Synthesis and antitumor activity of 1, 2-benzothiazines imidazolo ［1, 2-b］［1, 3, 4］ triazazole derivatives

WANG Xin; ZHAO Xiaomei; ZHANG Pingping; JI Xia; HU Guoqiang

doi:10.11665/j.issn.1000-5048.20190505

Journal of China Pharmaceutical University > 2019 > 50(5): 540-543. > DOI: 10.11665/j.issn.1000-5048.20190505

WANG Xin, ZHAO Xiaomei, ZHANG Pingping, JI Xia, HU Guoqiang. Synthesis and antitumor activity of 1, 2-benzothiazines imidazolo ［1, 2-b］［1, 3, 4］ triazazole derivatives[J]. Journal of China Pharmaceutical University, 2019, 50(5): 540-543. DOI: 10.11665/j.issn.1000-5048.20190505

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Synthesis and antitumor activity of 1, 2-benzothiazines imidazolo ［1, 2-b］［1, 3, 4］ triazazole derivatives

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In this study, triazazole moiety was introduced to piroxicam, a nonsteroidal anti-inflammatory drug, via bioisosterism to produce eight target analogs, which were structurally characterized by ¹H NMR and MS. These target compounds were tested for inhibitory activities on pancreatic cancer cell(Capan-1)and leukemia cell(L1210). The results showed that compound 6b had good antiproliferative activity against Capan-1 cells(IC₅₀=3. 6±0. 5 μmol/L); while compound 6a had good antiproliferative activity against L1210 cells(IC₅₀=1. 8±0. 2 μmol/L), indicating that the introduction of the imidazolo［1, 2-b］［1, 3, 4］triazazole moiety could be helpful to improve the antitumor activity of these compounds.
- imidazolo［1,2-b］［1,3,4］triazazole,
- synthesize,
- antitumor activity

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[1]	Zhou XL,Fan W,Yang G,et al.The clinical significance of PR,ER,NF-κB,and TNF-α in breast cancer[J].Dis Markers,2014,2014(6):494581-494587.
[2]	Stairs DB,Bayne LJ,Rhoades B,et al.Deletion of p120-catenin results in a tumor microenvironment with inflammation and cancer that establishes it as a tumor suppressor gene[J].Cancer Cell,2011,19(4):470-483.
[3]	Feng LS,Xu L,Fan J,et al.1,2,4-Triazole derivatives and their anti-tubercular agents[J].World Notes Antibiot(国外医药抗生素分册),2017,38(5):230-237.
[4]	Li Z.Design,synthesis and antitumor evaluation of[1,2,3] trazolo[4.5-D]pyromidine derivatives as LSD1 inhibitors(新型[1,2,3] 三氮唑并[4,5-d]嘧啶类LSD1抑制剂的设计、合成及其抗肿瘤活性研究)[D].Henan:Zhengzhou University,2018.
[5]	Wang S.Design,synthesis and biological evaluation of[1,2,4] trazolo[1.5-a]pyromidines as potent lysine specific demethylase 1(LSD1/KDM1A)inhibitors([1,2,4] 三氮唑并[1,5-a]嘧啶类LSD1抑制剂的设计、合成及其抗肿瘤活性评价)[D].Henan:Zhengzhou University,2017.
[6]	Zhao XL,Zhao YF,Xu DS,et al.Synthesis and antitumor activities of[1,2,4] triazolo[1,5-a]pyrimidines[J].Chin J Med Chem(中国药物化学杂志),2007,17(5):269-273,294.
[7]	Zhang ZQ,Fu B,Wang BG,et al.Synthesis and antifungal activities of novel trizole derivatives with dithiocarbamates side chain[J].Pharm Care Res(药学服务与研究),2016,16(2):94-97.
[8]	Zhan Y,Shu N,Guo N,et al.Advances in therepeutic drug monitoring for trozole antifungal agents[J].Chin J Clin Pharmacol Ther(中国临床药理学与治疗学),2014,19(6):706-711.
[9]	Lü XY,Shan J,Qiu T.Synthesis and fungicidal activities of novel 1,2,4-triazole derivatives[J].Chin J Synth Chem(合成化学),2018,26(12):888-894.
[10]	Wen YN,Yuan WY,Wu YW,et al.Synthesis and antiviral activity of 1,2,3-triazole derivatives[J].Chin J Med Chem(中国药物化学杂志),2016,26(1):18-23.
[11]	Chen SL,Guo DF,Yu SW,et al.Synthesis of 1-(3-phenoxypropyl)-1H-1,2,4-triazole derivatives and their anticonvulsant activities[J].J Jinggangshan Univ(Nat Sci)(井冈山大学学报自然科学版),2019,40(1):88-93.
[12]	Cui LJ,Wei CX.Synthesis and anticonvulsant activity study of 2-substituted-7-benzyloxy-4,5- dihydro-[1,2,4] triazolo[4,3-a]quinoline-1(2H)-ones[J].Guangdong Chem Ind(广东化工),2009,36(6):61-63.

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Synthesis and antitumor activity of 1, 2-benzothiazines imidazolo ［1, 2-b］［1, 3, 4］ triazazole derivatives

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