The Royal Society of Chemistry · S2 Methyl...

Transcript of The Royal Society of Chemistry · S2 Methyl...

S1

Benzofuranquinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO).

Synthesis and Biological Evaluation †

Catarina Carvalho, David Siegel, Martyn Inman, Rui Xiong, David Ross

and Christopher J. Moody

ELECTRONIC SUPPLEMENTARY INFORMATION

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2014

S2

Methyl 4,7-dihydro-5-methoxy-2-methyl-4,7-dioxobenzofuran-3-carboxylate 3a

c_car.cjr58_001001r

10 9 8 7 6 5 4 3 2 1 0Chemical Shift (ppm)

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.106.531.00

7.28

5.82

3.94

3.89

2.70

1.57

S3

Methyl 4,7-dihydro-6-methoxy-2-methyl-4,7-dioxobenzofuran-3-carboxylate 3b

c_car.cjr49_f1_001001r

9 8 7 6 5 4 3 2 1 0Chemical Shift (ppm)

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.056.251.00

7.28

5.87

3.96

3.88 2.70

1.55

c_car.CJR49_13C_2_002001r

220 200 180 160 140 120 100 80 60 40 20 0 -20Chemical Shift (ppm)

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

Nor

mal

ized

Inte

nsity

179.

88

169.

4616

5.26

162.

2915

8.13

148.

66

126.

99

113.

1110

8.23

77.3

377

.01

76.7

059

.90

56.8

952

.35

14.2

812

.64

S4

6-Methoxy-2-methyl-3-(morpholine-4-carbonyl)benzofuran-4,7-dione 3d

m_inm.MI-1927_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

Nor

mal

ized

Inte

nsity

3.162.068.861.00

7.29

5.80

3.90

3.86

3.84 3.

833.

823.

713.

353.

28

2.48

2.45

2.04

1.27 1.

251.

23

m_inm.MI-1927j_002001r

220 200 180 160 140 120 100 80 60 40 20 0Chemical Shift (ppm)

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

0.55

Nor

mal

ized

Inte

nsity

181.

21

168.

8416

1.29

159.

6715

9.40

147.

81

127.

11

115.

34

106.

92

77.3

477

.02

76.7

166

.64

66.5

6 57.0

3

47.3

042

.40

13.0

6

S5

Methyl 4,9-dihydro-2-methyl-4,9-dioxonaphtho[2,3-b]furan-3-carboxylate 3e

m_inm.MI-2569_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.043.032.082.00

8.23

8.22 8.22 8.21

7.80

7.79 7.

787.

777.

29

4.01

2.75

1.61

m_inm.MI-2569_001001r

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

0.55

0.60

0.65

0.70

Nor

mal

ized

Inte

nsity

178.

7917

3.51

164.

7516

2.55

151.

39

134.

1813

3.73

133.

6712

7.43

126.

54

113.

32

77.3

477

.02

76.7

0

52.3

9

14.2

2

S6

Methyl 4,7-dihydro-2-isopropyl-6-methoxy-4,7-dioxobenzofuran-3-carboxylate 3f

m_inm.MI-2562_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

6.101.031.00

7.29

5.86

3.96

3.88

3.68 3.

663.

65

1.60

1.39

1.37

m_inm.MI-2562_001001r

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

Nor

mal

ized

Inte

nsity

180.

15

172.

0816

9.30

162.

48 158.

38

148.

43

127.

09

111.

3910

7.97

77.3

377

.02

76.7

0

56.8

952

.42

27.8

6

20.5

317

.56

S7

Ethyl 4,7-dihydro-6-methoxy-4,7-dioxo-2-phenylbenzofuran-3-carboxylate 3g

m_inm.MI-2579_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.053.082.030.993.122.00

7.90

7.88

7.51

7.29

5.90

4.51

4.50

4.48

3.92

1.59

1.43

1.41

1.40

m_inm.MI-2579_001001r

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

0.55

0.60

0.65

0.70

Nor

mal

ized

Inte

nsity

180.

31

169.

0016

2.80

159.

3315

8.65

147.

77

131.

0912

8.90

127.

46

113.

