N-取代肌肽酰胺类衍生物的合成及生物活性

doi:10.7503/cjcu20140395

高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (12): 2567.doi: 10.7503/cjcu20140395

N-取代肌肽酰胺类衍生物的合成及生物活性

臧皓¹, 孙佳明¹, 黄晓光², 纪扬², 代婷婷¹, 高晓晨¹, 李晓东²(), 张辉¹()

1. 长春中医药大学中医药与生物工程研发中心, 长春 130117
2. 吉林省博大伟业制药有限公司, 长春 130117

收稿日期:2014-04-25 出版日期:2014-12-10 发布日期:2014-11-29
作者简介:联系人简介: 张辉, 男, 教授, 博士生导师, 主要从事中药化学研究. E-mail:zhanghui_8080@163.com;李晓东, 男, 高级工程师, 主要从事药物化学研究. E-mail:baoer88@126.com
基金资助:
国家自然科学基金(批准号: 81373936)、吉林省科技发展计划项目(批准号: 20140203015YY)和吉林省教育厅“双十”培育项目(批准号: 吉教科合字[2014]第71号)资助

Synthesis and Biological Activity of N-substituted Carnosine Amide Derivatives^†

ZANG Hao¹, SUN Jiaming¹, HUANG Xiaoguang², JI Yang², DAI Tingting¹, GAO Xiaochen¹, LI Xiaodong^2,^*(), ZHANG Hui^1,^*()

1. Development Center of Traditional Chinese Medicine and Bioengineering, Changchun University of Traditional Chinese Medicine, Changchun 130117, China
2. Jilin Province Bodaweiye Pharmaceutical Co. Ltd., Changchun 130117, China

Received:2014-04-25 Online:2014-12-10 Published:2014-11-29
Contact: LI Xiaodong,ZHANG Hui E-mail:baoer88@126.com;zhanghui_8080@163.com
Supported by:
† Supported by the National Natural Science Foundation of China(No.81373936), the Science and Technology Development Funds of Jilin Province, China(No.20140203015YY) and the “Double Ten” Development Project of Jilin Province Department of Education, China(No.JiJiaoKeHeZi[2014]No.71)

摘要/Abstract

摘要：

以肌肽为原料, 对伯氨基进行了结构修饰, 合成了11种肌肽衍生物. 化合物的结构经核磁共振、紫外-可见光谱及高分辨质谱分析确证. 丙烯醛清除活性测试结果表明, 在实验浓度下大部分化合物表现出一定的清除丙烯醛活性, 尤其是化合物4k对丙烯醛的清除活性高于肌肽. 脾细胞增殖活性测试结果表明, 在实验浓度下大部分化合物表现出一定的脾细胞增殖活性, 特别是化合物4b, 4d和4k对脾细胞的增殖活性高于阳性对照伴刀豆球蛋白A. 过氧化氢诱导血管内皮细胞损伤的预保护实验结果表明, 在实验浓度下大部分化合物表现出一定的预保护作用, 其中化合物4a, 4j和4k对过氧化氢诱导血管内皮细胞损伤的预保护作用大于肌肽. 血浆稳定性实验结果表明, 与肌肽相比, 11种化合物均具有很好的血浆稳定性.

关键词: 肌肽衍生物, 丙烯醛清除, 脾细胞增殖, 过氧化氢损伤预保护, 血浆稳定性

Abstract:

A series of carnosine derivatives were synthesized by modification of primary amino groups of carnosine, eleven target compounds were obtained and characterized by NMR, UV-Vis and HR-MS. Acrolein scavenging activity test results showed that most compounds exhibited some acrolein scavenging activities, especially compound 4k showed the highest acrolein scavenging activity which was stronger than carnosine. Spleen cell proliferation test results showed that most compounds exhibited some spleen cell proliferation activities, compounds 4b, 4d and 4k showed stronger spleen cell proliferation activities than the positive control conA. Hydrogen peroxide injury pre-protection results showed that most compounds exhibited some pre-protection effects, especially compounds 4a, 4j and 4k showed stronger ECV-304 cell pre-protection effects than carnosine. Plasma stability assay results showed that compared with carnosine, eleven compounds had good plasma stability.

