综述与进展

熊果酸的结构修饰与生物活性研究进展

  • 刘改枝 ,
  • 李金鑫 ,
  • 史礼君 ,
  • 刘萌芽 ,
  • 蔡邦荣
展开
  • 河南中医药大学药学院 郑州 450046

收稿日期: 2021-02-19

  修回日期: 2021-03-17

  网络出版日期: 2021-05-14

基金资助

中国博士后科学基金面上(2020M682311); 河南中医药大学博士基金(00104311-2019-33); 河南省科技攻关(202102310514)

Advances in the Study of Structural Modification and Biological Activities of Ursolic Acid

  • Gaizhi Liu ,
  • Jinxin Li ,
  • Lijun Shi ,
  • Mengya Liu ,
  • Bangrong Cai
Expand
  • College of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046
*Corresponding authors.E-mail: ;

Received date: 2021-02-19

  Revised date: 2021-03-17

  Online published: 2021-05-14

Supported by

National Natural Science Foundation of China Postdoctoral Science Foundation(2020M682311); Doctorʼs Fund of Henan University of Medicine(00104311-2019-33); Award for Science and Technology Tackling Key Problems Program of Henan Province(202102310514)

摘要

熊果酸是从药用植物、水果和蔬菜中提取的具有多种药理活性的五环三萜类化合物. 近年来, 熊果酸的药理作用得到了广泛的研究, 大量研究表明熊果酸具有多种药理活性, 包括抗癌、抗炎、抗氧化、抗菌、抗糖尿病等. 熊果酸虽然具有广泛的生物学活性, 但其水溶性差、生物利用度低等限制了在临床上的应用. 为了克服这些缺点, 国内外研究人员通过对熊果酸母体骨架进行化学修饰, 设计并开发了大量结构新颖、活性强的熊果酸衍生物. 对近年来合成的有进一步研究价值的熊果酸衍生物及其生物活性研究进展进行总结, 为以熊果酸为先导化合物的药物研究提供参考.

本文引用格式

刘改枝 , 李金鑫 , 史礼君 , 刘萌芽 , 蔡邦荣 . 熊果酸的结构修饰与生物活性研究进展[J]. 有机化学, 2021 , 41(8) : 2974 -2989 . DOI: 10.6023/cjoc202102032

Abstract

Ursolic acid (UA) belongs to a group of pentacyclic triterpenoids extracted from medicinal plants, fruits and vegetables. In recent years, the pharmacological action of ursolic acid has been widely studied. It has been reported that UA has a variety of pharmacological activities, including anti-cancer, anti-inflammation, anti-oxidation, anti-bacterial, anti-diabetes and so on. In spite of that UA shows the extensive therapeutic potential as a drug candidate, the poor water solubility and low bioavailability of UA limit its clinical application. To address these issue, large numbers of UA-based derivatives with enhanced activities and better physicochemical character have been developed by structural modification of its parent skeleton. In this paper, the research progress of the synthesized UA derivatives with therapeutic potential along with their biological activities is reviewed, which provides reference for further drug development using UA as a lead compound.

