Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives

doi:10.6023/cjoc202209040

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2126-2135.DOI: 10.6023/cjoc202209040 Previous Articles Next Articles

苦参碱缩氨基脲类化合物的合成及其体外抗肿瘤活性研究

庞盼杏^a, 宁蓉^a, 祝创^a, 黄文洁^a, 马献力^a, 蒋彩娜^a, 李芳耀^a^,^*(), 周小群^b^,^*()

a 桂林医学院药学院广西桂林 541004
b 桂林医学院人文与管理学院广西桂林 541004

收稿日期:2022-09-30 修回日期:2022-12-11 发布日期:2023-01-11
作者简介:
^†共同第一作者
基金资助:
国家级大学生创新创业训练计划(202010601021); 广西高校中青年科研基础能力提升(2019KY051); 广西自然科学基金(2018GXNSFAA281200); 桂林市科学研究与技术开发计划(20210227-1)

Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives

Panxing Pang^a, Rong Ning^a, Chuang Zhu^a, Wenjie Huang^a, Xianli Ma^a, Caina Jiang^a, Fangyao Li^a,*(), Xiaoqun Zhou^b,*()

a School of Pharmacy, Guilin Medical University, Guilin, Guangxi 541004
b College of Humanities and Management, Guilin Medical University, Guilin, Guangxi 541004

Received:2022-09-30 Revised:2022-12-11 Published:2023-01-11
Contact: * E-mail: lifangyao2006@163.com;zhouxqgy@163.com
About author:
^†These authors contributed equally to this work
Supported by:
National Innovation and Entrepreneurship Training Program for College Students(202010601021); Guangxi Young and Middle-Aged Scientific Research Basic Ability Improvement Project for Colleges and Universities(2019KY051); Natural Science Foundation of Guangxi Province(2018GXNSFAA281200); Project for Science Research and Technology Development of Guilin City(20210227-1)

1. .pdf(2190KB)

Abstract

In order to search for novel antitumor drugs with high efficiency and low toxicity, matrine semicarbazide derivatives were designed and synthesized. The antiproliferative activities of target compounds in four human cancer cell lines of A549 (lung), HepG2 (liver), Hela (epithelial cervical), MGC-803 (gastric) and a human normal cell of L-O2 (liver) were evaluated by methyl thiazolyl tetrazolium (MTT) assay. Biological screening results demonstrated that most of the derivatives exhibited more potent cytotoxicity against tumor cell lines superior to parent compound matrine. Among them, compounds of 14-formyl-15-chloro-matrine N-(3-chlorophenyl) semicarbazide (6c) and 14-formyl-15-chloro-matrine N-(3-nitrophenyl) semicarbazide (6f) displayed better antiproliferative activity with IC₅₀ values of (11.70±0.25) and (15.61±0.07) μmol/L toward A549 cells compared with camptothecin, and with IC₅₀ values of (11.32±1.07) and (9.27±2.03) μmol/L against MGC-803 cells. Moreover, they exhibited lower cytotoxicity against human normal liver cell line L-O2. Flow cytometry and JC-1 mitochondrial membrane potential detection showed that compound 6f could induce apoptosis of MGC803 cells and reduce the mitochondrial membrane potential. It would provide a new idea for the structural modification of matrine.

Key words: matrine, semicarbazide, synthesis, in vitro antitumor activity

Cite this article

Panxing Pang, Rong Ning, Chuang Zhu, Wenjie Huang, Xianli Ma, Caina Jiang, Fangyao Li, Xiaoqun Zhou. Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2126-2135.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 9

