H NMR spectrum of 9in CDCl3 ………………………………………………………..….S4

Full text

(1)

S

1

Supplementary Data

O-Aminoalkyl-O-Trimethyl-2,3-Dehydrosilybins: Synthesis and in vitro Effects toward Prostate Cancer Cells

Bao Vue

a

, Sheng Zhang

a

, Andre Vignau

a

, Guanglin Chen

a

, Xiaojie Zhang

a

, William Diaz

a

, Qiang Zhang

b,c

, Shilong Zheng

b,c

, Guangdi

Wang

b,c

, and Qiao-Hong Chen

a,

*

a

Department of Chemistry, California State University, Fresno, 2555 E. San Ramon Avenue, M/S SB70, Fresno, CA 93740, USA

b

Department of Chemistry and

c

RCMI Cancer Research Center, Xavier University of Louisiana, 1 Drexel Drive, New Orleans, LA

70125, USA

List of contents:

1

H NMR spectrum of

9

in CDCl

3

………..….S4

13

C NMR spectrum of

9

in CDCl

3

…………...………..….S5

1

H NMR spectrum of

10

in CDCl

3

……….…...S6

13

C NMR spectrum of

10

in CDCl

3

…………...………..…...S7

1

H NMR spectrum of

11

in CDCl

3

……….S8

13

C NMR spectrum of

11

in CDCl

3

…………...……….S9

1

H NMR spectrum of

12

in CDCl

3

……….S10

13

C NMR spectrum of

12

in CDCl

3

…………...……….S11

1

H NMR spectrum of

13

in CDCl

3

……….S12

13

C NMR spectrum of

13

in CDCl

3

…………...……….S13

1

H NMR spectrum of

14

in CDCl

3

……….S14

13

C NMR spectrum of

14

in CDCl

3

…………...……….S15

1

H NMR spectrum of

20

in CDCl

3

……….S16

13

C NMR spectrum of

20

in CDCl

3

…………...……….S17

1

H NMR spectrum of

21

in CDCl

3

……….S18

13

C NMR spectrum of

21

in CDCl

3

…………...……….S19

1

H NMR spectrum of

22

in CDCl

3

……….S20

13

C NMR spectrum of

22

in CDCl

3

…………...……….S21

1

H NMR spectrum of

23

in CDCl

(2)

S

2

1

H NMR spectrum of

23

in CDCl

3

……….S22

13

C NMR spectrum of

23

in CDCl

3

…………...……….S23

1

H NMR spectrum of

24

in CDCl

3

……….S24

13

C NMR spectrum of

24

in CDCl

3

…………...……….S25

1

H NMR spectrum of

25

in CDCl

3

……….S26

13

C NMR spectrum of

25

in CDCl

3

…………...……….S27

1

H NMR spectrum of

26

in CDCl

3

……….S28

13

C NMR spectrum of

26

in CDCl

3

…………...……….S29

1

H NMR spectrum of

27

in CDCl

3

……….S30

13

C NMR spectrum of

27

in CDCl

3

…………...……….S31

1

H NMR spectrum of

28

in CDCl

3

……….S32

13

C NMR spectrum of

28

in CDCl

3

…………...……….S33

1

H NMR spectrum of

29

in CDCl

3

……….S34

13

C NMR spectrum of

29

in CDCl

3

…………...……….S35

1

H NMR spectrum of

30

in CDCl

3

……….S36

13

C NMR spectrum of

30

in CDCl

3

…………...……….S37

1

H NMR spectrum of

31

in CDCl

3

……….S38

13

C NMR spectrum of

31

in CDCl

3

…………...……….S39

1

H NMR spectrum of

32

in CDCl

3

……….S40

13

C NMR spectrum of

32

in CDCl

3

…………...……….S41

1

H NMR spectrum of

33

in CDCl

3

……….S42

13

C NMR spectrum of

33

in CDCl

3

…………...……….S43

1

H NMR spectrum of

34

in CDCl

3

……….S44

13

C NMR spectrum of

34

in CDCl

3

…………...……….S45

1

H NMR spectrum of

35

in CDCl

3

……….S46

13

C NMR spectrum of

35

in CDCl

3

…………...……….S47

1

H NMR spectrum of

36

in CDCl

3

……….S48

13

C NMR spectrum of

36

in CDCl

3

…………...……….S49

1

H NMR spectrum of

37

in CDCl

3

……….S50

13

C NMR spectrum of

37

in CDCl

3

…………...……….S51

1

H NMR spectrum of

38

in CDCl

3

……….S52

13

C NMR spectrum of

38

in CDCl

3

…………...……….S53

1

H NMR spectrum of

39

in CDCl

(3)

S

3

13

C NMR spectrum of

39

in CDCl

3

…………...……….S55

1

H NMR spectrum of

40

in CDCl

3

……….S56

13

C NMR spectrum of

40

in CDCl

3

…………...……….S57

1

H NMR spectrum of

41

in CDCl

3

……….S58

13

C NMR spectrum of

41

in CDCl

3

…………...……….S59

1

H NMR spectrum of

42

in CDCl

3

……….S60

13

C NMR spectrum of

42

in CDCl

3

…………...……….S61

1

H NMR spectrum of

43

in CDCl

3

……….S62

13

C NMR spectrum of

43

in CDCl

3

…………...……….S63

1

H NMR spectrum of

44

in CDCl

3

……….S64

13

C NMR spectrum of

44

in CDCl

3

…………...……….S65

1

H NMR spectrum of

45

in CDCl

3

……….S66

13

C NMR spectrum of

45

in CDCl

3

…………...……….S67

____________

Corresponding author

.