参考文献

[1]
Tao, Y.-B.; Xing, Y.-L.; Fang, Z.-J.; Bi, L.-W.; Zhao, Z.-D. Chem. Ind. For. Prod. 2012, 32(1), 119. (in Chinese)
[1]
(陶渊博, 邢雅丽, 方芝娟, 毕良武, 赵振东, 林产化学与工业, 2012, 32(1), 119.)
[2]
Mlala, S.; Oyedeji, A. O.; Gondwe, M.; Oyedeji, O. O. Molecules 2019, 24(15), 2751.
[3]
López-Hortas, L.; P, P.-L.; Gonzá Lez-MuñOz, M. J.; Falqué, E.; Domí­Nguez, H. Food Res. Int. 2018, 103, 130.
[4]
Khwaza, V.; Oyedeji, O. O.; Aderibigbe, B. A. Int. J. Mol. Sci. 2020, 21(16), 5920.
[5]
Xiang, R.-Q.; Fan, Y. J. Pharm. Res. 2019, 38(2), 63. (in Chinese)
[5]
(向润清, 范源, 药学研究, 2019, 38(2), 63.)
[6]
Zhu, M. L.; Ge, W. Z.; Zhao, R. Acta Laser Biol. Sin. 2014, 23(5), 465. (in Chinese)
[6]
(朱美玲, 葛文中, 赵蕊, 激光生物学报, 2014, 23(5), 465.)
[7]
Wang, C.-Y.; Lin, C.-S.; Hua, C.-H.; Jou, Y.-J.; Liao, C.-R.; Chang, Y.-S.; Wan, L.; Huang, S.-H.; Hour, M.-J.; Wen, C.-L. Biomol. Ther. 2019, 27(1), 9.
[8]
Xu, J.; Wang, X.-D.; Zhang, H.-Y.; Yue, J.-Y.; Zhao, Y.-Q. Nat. Prod. Res. 2018, 34(6), 1.
[9]
Fontana, G.; Bruno, M.; Notarbartolo, M.; Labbozzetta, M.; Poma, P.; Spinella, A.; Rosselli, S. Bioorg. Chem. 2019, 90, 103054.
[10]
Tu, H. Y.; Huang, A.; Wei, B. L.; Gan, K. H.; Hour, T. C.; Yang, S. C.; Pu, Y. S.; Lin, C. N. Bioorg. Med. Chem. 2009, 17(20), 7265.
[11]
Gou, W.-F.; Luo, N.; Wei, H.-Q.; Wu, H.-Y.; Li, Y.-L. Pharm. Biol. 2020, 58(1), 707.
[12]
Tian, T.; Liu, X.; Lee, E. S.; Sun, J.; Feng, Z.; Zhao, L.; Zhao, C. Arch. Pharmacal Res. 2017, 40(4), 1.
[13]
Li, X.; Bai, X.; Wu, K.; Wang, Y. J.; Shi, W. Q.; Li, Y.; Yin, S. F. Chin. J. Org. Chem. 2012, 32(4), 703. (in Chinese)
[13]
(李霞, 白雪, 吴科, 王裕军, 石万棋, 李颖, 尹述凡, 有机化学, 2012, 32(4), 703.)
[14]
Mallavadhani, U. V.; Mahapatra, A.; Pattnaik, B.; Vanga, N.; Suri, N.; Saxena, A. K. Med. Chem. Res. 2013, 22(3), 1263.
[15]
Liu, M. C.; Yang, S. J.; Jin, L. H.; Hu, D. Y.; Xue, W.; Song, B. A. Eur. J. Med. Chem. 2012, 58(12), 128.
[16]
Liu, M. C.; Yang, S. J.; Jin, L. H.; Hu, D. Y.; Xue, W.; Yang, S. Med. Chem. Res. 2016, 25(10), 2267.
[17]
Liu, H.; Li, G.-B.; Zhang, D.-L.; Liu, Y.-M.; Gao, N. J. Third Milit. Med. Univ. 2017, 39(19), 1960. (in Chinese)
[17]
(刘涵, 李国兵, 张定林, 刘毅敏, 高宁, 第三军医大学学报, 2017, 39(19), 1960.)
[18]
Chen, Y.-H.; Hou, X.-Y.; Zhi, D.-F.; Li, C.; Tian, T.; Sun, J.-Y.; Zhao, L.-X.; Zhao, C.-H. Chin. J. Org. Chem. 2016, 36(4), 795. (in Chinese)
[18]