Key words: Carnosine derivative, Acrolein scavenging, Spleen cell proliferation, Hydrogen peroxide injury protection, Plasma stability

中图分类号:

O629.72

TrendMD:

臧皓, 孙佳明, 黄晓光, 纪扬, 代婷婷, 高晓晨, 李晓东, 张辉. N-取代肌肽酰胺类衍生物的合成及生物活性. 高等学校化学学报, 2014, 35(12): 2567.

ZANG Hao, SUN Jiaming, HUANG Xiaoguang, JI Yang, DAI Tingting, GAO Xiaochen, LI Xiaodong, ZHANG Hui. Synthesis and Biological Activity of N-substituted Carnosine Amide Derivatives^†. Chem. J. Chinese Universities, 2014, 35(12): 2567.

图/表 7

参考文献 22

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Compd.	Appearance	Yield(%)	m.p./℃	UV-Vis, λ_max/nm	HR-MS([M+H]⁺), m/z
4a	White solid	70.2	188—190	201	297.1503
4c	White solid	58.5	219—220	213	367.2246
4e	White solid	73.4	258—259	205, 239	345.1475
4f	White solid	94.2	156—158	205, 239	387.1927
4g	White solid	86.6	264—265	206, 238	365.0960
4h	White solid	52.3	263—265	206, 269	407.1637
4i	White solid	55.7	239—241	215, 258	345.1479
4j	White solid	56.9	243—245	216, 258	359.1643
4k	White solid	81.2	190—191	207	415.1373

Compd.	Appearance	Yield(%)	m.p./℃	UV-Vis, λ_max/nm	HR-MS([M+H]⁺), m/z
4a	White solid	70.2	188—190	201	297.1503
4c	White solid	58.5	219—220	213	367.2246
4e	White solid	73.4	258—259	205, 239	345.1475
4f	White solid	94.2	156—158	205, 239	387.1927
4g	White solid	86.6	264—265	206, 238	365.0960
4h	White solid	52.3	263—265	206, 269	407.1637
4i	White solid	55.7	239—241	215, 258	345.1479
4j	White solid	56.9	243—245	216, 258	359.1643
4k	White solid	81.2	190—191	207	415.1373