(4)

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

-50

0

50

100

150

200

250

300

350

400

450

500

550

600

650

NMR

SZ-208-4 CDCL3 HNMR 300MHZ

1

.2

2

2

.3

6

2

.9

7

2

.4

0

1

.2

6

3

.9

7

9

.7

1

3

.1

3

1

.0

0

0

.8

6

1

.0

0

2

.0

1

1

.0

5

1

.0

0

0

.8

9

0

.9

0

2

.0

1

2

2

.0

1

6

2

.3

0

3

2

.3

2

4

2

.3

4

4

2

.8

0

8

3

.2

3

0

3

.2

5

1

3

.2

7

1

3

.5

5

0

3

.5

6

1

3

.5

9

1

3

.6

0

4

3

.8

0

2

3

.8

1

8

3

.8

4

4

3

.8

5

1

3

.8

9

6

3

.9

1

1

3

.9

2

5

4

.0

6

1

4

.1

6

6

4

.9

8

3

5

.0

1

1

6

.1

8

3

6

.1

8

9

6

.2

2

2

6

.2

2

8

6

.9

1

7

6

.9

2

5

6

.9

4

5

6

.9

5

4

6

.9

7

4

6

.9

7

9

7.

0

2

6

7.

2

6

0

7.

5

1

2

7.

5

1

9

7.

5

4

1

7.

5

4

8

7.

5

8

8

7.

5

9

5

O

O

O

O

OH

O

N

H

CH

3

O

CH

3

O

CH

3

O

CH

3

O

CH

3

1

H NMR spectrum for compound 9

(5)

0

5000

10000

15000

20000

25000

30000

35000

40000

45000

NMR

SZ-208-4 CDCl3 CNMR 75MHZ

25

.7

3

4

.2

4

7.

5

5

6

.2

5

6

.2

5

6

.8

5

9

.9

6

1

.6

6

5

.2

7

6

.3

7

6

.7

7

7.

2

7

7.

6

7

8

.9

9

2

.9

9

6

.3

1

0

8

.7

1

1

0

.4

1

1

1

.5

1

1

7.

1

1

1

7.

2

1

2

0

.3

1

2

2

.0

1

2

3

.5

1

2

8

.3

1

4

0

.9

1

4

3

.7

1

4

5

.6

1

4

9

.6

1

5

0

.0

1

5

2

.6

1

5

8

.1

1

6

0

.4

1

6

2

.9

1

7

4

.4

O

O

O

O

OH

O

N

H

CH

3

O

CH

3

O

CH

3

O

CH

3

O

CH

3

13

C NMR spectrum for compound 9

(6)

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

-50

0

50

100

150

200

250

300

350

400

450

500

550

NMR

SZ-19-138 MeOD HNMR 300MHZ

6

.1

1

2

.0

5

6

.0

0

1

.2

0

7.

0

5

6

.5

5

3

.0

8

1

.0

6

0

.9

7

1

.0

0

3

.1

1

1

.0

9

1

.9

8

1

.0

7

6

1

.0

9

9

1

.1

2

3

1

.8

6

5

1

.9

4

2

2

.0

2

1

2

.6

4

8

2

.6

7

2

2

.6

9

6

2

.7

2

0

2

.7

4

5

2

.7

7

0

3

.2

9

9

3

.3

0

4

3

.3

1

0

3

.3

1

5

3

.3

2

1

3

.6

7

7

3

.7

1

2

3

.7

2

0

3

.7

5

1

3

.7

7

8

3

.8

3

3

3

.8

3

9

3

.9

2

5

4

.0

8

8

4

.8

6

8

4

.8

8

5

6

.2

3

3

6

.3

6

1

6

.9

1

5

6

.9

4

3

6

.9

7

1

7.

0

0

9

7.

0

3

2

7.

5

1

1

7.

5

4

8

O

O

O

O

OH

O

N

C

H

3

C

H

3

O

CH

3

O

CH

3

O

CH

3

O

CH

3

1

(7)

-2000

0

2000

4000

6000

8000

10000

12000

14000

16000

18000

20000

22000

24000

26000

28000

30000

NMR

SZ-19-138 MeOD CNMR 75MHZ

11

.0

2

6

.5

4

7.

9

5

0

.3

5

6

.4

5

6

.5

5

6

.6

6

0

.2

6

1

.9

6

7.