References 46

[1]	Bray, F.; Laversanne, M.; Weiderpass, E.; Soerjomataram, I. Cancer 2021, 127, 3029. doi: 10.1002/cncr.v127.16
[2]	Sung, H.; Ferlay, J.; Siegel, R. L.; Laversanne, M.; Soerjomataram, I.; Jemal, A.; Bray, F. Ca-Cancer J. Clin. 2021, 71, 209. doi: 10.3322/caac.v71.3
[3]	Alam, O.; Mullick, P.; Verma, S. P.; Gilani, S. J.; Khan, S. A.; Siddiqui, N.; Ahsan, W. Eur. J. Med. Chem. 2010, 45, 2467. doi: 10.1016/j.ejmech.2010.02.031
[4]	Sriram, D.; Stables, P. J.; Thirumurugan, R.; Induja, S.; Ragavendran, V. J.; Yogeeswari, P. Med. Chem. 2006, 2, 55. pmid: 16787356
[5]	Yogeeswari, P.; Sriram, D.; Veena, V.; Kavya, R.; Rakhra, K.; Ragavendran, J. V.; Mehta, S.; Thirumurugan, R.; Stables, J. P. Biomed. Pharmacother. 2005, 59, 51. pmid: 15740936
[6]	Xu, H.; Su, X.; Liu, X.Q.; Zhang, K. P.; Hou, Z.; Guo, C. Bioorg. Med. Chem. Lett. 2019, 29, 23.
[7]	Hania, M. M. E-J. Chem. 2009, 6, 508.
[8]	Gopi, C.; Dhanaraju, D. M. Beni-Suef Univ. J. Basic Appl. Sci. 2018, 7, 291.
[9]	Chipeleme, A.; Gut, J.; Rosenthal, P. J.; Chibale, K. Bioorg. Med. Chem. 2007, 15, 273. doi: 10.1016/j.bmc.2006.09.055
[10]	Queiroz, A. C.; Alves, M. A.; Barreiro, E. J.; Lima, L. M.; Alexandre-Moreira, M. S. Exp. Parasitol. 2019, 201, 57. doi: 10.1016/j.exppara.2019.04.003
[11]	Qazi, S. U.; Naz, A.; Hameed, A.; Osra, F. A.; Jalil, S.; Iqbal, J.; Ali Shah, S. A.; Mirza, A. Z. Bioorg. Chem. 2021, 115, 105209. doi: 10.1016/j.bioorg.2021.105209
[12]	Liu, Y.-B.; Peng, W.-L.; Yu, L.-J.; Xing, J.-H.; Chen, J.; Xia, X.-J.; Shen, D.-L. Agrochemicals 2010, 49, 407. (in Chinese)
	(刘永榜, 彭伟立, 郁林军, 邢家华, 陈杰, 夏旭建, 沈德隆, 农药, 2010, 49, 407.)
[13]	Ma, J. J.; Hu, G.; Xie, L. J.; Chen, L.; Xu, B. X.; Gong, P. Chem. Res. Chin. Univ. 2015, 31, 958. doi: 10.1007/s40242-015-5034-1
[14]	Jia, X. X.; Liu, Q.; Wang, S. Y.; Zeng, B. L.; Du, G. H.; Zhang, C.; Li, Y. Bioorg. Med. Chem. 2020, 28, 115557. doi: 10.1016/j.bmc.2020.115557
[15]	Afrasiabi, Z.; Sinn, E.; Lin, W. S.; Ma, Y. F.; Campana, C.; Padhye, S. J. Inorg. Biochem. 2005, 99, 1526. pmid: 15927263
[16]	Mishra, B. B.; Tiwari, V. K. Eur. J. Med. Chem., 2011, 46, 4769. doi: 10.1016/j.ejmech.2011.07.057
