樟脑磺酸噻唑腙类化合物的设计、合成及抗氧化应用

doi:10.6023/cjoc201901053

有机化学 ›› 2019, Vol. 39 ›› Issue (9): 2616-2624.DOI: 10.6023/cjoc201901053 上一篇下一篇

研究论文

樟脑磺酸噻唑腙类化合物的设计、合成及抗氧化应用

张强健^a, 王芸芸^a, 赵雨珣^a, 马崇慧^a, 徐徐^a,c, 谷文^a,c, 杨益琴^b,c, 王石发^a,c

a 南京林业大学化学工程学院南京 210037;
b 南京林业大学轻工与食品学院南京 210037;
c 南京林业大学林业资源高效加工利用协同创新中心南京 210037

收稿日期:2019-01-30 修回日期:2019-03-17 发布日期:2019-04-11
通讯作者: 王石发 E-mail:wangshifa65@163.com
基金资助:
国家自然科学基金（No.31470592）资助项目.

Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives

Zhang Qiangjian^a, Wang Yunyun^a, Zhao Yuxun^a, Ma Chonghui^a, Xu Xu^a,c, Gu Wen^a,c, Yang Yiqing^b,c, Wang Shifa^a,c

a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
b College of Light Industry and Food, Nanjing Forestry University, Nanjing 210037;
c Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037

Received:2019-01-30 Revised:2019-03-17 Published:2019-04-11
Contact: 10.6023/cjoc201901053 E-mail:wangshifa65@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31470592).

文章分享

1. 樟脑磺酸噻唑腙类化合物的设计、合成及抗氧化应用.PDF(3449KB)

摘要/Abstract

以樟脑衍生物樟脑磺酸为原料，经缩合、环化等反应，合成了22个樟脑磺酸噻唑腙类化合物，采用¹H NMR、¹³C NMR、HR-MS等方法对产物的结构进行表征，并研究了它们的抗氧化活性.结果表明，不同取代基的樟脑磺酸噻唑腙类化合物表现出不同的抗氧化活性，其中（2-（2-（4-（4-氰基苯基）噻唑-2-基）亚肼基）-7，7-二甲基双环[2.2.1]庚-1-基）甲磺酸（Q19）消除1，1-二苯基-2-三硝基苯肼（DPPH）自由基的IC₅₀值可达到176 μmol/L，（2-（2-（4-（4-氟苯基）噻唑-2-基）亚肼基）-7，7-二甲基双环[2.2.1]庚-1-基）甲磺酸（Q3）消除2，2-联氮-二（3-乙基-苯并噻唑-6-磺酸）二铵盐（ABTS）自由基的IC₅₀值可达到20.6 μmol/L，（E）-（7，7-二甲基-2-（2-（4-（3-甲苯基）噻唑-2-基）亚肼基）双环[2.2.1]庚-1-基）甲磺酸（Q8）对羟基自由基的消除率可达到66.2%，（2-（2-（4-（4-联苯基）噻唑-2-基）亚肼基）-7，7-二甲基双环[2.2.1]庚-1-基）甲磺酸（Q20）消除过氧自由基的IC₅₀值可达到20.7 μmol/L，均远超过阳性对照trolox的抗氧化活性.（2-（2-（4-（2-羟基苯基）噻唑-2-基）亚肼基）-7，7-二甲基双环[2.2.1]庚-1-基）甲磺酸（Q16）抑制酪氨酸酶的IC₅₀值可达154.9 μmol/L，也优于阳性对照曲酸.对樟脑磺酸基噻唑腙类化合物的抗氧化机理进行了探索.