9

7

7.

5

8

0

.3

9

4

.1

9

7.

0

1

0

9

.6

1

1

2

.3

1

1

2

.8

1

1

7.

9

1

1

8

.1

1

2

1

.6

1

2

3

.0

1

2

4

.4

1

3

0

.3

1

4

1

.9

1

4

5

.0

1

4

7.

2

1

5

0

.6

1

5

1

.1

1

5

3

.9

1

5

9

.7

1

6

1

.7

1

6

5

.0

1

7

5

.5

O

O

O

O

OH

O

N

C

H

3

C

H

3

O

CH

3

O

CH

3

O

CH

3

O

CH

3

13

C NMR spectrum for compound 10

(8)

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

-100

0

100

200

300

400

500

600

700

800

900

1000

1100

1200

NMR

SZ-19-165 CDCL3 HNMR 300MHZ

6

.2

2

4

.3

2

4

.0

0

2

.0

6

3

.9

8

1

.9

5

1

.0

1

4

.4

0

6

.0

2

3

.0

0

1

.8

5

1

.0

8

0

.9

5

1

.0

0

0

.9

1

1

.0

7

0

.9

5

1

.9

6

1

.0

5

0

.9

6

0

.8

6

5

0

.8

8

9

0

.9

1

3

1

.2

3

5

1

.3

5

6

1

.3

9

9

1

.4

9

6

1

.9

3

5

1

.9

5

7

1

.9

7

9

2

.0

0

1

2

.0

2

2

2

.4

6

0

2

.4

8

5

2

.5

0

9

2

.6

3

8

2

.6

6

1

2

.6

8

2

3

.5

6

4

3

.5

9

3

3

.6

0

5

3

.8

2

0

3

.8

2

8

3

.8

6

1

3

.8

7

0

3

.8

8

3

3

.9

0

7

3

.9

1

6

3

.9

4

1

4

.0

5

5

4

.0

7

5

4

.0

9

6

4

.1

0

8

4

.1

1

7

4

.1

4

5

5

.0

1

1

5

.0

3

9

6

.3

1

0

6

.3

1

7

6

.4

5

7

6

.4

6

4

6

.9

0

5

6

.9

3

3

6

.9

7

1

6

.9

7

7

7.

0

3

2

7.

0

6

0

7.

7

0

3

7.

7

1

0

7.

7

3

1

7.

7

3

8

7.

7

4

9

7.

7

5

5

O

O

O

O

OH

O

N

C

H

3

C

H

3

O

CH

3

O

CH

3

O

CH

3

O

CH

3

1

H NMR spectrum for compound 11

(9)

-5000

0

5000

10000

15000

20000

25000

30000

35000

40000

45000

50000

55000

NMR

SZ-19-165 CDCL3 CNMR 75MHZ

14

.2

2

0

.8

2

6

.7

2

8

.9

5

0

.5

5

3

.9

5

6

.1

5

6

.2

5

6

.5

6

0

.0

6

1

.7

6

6

.8

7

6

.4

7

8

.8

9

3

.0

9

6

.1

1

0

9

.5

1

1

0

.3

1

1

1

.5

1

1

7.

2

1

1

7.

3

1

2

0

.3

1

2

2

.3

1

2

4

.4

1

2

8

.5

1

4

1

.5

1

4

3

.8

1

4

5

.3

1

4

9

.6

1

4

9

.9

1

5

2

.0

1

5

8

.8

1

6

1

.1

1

6

3

.4

1

7

4

.2

O

O

O

O

OH

O

N

C

H

3

C

H

3

O

CH

3

O

CH

3

O

CH

3

O

CH

3

13

C NMR spectrum for compound 11

(10)

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

-50

0

50

100

150

200

250

300

350

400

450

500

550

600

650

700

750

800

850

900

NMR

SZ-19-177-2 CDCL3 HNMR 300MHZ

4

.0

4

2

.2

8

4

.2

2

2

.2

1

1

.1

4

4

.3

7

6

.1

8

2

.8

0

2

.3

7

0

.8

8

1

.0

2

1

.0

0

1

.0

0

1

.1

4

1

.0

6

2

.0

7

1

.9

9

1

.7

8

7

1

.8

7

8

2

.0

3

0

2

.0

5

1

2

.0

7

4

2

.0

9

9

2

.1

1

9

2

.5

6

9

2

.6

6

8

2

.6

8

2

2

.7

0

7

2

.7

3

1

3

.5

4

2

3

.5

5

5

3

.5

8

4

3

.5

9

7

3

.8

1

4

3

.8

2

2

3

.8

5

7

3

.8

7

8

3

.9

0

5

3

.9

1

5

3

.9

3

5

4

.0

6

5

4

.0

8

6

4

.1

0

7

4

.1

2

0

5

.0

0

8

5

.0

3

5

6

.3

0

9

6

.3

1

6

6

.4

6

2

6

.4

6

9

6

.9

2

8

6

.9

6

9

6

.9

7

4

7.

0

2

1

7.