[17]	Mondal, S.; Bandyopadhyay, S.; Ghosh, M. K.; Mukhopadhyay, S.; Roy, S.; Mandal, C. Anti-Cancer Agents Med. Chem. 2012, 12, 49. doi: 10.2174/187152012798764697
[18]	Newman, D. J.; Cragg, G. M.; Snader, K. M. J. Nat. Prod. 2003, 66, 1022. doi: 10.1021/np030096l pmid: 12880330
[19]	Huang, J. L.; Xu, H. Curr. Top. Med. Chem. 2016, 16, 3365. doi: 10.2174/1568026616666160506131012
[20]	Pan, J. L.; Hao, X.; Yao, H. W.; Ge, K. K.; Ma, L.; Ma, W. J. For. Res. 2019, 30, 1105. doi: 10.1007/s11676-019-00883-3
[21]	Sun, N.; Zhang, H.; Sun, P. P.; Khan, A.; Guo, J. H.; Zheng, X. Z.; Sun, Y. G.; Fan, K. H.; Yin, W.; Li, H. Q. Phytomedicine 2020, 77, 153289. doi: 10.1016/j.phymed.2020.153289
[22]	Zhang, B.; Liu, Z. Y.; Li, Y. Y.; Luo, Y.; Liu, M. L.; Dong, H. Y.; Wang, Y. X.; Liu, Y.; Zhao, P. T.; Jin, F. G.; Li, Z. C. Eur. J. Pharm. Sci. 2011, 44, 573. doi: 10.1016/j.ejps.2011.09.020 pmid: 22019524
[23]	Cheng, X. G.; He, H. Q.; Wang, W. X.; Dong, F. Y.; Zhang, H. H.; Ye, J. M.; Tan, C. C.; Wu, Y. H.; Lv, X. J.; Jiang, X. H.; Qin, X. J. Pest Manage. Sci. 2020, 76, 2711. doi: 10.1002/ps.v76.8
[24]	Zhou, S. K.; Zhang, R. L.; Xu, Y. F.; Bi, T. N. Molecules 2012, 17, 6481. doi: 10.3390/molecules17066481
[25]	Chen, M. H.; Gu, Y. Y.; Zhang, A. L.; Sze Daniel, M. Y.; Mo, S. L.; May Brian, H. Pharmacol. Res. 2021,171.
[26]	Zhang, X.; Hou, G. Q.; Liu, A. D.; Xu, H.; Guan, Y.; Wu, Y. S.; Deng, J.; Cao, X. Cell Death Dis. 2019, 10, 10. doi: 10.1038/s41419-018-1254-x
[27]	Liu, Z.-M.; Yang, X.-L.; Jiang, F.; Pan, Y.-C.; Zhang, L. J. Cell. Biochem. 2019, 121, 3.
[28]	Hu, J.; Wang, Y. Chin. Arch. Tradit. Chin. Med. 2021, 171. (in Chinese)
	(胡锦丹, 王宇, 中华中医药学刊, 2021, 171.)
[29]	Dai, M.; Cai, Z.; Chen, N.; Li, J.; Wen, J.; Tan, L.; Guo, D. J. South. Med. Univ. 2019, 39, 1239. (in Chinese)
	(戴美琴, 蔡茁, 陈娜娜, 李金州, 温嘉泳, 谭丽转, 郭丹, 南方医科大学学报, 2019, 39, 1239.)
[30]	Yang, J.; He, D.; Peng, Y.; Zhong, H.; Deng, Y.; Yu, Z.; Guan, C.; Zuo, Y.; Xu, Z. OncoTargets Ther. 2017, 10, 5209. doi: 10.2147/OTT.S149609 pmid: 29138573
[31]	Fu, S.; Zhao, N.; Jing, G.; Yang, X.; Liu, J.; Zhen, D.; Tang, X. Biomed. Pharmacother. 2020, 128, 110327. doi: 10.1016/j.biopha.2020.110327
[32]	Li, Z.; Luo, M. Y.; Cai, B.; Wu, L. C.; Huang, M. T.; Rashid, H.; Jiang, J.; Wang, L. S. Bioorg. Med. Chem. Lett. 2018, 28, 677. doi: 10.1016/j.bmcl.2018.01.017