(陈艳华, 侯熙彦, 支德福, 李常, 田甜, 孙竞阳, 赵龙铉, 赵春晖, 有机化学, 2016, 36(4), 795.)
[19]
Bai, K. K.; Chen, F. L.; Guo, H. H. Chin. J. New Drug 2012, 21(22), 2667. (in Chinese)
[19]
(白锴凯, 陈芬玲, 郭养浩, 中国新药杂志, 2012, 21(22), 2667.)
[20]
Cheng, W.; Dahmani, F. Z.; Zhang, J.; Xiong, H.; Wu, Y.; Yin, L.; Zhou, J.; Yao, J. Nanotechnol. 2017, 28(7), 075102.
[21]
Ahn, G. Y.; Paik, D. H.; Jeong, K. Y.; Baek, S. W.; Kang, R. H.; Lee, E. S.; Choi, S. W. Macromol. Res. 2018, 26(7), 1.
[22]
Bai, K. K.; Chen, F. L.; Guo, H. H. Chin. J. New Drug 2012, 21(13), 1536. (in Chinese)
[22]
(白锴凯, 陈芬玲, 郭养浩, 中国新药杂志, 2012, 21(13), 1536.)
[23]
Jiang, W.; Huang, R. Z.; Zhang, J.; Guo, T.; Zhang, M. T.; Huang, X. C.; Zhang, B.; Liao, Z. X.; Sun, J.; Wang, H. S. Bioorg. Chem. 2018, 79, 265.
[24]
Yu, Z.; Bai, K.-K.; Guo, Y.-H. Pharm. Biotechnol. 2010, 17(5), 382. (in Chinese)
[24]
(于舟, 白锴凯, 郭养浩, 药物生物技术, 2010, 17(5), 382.)
[25]
Dong, H.-Y.; Yang, X.; Xie, J.-J.; Xiang, L.; Li, Y.-F.; Ou, M.; Chi, T.; Liu, Z.; Yu, S.-H.; Gao, Y. Biochem. Pharmacol. 2015, 93(2), 151.
[26]
Hua, S. X.; Huang, R. Z.; Ye, M. Y.; Pan, Y. M.; Yao, G. Y.; Zhang, Y.; Wang, H. S. Eur. J. Med. Chem. 2015, 95(10), 435.
[27]
Huang, R. Z.; Hua, S. X.; Liao, Z. X.; Huang, X. C.; Wang, H. S. Med. Chem. Commun. 2017, 8(7), 1421.
[28]
Wang, J.-C.; Jiang, Z.; Xiang, L.-P.; Li, Y.-F.; Ou, M.-R.; Yang, X.; Shao, J.-W.; Lu, Y.-S.; Lin, L.-F.; Chen, J.-Z. Sci. Rep. 2014, 4, 5006.
[29]
Wiemann, J.; Heller, L.; Csuk, R. Bioorg. Med. Chem. Lett. 2016, 26(3), 907.
[30]
Yang, X.; Li, Y.; Jiang, W.; Ou, M.; Chen, Y.; Xu, Y.; Wu, Q.; Zheng, Q.; Wu, F.; Wang, L.; Zou, W.; Zhang, Y. J.; Shao, J. Chem. Biol. Drug Des. 2015, 86(6), 1397.
[31]
Bai, K. K.; Chen, F. L.; Zheng, Y. Q.; Guo, H. H. Chin. Pharm. J. 2012, 47(4), 265. (in Chinese)
[31]
(白锴凯, 陈芬玲, 郑允权, 郭养浩, 中国药学杂志, 2012, 47(4), 265.)
[32]
Shao, J. W.; Dai, Y. C.; Xue, J. P.; Wang, J. C.; Lin, F. P.; Guo, Y. H. Eur. J. Med. Chem. 2011, 46(7), 2652.
[33]
Popov, S. A.; Kornaukhova, L. M.; Shpatov, A. V.; Grigor'ev, I. A. Chem. Nat. Compd. 2016, 52(3), 555.
[34]
Wolfram, R. K.; Heller, L.; Csuk, R. Eur. J. Med. Chem. 2018, 152, 21.
[35]
Rashid, S.; Dar, B. A.; Majeed, R.; Hamid, A.; Bhat, B. A. Eur. J. Med. Chem. 2013, 66(66C), 238.
[36]
Yu, T.-T.; Li, L.; Cui, H.-B.; Meng, Y.-Q. Chem 2017, 80(11), 74.
[37]