0

5

0

7.

2

6

0

7.

6

9

1

7.

6

9

8

7.

7

2

0

7.

7

2

7

7.

7

4

0

7.

7

4

6

O

O

O

O

O

OH

O

O

O

N

C

H

3

CH

3

CH

3

O

CH

3

1

H NMR spectrum for compound 12

(11)

0

10000

20000

30000

40000

50000

60000

70000

80000

90000

NMR

SZ-177-2 CDCL3 CNMR 75MHZ

23

.6

2

8

.0

5

3

.0

5

4

.3

5

6

.1

5

6

.2

5

6

.5

6

0

.0

6

1

.7

6

6

.7

7

6

.4

7

8

.8

9

3

.0

9

6

.1

1

0

9

.5

1

1

0

.2

1

1

1

.4

1

1

7.

2

1

1

7.

3

1

2

0

.3

1

2

2

.2

1

2

4

.3

1

2

8

.5

1

4

1

.4

1

4

3

.8

1

4

5

.3

1

4

9

.6

1

4

9

.9

1

5

2

.1

1

5

8

.8

1

6

1

.0

1

6

3

.3

1

7

4

.2

O

O

O

O

O

OH

O

O

O

N

C

H

3

CH

3

CH

3

O

CH

3

13

C NMR spectrum for compound 12

(12)

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

-50

0

50

100

150

200

250

300

350

400

450

500

550

600

650

700

NMR

SZ-19-142 CDCL3 HNMR 300MHZ

2

.2

1

6

.2

0

1

.1

0

1

.0

9

1

6

.8

8

3

.2

2

1

.0

3

1

.0

2

1

.0

0

1

.1

1

1

.0

9

1

.9

8

2

.0

4

2

.0

4

5

2

.1

2

0

2

.1

8

1

2

.5

7

5

2

.6

7

3

2

.7

8

6

2

.9

9

1

3

.0

1

5

3

.0

3

9

3

.0

6

1

3

.5

4

3

3

.5

5

6

3

.5

8

6

3

.5

9

7

3

.7

6

2

3

.8

2

3

3

.8

7

0

3

.9

0

4

3

.9

1

4

3

.9

3

0

4

.0

3

7

4

.1

8

1

5

.0

0

7

5

.0

3

4

6

.2

9

3

6

.4

3

9

6

.9

0

4

6

.9

3

1

6

.9

7

0

7.

0

2

0

7.

0

4

8

7.

2

6

0

7.

6

9

5

7.

7

3

1

O

O

O

O

OH

O

N

O

O

CH

3

O

CH

3

O

CH

3

O

CH

3

1

H NMR spectrum for compound 13

CDCl3

, 300 MHz

(13)

-5000

0

5000

10000

15000

20000

25000

30000

35000

40000

45000

50000

55000

60000

65000

70000

75000

80000

85000

90000

NMR

SZ-19-142 CDCL3 CNMR 75MHZ

42

.3

5

3

.4

5

5

.4

5

6

.1

5

6

.2

5

6

.5

6

0

.0

6

1

.7

6

6

.2

6

6

.4

7

6

.4

7

8

.8

9

2

.9

9

6

.1

1

0

9

.5

1

1

0

.2

1

1

1

.4

1

1

7.

2

1

1

7.

2

1

2

0

.3

1

2

2

.2

1

2

4

.3

1

2

8

.4

1

4

1

.4

1

4

3

.8

1

4

5

.3

1

4

9

.6

1

4

9

.9

1

5

2

.1

1

5

8

.8

1

6

1

.0

1

6

3

.2

1

7

4

.2

O

O

O

O

OH

O

N

O

O

CH

3

O

CH

3

O

CH

3

O

CH

3

13

C NMR spectrum for compound 13

(14)

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

-50

0

50

100

150

200

250

300

350

400

450

500

550

600

SZ-19-139-purified HNMR 300MHZ

2

.1

8

3

.0

0

2

.1

7

7.

9

4

1

.2

8

1

.2

0

3

.3

9

6

.3

7

3

.0

2

2

.1

7

1

.3

5

1

.1

3

1

.0

3

1

.0

0

1

.1

8

1

.1

8

2

.2

8

2

.2

3

2

.0

1

6

2

.0

7

4

2

.5

5

4

2

.6

4

3

2

.6

6

6

2

.6

9

0

2

.7

1

8

2

.9

5

2

3

.5

4

8

3

.5

6

1

3

.5

9

0

3

.6

0

3

3

.8

2

5

3

.8

3

2

3

.8

6

6

3

.8

8

7

3

.9

1

3

3

.9

2

0

3

.9

4

3

4

.0

4

0

4

.0

6

0

4

.0

8

0

4

.1

1

0

4

.1

7

5

5

.0

1

2

5

.0

4

0

6

.3

0

0

6

.3

0

6

6

.4

3

8

6

.4

4

5

6

.9

1

2

6

.9

4

0

6

.9

6

8

6

.9

7

3

7.

0

2

0

7.