关键词: 樟脑磺酸, 噻唑腙, 抗氧化活性

A series of camphorsulfonic acid thiazolylhydrazone derivatives were synthesized by using camphorsulfonic acid derivated from natural camphor as the starting material in three steps, including condensation with aminothiourea and cyclization with bromoacetophenone. Their structures were characterized by ¹H NMR, ¹³C NMR and HR-MS, and their antioxidant activities were also investigated. The results showed that these compounds had good antioxidant activities compared with the positive control trolox. Among of them, (2-(2-(4-(4-cyanophenyl)thiazol-2-yl)indenyl)-7,7-dimethylbicyclo-[2.2.1]hept-1-yl)methanesulfonic acid (Q19) exhibited the relatively strong 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity with IC₅₀ value of 176 μmol/L, (2-(2-(4-(4-fluorophenyl)thiazol-2-yl)hydrazino)-7,7-dimethylbicyclo-[2.2.1]hept-1-yl)methanesulfonic acid (Q3) exhibited the relatively strong diammonium 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) radical scavenging activity with IC₅₀ value of 20.6 μmol/L, (E)-(7,7-dimethyl-2-(2-(4-(3-methyl)-thiazol-2-yl)indenyl)bicyclo[2.2.1]hept-1-yl)-sulfonic acid (Q8) exhibited the strong hydroxyl radical scavenging activity with scavenge rate 66.2%, (2-(2-(4-(4-biphenyl)thiazol-2-yl)indenyl)-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methane-sulfonic acid (Q20) exhibited the relatively strong superoxide radical scavenging activity with IC₅₀ value of 20.7 μmol/L. Compared with the positive control kojic acid, (2-(2-(4-(2-hydroxyphenyl)thiazol-2-yl)arylene)-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonic acid (Q16) exhibited remarkable tyrosinase inhibitory activity with IC₅₀ value of 154.9 μmol/L. It was known from the structure-activity relationship that the structure of R gave great influence on the activities of thiazolylhydrazone derivatives.

Key words: camphorsulfonic acid, thiazolylhydrazone, antioxidant activity

引用此文

张强健, 王芸芸, 赵雨珣, 马崇慧, 徐徐, 谷文, 杨益琴, 王石发. 樟脑磺酸噻唑腙类化合物的设计、合成及抗氧化应用[J]. 有机化学, 2019, 39(9): 2616-2624.

Zhang Qiangjian, Wang Yunyun, Zhao Yuxun, Ma Chonghui, Xu Xu, Gu Wen, Yang Yiqing, Wang Shifa. Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives[J]. Chin. J. Org. Chem., 2019, 39(9): 2616-2624.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Limtrakul, P.; Yodkeeree, S.; Thippraphan, P. BMC Com-plementary Altern. Med. 2016, 16, 497.
[2] Gragnani, A.; Cornick, S.; Chominski, V. Adv. Aging Res. 2014, 3, 265.
[3] Pedrosa, T.; Barros, A.; Nogueira, J. Arch. Dermatol. Res. 2016, 308, 643.
[4] Delalle-Lozica, N. Acta Clin. Croat. 2010, 49, 529.
[5] Jae, Y. L.; Young-Rak, C.; Ju, H. P. Toxicol. Rep. 2019, 6, 10.
[6] Limtrakul, P.; Yodkeeree, S.; Thippraphan, P. BMC Com-plementary Altern. Med. 2016, 16, 497.
[7] Alfredo, G.; Sarita, M. C.; Verônica, C. Adv. Aging Res. 2014, 3, 265.
[8] Laguerre, M.; Lecomte, J.; Villeneuve, P. Prog. Lipid Res. 2007, 46, 244.
[9] Amorati, R.; Foti, M.; Valgimigli, L. J. Agric. Food Chem. 2013, 61, 10835.
[10] Liu, Y.; Huang, G.; Hu, J. Int. J. Biol. Macromol. 2018, 111, 1304.
[11] Didem, ?.; Suat, S.; Burak, B. Bioorg. Chem. 2018, 81, 168.
[12] Li, X.; Huang, J.; Wang, Z. Sep. Purif. Technol. 2014, 124, 201.
[13] Adelakun, O.; Kudanga, T.; Parker, A. J. Mol. Catal. B:Enzym. 2012, 74, 29.
[14] Adom, K.; Liu, R. J. Agric. Food Chem. 2005, 53, 6572.
[15] Erzsébet, I.; Amir, M.; Vered, M. Free Radical Biol. Med. 2019, 131, 1.
[16] Jae, Y.; Young, R.; Ju, H. Toxicol. Rep. 2019, 6, 10.
[17] Olanow, C. Trends Neurosci. 1993, 16, 439.
[18] Bennett, S.; Grant, M.; Aldreda, S. J. Alzheimer's Dis. 2009, 17, 245.
[19] Rietveld, I.; Barrio, M.; Veglio, N. Thermochim. Acta 2010, 511, 43.
[20] Andersson, O.; Ross, R.; Jezowski, A. Mol. Phys. 1990, 70, 1065.
[21] Kisiel, Z.; Desyatnyk, O.; Bia?kowska-Jaworska, E. Phys. Chem. Chem. Phys. 2003, 5, 820.
[22] Hargrave, K.; Hess, F.; Oliver, J. J. Med. Chem. 1983, 26, 1158.
[23] Patt, W.; Hamilton, H.; Taylor, M. J. Med. Chem. 1992, 35, 2562.
[24] Kamble, R.; Meshram, R.; Hese, S. Comput. Biol. Chem. 2016, 61, 86.
[25] Jaen, J.; Wise, L.; Caprathe, B. J. Med. Chem. 1990, 33, 311.
[26] Mohammad, H.; Reddy, P.; Monteleone, D. Eur. J. Med. Chem. 2015, 94, 306.
[27] Ergenç, N.; Çapan, G.; Günay, N. Arch. Pharm. (Weinheim, Ger.) 1999, 332, 343.
[28] Bell, F.; Cantrell, A.; Hoegberg, M. J. Med. Chem. 1995, 38, 4929.
[29] Badorc, A.; Bordes, M.; Cointet, P. Med. Chem. 1997, 40, 3393.
[30] Khan, K.; Qurban, S.; Salar, U. Bioorg. Chem. 2016, 68, 245.
[31] Wang, G.; Peng, Z.; Gong, Z. Bioorg. Chem. 2018, 78, 195.
[32] Paudel, Y. N.; Ali, M. R.; Shah, S. Biomed. Pharmacother. 2017, 89, 651.
[33] Rui, J.; Zhang, Q.; Wang, X. Chin. J. Org. Chem. 2017, 37, 218(in Chinese). (芮坚, 张齐, 王欣, 有机化学, 2017, 37, 218.)
[34] Sun, N.; Wang, X.; Ding, Z. Chin. J. Org. Chem. 2016, 36, 2489. (in Chinese). (孙楠, 王欣, 丁志彬, 有机化学, 2016, 36, 2489.)
[35] Wang, Y.; Gu, W.; Shan, Y. Bioorg. Med. Chem. Lett. 2017, 27, 2360.
[36] Yang, J.; Xu, X.; Rui, J. Spectrochim. Acta, Part A 2017, 183, 60.
[37] Yang, J.; Xu, H.; Xu, X. Dyes Pigm. 2016, 128, 75.
[38] Vinícius, G. M.; Marina, F. R.; Thales, K. J. Mol. Graphics Modell. 2019, 86, 106.