[33]	Wei, J.; Liang, Y.; Wu, L. Molecules 2021, 26, 417. doi: 10.3390/molecules26020417
[34]	Sun, X.; Zhuo, X.-B.; Hu, Y.-P.; Zheng, X.; Zhao, Q.-J. Mol. Cell. Biochem. 2018, 449, 47. doi: 10.1007/s11010-018-3341-9
[35]	Rashid, H.; Xu, Y.; Muhammad, Y.; Wang, L.; Jiang, J. Eur. J. Med. Chem. 2019, 161, 205. doi: 10.1016/j.ejmech.2018.10.037
[36]	Wang, M.; Huang, L.; Su, Y.; Xu, Y.-H.; Huang, L.-Y.; Zhou, X.-Q.; Li, F.-Y. Chemistry 2019, 82, 57. (in Chinese)
	(王妙, 黄琳, 苏燕, 许英红, 黄铃月, 周小群, 李芳耀, 化学通报, 2019, 82, 57.)
[37]	Xin, M.; Pang, F.-H.; Huang, L.; Zhou, X.-Q.; Wang, M.-D.; Li, J.-L.; Li, F.-Y. Chin. J. Synth. Chem. 2020, 28, 483. (in Chinese)
	(辛懋, 庞富华, 黄琳, 周小群, 王萌迪, 李金林, 李芳耀, 合成化学, 2020, 28, 483.)
[38]	Li, F.-Y.; Huang, L.; Li, Q.; Wang, X.; Ma, X. L.; Jiang, C. N.; Zhou, X. Q.; Duan, W. G.; Lei, F. H. Molecules 2019, 24, 4191. doi: 10.3390/molecules24224191
[39]	Huang, L.; Huang, R.; Pang, F. H.; Li, A. K.; Huang, G. B.; Zhou, X. Q.; Li, Q.; Li, F. Y.; Ma, X. L. RSC Adv. 2020, 10, 18008. doi: 10.1039/d0ra02432e pmid: 35517208
[40]	Li, F. Y.; Huang, L.; Zhou, X. Q.; Li, Q.; Ma, X. L; Duan, W. G.; Wang, X. Chin. J. Org. Chem. 2020, 40, 2845. (in Chinese)
	(李芳耀, 黄琳, 周小群, 李倩, 马献力, 段文贵, 王秀, 有机化学, 2020, 40, 2845.) doi: 10.6023/cjoc202003062
[41]	Zheng, W. L.; Ma, X. L.; Zhou, X. Q.; Li, F. Y.; Xin, M.; Jiang, C. N. Chem. Ind. For. Prod. 2019, 39, 41. (in Chinese)
	(郑万里, 马献力, 周小群, 李芳耀, 辛懋, 蒋彩娜, 林产化学与工业, 2019, 39, 41.)
[42]	Wang, K.; Zheng, W. L; Jiang, C. N.; Zhou, X. Q.; Li, F. Y.; Xin, M.; Ma, X. L. Chem. Res. Appl. 2020, 32, 1377. (in Chinese)
	(王珂, 郑万里, 蒋彩娜, 周小群, 李芳耀, 辛懋, 马献力, 化学研究与应用, 2020, 32, 1377.)
[43]	Huang, J. L.; Lv, M.; Xu, H. RSC Adv. 2017, 7, 15997. doi: 10.1039/C7RA00954B
[44]	Xu, H.; Su, X.; Liu, X. Q.; Zhang, K. P.; Hou, Z.; Guo, C. Bioorg. Med. Chem. Lett. 2019, 29, 126726. doi: 10.1016/j.bmcl.2019.126726
[45]	Dai, B.; Ma, X.; Tang, Y.; Xu, L.; Guo, S.; Chen, X.; Lu, S.; Wang, G.; Liu, Y. Bioorg. Med. Chem. 2021, 29, 115891. doi: 10.1016/j.bmc.2020.115891
[46]	Ly, J. D.; Grubb, D. R.; Lawen, A. Apoptosis 2003, 8, 115. doi: 10.1023/a:1022945107762 pmid: 12766472

