Synthesis, Anticancer Evaluation, and Preliminary Mechanism Study of 1,3,4-Oxadiazole Derivatives Targeting K562 Tumor Cells

doi:10.6023/cjoc202601044

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (10): 4034-4049.DOI: 10.6023/cjoc202601044 Previous Articles Next Articles

ARTICLES

靶向K562肿瘤细胞的1,3,4-噁二唑衍生物的合成、抗癌活性评价及初步作用机制研究

吴越友^a, 何丹丹^a, 冯念林^a, 张依^a, 刘丹丹^a, 周玥^a, 李晨晨^a^,^*(), 王贞超^a^,^b^,^*()

^a 贵州大学药学院贵阳 550025
^b 贵州大学精细化工研究开发中心绿色农药全国重点实验室绿色农药与农业生物工程教育部重点实验室贵阳 550025

收稿日期:2026-03-24 修回日期:2026-05-26 发布日期:2026-06-26
通讯作者: 李晨晨, 王贞超
基金资助:
国家自然科学基金(32360689); 贵州省优秀青年学者项目(GCC[2023]072); 国家重点研发计划(2023YFD1400400); 贵州省基础研究计划(自然科学)青年引导(QN[2025]010); 贵州省基础研究计划(自然科学)青年引导(QN[2025]009)

Synthesis, Anticancer Evaluation, and Preliminary Mechanism Study of 1,3,4-Oxadiazole Derivatives Targeting K562 Tumor Cells

Yueyou Wu^a, Dandan He^a, Nianlin Feng^a, Yi Zhang^a, Dandan Liu^a, Yue Zhou^a, Chenchen Li^a^,^*(), Zhenchao Wang^a^,^b^,^*()

^a School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025
^b Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, State Key Laboratory of Green Pesticides, Center for R&D of Fine Chemicals, Guizhou University, Guiyang 550025

Received:2026-03-24 Revised:2026-05-26 Published:2026-06-26
Contact: Chenchen Li, Zhenchao Wang
Supported by:
National Natural Science Foundation of China(32360689); Guizhou Provincial Foundation for Excellent Scholars Program(GCC[2023]072); National Key Research and Development Program of China(2023YFD1400400); Youth Guidance Project of the Guizhou Provincial Basic Research Program (Natural Science)(QN[2025]010); Youth Guidance Project of the Guizhou Provincial Basic Research Program (Natural Science)(QN[2025]009)

1. .pdf(8392KB)

Abstract

Chronic myeloid leukemia (CML) is a hematological malignancy characterized by aberrant myeloid cell proliferation, and the emergence of drug resistance to conventional tyrosine kinase inhibitors necessitates novel antitumor agents. Based on the pharmacophore of indole, 1,3,4-oxadiazole, and benzenesulfonamide, which possess antitumor potential, 30 novel hybrid derivatives were designed and synthesized, aiming to enhance activity and selectivity. Among these compounds, N-(5-(1H-indol-3-yl)-1,3,4-oxadiazol-2-yl)-3,4,5-trifluorobenzenesulfonamide (XL-10) demonstrated potent antiproliferative effects against CML K562 cells, exhibiting an IC₅₀ value of (6.69±0.35) μmol/L. Mechanistic investigations revealed that XL-10 induced apoptosis in K562 cells by disrupting redox homeostasis, as evidenced by elevated reactive oxygen species (ROS) levels and reduced mitochondrial membrane potential. Flow cytometry analysis indicated that XL-10 arrests K562 cells at the G2/M phase through regulation of key cell cycle proteins including Cyclin B1 and Cyclin-dependent kinase 1 (CDK1), while Western blot assays confirmed its modulation of the mitogen-activated protein kinase (MAPK) and phosphatidylinositol 3-kinase/protein kinase B (PI3K-AKT) signaling pathways. These findings elucidate the antitumor mechanisms of XL-10 and highlight its potential as a promising lead compound for the development of targeted CML therapies.