樟脑磺酸噻唑腙类化合物的设计、合成及抗氧化应用

Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 8

编辑推荐

相关统计

本文评价

[1]	赵婷, 农旭华, 王佳莉, 许宽毓, 唐敏敏, 易继凌, 韩长日, 陈光英. 长花龙血树茎中抗氧化活性的木脂素类成分研究[J]. 有机化学, 2023, 43(8): 2968-2972.
[2]	王斌, 曾尾女, 李杲钰, 肖媚, 韦方芳, 罗由萍, 钮智刚, 黄国雷, 郑彩娟. 红树来源真菌Daldinia eschscholtzii HJ004发酵产物中三个新的次级代谢产物[J]. 有机化学, 2023, 43(1): 332-337.
[3]	蔡瑾, 农旭华, 王斌, 曾尾女, 黄国雷, 张子怡, 郑彩娟. 红树来源真菌Eupenicillium sp. HJ002发酵产物中三个新的聚酮类化合物[J]. 有机化学, 2021, 41(7): 2905-2909.
[4]	张强健, 王芸芸, 赵雨珣, 马崇慧, 杨益琴, 徐徐, 谷文, 王石发. 诺蒎酮基噻唑腙类化合物的合成及对α-淀粉酶的抑制活性[J]. 有机化学, 2019, 39(5): 1372-1382.
[5]	吴建章, 李物兰, 陈玲姿, 楚生辉, 赵承光, 卫涛, 杨树林, 李校堃. 查尔酮及其螺杂环衍生物的合成、晶体结构、抗氧化活性研究[J]. 有机化学, 2012, 32(11): 2141-2147.
[6]	傅晓钟, 邢凤晶, 蓝燕宇, 王爱民, 王永林, 李靖, 周雯, 张伟, 刘影. 灯盏乙素苷元4-N-取代氨甲基苯甲酸酯的合成及体外抗氧化活性研究[J]. 有机化学, 2011, 31(07): 1043-1048.
[7]	张培全,曾和平. 5-[2-(8-羟基喹啉-2-基)乙烯基]-2-甲基-8-羟基喹啉的合成、抗氧化活性及促进鼠骨髓间质干细胞增殖的研究[J]. 有机化学, 2008, 28(06): 1035-1039.
[8]	蒋柳云,刘玉明. 两种槲皮素-Zn配合物的抗氧化活性及其结构的量子化学研究[J]. 有机化学, 2005, 25(06): 684-689.