0

2

5

7.

0

4

6

7.

0

7

6

7.

2

6

0

7.

7

1

1

7.

7

7

0

O

O

O

O

O

OH

O

O

O

N

N

C

H

3

C

H

3

CH

3

CH

3

O

CH

3

1

H NMR spectrum for compound 14

(15)

-2000

0

2000

4000

6000

8000

10000

12000

14000

16000

18000

20000

22000

24000

26000

NMR

SZ-19-139-purified CDCL3 CNMR 75MHZ

26

.1

4

4

.5

5

0

.9

5

4

.0

5

4

.3

5

6

.1

5

6

.6

6

0

.1

6

1

.7

6

6

.3

7

6

.5

7

7.

4

7

8

.8

9

2

.8

9

6

.2

1

0

9

.6

1

1

0

.3

1

1

1

.5

1

1

7.

2

1

1

7.

2

1

2

0

.3

1

2

2

.4

1

2

4

.4

1

2

8

.4

1

4

1

.5

1

4

3

.8

1

4

5

.3

1

4

9

.6

1

5

0

.0

1

5

2

.0

1

5

8

.8

1

6

1

.1

1

6

3

.2

1

7

4

.2

O

O

O

O

O

OH

O

O

O

N

N

C

H

3

C

H

3

CH

3

CH

3

O

CH

3

13

C NMR spectrum for Compound 14

(16)

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

9.5

E:

BV-48-23-R2-CDCL3

2

.3

5

5

.7

9

1

.8

9

1

.1

9

4

.6

6

7.

2

8

3

.6

7

1

.8

0

1

.1

7

1

.1

2

1

.0

0

1

.0

1

0

.9

7

1

.1

4

1

.2

6

1

.0

1

1

.9

9

2

.2

2

0

2

.2

9

1

2

.3

2

9

2

.8

8

3

3

.4

2

3

3

.4

8

3

3

.5

2

5

3

.5

4

8

3

.5

5

8

3

.5

8

9

3

.5

9

9

3

.8

3

1

3

.8

6

2

3

.8

9

6

3

.9

0

9

3

.9

3

7

3

.9

7

9

4

.0

0

6

4

.1

6

4

4

.1

8

9

5

.0

4

1

5

.0

6

6

6

.3

3

1

6

.4

6

8

6

.9

0

1

6

.9

2

8

6

.9

8

3

7.

0

2

3

7.

0

5

1

7.

0

8

6

7.

1

2

0

7.

2

6

0

7.

6

3

3

7.

6

5

3

O

O

O

O

OH

O

O

C

H

3

N

CH

3

CH

3

O

CH

3

O

CH

3

O

CH

3

(17)

linker nmr

bv-17-23-r2- cdcl3

2

5

.5

7

4

2

.4

1

4

3

.4

7

5

6

.0

0

5

6

.1

4

5

6

.2

5

5

6

.6

6

6

1

.5

1

6

9

.4

3

7

6

.4

7

7

6

.7

8

7

7.

2

0

7

7.

6

2

7

8

.8

9

9

2

.6

8

9

6

.3

3

1

0

9

.0

4

1

1

0

.4

2

1

1

1

.5

1

1

1

7.

1

6

1

1

7.

6

6

1

2

0

.3

8

1

2

2

.3

3

1

2

3

.4

6

1

2

8

.3

6

1

3

9

.7

3

1

4

4

.0

1

1

4

5

.9

9

1

4

9

.5

5

1

4

9

.9

3

1

5

3

.5

7

1

5

9

.0

6

1

6

0

.9

4

1

6

4

.6

0

1

7

4

.5

4

O

O

O

O

OH

O

O

C

H

3

N

CH

3

CH

3

O

CH

3

O

CH

3

O

CH

3

13

C NMR spectrum for compound 20

(18)

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

-100

0

100

200

300

400

500

600

700

800

900

1000

1100

andre vignau

av 39-36 dimethylamaine 5c

3

.9

4

5

.8

5

1

.8

9

1

.0

6

1

3

.4

3

2

.0

2

1

.0

3

0

.9

9

1

.0

0

0

.9

9

1

.1

2

1

.0

5

1

.9

9

1

.9

2

1

.6

5

6

1

.6

7

2

1

.6

9

6

1

.7

1

5

1

.7

3

0

1

.7

5

1

1

.7

7

3

2

.2

8

7

2

.4

2

6

2

.4

5

0

2

.4

7

5

3

.5

4

1

3

.5

5

4

3

.5

8

2

3

.5

9

5

3

.8

0

8

3

.8

1

7

3

.8

5

7

3

.8

8

1

3

.9

0

0

3

.9

0

7

3

.9

3

4

3

.9

9

0

4

.0

1

0

4

.0

3

0

4

.0

5

0

4

.1

0

7

4

.1

1

8

4

.1

3

3

4

.1

4

4

5

.0

2

7

5

.0

5

4

6

.3

1

1

6

.3

1

8

6

.4

5

1

6

.4

5

8

6

.8

9

8

6

.9

2

5

6

.9

6

6

6

.9

7

1

7.