Key words: K562 cell, anticancer activity, nitrogen-containing heterocycle, chronic myeloid leukemia, 1,3,4-oxadiazole

Cite this article

Yueyou Wu, Dandan He, Nianlin Feng, Yi Zhang, Dandan Liu, Yue Zhou, Chenchen Li, Zhenchao Wang. Synthesis, Anticancer Evaluation, and Preliminary Mechanism Study of 1,3,4-Oxadiazole Derivatives Targeting K562 Tumor Cells[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 4034-4049.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 11

Figure 1. Design strategy of the target compounds

Scheme 1. Synthetic route of compounds XL-1~XL-20 and WG-1~WG-10

Compd.	Inhibition rate^a/% of 10 μmol/L
Compd.	PC-3	A549	K562	HEK
XL-1	—	14.03±2.81	3.52±2.35	18.47±3.32
XL-2	—	20.97±3.68	6.32±1.36	8.62±1.93
XL-3	34.80±2.15	33.18±3.66	6.51±2.39	4.17±3.58
XL-4	9.49±2.9	18.34±4.23	10.30±1.38	12.19±2.55
XL-5	7.98±4.56	19.32±1.99	26.85±2.01	8.31±2.35
XL-6	6.72±4.65	15.36±0.86	31.41±1.63	-5.18±2.80
XL-7	4.21±2.49	12.82±2.46	15.65±2.51	0.69±0.33
XL-8	12.14±1.25	22.65±10.61	10.63±2.54	7.32±5.36
XL-9	30.86±1.43	24.07±2.96	13.28±2.12	19.30±2.12
XL-10	53.72±1.48	18.63±3.04	87.20±1.79	13.13±2.04
XL-11	—	6.33±3.21	14.57±1.72	20.03±3.32
XL-12	—	16.12±5.06	6.75±0.99	15.69±1.93
XL-13	—	17.41±2.36	10.61±0.32	-23.56±3.58
XL-14	—	15.41±0.92	30.55±1.67	12.27±2.55
XL-15	—	15.32±1.14	38.33±1.06	14.61±2.35
XL-16	—	32.55±1.83	13.60±2.67	-14.77±2.80
XL-17	—	31.87±3.16	8.05±1.58	5.42±0.33
XL-18	35.26±3.19	31.03±3.50	20.24±0.43	6.56±5.36
XL-19	—	15.49±0.29	6.08±1.82	13.04±2.12
XL-20	—	—	5.00±1.26	9.56±2.04
WG-1	12.68±3.36	11.81±1.39	—	23.29±2.98
WG-2	—	13.78±1.68	—	23.80±5.13
WG-3	—	7.72±1.55	—	18.99±4.76
WG-4	—	18.52±3.39	12.94±8.88	22.84±1.46
WG-5	14.71±3.60	20.01±0.38	15.60±7.04	16.43±5.60
WG-6	—	17.62±0.83	10.18±5.98	21.50±0.32
WG-7	10.78±3.59	19.04±1.91	11.23±4.79	22.14±1.75
WG-8	10.03±2.30	13.96±0.97	1.56±3.06	17.83±4.43
WG-9	13.12±5.10	12.08±1.14	25.58±2.34	22.65±3.06
WG-10	29.96±6.66	15.28±1.13	3.24±5.68	17.84±2.60
5-Fu^b	62.46±2.79	54.52±1.31
Ima^c			97.58±0.51

Table 1. Preliminary evaluation of the antitumor activity of the target compounds

Compd.	IC₅₀±SD^a/(μmol•L^-1)
XL-10	6.69±0.35
Ima^b	0.39±0.11

Table 2. IC50 of compound XL-10 for antitumor activity

Figure 2. Analysis of the structure-activity relationship of the target compound

Figure 3. (a~e) Apoptosis detection in K562 cells following 24 h exposure to compound XL-10 using Annexin V-FITC/PI dual-staining flow cytometry (DMSO served as the negative control, while Ima was used as the positive reference), and (f) statistical analysis conducted using one-way ANOVA followed by Dunnett’s multiple comparisons test in GraphPad Prism (****p<0.0001 indicating significant differences)

