辅助材料
α-(异吲哚啉酮-2-基)戊二酰亚胺含氟类似物的合成与白血病细胞 K562 抑制活性
任玉杰*
陈衍炽
上海应用技术学院化学与环境工程学院 上海 201418
本PDF文件提供了合成化合物的1H NMR（13C NMR）和 HRMS（GCMS、LCMS）图
谱：
Spectra of lenalidomide ( 1H NMR, 13C NMR, HRMS )………………………………………S2
Spectra of 10a ( 1H NMR, 13C NMR, HRMS )…………………………………………………S3
Spectra of 10b ( 1H NMR, 13C NMR, HRMS )…………………………………………………S5
Spectra of 10c ( 1H NMR, 13C NMR, HRMS )…………………………………………………S6
Spectra of 10d ( 1H NMR, 13C NMR, HRMS )…………………………………………………S8
Spectra of 14a ( 1H NMR, 13C NMR, HRMS )…………………………………………………S9
Spectra of 14b ( 1H NMR, 13C NMR, HRMS )…………………………………………………S11
Spectra of 15 ( 1H NMR, 13C NMR, LCMS ) …………………………………………………S12
Spectra of 2 ( 1H NMR, HRMS ) ………………………………………………………………S14
Spectra of 3 ( 1H NMR, HRMS ) ………………………………………………………………S15
Spectra of 4 ( 1H NMR, HRMS ) ………………………………………………………………S16
Spectra of 2-bromomethyl-3-nitro-benzoic acid methyl ester ( 1H NMR, HRMS )……………S17
Spectra of 3-(4-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione ( 1H NMR, HRMS )
…………………………………………………………………………………………………S18
Spectra of 6a ( 1H NMR, HRMS )………………………………………………………………S19
Spectra of 6d ( 1H NMR, HRMS )………………………………………………………………S20
Spectra of 8a ( 1H NMR, GCMS )………………………………………………………………S21
Spectra of 8d ( 1H NMR, HRMS )………………………………………………………………S22
Spectra of 9a ( 1H NMR, HRMS )………………………………………………………………S23
Spectra of 9b ( 1H NMR, HRMS )………………………………………………………………S24
Spectra of 9c ( 1H NMR, HRMS )………………………………………………………………S25
Spectra of 9d ( 1H NMR, HRMS )………………………………………………………………S26
Spectra of 11a ( 1H NMR, HRMS ) ……………………………………………………………S27
Spectra of 11b ( 1H NMR, HRMS ) ……………………………………………………………S28
Spectra of 12a ( 1H NMR, HRMS ) ……………………………………………………………S29
Spectra of 12b ( 1H NMR, HRMS ) ……………………………………………………………S30
Spectra of 13a ( 1H NMR, HRMS ) ……………………………………………………………S31
Spectra of 13b ( 1H NMR, HRMS ) ……………………………………………………………S32
S1
O
O
NH
N
O
NH2
Lenalidomide
1
H NMR (DMSO-d6, 500 MHz) of lenalidomide:
13
C NMR (DMSO-d6, 100 MHz) of lenalidomide:
S2
HRMS spectra of lenalidomide
O
O
NH
N
O
F
3-(4-Fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (10a)
1
H NMR (DMSO-d6, 500 MHz) of 10a
S3
13
C NMR (DMSO-d6, 100 MHz) of 10a
HRMS spectra of 10a
S4
O
O
NH
N
O
F
3-(5-Fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (10b)
1
H NMR (DMSO-d6, 500 MHz) of 10b
13
C NMR (DMSO-d6, 100 MHz) of 10b
S5
HRMS spectra of 10b
O
F
O
NH
N
O
3-(6-Fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (10c)
1
H NMR (DMSO-d6, 500 MHz) of 10c
S6
13
C NMR (DMSO-d6, 100 MHz) of 10c
HRMS spectra of 10c
S7
F
O
O
NH
N
O
3-(7-Fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (10d)
1
H NMR (DMSO-d6, 500 MHz) of 10d
13
C NMR (DMSO-d6, 100 MHz) of 10d
S8
HRMS spectra of 10d
NH2
O
O
NH
N
O
F
3-(7-Amino-4-fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (14a)
1
H NMR (DMSO-d6, 500 MHz) of 14a
S9
13
C NMR (DMSO-d6, 100 MHz) of 14a
HRMS spectra of 14a
S10
O
H2N
O
NH
N
O
F
