534.9±50.0 °C(Predicted) | [density ]
1.531±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO:27.0(Max Conc. mg/mL);94.98(Max Conc. mM) | [form ]
powder | [pka]
13.59±0.40(Predicted) | [color ]
yellow to orange | [InChI]
1S/C13H12N6O2.C2HF3O2/c1-14-12-5-4-11(19(20)21)13(17-12)16-9-2-3-10-8(6-9)7-15-18-10;3-2(4,5)1(6)7/h2-7H,1H3,(H,15,18)(H2,14,16,17);(H,6,7) | [InChIKey]
DNBQMABUWGNHGB-UHFFFAOYSA-N | [SMILES]
CNC1=NC(NC2=CC=C(NN=C3)C3=C2)=C([N+]([O-])=O)C=C1.FC(F)(C(O)=O)F |
| Hazard Information | Back Directory | [Uses]
KRIBB 11 is a heat shock factor (HSF) inhibitor that induces apoptosis in cancer cells. KRIBB 11 exhibits anticancer properties. | [Biological Activity]
KRIBB11 is an inhibitor of the transcription factor He at Shock Factor 1 (HSF1) with an IC50 value of 1.2 μM. KRIBB11 blocks induction of HSF1 downstream target proteins such as HSP27 and HSP70 by impairing the recruitment of Positive Transcription Elongation Factor b (P-TEFb) to the HSF1 transcriptional complexpreventing HSF1-mediated gene expression KRIBB11 inhibits tumor growth in vivo and acts synergistically to increase apoptosis in cancer cells treated with the HSP90 inhibitors Geldanamycin and 17-AAG.''KRIBB11 is capable of preventing the proliferation of cancer cells. It has the ability to stimulate apoptosis and can arrest the cell cycle at G2/M phase. | [Synthesis]
Example 3 Preparation of N2-(1H-indazol-5-yl)-N6-methyl-3-nitropyridine-2,6-diamine
To a reaction flask containing methanol with 40% aqueous methylamine (20 mL) was added 2-(1H-indazol-5-ylamino)-6-methoxy-3-nitropyridine (1 g) obtained by Example 1. The reaction mixture was stirred at 25°C for 1 hour. Subsequently, deionized water (20 mL) was slowly added to the reaction mixture and stirring was continued for 1 hour. After completion of the reaction, the reaction mixture was filtered and the solid product was washed with 30% aqueous methanol (5 mL). The resulting solid product was dried under vacuum at 50-60 °C to afford the target compound N2-(1H-indazol-5-yl)-N6-methyl-3-nitropyridine-2,6-diamine (0.82 g, 82% yield). Melting point: 238-240 °C. 1H-NMR (DMSO-d6, δ, ppm): 2.86 (d, 3H), 6.09 (d, 1H), 7.51 (d, 1H), 7.57 (d, 1H), 8.05 (t, 2H), 8.24 (d, 2H), 10.97 (s, 1H), 13.05 (br s, 1H). | [storage]
Store at -20°C | [References]
[1] Patent: US6743795, 2004, B1. Location in patent: Page/Page column 8 |
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