Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3157-3170.DOI: 10.6023/cjoc202102046 Previous Articles Next Articles
ARTICLES
李英俊a,*(), 林乐弟a, 靳焜b, 高立信c, 盛丽c, 刘季红d, 李佳c,*()
收稿日期:
2021-02-24
修回日期:
2021-04-02
发布日期:
2021-05-14
通讯作者:
李英俊, 李佳
基金资助:
Yingjun Lia(), Ledi Lina, Kun Jinb, Lixin Gaoc, Li Shengc, Jihong Liud, Jia Lic()
Received:
2021-02-24
Revised:
2021-04-02
Published:
2021-05-14
Contact:
Yingjun Li, Jia Li
Supported by:
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Yingjun Li, Ledi Lin, Kun Jin, Lixin Gao, Li Sheng, Jihong Liu, Jia Li. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Arylaminoacetylhydrazone Derivatives Containing Carbazole Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3157-3170.
Position | δH | 1H-1H COSY A (B) | NOESY A (B) | |
---|---|---|---|---|
A | B | |||
1 (1') | 7.65 (d, J=8.5 Hz) | — | H-2 (—) | H-16 (—) |
2 (2') | 7.92 (dd, J=8.5, 1.0 Hz) | 7.87 (dd, J=8.5, 1.0 Hz) | H-1,4 (H-4') | H-9/H-9' |
3 (3') | / | / | / | / |
4 (4') | 8.48 | 8.46 | H-2 (—) | / |
5 (5') | 8.25 (d, J=7.5 Hz) | 8.21 (d, J=7.5 Hz) | H-6 (H-6') | / |
6 (6') | 7.244 (t, J=7.5 Hz) | 7.237 (t, J=7.5 Hz) | H-5,7 (H-5') | / |
7 (7') | 7.48 (t, J=7.0 Hz) | — | H-6,8 (—) | / |
8 (8') | 7.61 (d, J=8.0 Hz) | — | H-7 (—) | H-16 (—) |
9 (9') | 8.22 | 8.41 | / | H-2/H-2'/H-10/H-10' |
10 (10') | 11.59 | 11.56 | / | H-9/H-9'/–/H-12' |
11 (11') | / | / | / | / |
12 (12') | 4.51 (d, J=6.0 Hz) | 4.04 (d, J=6.0 Hz) | H-13 (—) | (—)/H-10'/H-14/H-14' |
13 (13') | 7.47 | — | H-12 (—) | H-14 (—) |
14 (14') | 6.79 (d, J=9.0 Hz) | 6.74 (d, J=9.0 Hz) | H-15 (H-15') | H-12/H-12'/H-13 |
15 (15') | 8.04 (d, J=9.0 Hz) | 8.06 (d, J=9.0 Hz) | H-14 (H-14') | / |
16 (16') | 4.40 (t, J=6.5 Hz) | 4.38 (t, J=6.5 Hz) | / | H-1/H-8 |
Position | δH | 1H-1H COSY A (B) | NOESY A (B) | |
---|---|---|---|---|
A | B | |||
1 (1') | 7.65 (d, J=8.5 Hz) | — | H-2 (—) | H-16 (—) |
2 (2') | 7.92 (dd, J=8.5, 1.0 Hz) | 7.87 (dd, J=8.5, 1.0 Hz) | H-1,4 (H-4') | H-9/H-9' |
3 (3') | / | / | / | / |
4 (4') | 8.48 | 8.46 | H-2 (—) | / |
5 (5') | 8.25 (d, J=7.5 Hz) | 8.21 (d, J=7.5 Hz) | H-6 (H-6') | / |
6 (6') | 7.244 (t, J=7.5 Hz) | 7.237 (t, J=7.5 Hz) | H-5,7 (H-5') | / |
7 (7') | 7.48 (t, J=7.0 Hz) | — | H-6,8 (—) | / |
8 (8') | 7.61 (d, J=8.0 Hz) | — | H-7 (—) | H-16 (—) |
9 (9') | 8.22 | 8.41 | / | H-2/H-2'/H-10/H-10' |
10 (10') | 11.59 | 11.56 | / | H-9/H-9'/–/H-12' |
11 (11') | / | / | / | / |
12 (12') | 4.51 (d, J=6.0 Hz) | 4.04 (d, J=6.0 Hz) | H-13 (—) | (—)/H-10'/H-14/H-14' |
13 (13') | 7.47 | — | H-12 (—) | H-14 (—) |
14 (14') | 6.79 (d, J=9.0 Hz) | 6.74 (d, J=9.0 Hz) | H-15 (H-15') | H-12/H-12'/H-13 |
15 (15') | 8.04 (d, J=9.0 Hz) | 8.06 (d, J=9.0 Hz) | H-14 (H-14') | / |
16 (16') | 4.40 (t, J=6.5 Hz) | 4.38 (t, J=6.5 Hz) | / | H-1/H-8 |
Compd. | X | R | PTP1Ba | |
---|---|---|---|---|
Inhibition/% at 20 μg/mL | IC50/(μmol•L–1) | |||
3a | 4-OCH3 | C2H5 | 93.19±1.27 | 9.91±1.72 |
3b | 4-OCH3 | n-C3H7 | 93.92±1.48 | 9.00±0.63 |
