Synthesis and cytotoxicity study of cembrane triazole derivatives

CHENG Weihua; WANG Wenqian; SHANG Hai; ZHANG Hongwu; GUO Qiang; CHEN Hong; ZOU Zhongmei

doi:10.11665/j.issn.1000-5048.20180108

Journal of China Pharmaceutical University > 2018 > 49(1): 56-63. > DOI: 10.11665/j.issn.1000-5048.20180108

CHENG Weihua, WANG Wenqian, SHANG Hai, ZHANG Hongwu, GUO Qiang, CHEN Hong, ZOU Zhongmei. Synthesis and cytotoxicity study of cembrane triazole derivatives[J]. Journal of China Pharmaceutical University, 2018, 49(1): 56-63. DOI: 10.11665/j.issn.1000-5048.20180108

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Synthesis and cytotoxicity study of cembrane triazole derivatives

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A series of triazole derivatives were designed and synthesized based on a natural product cembrane separated from Croton laevigatus Vahl which showed potential antitumor activity against HeLa cells. Twelve novel compounds were synthesized and their structures were characterized by ¹H NMR, ¹³C NMR and HRMS. Their cytotoxicities in vitro were evaluated for HeLa, K562 and K562/A02 cells by MTT assay. The results showed that some cembrane derivatives possessed antitumor activities. Substituted triazole connected to cembrane derivatives exhibited potent activity toward drug-resistant K562/A02 cells.
- cembrane,
- triazole,
- synthesis,
- structural modification,
- cytotoxicity,
- anti-drug-resistance activity

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[1]	Thao NP,Luyen BTT,Ngan NTT,et al.New anti-inflammatory cembranoid diterpenoids from the Vietnamese soft coral Lobophytum crassum[J].Bioorg Med Chem Lett,2014,24(1):228-232.
[2]	Peres MT,Delle Monache F,Cruz AB,et al.Chemical composition and antimicrobial activity of Croton urucurana Baillon(Euphorbiaceae)[J].J Ethnopharmacol,1997,56(3):223-226.
[3]	Tsacheva I,Rostan J,Iossifova T,et al.Complement inhibiting properties of dragon′s blood from Croton draco[J].Z Naturforsch C,2004,59(7/8):528-532.
[4]	Su JH,Ahmed AF,Sung PJ,et al.Manaarenolides AI,diterpenoids from the soft coral Sinularia manaarensis[J].J Nat Prod,2006,69(8):1134-1139.
[5]	Hassan HM,Sallam AA,Mohammed R,et al.Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors[J].Bioorg Med Chem,2011,19(16):4928-4934.
[6]	Fahmy H,Zjawiony JK,Konoshima T,et al.Potent skin cancer chemopreventing activity of some novel semi-synthetic cembranoids from marine sources[J].Mar Drugs,2006,4(2):28-36.
[7]	Huang HC,Ahmed AF,Su JH,et al.Crassocolides A-F,cembranoids with a transfused lactone from the soft coral Sarcophyton crassocaule[J].J Nat Prod,2006,69(11):1554-1559.
[8]	Sánchez MC,Ortega MJ,Zubía E,et al.Cembrane diterpenes from the gorgonian Lophogorgia peruana[J].J Nat Prod,2006,69(12):1749-1755.
[9]	Wen T,Ding Y,Deng Z,et al.Sinulaflexiolides A-K,cembrane-type diterpenoids from the Chinese soft coral Sinularia flexibilis[J].J Nat Prod,2008,71(7):1133-1140.
[10]	Cuzick J.Anastrozole[J].Drugs Today,2005: 41(4):227-239.
[11]	Ribatti D,Vacca A,Falco GD,et al.Angiogenesis and anti-angiogenesis in neuroblastoma[J].Eur J Cancer,2002,38(6):750-757.
[12]	Guo L,Li ZS,Wang HL,et al.Carboxyamido-triazole inhibits proliferation of human breast cancer cell via G₂/M cell cycle arrest and apoptosis[J].Eur J Pharmacol,2006,538(1/2/3):15-22.
[13]	Cheng WH,Cao B,Shang H,et al.Synthesis and evaluation of novel podophyllotoxin derivatives as potential antitumor agents[J].Eur J Med Chem,2014,85:498-507.
[14]	Mahadevan D.Will MDR-1/P-gp modulators provide clinical benefit in hematologic malignancies[J]?Leuk Res,2006,30(9):1077-1078.

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