Figure 4. (a~e) Mitochondrial-membrane-potential detection in K562 cells after 24-h treatment with compound XL-10 by JC-1-staining flow cytometry (DMSO served as the negative control, while Ima was used as the reference compound), and (f) statistical significance determined by one-way ANOVA with Dunnett’s multiple comparisons test using GraphPad Prism (****p<0.0001 indicates highly significant differences)

Figure 5. (a) Intracellular ROS detection in K562 cells after 12-h treatment with compound XL-10 using ROS-specific fluorescent-staining flow cytometry (DMSO served as the negative control, while Ima was used as the positive control), and (b) statistical analysis performed using one-way ANOVA with Dunnett’s multiple comparisons test in GraphPad Prism (**p<0.01, ***p<0.001, and ****p<0.0001 indicating significant increases in ROS generation)

Figure 6. (a~e) Analysis of cell cycle distribution in K562 cells upon 24-hour treatment with compound XL-10 at concentrations of 3, 6, and 12 μmol/L, using cell cycle staining followed by flow cytometry (DMSO served as the negative control, while Ima was used as the reference compound), and (f) statistical analysis conducted using two-way ANOVA with Dunnett’s multiple comparisons test in GraphPad Prism

Figure 7. (a) Number of differentially expressed genes (DEGs) in K562 cells after 24 h XL-10 treatment versus DMSO control, (b) Gene Ontology (GO) enrichment analysis of DEGs (The top 10 significantly enriched GO terms within each domain are highlighted), (c) volcano plot of genome-wide transcriptional variations between XL-10 and DMSO treatment groups, and (d) KEGG pathway enrichment analysis based on quantitative transcriptomic profiling of XL-10-treated K562 cells

Figure 8. Protein expression profiling of K562 cells treated with compound XL-10 (a) Expression changes of apoptosis-associated proteins; (b) expression variations of cell cycle-regulating proteins; (c) alterations of proteins involved in MAPK and PI3K-AKT signaling pathways. All data are expressed as mean±SD from three independent experiments (*p<0.05, ** p<0.001, ***p<0.0001)