Compd.	¹H NMR(D₂O, 600 MHz), δ	¹³C NMR(D₂O, 150 MHz), δ
4a	8.45(s, 1H), 7.16(s, 1H), 4.41(dd, J=7.8, 4.8 Hz, 1H), 3.32(q, J=6.6 Hz, 2H), 3.16(q, J=4.8 Hz, 1H), 3.00(q, J=8.4 Hz, 1H), 2.40(t, J=6.6 Hz, 2H), 2.09(t, J=7.2 Hz, 2H), 1.47(q, J=7.2 Hz, 2H), 0.78(t, J=7.2 Hz, 3H)	176.3, 175.6, 172.5, 132.5, 129.2, 115.9, 53.3, 36.8, 34.9, 34.3, 26.7, 18.1, 11.8
4c	8.47(s, 1H), 7.17(s, 1H), 4.42(t, J=7.8, 5.4 Hz, 1H), 3.33(q, J=6.6 Hz, 2H), 3.17(q, J=5.4 Hz, 1H), 3.01(q, J=7.8 Hz, 1H), 2.41(t, J=6.6 Hz, 2H), 2.12(t, J=7.2 Hz, 2H), 1.47(s, 2H), 1.19(s, 10H), 0.78(t, J=7.2 Hz, 3H)	176.5, 175.5, 172.4, 132.5, 129.2, 115.9, 53.3, 34.9, 34.9, 34.3, 30.2, 27.5, 27.4, 27.3, 26.7, 24.5, 21.2, 12.6
4e	8.17(s, 1H), 7.52(d, J=7.8 Hz, 2H), 7.28(d, J=8.4 Hz, 2H), 7.05(s, 1H), 4.44(s, 1H), 3.54(q, J=6.0 Hz, 2H), 3.13(t, J=4.2 Hz, 1H), 2.98(q, J=8.4 Hz, 1H), 2.56(d, J=6.6 Hz, 1H), 2.50(d, J=6.6 Hz, 1H), 2.34(s, 1H)	175.6, 172.7, 169.7, 142.5, 132.2, 129.6, 129.1, 128.6, 128.6, 126.2, 126.2, 115.5, 53.0, 35.5, 34.5, 26.5, 19.7
4f	8.15(s, 1H), 7.59(d, J=8.4 Hz, 2H), 7.53(d, J=8.4 Hz, 2H), 7.06(s, 1H), 4.45(dd, J=8.4, 4.8 Hz, 1H), 3.52—3.58(m, 2H), 3.14(q, J=4.8 Hz, 1H), 2.97(q, J=8.4 Hz, 1H), 2.51—2.57(m, 2H), 1.26(s, 9H)	175.6, 172.7, 169.5, 155.5, 132.1, 129.6, 129.1, 126.1, 126.1, 125.0, 125.0, 115.6, 53.0, 35.5, 34.5, 33.6, 29.5, 29.5, 29.5, 26.6
4g	8.32(d, 1H), 7.57(d, J=8.4 Hz, 2H), 7.44(d, J=8.4 Hz, 2H), 7.09(s, 1H), 4.44(dd, J=8.4, 4.8 Hz, 1H), 3.51—3.56(m, 2H), 3.15(q, J=4.8 Hz, 1H), 2.99(q, J=8.4 Hz, 1H), 2.50—2.55(m, 2H)	175.5, 172.6, 168.8, 136.8, 132.2, 131.1, 129.0, 128.0, 128.0, 127.7, 127.7, 115.6, 53.0, 35.6, 34.5, 26.5
4h	8.53(s, 1H, —COOH),8.20(d, J=7.8 Hz, 1H, imidazole NH)7.91(d, J=8.4Hz, 2H), 7.75(d, J=8.4 Hz, 2H), 7.73(s, 1H, —CONH), 7.72(s, 1H, —CONH), 7.55(s, 1H), 7.49(t, J=7.8 Hz, 2H), 7.41(d, J=7.8 Hz, 1H), 6.81(s, 1H), 4.44(d, J=5.4 Hz, 1H), 3.45(d, J=6.0 Hz, 2H), 2.95(q, J=5.4 Hz, 1H), 2.84(q, J=5.4 Hz, 1H), 2.41(q, J=7.2 Hz, 2H)	173.1, 170.3, 165.8, 142.6, 142.6, 139.2, 134.7, 133.3, 133.3, 129.0, 129.0, 128.0, 127.8, 127.8, 126.8, 126.8, 126.4, 126.4, 52.3, 36.0, 35.2, 28.9
4i	8.34(s, 1H), 7.31(t, J=7.2 Hz, 2H), 7.26(t, J=7.2 Hz, 1H), 7.21(d, J=7.2 Hz, 2H), 7.09(s, 1H), 4.36(q, J=5.4 Hz, 1H), 3.49(s, 2H), 3.34(t, J=6.0 Hz, 2H), 3.07(d, J=4.8 Hz, 1H), 2.94(d, J=7.8 Hz, 1H), 2.40(t, J=6.0 Hz, 2H)	175.7, 173.8, 172.4, 134.1, 132.6, 129.4, 128.3, 128.3, 128.1, 128.1, 126.5, 116.0, 53.4, 41.5, 35.1, 34.3, 26.8
4j	8.45(s, 1H), 7.27(t, J=7.2 Hz, 2H), 7.15—7.20(m, 4H), 4.38(q, J=5.4 Hz, 1H), 3.22(t, J=6.6 Hz, 2H), 3.17(q, J=5.4 Hz, 1H), 3.14(q, J=5.4 Hz, 1H), 2.98(q, J=7.8 Hz, 1H), 2.82(t, J=7.2 Hz, 2H), 2.44(t, J=7.2 Hz, 2H), 2.26(t, J=6.6 Hz, 2H)	175.5, 174.9, 172.3, 139.7, 132.3, 129.0, 127.9, 127.9, 127.6, 127.6, 125.6, 115.8, 53.2, 36.5, 34.7, 34.1, 30.5, 26.6
4k	8.49(d, J=1.2 Hz, 1H), 7.18(s, 1H), 4.43(dd, J=7.8, 5.4 Hz, 1H), 3.62(s, 1H), 3.34(q, J=6.6 Hz, 2H), 3.15—3.19(m, 2H), 3.12(d, J=6.6 Hz, 1H), 3.01(t, J=7.2 Hz, 1H), 2.41(q, 3H), 2.15(t, J=7.2 Hz, 2H), 1.92(t, J=7.2 Hz, 1H), 1.66(s, 1H), 1.50—1.56(m, 3H), 1.32(t, J=7.8 Hz, 2H)	176.1, 175.5, 172.4, 132.4, 129.1, 115.9, 55.7, 53.3, 39.5, 37.3, 34.9, 34.6, 34.3, 32.9, 26.9, 26.7, 24.2