Yan-Qiu, M.; Dan, L.; Zhong-Wei, B.; Ling-Li, C.; Hong-Ru, A. Acta Pharm. Sin. 2011, 46(5), 556. (in Chinese)
[37]
(孟艳秋, 刘丹, 白忠伟, 蔡伶俐, 艾宏儒, 药学学报, 2011, 46(5), 556.)
[38]
Meng, Y.-Q.; Song, Y.-L.; Yan, Z.-K.; Xia, Y. Molecules 2010, 15(6), 4033.
[39]
Xu, C.-D.; Meng, Y.-Q. J. Shenyang Univ. Chem. Technol. 2020, 34(1), 18. (in Chinese)
[39]
(徐川东, 孟艳秋, 沈阳化工大学学报, 2020, 34(1), 18.)
[40]
Meng, Y.-Q.; Xu, C.-D.; Yu, T.-T.; Li, W.; Li, Q.-W.; Li, X.-X. J. Asian Nat. Prod. Res. 2019, 24(4), 359.
[41]
Meng, Y.-Q.; Ding, Y.; Yang, Z.; Zhang, M. Drugs Clin. 2014, 29(2), 116. (in Chinese)
[41]
(孟艳秋, 丁一, 张萌, 杨哲, 现代药物与临床, 2014, 29(2), 116.)
[42]
Yao, Y.; Zhang, X.; Wang, Z.; Zheng, C.; Li, P.; Huang, C.; Tao, W.; Xiao, W.; Wang, Y.; Huang, L.; Yang, L. J. Ethnopharmacol. 2013, 150(2), 619.
[43]
Zhang, L.-F.; Meng, Y.-Q. J. Shenyang Univ. Chem. Technol. 2016, 30(2), 117. (in Chinese)
[43]
(张良锋, 孟艳秋, 沈阳化工大学学报, 2016, 30(2), 117.)
[44]
Li, A. L.; Hao, Y.; Wang, W. Y.; Liu, Q. S.; Gu, W. Int. J. Mol. Sci. 2020, 21(8), 2876.
[45]
Jin, X. Y.; Chen, H.; Li, D. D.; Li, A. L.; Gu, W. J. Enzyme Inhib. Med. Chem. 2019, 34(1), 955.
[46]
Liu, X.-Y.; Gao, X.-Q.; Jin, X.-J.; Zhao, C.-H.; Feng, Z.-H.; Sui, Y.; Zhao, L.-X.; Yan, X. Chin. J. Org. Chem. 2018, 38(12), 99. (in Chinese)
[46]
(刘新宇, 高雪琴, 金学军, 赵春晖, 冯中华, 隋悦, 赵龙铉, 阎欣, 有机化学, 2018, 38(12), 99.)
[47]
Zhang, T.; He, B.-E.; Yuan, H.; Feng, G.-L.; Chen, F.-L.; Wu, A.-Z.; Zhang, L.-L.; Lin, H.-R.; Zhuo, Z.-J.; Wang, T. Chem. Biodiversity 2019, 16(6), e1900111.
[48]
Wu, J.; Zhang, Z. H.; Zhang, L. H.; Jin, X. J.; Ma, J.; Piao, H. R. Bioorg. Med. Chem. Lett. 2019, 29(6), 853.
[49]
Fan, H.-T.; Geng, L.; Yang, F.; Dong, X.; He, D.; Zhang, Y. Eur. J. Med. Chem. 2019, 176, 61.
[50]
Pei, T.; Wang, Y.-Y. J. Chin. Pharm. Univ. 2017, 48(1), 31. (in Chinese)
[50]
(裴婷, 王玉英, 中国药科大学学报, 2017, 48(1), 31.)
[51]
Chen, Y.; Li, C.; Zheng, Y.; Gao, Y.; Hu, J.; Chen, H. Bioorg. Med. Chem. Lett. 2017, 27(4), 1007.
[52]
Li, W.; Zhang, H.; Nie, M.; Wang, W.; Liu, Z.; Chen, C.; Chen, H.; Liu, R.; Baloch, Z.; Ma, K. Oncol. Lett. 2018, 15(2), 2323.
[53]
Dar, B. A.; Lone, A. M.; Shah, W. A.; Qurishi, M. A. Eur. J. Med. Chem. 2016, 111, 26.
[54]
Finlay, H. J.; Honda, T.; Gribble, G. W.; Danielpour, D.; Benoit, N. E.; Suh, N.; Williams, C.; Sporn, M. B. Bioorg. Med. Chem. Lett. 1997, 7(13), 1769.
