Novel cyclopropane indolinone derivatives
a technology of cyclopropane indolinone and derivatives, which is applied in the field of new cyclopropane indolinone derivatives, can solve the problems of severe affecting the health and quality of life of affected individuals, and achieve the effects of lowering blood glucose, treatment or prophylaxis of diseases
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example 1
(1R,2S) and (1S,2R)-3-((2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)methyl)benzoic acid
[0446]
Synthesis of (Z)-3-(4-chloro-benzylidene)-1,3-dihydro-indol-2-one
[0447]Oxindole (0.13 g, 1 mmol), 4-chlorobenzaldehyde (0.17 g, 1.2 mmol) were mixed in alcohol; then pyrrolidine (0.17 ml, 2 mmol) was added. The mixture was refluxed for 3 hours. The formed precipitates was collected by filtration and washed with alcohol twice to give the title compound as yellow powder (0.24 g, 92%). LC / MS m / e calcd. for C15H10ClNO 255, observed (M+H)+: 256.1.
Synthesis of (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one
[0448]
[0449]A solution of dimethylsulfoxoniummethylide was prepared as under argon from a 60% NaH mineral oil dispersion (88 mg, 2.2 mmol), trimethylsulfoxoniumiodide (484 mg, 2.2 mmol), and DMSO (10 mL). After 20 min, a solution of (Z)-3-(4-chloro-benzylidene)-1,3-dihydro-indol-2-one (510 mg, 2 mmol) in THF (5 mL) was added dropwise over 20 min...
example 2
(1R,2R) and (1S,2S)-3-((2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)methyl)benzoic acid
[0454]
[0455]The title compound was prepared in analogy to Example 1 starting from methyl-(3-bromomethyl)-benzoate (commercially available), (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC / MS m / e calcd. for C24H18ClNO3: 403.1, observed (M+H)+: 404.2. 1H NMR (400 MHz, DMSO-d6) δppm 2.26 (dd, J=8.97, 4.67 Hz, 1H) 2.34 (dd, J=8.34, 4.80 Hz, 1H) 3.34 (t, J=8.72 Hz, 1H) 4.84-5.01 (m, 2H) 6.95 (d, J=7.58 Hz, 1H) 7.04 (t, J=7.45 Hz, 1H) 7.14-7.23 (m, 2H) 7.29-7.37 (m, 4H) 7.41-7.52 (m, 2H) 7.76 (s, 1H) 7.83 (d, J=7.58 Hz, 1H) 13.05 (br. s., 1H).
example 3
(1S,2R) and (1R,2S)-3-((2-(3-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)methyl)benzoic acid
[0456]
[0457]The title compound was prepared in analogy to Example 1 starting from methyl-(3-bromomethyl)-benzoate (commercially available), (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC / MS m / e calcd. for C24H18ClNO3: 403.1, observed (M+H)+: 404.1. 1H NMR (400 MHz, DMSO-d6) δppm 2.10 (dd, J=9.22, 4.93 Hz, 1H) 2.45 (dd, J=7.96, 4.93 Hz, 1H) 3.19-3.25 (m, 1H) 5.10 (s, 2H) 6.17 (d, J=7.33 Hz, 1H) 6.71 (t, J=7.58 Hz, 1H) 6.95 (d, J=7.83 Hz, 1H) 7.08 (t, J=7.71 Hz, 1H) 7.27 (s, 1H) 7.30-7.37 (m, 2H) 7.42 (s, 1H) 7.50 (t, J=7.58 Hz, 1H) 7.60 (d, J=7.83 Hz, 1H) 7.80-7.99 (m, 2H).
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