Compd.	¹H NMR(D₂O, 600 MHz), δ	¹³C NMR(D₂O, 150 MHz), δ
4a	8.45(s, 1H), 7.16(s, 1H), 4.41(dd, J=7.8, 4.8 Hz, 1H), 3.32(q, J=6.6 Hz, 2H), 3.16(q, J=4.8 Hz, 1H), 3.00(q, J=8.4 Hz, 1H), 2.40(t, J=6.6 Hz, 2H), 2.09(t, J=7.2 Hz, 2H), 1.47(q, J=7.2 Hz, 2H), 0.78(t, J=7.2 Hz, 3H)	176.3, 175.6, 172.5, 132.5, 129.2, 115.9, 53.3, 36.8, 34.9, 34.3, 26.7, 18.1, 11.8
4c	8.47(s, 1H), 7.17(s, 1H), 4.42(t, J=7.8, 5.4 Hz, 1H), 3.33(q, J=6.6 Hz, 2H), 3.17(q, J=5.4 Hz, 1H), 3.01(q, J=7.8 Hz, 1H), 2.41(t, J=6.6 Hz, 2H), 2.12(t, J=7.2 Hz, 2H), 1.47(s, 2H), 1.19(s, 10H), 0.78(t, J=7.2 Hz, 3H)	176.5, 175.5, 172.4, 132.5, 129.2, 115.9, 53.3, 34.9, 34.9, 34.3, 30.2, 27.5, 27.4, 27.3, 26.7, 24.5, 21.2, 12.6
4e	8.17(s, 1H), 7.52(d, J=7.8 Hz, 2H), 7.28(d, J=8.4 Hz, 2H), 7.05(s, 1H), 4.44(s, 1H), 3.54(q, J=6.0 Hz, 2H), 3.13(t, J=4.2 Hz, 1H), 2.98(q, J=8.4 Hz, 1H), 2.56(d, J=6.6 Hz, 1H), 2.50(d, J=6.6 Hz, 1H), 2.34(s, 1H)	175.6, 172.7, 169.7, 142.5, 132.2, 129.6, 129.1, 128.6, 128.6, 126.2, 126.2, 115.5, 53.0, 35.5, 34.5, 26.5, 19.7
4f	8.15(s, 1H), 7.59(d, J=8.4 Hz, 2H), 7.53(d, J=8.4 Hz, 2H), 7.06(s, 1H), 4.45(dd, J=8.4, 4.8 Hz, 1H), 3.52—3.58(m, 2H), 3.14(q, J=4.8 Hz, 1H), 2.97(q, J=8.4 Hz, 1H), 2.51—2.57(m, 2H), 1.26(s, 9H)	175.6, 172.7, 169.5, 155.5, 132.1, 129.6, 129.1, 126.1, 126.1, 125.0, 125.0, 115.6, 53.0, 35.5, 34.5, 33.6, 29.5, 29.5, 29.5, 26.6
4g	8.32(d, 1H), 7.57(d, J=8.4 Hz, 2H), 7.44(d, J=8.4 Hz, 2H), 7.09(s, 1H), 4.44(dd, J=8.4, 4.8 Hz, 1H), 3.51—3.56(m, 2H), 3.15(q, J=4.8 Hz, 1H), 2.99(q, J=8.4 Hz, 1H), 2.50—2.55(m, 2H)	175.5, 172.6, 168.8, 136.8, 132.2, 131.1, 129.0, 128.0, 128.0, 127.7, 127.7, 115.6, 53.0, 35.6, 34.5, 26.5