0310

7.44

77.3

477

.02

76.7

162

.40 57

.02

13.8

9

S8

tert-Butyl 4,7-dihydro-6-methoxy-2-methyl-4,7-dioxobenzofuran-3-carboxylate 3c

m_inm.MI-2601_001001r

9 8 7 6 5 4 3 2 1Chemical Shift (ppm)

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

10.383.113.131.00

7.29

5.85

3.88

2.67

1.64

m_inm.MI-451-J_002001r

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

Nor

mal

ized

Inte

nsity

179.

89

164.

4116

0.94

158.

09

148.

39

127.

22

108.

19

82.7

077

.33

77.0

276

.70

56.8

1

28.1

327

.66 14

.17

S9

4,7-Dihydro-6-methoxy-2-methyl-4,7-dioxobenzofuran-3-carboxylic acid 4

m_inm.MI-2607_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.133.141.00

7.28

6.00

3.98

2.86

m_inm.MI-2607N_001001r

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

185.

79

169.

4616

7.99 16

0.70

160.

69

147.

24

125.

33

112.

8610

5.93

77.3

5 77.0

376

.71

57.6

9

14.5

2

S10

4,7-Dihydro-3-hydroxymethyl-5-methoxy-2-methylbenzofuran-4,7-dione 5a

c_car.cjr86_2_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.100.843.152.061.00

7.28

5.81 4.

64

3.89

2.44

1.57

S11

Methyl 4,7-dihydroxy-6-methoxy-2-methylbenzofuran-3-carboxylate 10b

c_car.cjr54_av3400_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

1.282.763.131.000.980.99

9.78

8.70

6.41

3.94 3.

78

3.31

2.66

2.50

c_car.cjr54_av400_001001r

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

168.

1016

2.54

147.

10

141.

97

124.

81

108.

6410

7.63

97.2

6

57.1

053

.53

40.6

040

.40

40.1

939

.97

39.7

739

.56

39.3

5

15.1

7

S12

4,7-Dihydro-3-hydroxymethyl-6-methoxy-2-methylbenzofuran-4,7-dione 5b

c_car.cjr83_3_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.514.122.291.00

7.28

5.85

4.62

3.90

2.45

c_car.cjr83_13c_001001r

0.05

0.10

0.15

0.20

0.25

0.30

Nor

mal

ized

Inte

nsity

184.

61

168.

47

160.

1415

6.71

148.

27

129.

44

121.

01

106.

35

77.3

377

.01

76.7

0

57.1

154

.93

12.3

5

S13

4,9-Dihydro-3-(hydroxymethyl)-2-methylnaphtho[2,3-b]furan-4,9-dione 5c

m_inm.MI-2582_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.220.722.042.032.01

8.25 8.25

8.23 8.19

7.80 7.

797.

79 7.78

7.29

4.71

2.51

m_inm.MI-2582_001001r

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

Nor

mal

ized

Inte

nsity

183.

28

172.

97

156.

03

134.

3713

3.76

132.

8012

7.04

120.

74

77.3

377

.01

76.7

0

55.0

3 12.2

7

S14

4,7-Dihydro-3-(hydroxymethyl)-2-isopropyl-6-methoxybenzofuran-4,7-dione 5d

m_inm.MI-2568_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

6.331.034.022.051.00

7.29

5.85

4.64

3.91

3.21 3.

203.

18 1.61

1.37

1.35

m_inm.MI-2568_001001r

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

Nor

mal

ized

Inte

nsity

184.

82

168.

4216

4.79

160.

22

148.

17

129.

49 119.

30

106.

29

77.3

477

.02

76.7

0

57.1

154

.65

26.9

821

.03

S15

4,7-Dihydro-5-Methoxy-3-(methoxymethyl)-2-methylbenzofuran-4,7-dione 6

S16

4,7-Dihydro-3-(2,4,6-trifluorophenoxy)methyl-5-methoxy-2-methylbenzofuran-4,7-dione 7a

CJR300 13C-NMR 3-((2,4,6-TRIFLUOROPHENOXY)METHYL)-5-METHOXY-2-METHYLBENZOFURAN-4,7-DIONE 215.MRC

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

0.55

0.60

0.65

0.70

Nor

mal

ized

Inte

nsity

177.