References 40

[1]	Soverini S.; Mancini M.; Bavaro L.; Cavo M.; Martinelli G. Mol. Cancer 2018, 17, 49. doi: 10.1186/s12943-018-0780-6 pmid: 29455643
[2]	Cortes J.; Pavlovsky C.; Saußele S. Lancet 2021, 398, 1914. doi: 10.1016/S0140-6736(21)01204-6 pmid: 34425075
[3]	Braun T. P.; Eide C. A.; Druker B. J. Cancer Cell 2020, 37, 530. doi: 10.1016/j.ccell.2020.03.006
[4]	Hochhaus A.; Larson R. A.; Guilhot F.; Radich J. P.; Branford S.; Hughes T. P.; Baccarani M.; Deininger M. W.; Cervantes F.; Fujihara S.; Ortmann C.; Menssen H. D.; Kantarjian H.; O’Brien S. G.; Druker B. J. N. Engl. J. Med. 2017, 376, 917. doi: 10.1056/NEJMoa1609324
[5]	Shah N. P.; Tran C.; Lee F. Y.; Chen P.; Norris D.; Sawyers C. L. Science 2004, 305, 399. doi: 10.1126/science.1099480
[6]	Atallah E.; Schiffer C. A.; Radich J. P.; Weinfurt K. P.; Zhang M.; Pinilla-Ibarz J.; Kota V.; Larson R. A.; Moore J. O.; Mauro M. J.; Deininger M. W. N.; Thompson J. E.; Oehler V. G.; Wadleigh M.; Shah N. P.; Ritchie E. K.; Silver R. T.; Cortes J.; Lin L.; Visotcky A.; Baim A.; Harrell J.; Helton B.; Horowitz M.; Flynn K. E. JAMA Oncol. 2021, 7, 42. doi: 10.1001/jamaoncol.2020.5774 pmid: 33180106
[7]	Jabbour E.; Kantarjian H. Am. J. Hematol. 2020, 95, 691. doi: 10.1002/ajh.25792 pmid: 32239758
[8]	Osman A. E. G.; Deininger M. W. Blood Rev. 2021, 49, 100825. doi: 10.1016/j.blre.2021.100825
[9]	Kamal A.; Surendranadha Reddy J.; Janaki Ramaiah M.; Dastagiri D.; Vijaya Bharathi E.; Ameruddin Azhar M.; Sultana F.; Pushpavalli S. N. C. V.; Pal-Bhadra M.; Juvekar A.; Sen S.; Zingde S. Eur. J. Med. Chem. 2010, 45, 3924. doi: 10.1016/j.ejmech.2010.05.047
[10]	Uppar P. M.; Kim N. Y.; Harish K. K.; Beeraka N. M.; Gaonkar S. L.; Madegowda M.; Sethi G.; Rangappa K. S.; Nikolenko V. N.; Chinnathambi A.; Alharbi S. A.; Ahn K. S.; Basappa B. Chem. Biol. Interact. 2025, 415, 111528. doi: 10.1016/j.cbi.2025.111528
[11]	Olgen S.; Kaleli S. N. B.; Karaca B. T.; Demirel U. U.; Bristow H. K. Curr. Med. Chem. 2024, 31, 3798. doi: 10.2174/0929867330666230626143911
[12]	Cros S.; Wright M.; Morimoto M.; Lataste H.; Couzinier J. P.; Krikorian A. Semin. Oncol. 1989, 16, 15. pmid: 2711203
[13]	Anderson R.; Makvandi M.; Xu K.; Lieberman B. P.; Zeng C.; Pryma D. A.; Mach R. H. Nucl. Med. Biol. 2016, 43, 752. doi: 10.1016/j.nucmedbio.2016.08.007
[14]	Prieto-Domínguez N.; Méndez-Blanco C.; Carbajo-Pescador S.; Fondevila F.; García-Palomo A.; González-Gallego J.; Mauriz J. L. Oncotarget 2017, 8, 85858. doi: 10.18632/oncotarget.v8i49
[15]	Paik J.; Dhillon S. Drugs 2018, 78, 1247. doi: 10.1007/s40265-018-0952-0
[16]	Glomb T.; Szymankiewicz K.; Wiątek P. Molecules 2018, 23, 3361. doi: 10.3390/molecules23123361
[17]	Ahsan M. J. Mini-Rev. Med. Chem. 2022, 22, 164. doi: 10.2174/1389557521666210226145837
[18]	Allawi M. M.; Razzak Mahmood A. A.; Tahtamouni L. H.; Saleh A. M.; Kanaan S. I.; Saleh K. M.; AlSakhen M. F.; Himsawi N.; Yasin S. R. Future Med. Chem. 2024, 16, 1313. doi: 10.1080/17568919.2024.2347084