0

2

4

7.

0

5

5

7.

2

6

0

7.

7

0

4

7.

7

1

2

7.

7

1

5

7.

7

2

1

7.

7

3

4

7.

7

4

1

O

O

O

O

O

OH

O

O

O

C

H

3

N

CH

3

CH

3

CH

3

CH

3

O

CH

3

1

H NMR spectrum for compound 21

(19)

-500

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

6500

7000

7500

andre vignau

av 39-36 dimethylamaine 5c c13

2

3

.4

8

2

7.

8

8

4

4

.7

6

5

5

.7

3

5

6

.0

0

5

6

.0

3

5

6

.3

8

5

9

.1

0

6

1

.4

8

7

1

.8

4

7

6

.2

0

7

6

.6

2

7

7.

0

4

7

7.

4

7

7

8

.6

7

9

2

.3

1

9

5

.7

7

1

0

9

.4

1

1

1

0

.1

6

1

1

1

.3

0

1

1

6

.9

8

1

1

7.

1

5

1

2

0

.1

8

1

2

2

.3

6

1

2

4

.3

1

1

2

8

.4

5

1

4

0

.4

0

1

4

3

.6

0

1

4

5

.1

6

1

4

9

.4

0

1

4

9

.7

2

1

5

2

.3

2

1

5

8

.7

7

1

6

0

.9

6

1

6

3

.8

9

1

7

4

.1

1

O

O

O

O

O

OH

O

O

O

C

H

3

N

CH

3

CH

3

CH

3

CH

3

O

CH

3

13

C NMR spectrum for compound 21

(20)

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

-50

0

50

100

150

200

250

300

350

400

450

500

550

600

650

700

750

andre vignau

av 37-30

2

.2

8

2

.1

8

2

.1

5

5

.9

3

1

.9

8

1

.9

6

1

3

.6

7

2

.3

0

1

.1

2

1

.0

7

2

.0

0

1

.0

6

1

.1

3

2

.0

8

2

.0

6

1

.3

6

9

1

.4

1

8

1

.4

4

0

1

.4

6

6

1

.5

0

8

1

.5

3

3

1

.5

4

3

1

.5

5

8

1

.5

8

5

1

.6

0

8

1

.6

7

8

1

.7

0

0

1

.7

2

3

1

.7

4

7

1

.7

7

0

2

.3

3

6

2

.3

9

2

2

.4

1

9

2

.4

4

4

3

.5

4

2

3

.5

5

4

3

.5

8

3

3

.5

9

6

3

.8

1

1

3

.8

2

0

3

.8

5

1

3

.8

9

5

3

.9

0

3

3

.9

2

6

3

.9

8

0

4

.0

0

1

4

.0

1

3

4

.0

3

4

4

.1

2

6

4

.1

4

0

4

.1

5

2

4

.1

6

3

5

.0

4

2

5

.0

6

8

6

.3

0

3

6

.3

1

0

6

.4

4

6

6

.4

5

3

6

.8

9

6

6

.9

2

3

6

.9

7

4

6

.9

7

9

7.

0

1

5

7.

0

4

4

7.

2

6

0

7.

6

7

0

7.

6

9

3

7.

7

0

3

7.

7

1

0

7.

7

1

6

7.

7

3

8

O

O

O

O

O

OH

O

O

O

C

H

3

CH

3

CH

3

N

CH

3

CH

3

O

CH

3

1

H NMR sepctrum for compound 22

(21)

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

andre vignau

av 37-30 c13

2

3

.7

3

2

6

.1

4

2

9

.8

5

4

4

.4

6

5

5

.7

2

5

5

.9

9

5

6

.0

4

5

6

.3

5

5

9

.0

5

6

1

.4

5

7

2

.0

4

7

6

.1

2

7

6

.6

3

7

7.

4

7

7

8

.6

9

9

2

.3

0

9

5

.7

5

1

0

9

.4

2

1

1

0

.1

7

1

1

1

.3

1

1

1

6

.9

2

1

1

7.

1

8

1

2

0

.1

5

1

2

2

.3

8

1

2

4

.3

2

1

2

8

.5

3

1

4

0

.4

7

1

4

3

.5

5

1

4

5

.1

4

1

4

9

.3

9

1

4

9

.6

9

1

5

2

.3

2

1

5

8

.7

7

1

6

0

.9

6

1

6

3

.8

7

1

7

4

.1

0

O

O

O

O

O

OH

O

O

O

C

H

3

CH

3

CH

3

N

CH

3

CH

3

O

CH

3

13

C NMR spectrum for compound 22

(22)

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

linker nmr

bv-17-232 cdcl3

5

.9

7

1

.9

4

6

.4

4

1

.0

6

5

.0

3

5

.7

2

2

.5

3

1

.6

3

0

.8

9

1

.0

8

1

.0

0

0

.9

3

4

.3

3

1

.9

8

1

.1

6

3

1

.1

8

5

1

.2

0

9

2

.0

8

0

2

.1

0

5

2

.1

2

4

2

.7

6

0

2

.7

8

6

2

.8

3

9

2

.8

6

1

2

.8

6

1

2

.9

2

6

3

.0

2

1

3

.0

4

8

3

.0

7

1

3

.5

5

4

3

.5

8

8

3

.5

9

7

3

.8

2

7

3

.8

6

3

3

.9

0

6

3

.9

3

9

4

.0

1

0

4

.0

2

6

4

.1

3

0

4

.1

5

7

5

.0

1

8

5

.0

4

5

6

.3

2

7

6

.4

6

6

6

.9

0

1

6

.9

2

8

6

.9

6

9

7.

