Chromenone derivatives with antitumor activity
A compound, alkyl technology, used in the prevention or treatment of warm-blooded animals such as human cancer drugs, the production of the chromenone derivatives, the new chromenone derivatives or the field of pharmaceutically acceptable salts thereof, can solve the problem. Insufficient selectivity, etc.
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Embodiment 8
[0534] Wherein, the compound of formula I is a single optically active enantiomer (the chiral center is the group methyl and -N-phenyl (R 4 )(R 5 )(R 6 )(R 7 )(R 8 ) attached carbon atom), compounds of formula XVII can be prepared using procedures similar to those outlined in the following schemes (see Example 8.00 herein for more details on this particular example):
[0535]
[0536] Among them, Ti(OEt) 4 is tetraethoxytitanium(IV), (R)-H2NSOtBu is (R)-2-methylpropane-2-sulfinamide, DCM is dichloromethane, MeOH is methanol and THF is tetrahydrofuran.
[0537] For example, the compound of formula II can be combined with R 3 NH 2 The single optically active enantiomer of formula XVII is prepared by reaction of the chiral equivalent of , such as a chiral sulfenamide (eg (R)-2-methylpropane-2-sulfinamide) to give the corresponding imine. The reaction is conveniently carried out in the presence of a Lewis acid such as tetraethoxytitanium(IV). The reaction is convenientl...
Embodiment 100
[0715] N-(2-(dimethylamino)ethyl)-8-(1-(4-fluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6- Formamide
[0716]
[0717] Titanium(IV) chloride (0.129 mL, 0.13 mmol) was added to 8-acetyl-N-(2-(dimethylamino)ethyl)-2-morpholino-4- Stirred suspension of oxo-4H-chromene-6-carboxamide (100 mg, 0.26 mmol), 4-fluoroaniline (0.042 mL, 0.44 mmol) and triethylamine (0.108 mL, 0.77 mmol) in DCM (2 mL) in the liquid. The resulting solution was stirred at 23 °C for 2 days. Add saturated sodium carbonate solution and extract with DCM. The organic phase was washed with water and brine, dried over magnesium sulfate and concentrated to provide the crude imine. The imine was diluted with DCM and MeOH and acetic acid (0.030 mL, 0.52 mmol) and sodium cyanoborohydride (32.4 mg, 0.52 mmol) were added. The resulting solution was stirred at room temperature for 30 minutes. Sodium carbonate solution was added and extracted with DCM. The organic phase was washed with water and brine,...
Embodiment 101
[0754] N-(2-(dimethylamino)ethyl)-8-(1-(3-fluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6- Formamide
[0755]
[0756] N-(2-(Dimethylamino)ethyl)-8-(1-(3-fluorophenylamino)ethyl)-2-morpholino- 4-Oxo-4H-chromene-6-carboxamide (28.0 mg, 18.7%). Mass Spectrum: M+H + 483. NMR spectrum: (CDC1 3 )1.62(d,3H),2.27(s,6H),2.52(t,2H),3.44-3.58(m,6H),3.78-3.89(m,4H),4.55(bs,1H),4.92-5.02 (m,1H),5.56(s,1H),6.14(ddd,1H),7.27(dd,1H),7.36(ddd,1H),6.95(bs,1H),7.03(dd,1H),8.28( d,1H), 8.35(d,1H).
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