3417

5.44

159.

8715

9.01

149.

9114

7.34

124.

74

114.

7810

5.46

101.

0510

0.78

100.

51

77.3

177

.00

76.6

864

.74 56

.82

29.6

8 12.0

5

S17

4,9-Dihydro-2-methyl-3-(2,4,6-trifluorophenoxy)methylnaphtho[2,3-b]furan-4,9-dione 7b

m_inm.MI-2605_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.102.092.082.082.00

8.24

8.21

8.15 7.78 7.

77 7.76

7.75

7.28

6.72 6.

706.

68

5.36

2.56

m_inm.mi2605_001001r

0.01

0.02

0.03

0.04

0.05

0.06

0.07

0.08

0.09

Nor

mal

ized

Inte

nsity

181.

36

173.

25

160.

4115

5.34

151.

12

133.

8813

3.77

133.

1913

1.53

126.

85

115.

65

101.

0410

0.82

100.

61

77.2

877

.02

76.7

7

65.0

0

29.7

1

12.3

5

S18

4,7-Dihydro-3-hydroxymethyl-2-methyl-5-(pentylamino)benzofuran-4,7-dione 8a

c_car.cjr233_1_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.104.193.032.302.000.960.93

7.29

5.87

5.31

4.63

3.20

3.18

3.17

3.15

2.41

1.73 1.

711.

701.

401.

391.

390.

970.

960.

94

c_car.cjr233_001001r

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

Nor

mal

ized

Inte

nsity

180.

7617

5.18

152.

9414

7.93

118.

95 95.8

0

77.3

577

.03

76.7

1

55.0

6

43.0

8

29.1

427

.81

22.3

113

.93

11.8

5

S19

4,7-Dihydro-5-(3-(dimethylamino)propylamino)-3-(hydroxymethyl)-2-methylbenzofuran-4,7-dione 8b

c_car.cjr231_f2_2_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

2.079.482.242.081.000.94

7.28

5.26

4.61

3.29

3.28

2.56

2.40

2.37

1.90 1.

88

1.27

S20

4,7-Dihydro-3-(2,4,6-trifluorophenoxy)methyl-5-(3-(dimethylamino)propylamino)-2-methylbenzofuran-4,7-dione 8c

c_car.cjr301_f1_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

3.306.582.092.082.001.02

7.29

6.71

6.68

6.66

5.27

5.20

3.26

3.25

2.50

2.48

2.41

2.32

1.86 1.

851.

83

c_car.cjr301_f1_1_001001r

0.05

0.10

0.15

0.20

Nor

mal

ized

Inte

nsity

178.

9817

5.14

156.

8815

2.98

149.

02

122.

45 113.

8410

1.00 10

0.73

94.9

5

77.3

377

.01

76.7

065

.01

57.9

8

45.1

942

.80 24

.67

11.7

3

S21

4,7-Dihydro-5-(2-(Dimethylamino)ethylamino)-2-(hydroxymethyl)-3-methylbenzofuran-4,7-dione 8d

c_car.cjr454_2_001001r

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

Nor

mal

ized

Inte

nsity

9.322.162.000.990.92

7.28

6.51

5.26

4.66

3.18

3.17 2.65 2.

63

2.32

2.29

2.03

c_car.cjr454_2_dpx400_001001r

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

Nor

mal

ized

Inte

nsity

179.

1317

5.29

153.

98

148.

52

123.

3611

7.29

96.1

1

77.3

577

.03

76.7

1

56.4

354

.82

45.0

839

.91

8.53

S22

Methyl 4,7-dihydroxy-6-methoxy-2-methylbenzofuran-3-carboxylate 10a

c_car.cjr62_001001r

0.05

0.10

0.15

0.20

0.25

0.30

Nor

mal

ized

Inte

nsity

168.

1216

3.91

143.

1413

4.38

131.

89

115.

39

101.

40 57.5

553

.56

40.6

240

.42

40.2

040

.00

39.7

939

.58

39.3

7

15.4

8

The Royal Society of Chemistry · S2 Methyl...

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Transcript of The Royal Society of Chemistry · S2 Methyl...

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