[19]	Asati V.; Bhupal R.; Bhattacharya S.; Kaur K.; Gupta G. D.; Pathak A.; Mahapatra D. K. Anticancer Agents Med. Chem. 2023, 23, 404. doi: 10.2174/1871520622666220607143040
[20]	Loscocco F.; Visani G.; Galimberti S.; Curti A.; Isidori A. Front Oncol. 2019, 9, 939. doi: 10.3389/fonc.2019.00939
[21]	Tantak M. P.; Kumar A.; Noel B.; Shah K.; Kumar D. ChemMedChem 2013, 8, 1468. doi: 10.1002/cmdc.v8.9
[22]	Kaur K.; Jaitak V. Anti-Cancer Agents Med. Chem. 2019, 19, 962. doi: 10.2174/1871520619666190312125602
[23]	Shu B.; Yu Q.; Hu D.; Che T.; Zhang S.; Li D. Bioorg. Med. Chem. Lett. 2020, 30, 126925. doi: 10.1016/j.bmcl.2019.126925
[24]	Sagredou S.; Dalezis P.; Nikoleousakos N.; Nikolaou M.; Voura M.; Almpanakis K.; Panayiotidis M. I.; Sarli V.; Trafalis D. T. OncoTargets Ther. 2020, 13, 7369. doi: 10.2147/OTT.S254856 pmid: 32801761
[25]	Fu X.; Huang J.; Li N.; Liu Y.; Liu Q.; Yuan S.; Xu Y.; Chen Y.; Zhao Y.; Song J.; Zhang S.; Bai Y. Eur. J. Med. Chem. 2023, 262, 115883. doi: 10.1016/j.ejmech.2023.115883
[26]	Puri S.; Stefan K.; Khan S. L.; Pahnke J.; Stefan S. M.; Juvale K. J. Med. Chem. 2023, 66, 657. doi: 10.1021/acs.jmedchem.2c01612
[27]	Wang Z.; Cai J.; Cheng J.; Yang W.; Zhu Y.; Li H.; Lu T.; Chen Y.; Lu S. J. Med. Chem. 2021, 64, 2878. doi: 10.1021/acs.jmedchem.0c01851
[28]	Ju Z.; Su M.; Hong J.; La Kim E.; Moon H. R.; Chung H. Y.; Kim S.; Jung J. H. Eur. J. Med. Chem. 2019, 180, 86. doi: 10.1016/j.ejmech.2019.07.016
[29]	Boschelli D. H.; Connor D. T.; Bornemeier D. A.; Dyer R. D.; Kennedy J. A.; Kuipers P. J.; Okonkwo G. C.; Schrier D. J.; Wright C. D. J. Med. Chem. 1993, 36, 1802. pmid: 8515419
[30]	Ullah H.; Aslam M. W.; Rahim F.; Hussain A.; Perviaz M. Chem. Data Collect. 2023, 45, 101031. doi: 10.1016/j.cdc.2023.101031
[31]	Thompson C. B. Science 1995, 267, 1456. doi: 10.1126/science.7878464 pmid: 7878464
[32]	Gregory C. D. Immunol Rev. 2023, 319, 100. doi: 10.1111/imr.v319.1
[33]	Gottlieb E.; Armour S. M.; Harris M. H.; Thompson C. B. Cell Death Differ. 2003, 10, 709. doi: 10.1038/sj.cdd.4401231 pmid: 12761579
[34]	Begum H. M.; Shen K. WIREs Mech. Dis. 2023, 15, e1595.
[35]	Glorieux C.; Liu S.; Trachootham D.; Huang P. Nat. Rev. Drug Discovery 2024, 23, 583. doi: 10.1038/s41573-024-00979-4
[36]	Harris I. S.; Denicola G. M. Trends Cell Biol. 2020, 30, 440. doi: S0962-8924(20)30058-1 pmid: 32303435
[37]	Moloney J. N.; Cotter T. G. Semin. Cell Dev. Biol. 2018, 80, 50. doi: 10.1016/j.semcdb.2017.05.023
[38]	Matthews H. K.; Bertoli C.; de Bruin R. A. M. Nat. Rev. Mol. Cell Biol. 2022, 23, 74. doi: 10.1038/s41580-021-00404-3
[39]	Corrales E.; Levit-Zerdoun E.; Metzger P.; Mertes R.; Lehmann A.; Münch J.; Lemke S.; Kowar S.; Boerries M. Cell Commun. Signaling 2022, 20, 187. doi: 10.1186/s12964-022-00989-y
[40]	Irvine M.; Stewart A.; Pedersen B.; Boyd S.; Kefford R.; Rizos H. Oncogenesis 2018, 7, 72. doi: 10.1038/s41389-018-0081-3 pmid: 30237495