Complex	6a
Empirical formula	C₂₃H₂₈ClN₅O
Formula weight (M_r)	425.95
Crystal system	Orthorhombic
Space group	P2₁2₁2₁
a/nm	0.52876(1)
b/nm	1.53224(3)
c/nm	2.68038(5)
V/nm³	2.17161(7)
Z	4
F(000)	904
D_x/(Mg•m^–3)	1.303
Cu Kα radiation (λ)/nm	0.154184
μ/mm^–1	1.75
T/K	293
Measured reflections	16468
Independent reflections	4367
Reflections with I>2(I)	3707
R_int	0.052

Complex	6a
Empirical formula	C₂₃H₂₈ClN₅O
Formula weight (M_r)	425.95
Crystal system	Orthorhombic
Space group	P2₁2₁2₁
a/nm	0.52876(1)
b/nm	1.53224(3)
c/nm	2.68038(5)
V/nm³	2.17161(7)
Z	4
F(000)	904
D_x/(Mg•m^–3)	1.303
Cu Kα radiation (λ)/nm	0.154184
μ/mm^–1	1.75
T/K	293
Measured reflections	16468
Independent reflections	4367
Reflections with I>2(I)	3707
R_int	0.052

Compd.	R	IC₅₀^a/(μmol•L^–1)
Compd.	R	L-O2	MGC803	HeLa	A549	Hepg2
6a	H	30.46±0.12	17.41±1.52	24.86±0.70	46.53±0.40	83.93±1.30
6b	2-Cl	76.50±2.82	11.66±1.31	17.30±2.04	25.48±2.72	>100
6c	3-Cl	27.45±2 47	11.32±1.07	16.94±1.97	11.70±0.25	35.82±1.93
6d	4-Cl	12.77±1.87	14.36±2.99	15.47±1.24	45.48±1.11	46.75±1.59
6e	2-NO₂	31.46±0.98	17.47±2.58	32.51±0.14	33.31±0.03	>100
6f	3-NO₂	63.99±2.71	9.27±2.03	50.84±0.91	15.61±0.07	27.59±2.02
6g	4-NO₂	33.24±0.74	21.70±1.89	30.21±1.71	63.74±1.21	>100
6h	2-Br	45.85±1.47	23.63±0.22	38.34±0.65	71.39±4.84	59.82±2.85
6i	4-Br	12.36±2.64	13.73±1.57	16.34±1.87	20.72±0.49	>100
6j	2-F	32.90±0.36	14.16±2.35	30.09±2.69	49.90±1.70	>100
6k	3-F	26.70±1.64	16.46±1.99	23.50±2.8	62.73±2.42	38.64±4.47
6l	4-F	11.94±1.85	17.28±1.27	15.94±1.41	41.49±1.46	31.40±2.31
6m	2-CH₃	27.49±2.22	20.84±0.11	21.34±2.36	56.86±1.57	56.90±2.43
6n	3-CH₃	33.48±2.23	19.73±1.04	25.35±0.19	45.11±1.32	53.94±2.67
6o	4-CH₃	18.02±2.13	13.81±0.23	21.21±0.60	53.44±2.18	92.76±3.05
苦参碱		>100	>100	>100	>100	>100
喜树碱^b		4.44±2.54	8.13±2.13	2.00±0.8	20.34±1.53	2.30±1.19

Compd.	R	IC₅₀^a/(μmol•L^–1)
Compd.	R	L-O2	MGC803	HeLa	A549	Hepg2
6a	H	30.46±0.12	17.41±1.52	24.86±0.70	46.53±0.40	83.93±1.30
6b	2-Cl	76.50±2.82	11.66±1.31	17.30±2.04	25.48±2.72	>100
6c	3-Cl	27.45±2 47	11.32±1.07	16.94±1.97	11.70±0.25	35.82±1.93
6d	4-Cl	12.77±1.87	14.36±2.99	15.47±1.24	45.48±1.11	46.75±1.59
6e	2-NO₂	31.46±0.98	17.47±2.58	32.51±0.14	33.31±0.03	>100
6f	3-NO₂	63.99±2.71	9.27±2.03	50.84±0.91	15.61±0.07	27.59±2.02
6g	4-NO₂	33.24±0.74	21.70±1.89	30.21±1.71	63.74±1.21	>100
6h	2-Br	45.85±1.47	23.63±0.22	38.34±0.65	71.39±4.84	59.82±2.85
6i	4-Br	12.36±2.64	13.73±1.57	16.34±1.87	20.72±0.49	>100
6j	2-F	32.90±0.36	14.16±2.35	30.09±2.69	49.90±1.70	>100
6k	3-F	26.70±1.64	16.46±1.99	23.50±2.8	62.73±2.42	38.64±4.47
6l	4-F	11.94±1.85	17.28±1.27	15.94±1.41	41.49±1.46	31.40±2.31
6m	2-CH₃	27.49±2.22	20.84±0.11	21.34±2.36	56.86±1.57	56.90±2.43
6n	3-CH₃	33.48±2.23	19.73±1.04	25.35±0.19	45.11±1.32	53.94±2.67
6o	4-CH₃	18.02±2.13	13.81±0.23	21.21±0.60	53.44±2.18	92.76±3.05
苦参碱		>100	>100	>100	>100	>100
喜树碱^b		4.44±2.54	8.13±2.13	2.00±0.8	20.34±1.53	2.30±1.19

苦参碱缩氨基脲类化合物的合成及其体外抗肿瘤活性研究

Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 9

References 46

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[14]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.