3c | 4-OCH3 | n-C4H9 | 91.82±0.32 | 9.31±0.16 |
3d | 4-OCH3 | n-C5H11 | 81.15±2.86 | 7.68±1.56 |
3e | 4-OCH3 | n-C6H13 | 76.38±10.73 | 5.26±1.66 |
3f | 4-OCH3 | n-C7H15 | 74.15±1.24 | 5.38±2.74 |
3g | 4-OCH3 | n-C8H17 | 53.68±0.33 | 7.76±0.54 |
3h | 3-Cl | C2H5 | 90.21±1.19 | 7.09±1.11 |
3i | 3-Cl | n-C3H7 | 95.32±0.16 | 5.80±0.72 |
3j | 3-Cl | n-C4H9 | 95.24±0.15 | 3.88±0.02 |
3k | 3-Cl | n-C5H11 | 96.46±0.24 | 6.67±0.18 |
3l | 3-Cl | n-C6H13 | 96.03±1.67 | 4.14±0.13 |
3m | 3-Cl | n-C7H15 | 93.34±0.21 | 4.51±0.23 |
3n | 3-Cl | n-C8H17 | 83.08±3.72 | 5.48±2.58 |
3o | 4-NO2 | n-C3H7 | 77.04±1.71 | 5.59±0.98 |
3p | 4-NO2 | n-C4H9 | 74.05±2.13 | 4.08±1.38 |
3q | 4-NO2 | n-C5H11 | 73.23±0.85 | 5.57±1.33 |
3r | 4-NO2 | n-C6H13 | 95.37±1.33 | 4.41±1.17 |
3s | 4-NO2 | n-C7H15 | 96.39±0.24 | 3.27±0.47 |
3t | 4-NO2 | n-C8H17 | 96.70±1.63 | 2.78±0.04 |
Compd. | X | R | PTP1Ba | |
---|---|---|---|---|
Inhibition/% at 20 μg/mL | IC50/(μmol•L–1) | |||
3a | 4-OCH3 | C2H5 | 93.19±1.27 | 9.91±1.72 |
3b | 4-OCH3 | n-C3H7 | 93.92±1.48 | 9.00±0.63 |
3c | 4-OCH3 | n-C4H9 | 91.82±0.32 | 9.31±0.16 |
3d | 4-OCH3 | n-C5H11 | 81.15±2.86 | 7.68±1.56 |
3e | 4-OCH3 | n-C6H13 | 76.38±10.73 | 5.26±1.66 |
3f | 4-OCH3 | n-C7H15 | 74.15±1.24 | 5.38±2.74 |
3g | 4-OCH3 | n-C8H17 | 53.68±0.33 | 7.76±0.54 |
3h | 3-Cl | C2H5 | 90.21±1.19 | 7.09±1.11 |
3i | 3-Cl | n-C3H7 | 95.32±0.16 | 5.80±0.72 |
3j | 3-Cl | n-C4H9 | 95.24±0.15 | 3.88±0.02 |
3k | 3-Cl | n-C5H11 | 96.46±0.24 | 6.67±0.18 |
3l | 3-Cl | n-C6H13 | 96.03±1.67 | 4.14±0.13 |
3m | 3-Cl | n-C7H15 | 93.34±0.21 | 4.51±0.23 |
3n | 3-Cl | n-C8H17 | 83.08±3.72 | 5.48±2.58 |
3o | 4-NO2 | n-C3H7 | 77.04±1.71 | 5.59±0.98 |
3p | 4-NO2 | n-C4H9 | 74.05±2.13 | 4.08±1.38 |
3q | 4-NO2 | n-C5H11 | 73.23±0.85 | 5.57±1.33 |
3r | 4-NO2 | n-C6H13 | 95.37±1.33 | 4.41±1.17 |
3s | 4-NO2 | n-C7H15 | 96.39±0.24 | 3.27±0.47 |
3t | 4-NO2 | n-C8H17 | 96.70±1.63 | 2.78±0.04 |
Est. free energy/ (kJ/mol) of binding | No. of H-bond | H-bond (length/nm) | Polar (length/nm) | Hydrophobic (length/nm) | π-π (length/nm) |
---|---|---|---|---|---|
–25.75 | 5 | N(2)-VAL184 (0.349) | H(26)-GLU186 (0.245) | C(9)-PRO180 (0.352) | C(4)-TYR152 (0.382) |
N(3)-VAL184 (0.300) | O(2)-ARG268 (0.370) | C(10)-PRO180 (0.314) | |||
N(4)-VAL184 (0.306) | O(3)-ARG268 (0.336) | C(11)-PRO180 (0.355) | |||
N(2)-GLU186 (0.265) | N(5)-ARG268 (0.387) | C(21)-PRO180 (0.324) | |||
N(3)-GLU186 (0.267) |
Est. free energy/ (kJ/mol) of binding | No. of H-bond | H-bond (length/nm) | Polar (length/nm) | Hydrophobic (length/nm) | π-π (length/nm) |
---|---|---|---|---|---|
–25.75 | 5 | N(2)-VAL184 (0.349) | H(26)-GLU186 (0.245) | C(9)-PRO180 (0.352) | C(4)-TYR152 (0.382) |
N(3)-VAL184 (0.300) | O(2)-ARG268 (0.370) | C(10)-PRO180 (0.314) | |||
N(4)-VAL184 (0.306) | O(3)-ARG268 (0.336) | C(11)-PRO180 (0.355) | |||
N(2)-GLU186 (0.265) | N(5)-ARG268 (0.387) | C(21)-PRO180 (0.324) | |||
N(3)-GLU186 (0.267) |
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