0

1

6

7.

0

4

7

7.

0

7

7

7.

2

6

0

7.

5

6

4

7.

6

8

8

7.

8

0

9

O

O

O

O

OH

O

O

C

H

3

N

CH

3

CH

3

O

CH

3

O

CH

3

O

CH

3

1

(23)

linker nmr

bv-17-232 cdcl3

1

0

.0

7

2

6

.3

6

4

6

.8

7

4

9

.9

2

5

5

.9

3

5

6

.1

6

5

6

.2

2

5

6

.5

8

6

1

.6

5

7

0

.0

2

7

6

.4

5

7

6

.7

8

7

7.

2

0

7

7.

6

2

7

8

.8

6

9

2

.5

4

9

6

.0

5

1

0

9

.4

4

1

1

0

.3

4

1

1

1

.4

7

1

1

7.

2

6

1

1

7.

3

6

1

2

0

.3

7

1

2

2

.4

3

1

2

4

.1

3

1

2

8

.4

8

1

4

0

.2

2

1

4

3

.8

7

1

4

5

.5

5

1

4

9

.5

7

1

4

9

.9

1

1

5

2

.8

5

1

5

8

.9

7

1

6

1

.0

7

1

6

4

.2

2

1

7

4

.2

4

O

O

O

O

OH

O

O

C

H

3

N

CH

3

CH

3

O

CH

3

O

CH

3

O

CH

3

13

C NMR spectrum for compound 23

(24)

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

9.5

0

50

100

150

200

250

300

350

400

450

500

Andre

AV-39-35-R2 HNMR CDCl3 300MHZ

5

.8

6

3

.7

5

4

.7

4

2

.5

4

1

.2

1

1

5

.4

0

1

.1

1

1

.0

0

1

.0

0

0

.9

9

1

.1

2

0

.9

6

1

.9

8

1

.9

7

1

.0

3

6

1

.0

5

9

1

.0

8

3

1

.2

3

8

1

.5

9

0

1

.7

1

1

1

.7

3

1

1

.7

9

9

2

.5

9

6

2

.6

1

8

2

.6

4

1

2

.6

6

5

2

.9

6

4

3

.5

3

6

3

.5

4

7

3

.5

7

7

3

.5

8

8

3

.8

1

2

3

.8

5

1

3

.8

9

8

3

.9

2

6

3

.9

5

2

3

.9

8

1

4

.0

0

2

4

.0

2

2

4

.1

1

4

4

.1

3

9

5

.0

2

1

5

.0

4

7

6

.3

0

9

6

.4

5

0

6

.8

9

2

6

.9

1

9

6

.9

6

6

7.

0

1

4

7.

0

4

4

7.

2

6

0

7.

7

0

8

7.

7

2

9

O

O

O

O

O

OH

O

O

O

C

H

3

CH

3

CH

3

N

CH

3

CH

3

O

CH

3

1

H NMR spectrum for compound 24

(25)

-500

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

6500

7000

7500

Andre

AV-39-35-R2 CNMR CDCL3 75MHZ

1

1

.3

4

2

2

.9

3

2

8

.6

9

4

7.

1

4

5

2

.6

7

5

6

.3

7

5

6

.6

4

5

7.

0

0

6

2

.0

8

7

2

.5

0

7

6

.8

4

7

7.

2

8

7

7.

7

0

7

8

.1

2

7

9

.3

1

9

2

.9

4

9

6

.4

1

1

1

0

.0

0

1

1

0

.7

7

1

1

1

.9

1

1

1

7.

6

3

1

1

7.