靶向K562肿瘤细胞的1,3,4-噁二唑衍生物的合成、抗癌活性评价及初步作用机制研究

Synthesis, Anticancer Evaluation, and Preliminary Mechanism Study of 1,3,4-Oxadiazole Derivatives Targeting K562 Tumor Cells

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 11

References 40

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wenbo Wang, Guichuan Chen, Jinbo Wang, Yang Zhao, Qilin Wang. Applications of Pyridinium 1,4-Zwitterionic Thiolates in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 1845-1870.
[2]	Weishu Zhang, Lifei Nie, Khurshed Bozorov, Haji Akber Aisa, Jiangyu Zhao. Synthesis of Diethyl 2,5-Diaminothiophene-3,4-dicarboxylate Derivatives and Antitumor Activity Study [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2543-2552.
[3]	Jiantao Zhang, Cong Zhang, Zidong Zheng, Peng Zhou, Weibing Liu. Research Progress of Sulfoxonium Ylides in the Construction of Five/Six-Membered Nitrogen-Containing Heterocycles [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2745-2759.
[4]	Jing Zhao, Zhe Jin, Run Wang, Xin'geng Zhang, Yingmei Han, Chun Hu, Xiaoping Liu, Chuanming Zhang, Liping Jin. Design, Synthesis and Anticancer Activity of 2-((Pyridin- 2-ylmethyl)thio)-1H-benzimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2172-2183.
[5]	Yan Zeng, Lifei Nie, Chao Niu, Aytilla Mamatjan, Khurshed Bozorov, Jiangyu Zhao, Haji Akber Aisa. Synthesis and Biological Activities of Dihydrooxazolo[5,4-d]-pyrrolo[1,2-a]pyrimidinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 543-556.
[6]	Shenghui Wang, Yongfeng Guan, Xiujuan Liu, Xinying Yuan, Guangxi Yu, Yinru Li, Yanbing Zhang, Jian Song, Wen Li, Saiyang Zhang. Design, Synthesis and Anticancer Activity Studies of Novel Quinoline-Indole Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3617-3624.
[7]	Xin Liu, Runmei Xu, Lin Wang, Yaxue Liu, Zhihao Chen, Wei Qin, Yushun Tian. Synthesis and Evaluation in vitro of Dihydrothiophenopyridine-Chalcone Derivatives as Anticancer Activity Agents [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3550-3559.
[8]	Jiantao Zhang, Peng Zhou, Duoduo Xiao, Weibing Liu. Research Progress of 1,3,5-Triazinanes in the Synthesis of Nitrogen-Containing Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4154-4166.
[9]	Maihesuti Liwaliding, Yu Junjie, Wang Qi, Cao Jianguo, Huang Guozheng. Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2764-2771.
[10]	Mao Zewei, Liu Bei, Zhu Ping, Zhang Lijun, Zhu Jiahong, Wu Linze, Wan Chunping. Synthesis and Biological Evaluation of Piperazine Substituted 3-Aryl-5-furanyldihydropyrazole Amide Derivatives [J]. Chin. J. Org. Chem., 2018, 38(8): 2167-2173.
[11]	Huang Xinwei, Liu Jianli. Synthesis and Anticancer Activities of Novel Pyranocoumarin Fused Pyrimidine Based on Cyanoenamine [J]. Chin. J. Org. Chem., 2018, 38(5): 1233-1241.
[12]	Zhang Lei, Liu Lai, Zheng Chengyue, Wang Yang, Wang Jing, Yao Qizheng. Synthesis of Novel Indirubin Derivatives and Their Effects on the Proliferation, Cell Cycle and Apoptosis in Acute Myeloblastic Leukemia HL-60 Cells [J]. Chin. J. Org. Chem., 2017, 37(6): 1523-1529.
[13]	Liu Juanjuan, Lu Yanju, Wang Jing, Bi Liangwu, Zhao Zhendong. Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid [J]. Chin. J. Org. Chem., 2017, 37(3): 731-738.
[14]	Imerhasan Mukhtar, Helil Setiwaldi, Mahmud Muhammed Amin. Synthesis and in vitro Anticancer Activity of N-Methylisoxazolinium-Salts with Carboxyl or Ester Groups against Cell Division Cycle 25B Phosphatase and Protein Tyrosine Phosphatase-1 [J]. Chin. J. Org. Chem., 2017, 37(2): 496-502.
[15]	Li Zemin, Huang Daorui, Ma Congming, Xu Xiaojuan, Liu Zuliang, Yao Qizheng. Convenient Aminative Ring-Opening Reaction of 7-Amino-6-nitro-[1,2,5]oxadiazolo[3,4-b]pyridine-1-oxide and Antitumor Activity of Corresponding Products [J]. Chin. J. Org. Chem., 2016, 36(9): 2236-2241.