[55]
Gu, W.; Jin, X. Y.; Li, D. D.; Wang, S. F.; Tao, X. B.; Chen, H. Bioorg. Med. Chem. Lett. 2017, 27(17), 4128.
[56]
Gu, W.; Hao, Y.; Zhang, G.; Wang, S. F.; Miao, T. T.; Zhang, K. P. Bioorg. Med. Chem. Lett. 2015, 25(3), 554.
[57]
Lin, R. X.; Gong, L. L.; Fan, L. M.; Zhao, Z. K.; Yang, S. L. Int. J. Clin. Exp. Pathol. 2015, 8(2), 1427.
[58]
Mendes, V. I. S.; Bartholomeusz, G. A.; Ayres, M.; Gandhi, V.; Salvador, J. A. R. Eur. J. Med. Chem. 2016, 123, 317.
[59]
Sun, L.; Li, B.; Su, X.; Chen, G.; Li, Y.; Yu, L.; Li, L.; Wei, W. J. Med. Chem. 2017, 60(15), 6638.
[60]
Jin, X.-Y.; Chen, H.; Tao, X.-B.; Wang, S.; Gu, W. J. For. Eng. 2018, (1), 54.
[61]
Pan, H.-S.; Li, L.; Cui, H.-B.; Yang, L.-N.; Yu, T.-T.; Meng, Y.-Q. Acta Pharm. Sin. 2017, 52(12), 1890. (in Chinese)
[61]
(潘洪双, 李磊, 崔华博, 杨丽娜, 于婷婷, 孟艳秋, 药学学报, 2017, 52(12), 1890.)
[62]
Meng, Y.-Q.; Cao, J.; Tang, Y.; Lu, X.-Y.; Liu, L.-W. Chin. J. Org. Chem. 2016, 36(5), 1080. (in Chinese)
[62]
(孟艳秋, 曹佳, 汤义, 鹿学宇, 刘立伟, 有机化学, 2016, 36(5), 1080.)
[63]
Wang, Y.-Y.; Xiong, H. Strait. Pharm. J. 2017, 29(2), 268. (in Chinese)
[63]
(王玉英, 熊慧, 海峡药学, 2017, 29(2), 268.)
[64]
Wang, Y.-Y.; Xiong, H. Strait. Pharm. J. 2016, 28(12), 273. (in Chinese)
[64]
(王玉英, 熊慧, 海峡药学, 2016, 28(12), 273.)
[65]
Wei, Z.; Di, H.; Zhou, Y.; Zhang, Y.; Qiang, S.; Li, J. Y.; Hu, L. H.; Jia, L. Biochim. Biophys. Acta. Gen. Subj. 2006, 1760(10), 1505.
[66]
Guzmán-Ávila, R.; Flores-Morales, V.; Paoli, P.; Camici, G.; Ramírez-Espinosa, J. J.; Cerón-Romero, L.; Navarrete-Vázquez, G.; Hidalgo-Figueroa, S.; Yolanda, R. M.; Villalobos-Molina, R. Drug Dev. Res. 2018, 79(2). 70.
[67]
Kazmi, I.; Rahman, M.; Afzal, M.; Gupta, G.; Saleem, S.; Afzal, O.; Shaharyar, M. A.; Nautiyal, U.; Ahmed, S.; Anwar, F. Fitoterapia 2012, 83(1), 142.
[68]
Wu, P. P.; Zhang, K.; Lu, Y. J.; He, P.; Zhao, S. Q. Eur. J. Med. Chem. 2014, 80, 502.
[69]
Wu, P. P.; Zhang, B. J.; Cui, X. P.; Yang, Y.; Jiang, Z. Y.; Zhou, Z. H.; Zhong, Y. Y.; Mai, Y. Y.; Ouyang, Z.; Chen, H. S. Sci. Rep. 2017, 7, 45578.
[70]
Gao, Y.; Li, Z.; Xie, X.; Wang, C.; You, J.; Mo, F.; Jin, B.; Chen, J.; Shao, J.; Chen, H.; Jia, L. Eur. J. Pharm. Sci. 2015, 70, 55.
[71]
Chen, L.; Yang, X. S.; Yang, X.; Ye, L. H.; Hao, X. J. J. Chin. Pharm. Univer. 2010, 41(3), 222. (in Chinese)
[71]
(陈磊, 杨小生, 杨娟, 叶林虎, 郝小江, 中国药科大学学报, 2010, 41(3), 222.)
