Structure Characterization and Analgesic Activity of Novel Pyrazolo[3,4-d]pyrimidin-4-one Derivatives

doi:10.11938/cjmr20222995

Abstract

Abstract:

Three compounds of novel pyrazolo[3,4-d]pyrimidin-4-one derivatives (A~C) were synthesized through a multi-step reaction using ethyl-2-cyano-3-ethoxyacrylate and 3,4-dimethylphenylhydrazine. The structures of these compounds were identified by nuclear magnetic resonance (NMR, i.e., ¹H NMR, ¹³C NMR), and liquid chromatography-mass spectrum (LC-MS), and the ¹H NMR signals of each compound were fully assigned. The in vivo analgesic activity of synthesized compound A was preliminarily evaluated through mass spectrometry brain imaging and formalin induced pain model in mice. The imaging data and results showed that compound A could cross the blood-brain barrier and penetrate into the brain of mice, and produce a dose-dependent analgesic activity. This study provided a piece of fundamental research data on structural and in vivo activity for developing anti-pain drugs based on pyrazolo[3,4-d]pyrimidin-4-one scaffold.

Key words: pyrazolo[3,4-d]pyrimidin-4-one, ¹H NMR, ¹³C NMR, mass spectrometry imaging, analgesic activity

CLC Number:

O482.53

ZHAI Chonggang,WANG Pengcheng,SHAN Yubao,LAN Yu,HU Rui,YANG Yunhuang. Structure Characterization and Analgesic Activity of Novel Pyrazolo[3,4-d]pyrimidin-4-one Derivatives[J]. Chinese Journal of Magnetic Resonance, 2023, 40(1): 1-9.

Figures/Tables 8

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Table 1

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References 14

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编号	δ_H	氢原子个数	谱峰裂分(J/Hz)	归属
1	1.39	2	p (5.9)	H-20
2	1.49	4	p (5.5)	H-19, H-21
3	1.89	2	p (6.6)	H-14
4	2.28	3	s	H-16
5	2.31	3	s	H-17
6	2.33	4	t (6.8)	H-18, H-22
7	2.43	2	t (7.0)	H-15
8	2.62	3	s	H-12
9	4.25	2	t (6.2)	H-13
10	7.31	1	d (8.1)	H-2
11	7.71	1	dd (8.1/2.3)	H-1
12	7.74	1	d (2.3)	H-5
13	8.31	1	s	H-9

编号	δ_H	氢原子个数	谱峰裂分(J/Hz)	归属
1	1.91	2	p (6.5)	H-14
2	2.28	3	s	H-16
3	2.31	3	s	H-17
4	2.38	4	t (6.8)	H-18, H-21
5	2.48	2	t (7.0)	H-15
6	2.62	3	s	H-12
7	3.58	4	t (4.5)	H-19, H-20
8	4.27	2	t (6.3)	H-13
9	7.31	1	d (8.1)	H-2
10	7.71	1	dd (8.1/2.3)	H-1
11	7.75	1	d (2.3)	H-5
12	8.31	1	s	H-9

编号	δ_H	氢原子个数	谱峰裂分(J/Hz)	归属
1	1.95	2	p (6.6)	H-14
2	2.28	3	s	H-16
3	2.31	3	s	H-17
4	2.52	2	t (7.0)	H-15
5	2.55	4	t (6.8)	H-18, H-21
6	2.64	3	s	H-12
7	3.13	4	t (5.5)	H-19, H-20
8	4.29	2	t (6.2)	H-13
9	6.77	1	t (7.3)	H-25
10	6.93	2	d (8.1)	H-23, H-27
11	7.21	2	dd (8.7/7.2)	H-24, H-26
12	7.30	1	d (8.2)	H-2
13	7.71	1	dd (8.2/2.3)	H-1
14	7.75	1	d (2.3)	H-5
15	8.31	1	s	H-9

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