4h	8.53(s, 1H, —COOH),8.20(d, J=7.8 Hz, 1H, imidazole NH)7.91(d, J=8.4Hz, 2H), 7.75(d, J=8.4 Hz, 2H), 7.73(s, 1H, —CONH), 7.72(s, 1H, —CONH), 7.55(s, 1H), 7.49(t, J=7.8 Hz, 2H), 7.41(d, J=7.8 Hz, 1H), 6.81(s, 1H), 4.44(d, J=5.4 Hz, 1H), 3.45(d, J=6.0 Hz, 2H), 2.95(q, J=5.4 Hz, 1H), 2.84(q, J=5.4 Hz, 1H), 2.41(q, J=7.2 Hz, 2H)	173.1, 170.3, 165.8, 142.6, 142.6, 139.2, 134.7, 133.3, 133.3, 129.0, 129.0, 128.0, 127.8, 127.8, 126.8, 126.8, 126.4, 126.4, 52.3, 36.0, 35.2, 28.9
4i	8.34(s, 1H), 7.31(t, J=7.2 Hz, 2H), 7.26(t, J=7.2 Hz, 1H), 7.21(d, J=7.2 Hz, 2H), 7.09(s, 1H), 4.36(q, J=5.4 Hz, 1H), 3.49(s, 2H), 3.34(t, J=6.0 Hz, 2H), 3.07(d, J=4.8 Hz, 1H), 2.94(d, J=7.8 Hz, 1H), 2.40(t, J=6.0 Hz, 2H)	175.7, 173.8, 172.4, 134.1, 132.6, 129.4, 128.3, 128.3, 128.1, 128.1, 126.5, 116.0, 53.4, 41.5, 35.1, 34.3, 26.8
4j	8.45(s, 1H), 7.27(t, J=7.2 Hz, 2H), 7.15—7.20(m, 4H), 4.38(q, J=5.4 Hz, 1H), 3.22(t, J=6.6 Hz, 2H), 3.17(q, J=5.4 Hz, 1H), 3.14(q, J=5.4 Hz, 1H), 2.98(q, J=7.8 Hz, 1H), 2.82(t, J=7.2 Hz, 2H), 2.44(t, J=7.2 Hz, 2H), 2.26(t, J=6.6 Hz, 2H)	175.5, 174.9, 172.3, 139.7, 132.3, 129.0, 127.9, 127.9, 127.6, 127.6, 125.6, 115.8, 53.2, 36.5, 34.7, 34.1, 30.5, 26.6
4k	8.49(d, J=1.2 Hz, 1H), 7.18(s, 1H), 4.43(dd, J=7.8, 5.4 Hz, 1H), 3.62(s, 1H), 3.34(q, J=6.6 Hz, 2H), 3.15—3.19(m, 2H), 3.12(d, J=6.6 Hz, 1H), 3.01(t, J=7.2 Hz, 1H), 2.41(q, 3H), 2.15(t, J=7.2 Hz, 2H), 1.92(t, J=7.2 Hz, 1H), 1.66(s, 1H), 1.50—1.56(m, 3H), 1.32(t, J=7.8 Hz, 2H)	176.1, 175.5, 172.4, 132.4, 129.1, 115.9, 55.7, 53.3, 39.5, 37.3, 34.9, 34.6, 34.3, 32.9, 26.9, 26.7, 24.2