3-(6-Amino-5-fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (14b)
1
H NMR (DMSO-d6, 500 MHz) of 14a
13
C NMR (DMSO-d6, 100 MHz) of 14b
S11
HRMS spectra of 14b
O
O
N
OH
O
O 2N
F
NH
O
2-{[(2,6-Dioxo-piperidin-3-yl)-hydroxy-amino]-methyl}-4-fluoro-5-nitro-benzoic acid methyl ester (15)
1
H NMR (DMSO-d6, 500 MHz) of 15
S12
13
C NMR (DMSO-d6, 100 MHz) of 15
LC-MS (ES-API) spectra of 15
S13
O
O
HO
NH2
HN
O
O
2-tert-Butoxycarbonylamino-4-carbamoyl-butyric acid (2)
1
H NMR (DMSO-d6, 500 MHz) of 2
S14
HRMS spectra of 2
O
HN
H
N
O
O
O
(2,6-Dioxo-piperidin-3-yl)-carbamic acid tert-butyl ester (3)
1
H NMR (DMSO-d6, 500 MHz) of 3
HRMS spectra of 3
S15
O
HN
NH2·HCl
O
3-amino-piperidine-2,6-dione hydrochloride (4)
1
H NMR (DMSO-d6, 500 MHz) of 4
S16
O
O
Br
NO 2
2-Bromomethyl-3-nitro-benzoic acid methyl ester
1
H NMR (CDCl3, 500 MHz) of 2-bromomethyl-3-nitro-benzoic acid methyl ester
HRMS spectra of 2-bromomethyl-3-nitro-benzoic acid methyl ester
S17
NO
2
O
N
HN
O
O
3-(4-Nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione
1
H NMR (DMSO-d6, 500 MHz) of 3-(4-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine
-2,6-dione
HRMS spectra of 3-(4-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine -2,6-dione
S18
NH2
O
O
3-Amino-2-methyl-benzoic acid methyl ester (6a)
1
H NMR (DMSO-d6, 500 MHz) of 6a
HRMS spectra of 6a
S19
NH2 O
O
2-Amino-6-methyl-benzoic acid methyl ester (6d)
1
H NMR (CDCl3, 500 MHz) of 6d
HRMS spectra of 6d
S20
O
O
F
3-Fluoro-2-methyl-benzoic acid methyl ester (8a)
1
H NMR (DMSO-d6, 500 MHz) of 8a
GC-MS spectra of 8a
S21
F
O
O
2-Fluoro-6-methyl-benzoic acid methyl ester (8d)
1
H NMR (CDCl3, 500 MHz) of 8d
HRMS spectra of 8d
S22
O
O
Br
F
2-Bromomethyl-3-fluoro-benzoic acid methyl ester (9a)
1
H NMR (CDCl3, 500 MHz) of 9a
HRMS spectra of 9a
S23
O
F
O
Br
2-Bromomethyl-4-fluoro-benzoic acid methyl ester (9b)
1
H NMR (CDCl3, 500 MHz) of 9b
HRMS spectra of 9b
S24
O
F
O
Br
2-Bromomethyl-5-fluoro-benzoic acid methyl ester (9c)
1
H NMR (CDCl3, 500 MHz) of 9c
HRMS spectra of 9c
S25
F
O
O
Br
2-Bromomethyl-6-fluoro-benzoic acid methyl ester (9d)
1
H NMR (CDCl3, 500 MHz) of 9d
HRMS spectra of 9d
S26
NO 2 O
O
F
3-Fluoro-2-methyl-6-nitro-benzoic acid methyl ester (11a)
1
H NMR (CDCl3, 500 MHz) of 11a
HRMS spectra of 11a
S27
O
O2N
O
F
4-Fluoro-2-methyl-5-nitro-benzoic acid methyl ester (11b)
1
H NMR (CDCl3, 500 MHz) of 11b
HRMS spectra of 11b
S28
NO2 O
O
Br
F
2-Bromomethyl-3-fluoro-6-nitro-benzoic acid methyl ester (12a)
1
H NMR (CDCl3, 500 MHz) of 12a
HRMS spectra of 12a
S29
O
O 2N
O
Br
F
2-Bromomethyl-4-fluoro-5-nitro-benzoic acid methyl ester (12b)
1
H NMR (CDCl3, 500 MHz) of 12b
HRMS spectra of 12b
S30
NO2
O
O
NH
N
O
F
3-(4-Fluoro-7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (13a)
1
H NMR (DMSO-d6, 500 MHz) of 13a
HRMS spectra of 13a
S31
O
O2N
O
NH
N
O
F
3-(5-Fluoro-6-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (13b)
1
H NMR (DMSO-d6, 500 MHz) of 13b
HRMS spectra of 13b
S32