7

3

1

2

0

.8

1

1

2

2

.9

8

1

2

4

.8

9

1

2

9

.0

8

1

4

1

.0

0

1

4

4

.2

4

1

4

5

.8

3

1

5

0

.0

1

1

5

0

.3

3

1

5

2

.9

7

1

5

9

.4

0

1

6

1

.5

6

1

6

4

.5

4

1

7

4

.7

6

O

O

O

O

O

OH

O

O

O

C

H

3

CH

3

CH

3

N

CH

3

CH

3

O

CH

3

13

C NMR spectrum for compound 24

(26)

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

-50

0

50

100

150

200

250

300

350

400

450

500

550

600

650

700

andre vignau

av 37-16 diethylamine

6 .1 4 1 .9 5 2 .2 4 2 .0 5 2 .0 8 4 .0 0 1 .3 8 1 3 .2 0 2 .1 2 1 .0 8 0 .8 5 0 .8 6 0 .8 6 1 .0 6 1 .0 2 2 .0 3 1 .7 8 1 .0 9 4 1 .1 0 7 1 .1 1 8 1 .1 3 2 1 .1 5 6 1 .3 6 7 1 .4 1 4 1 .4 3 6 1 .4 6 3 1 .5 1 1 1 .5 3 6 1 .5 4 8 1 .5 6 3 1 .6 1 2 1 .7 0 1 1 .7 2 5 1 .7 4 8 1 .7 7 0 2 .6 0 1 2 .6 2 7 2 .6 5 5 2 .7 1 7 2 .7 4 1 2 .7 6 5 2 .7 8 9 3 .5 5 0 3 .5 6 2 3 .5 9 1 3 .6 0 4 3 .6 3 4 3 .8 2 5 3 .8 3 4 3 .8 6 1 3 .8 7 6 3 .9 0 2 3 .9 0 9 3 .9 3 4 4 .1 3 2 4 .1 4 4 4 .1 5 8 4 .1 6 8 5 .0 6 1 5 .0 8 8 6 .3 1 5 6 .3 2 2 6 .4 5 9 6 .4 6 6 6 .9 0 2 6 .9 2 9 6 .9 7 8 6 .9 8 4 7. 0 3 5 7. 0 6 6 7. 2 6 0 7. 6 8 3 7. 6 9 0 7. 6 9 9 7. 7 0 6 7. 7 1 4 7. 7 2 1

O

O

O

O

O

OH

O

O

O

C

H

3

CH

3

CH

3

N

CH

3

CH

3

O

CH

3

1

H NMR spectrum for compound 25

(27)

-5000

0

5000

10000

15000

20000

25000

30000

35000

40000

45000

50000

55000

60000

65000

70000

75000

andre vignau

av 39-16 c13

9

.3

9

2

3

.7

2

2

9

.5

2

4

6

.3

3

5

1

.1

4

5

5

.7

4

5

6

.0

0

5

6

.0

6

5

6

.3

8

6

1

.4

5

7

1

.7

2

7

6

.1

2

7

6

.6

2

7

7.

0

4

7

7.

4

6

7

8

.6

7

9

2

.3

4

9

5

.8

2

1

0

9

.4

3

1

1

0

.2

1

1

1

1

.3

3

1

1

7.

0

0

1

1

7.

2

3

1

2

0

.1

5

1

2

2

.3

4

1

2

4

.1

8

1

2

8

.5

1

1

4

0

.3

3

1

4

3

.5

8

1

4

5

.2

6

1

4

9

.3

9

1

4

9

.7

0

1

5

2

.5

3

1

5

8

.8

1

1

6

0

.9

6

1

6

3

.9

2

1

7

4

.0

7

O

O

O

O

O

OH

O

O

O

C

H

3

CH

3

CH

3

N

CH

3

CH

3

O

CH

3

13

C NMR spectrum for compound 25

(28)

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

linker nmr

bv-48-52-r1 cdcl3

6

.2

6

4

.0

7

2

.1

9

3

.8

6

1

.8

1

1

.1

0

0

.7

0

3

.5

1

6

.2

7

2

.9

0

1

.8

3

0

.9

9

1

.0

1

1

.0

0

1

.0

1

1

.0

2

1

.0

4

2

.1

1

2

.0

8

0

.8

3

9

9

0

.8

6

4

1

0

.8

8

8

2

1

.4

9

9

3

1

.5

2

3

3

1

.5

4

7

7

1

.5

7

2

7

1

.5

9

8

3

1

.6

2

1

0

2

.0

0

3

7

2

.0

2

7

8

2

.0

5

2

2

2

.5

6

7

5

2

.5

9

3

2

2

.6

1

7

7

2

.8

4

7

0

2

.8

9

2

8

2

.9

1

0

7

2

.9

7

3

0

3

.5

4

0

4

3

.5

5

1

8

3

.5

8

2

1

3

.5

9

3

1

3

.8

2

1

7

3

.8

5

4

9

3

.9

0

3

6

3

.9

3

3

6

4

.0

0

0

2

4

.0

1

6

0

4

.0

3

3

8

4

.0

7

9

1

4

.1

1

8

5

4

.1

4

4

6

5

.0

1

8

8

5

.0

4

5

6

6

.3

1

9

8

6

.4

5

7

6

6

.8

9

5

1

6

.9

2

2

4

6

.9

6

8

5

7.

0

1

4

1

7.

0

3

6

7

7.

0

6

3

0

7.

2

5

9

7

7.

6

8

2

6

7.

7

0

8

2

O

O

O

O O

OH

N

CH3

CH3 O

C H3

O CH3

O CH3

O CH3

1

H NMR spectrum for compound 26

Figure

Updating...

References

Updating...