Compd.	Scavenging ratio(%)			Compd.	Scavenging ratio(%)
Compd.	1 h	2 h	3 h	Compd.	1 h	2 h	3 h
4a	25.6±0.9	30.4±0.4	37.0±0.5	4h	38.7±0.6	51.5±1.6	60.5±0.5
4b	22.0±0.6	32.9±2.3	40.3±1.2	4i	21.0±0.6	26.5±1.2	40.7±1.2
4c	21.9±0.4	42.6±0.8	55.5±1.2	4j	14.9±0.4	28.6±0.8	43.6±1.1
4d	22.2±1.4	31.7±1.8	40.5±1.6	4k	56.0±2.1	75.2±1.0	92.1±1.1
4e	28.0±1.1	39.1±1.5	55.8±2.0	Carnosine	46.6±1.8	74.7±2.0	88.0±2.3
4f	21.3±0.7	38.5±0.5	58.4±0.5	β-Alanine	12.3±1.5	27.6±1.7	41.1±2.0
4g	22.9±1.4	39.7±1.2	58.2±0.4	GABA	10.4±0.8	23.4±0.4	39.0±2.3

N-取代肌肽酰胺类衍生物的合成及生物活性

Synthesis and Biological Activity of N-substituted Carnosine Amide Derivatives^†

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Compd.	OD value^*	Proliferation rate(%)	Compd.	OD value^*	Proliferation rate(%)
4a	0.830±0.097	58.0	4h	0.782±0.094	48.9
4b	1.171±0.122	123.1	4i	0.563±0.108	7.3
4c	0.859±0.087	63.6	4j	0.613±0.134	16.8
4d	1.066±0.119	103.0	4k	0.917±0.042	74.7
4e	0.693±0.056	32.0	Carnosine	0.499±0.066	-4.9
4f	0.732±0.111	39.5	Blank	0.525±0.079	0
4g	0.656±0.157	24.9	ConA	0.882±0.071	68.0

Compd.	OD value	Proliferation rate(%)	Compd.	OD value	Proliferation rate(%)
4a	2.638±0.055	53.6	4h	2.239±0.104	30.4
4b	2.385±0.033	38.9	4i	2.403±0.184	40.0
4c	2.237±0.075	30.3	4j	2.720±0.144	58.4
4d	2.308±0.086	34.4	4k	2.767±0.013	61.2
4e	2.006±0.223	16.8	Carnosine	2.510±0.130	46.2
4f	2.080±0.071	21.1	Blank	1.717±0.191	0
4g	2.353±0.255	37.0	H₂O₂	1.258±0.179	-26.7

Compd.	Plasma stability assay
Compd.	0.5 h	1 h	1.5 h	2 h
4a	99.7±0.1	99.3±0.1	99.1±0.1	99.0±0.1
4b	99.6±0.1	99.4±0.1	99.1±0.1	98.7±0.1
4c	99.5±0.1	99.1±0.1	98.9±0.1	98.7±0.1
4d	99.7±0.1	99.6±0.1	99.4±0.1	99.3±0.1
4e	99.9±0.1	99.3±0.1	99.0±0.1	98.6±0.1
4f	99.7±0.1	99.6±0.1	99.3±0.1	99.0±0.1
4g	99.7±0.1	99.4±0.1	99.1±0.1	98.8±0.1
4h	99.9±0.1	99.6±0.1	99.3±0.1	99.1±0.1
4i	99.8±0.1	99.1±0.1	98.4±0.1	98.0±0.1
4j	99.9±0.1	99.6±0.1	99.4±0.1	99.2±0.1
4k	99.7±0.1	99.5±0.1	99.3±0.1	99.0±0.1

N-取代肌肽酰胺类衍生物的合成及生物活性

Synthesis and Biological Activity of N-substituted Carnosine Amide Derivatives†

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Synthesis and Biological Activity of N-substituted Carnosine Amide Derivatives^†