[72]
Zhang, L.; Dong, J.; Liu, J.; Zhang, L.; Kong, L.; Yao, H.; Sun, H. Med. Chem. 2013, 9(1), 118.
[73]
Chen, C.; Sun, R.; Sun, Y.; Chen, X.; Chen, D. Bioorg. Med. Chem. Lett. 2019, 30(2), 126824.
[74]
Wei, Z. Y.; Chi, K. Q.; Wang, K. S.; Wu, J.; Liu, L. P.; Piao, H. R. Bioorg. Med. Chem. Lett. 2018, 28(10), 1797.
[75]
Nelson, A. T.; Camelio, A. M.; Claussen, K. R.; Cho, J.; Tremmel, L.; Digiovanni, J.; Siegel, D. Bioorg. Med. Chem. Lett. 2015, 25(19), 4342.
[76]
Zhang, C.; Xu, S. H.; Ma, B. L.; Wang, W. W.; Yu, B. Y.; Zhang, J. Bioorg. Med. Chem. Lett. 2017, 27(11), 2575.
[77]
Li, C. H.; Yang, C. L.; Zhang, K.; Shi, W. Q.; Li, J. Z.; Li, Y.; Yin, S. F. Chin. J. Org. Chem. 2012, 32(1), 133. (in Chinese)
[77]
(李财虎, 杨聪玲, 张宽, 石万棋, 李剑忠, 李颖, 尹述凡, 有机化学, 2012, 32(1), 133.)
[78]
Tan, J.; Huang, W.; Chen, S.-L.; Yue, Y. Acta Pharm. Sin. 2016, 51(6), 938. (in Chinese)
[78]
(谭娟, 黄微, 陈善龙, 岳源, 药学学报, 2016, 51(6), 938.)
[79]
Li, C.; Chen, J.; Yuan, W.; Zhang, W.; Chen, H.; Tan, H. Iubmb. Life 2020, 72(4), 632.
[80]
Fu, H. J.; Zhou, Y. R.; Bao, B. H.; Jia, M. X.; Zhao, Y.; Zhang, L.; Li, J. X.; He, H. L.; Zhou, X. M. J. Med. Chem. 2014, 57(11), 4692.
[81]
Fu, H. J.; Zhao, Y.; Zhou, Y. R.; Bao, B. H.; Du, Y.; Li, J. X. Eur. J. Pharm. Sci. 2015, 76, 33.
[82]
Yu, S. G.; Zhang, C. J.; Xu, X. E.; Sun, J. H.; Zhang, L.; Yu, P. F. Int. J. Clin. Exp. Pathol. 2014, 8(4), 3681.
[83]
Kong, L.-B.; Li, S.-S.; Liao, Q.-J.; Zhang, Y.-N.; Sun, R.-N.; Zhu, X.-D.; Zhang, Q.-H.; Wang, J.; Wu, X.-Y.; Fang, X.-N. Antiviral Res. 2013, 98(1), 44.
[84]
Zhong, Y.; Dai, Z.; Xu, Y.; Teng, Y.; Wu, B. Eur. J. Pharm. Sci. 2012, 45(1-2), 110.
[85]
Li, S.-M.; Jia, X.-H.; Li, H.; Ye, Y.-L.; Song, G.-P. Bioorg. Med. Chem. Lett. 2020, 30(22), 127518.
[86]
Song, G.; Shen, X.; Li, S.; Li, Y.; Liu, Y.; Zheng, Y.; Lin, R.; Fan, J.; Ye, H.; Liu, S. Eur. J. Med. Chem. 2015, 93, 431.
[87]
Luan, T.; Jin, C. M.; Gong, G. H.; Quan, Z. S. J. Enzyme Inhib. Med. Chem. 2019, 34(1), 761.
[88]
Sifaoui, I.; Rodríguez-Expósito, R. L.; Reyes-Batlle, M.; Rizo- Liendo, A.; Piero, J. E.; Bazzocchi, I. L.; Lorenzo-Morales, J.; Jiménez, I. A. Pathogens 2019, 8(3), 130.
[89]
Wang, P. Y.; Xiang, M.; Luo, M.; Liu, H. W.; Zhou, X.; Wu, Z. B.; Liu, L. W.; Li, Z.; Yang, S. Pest. Manage. Sci. 2020, 76(8), 2746.
[90]
Cunha, L. C. S.; Silva, M. L. a. E.; Furtado, N. a. X. C.; Vinholis, A. H. C.; Martins, C. H. G.; Filho, A. A. D. S.; Cunha, W. R. Z. Naturforsch., C: J. Biosci. 2007, 62(9-10), 668.
[91]
Do Nascimento, P. G. G.; Lemos, T. L. G.; Bizerra, A. M. C.; Arriaga, Â. M. C.; Ferreira, D. A.; Santiago, G. M. P.; Braz-Filho, R.; Costa, J. G. M. Molecules 2014, 19(1), 1317.
[92]
Dwivedi, G. R.; Maurya, A.; Yadav, D. K.; Khan, F.; Darokar, M. P.; Srivastava, S. K. Chem. Biol. Drug Des. 2015, 86(3), 272.
[93]
Jabeen, M.; Ahmad, S.; Shahid, K.; Sadiq, A.; Rashid, U. Front. Chem. 2018, 6, 55.
[94]
Huang, L. R.; Luo, H.; Yang, X. S.; Lei, C.; Zhang, J. X.; Wang, D. P.; Hao, X. J. Med. Chem. Res. 2014, 23(11), 4631.
[95]
Meng, Y.-C.; Zhan, J.-H.; Xiao, S.-P.; Tan, Y.; Liao, M.-F.; Zhang, Y.-L.; Li, L.; Pei, G. J. Hunan Univ. Chin. Med. 2017, 37(5), 493. (in Chinese)
[95]
(孟英才, 詹济华, 肖水平, 谭洋, 廖美芳, 张雨林, 李玲, 裴刚, 湖南中医药大学学报, 2017, 37(5), 493.)
[96]
Gnoatto, S.; Dalla-Vechia, L., Cl; Dassonville-Klimpt, A.; Da-Nascimento, S.; Mossalayi, D.; Guillon, J.; Gosmann, G.; Sonnet, P. J. Enzyme Inhib. Med. Chem. 2008, 23(5), 604.
[97]
Innocente, A. M.; Silva, G. N. S.; Laura Nogueira, C.; Moraes, M. S.; Myna, N.; Pascal, S.; Grace, G.; Garcia, C. R. S.; Gnoatto, S. C. B. Molecules 2012, 17(10), 12003.
[98]
Silva, G. N. D.; Maria, N. R.; Schuck, D. C.; Cruz, L. N.; Moraes, M. S. D.; Nakabashi, M.; Graebin, C.; Gosmann, G.; Garcia, C. R.; Gnoatto, S. C. Malar. J. 2013, 12(1), 89.
[99]
Cargnin, S. T.; Staudt, A. F.; Medeiros, P.; Sol, D. D. M. S.; Santos, A. P. D. a. D.; Zanchi, F. B.; Gosmann, G.; Puyet, A.; Teles, C. B. G.; Gnoatto, S. B. Bioorg. Med. Chem. Lett. 2018, 28(3), 265.
[100]
Bitencourt, F. G.; Vieira, P. D. B.; Meirelles, L. C.; Rigo, G. V.; Silva, E. F. D.; Gnoatto, S. C. B.; Tasca, T. Parasitol. Res. 2018, 117(5), 1.
[101]
Loesche, A.; Köwitsch, A.; Lucas, S. D.; Al-Halabi, Z.; Sippl, W., Al-Harrasi, A; Csuk, R. Bioorg. Chem. 2019, 85, 23.
[102]
Imran, K.; Muhammad, A.; Gaurav, G.; Firoz, A. CNS Neurosci. Ther. 2012, 18(9), 799.
[103]
Kazmi, I.; Gupta, G.; Afzal, M.; Anwar, F. Asian Pac. J. Trop. Dis. 2012, 2(Suppl. 1), S453.
[104]
Imran, K.; Gaurav, G.; Muhammad, A.; Mahfoozur, R.; Firoz, A. CNS Neurosci. Ther. 2012, 18 (8), 707.
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