Synthesis and Bioactivity of Novel Bis-heterocyclic Amide Modified Sulfide Derivatives

doi:10.11944/j.issn.1000-0518.2017.03.160352

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (3): 308-315.DOI: 10.11944/j.issn.1000-0518.2017.03.160352

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Synthesis and Bioactivity of Novel Bis-heterocyclic Amide Modified Sulfide Derivatives

ZHANG Chenglu(),XI Huan,SHA Yuting,SUN Xiaona,LI Chuanyin,WANG Jing,LI Yizheng

College of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian,Liaoning 116029,China

Received:2016-09-02 Accepted:2016-11-28 Published:2017-02-27 Online:2017-02-27
Contact: ZHANG Chenglu
Supported by:
Supported by Technology Research Program of Liaoning Provincial Department of Education(No.2009A426)

Abstract

Abstract:

Sixteen novel double-heterocyclic modified amide sulfide derivatives containing 1,2,4-triazole and 1,3,4-thiadiazole were designed and synthesized, and their structures were characterized. The inhibitory activities of synthesized molecules against cell division cycle 25B(Cdc25B) of protein tyrosine phosphatase 1B(PTP1B) were evaluated. The results show that all target molecules exhibit good inhibitory activity against PTP1B. Compounds 8-C-d and 8-D-c have the optimal inhibition. Their half maximal inhibitory concentration(IC₅₀) values are (1.19±0.22) mg/L and (1.08±0.09) mg/L, respectively, which are lower than that of positive reference oleanolic acid(IC₅₀=(1.27±0.19) mg/L). They are expected to be anti-diabetic drug leading compounds. The target molecules also exhibit good inhibitory activities against Cdc25B. The IC₅₀ values of compounds 8-A-d, 8-C-d and 8-D-c are higher than that of positive reference Na₃VO₄(IC₅₀=(1.25±0.14) mg/L), which are expected to be anticancer drug leading compounds.

Key words: triazole, thiadiazole, protein tyrosine phosphatase 1B, cell division cycle 25B, inhibitors

ZHANG Chenglu, XI Huan, SHA Yuting, SUN Xiaona, LI Chuanyin, WANG Jing, LI Yizheng. Synthesis and Bioactivity of Novel Bis-heterocyclic Amide Modified Sulfide Derivatives[J]. Chinese Journal of Applied Chemistry, 2017, 34(3): 308-315.

References

[1]	Radwan A A,eLthair K .E H. Synthesis and In-Silico Studies of Some Diaryltriazole Derivatives as Potential Cyclooxygenase Inhibitors[J]. Arch Pharmacal Res,2013,36(5):553-563.
[2]	Marino J P Jr,Fisher P W,Hofmann G A,et al. Highly Potent Inhibitors of Methionine Aminopeptidase-2 Based on a 1,2,4-Triazol Pharmacophore[J]. Med Chem,2007,50(16):3777-3785.
[3]	Wang B L,Shi Y X,Ma Y,et al.Synthesis and Biological Activity of Some Novel Trifluoromethy-Substituted 1,2,4-Triazole and Bis(1,2,4-Triazole) Mannich Bases Containing Piperazine Rings[J]. Agric Food Chem,2010,58(9):5515-5522.
[4]	Thottempudi V,Shreeve J M. Synthesis and Promising Properties of a New Family of High-Density Energetic Salts of 5-Nitro-3-trinitromethyl-1H-1,2,4-Triazole and 5,5'-Bis(trinitromethyl)-3,3'-azo-1H-1,2,4-triazole[J]. J Am Chem Soc,2011,133(49):19982-19992.
[5]	YANG Haikui,XU Wanfu,DUAN Anna,et al.Syntheses and Biological Activities of Novel Imine and Imide Derivatives Bearing 1,2,4-Triazole Moiety[J]. Chem J Chinese Univ,2014,35(3):555-563(in Chinese). 杨海葵,许万福,段安娜,等. 含1,2,4-三唑环的亚胺及酰亚胺类化合物的合成及生物活性[J]. 高等学校化学学报,2014,35(3):555-563.
[6]	Oruç E E,Rollas S F,Shvets N,et al.1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure Antituberculosis Activity Relationship Investigation[J]. J Med Chem,2004,47(27):6760-6767.
[7]	Yang S J,Choe J H,Abdildinova A,et al.A Highly Efficient Diversification of 2-Amino/Amido-1,Highly Efficient Diversification of 2-Amino/Amido-1,3,4-oxadiazole and 1,3,4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate on Solid-Phase[J]. ACS Comb Sci,2015,17(12):732-741.
[8]	Fan Z J,Yang Z K,Zhang H K,et al.Synthesis, Crystal Structure, and Biological Activity of 4-Methy-1,2,3-thiadiazole-Containing 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles[J]. Agric Food Chem, 2010,58(5):2630-2636.
[9]	Xia J,Zou L H,Lai G Y,et al.Synthesis, Fungicidal Activity, and 3D-QSAR of Pyridazinone-Substituted 1,3,4-Oxadiazoles and 1,3,4-Thiadiazoles[J]. Agric Food Chem,2002,50(13):3757-3760.
[10]	CHEN Danping,WU Wenneng,LI Feifei,et al.Research and Application of Five-member Heterocyclic Fungicides[J]. Mod Agrochem,2014,2(13):5-10(in Chinese). 陈丹萍,吴文能,李飞飞,等. 五元杂环类杀菌活性化合物的研究进展[J]. 现代农药,2014,2(13):5-10.
[11]	Moriyama K,Suzuki T,Negishi K,et al.Effects of Introduction of Hydrophobic Group on Ribavirin Base on Mutation Induction and Anti-RNA Viral Activity[J]. J Med Chem,2008,51(1):159-166.
[12]	SHEN Suwen,LIU Yongfeng,ZHOU Sujin,et al.4 Antagonistic Bacteria and Streptomycin, Rice Research Article Bacterial Spot Disease Bismerthiazol Cooperative Control[J]. Jiangsu Agric Sci,2010,(4):98-100(in Chinese). 沈素文,刘永锋,周苏津,等. 4株拮抗细菌与链霉素、叶枯唑协同控制水稻细菌性条斑病研究[J]. 江苏农业科学,2010,(4):98-100.
[13]	Jida M,Soueidan M,Willand N,,et al.A Facile and Rapid Synthesis of N-Benzyl-2-substituted Piperazines[J]. Tetrahedron Lett,2011,52(4):1705-1708.
[14]	Xiong W F,Qi C R,He H T,et al.Base-Promoted Coupling of Carbon Dioxide, Amines, and N-Tosylhydrazones:A Novel and Versatile Approach to Carbamates[J]. Angew Chem Int Ed,2015,54(10):3084-3087.
[15]	Rakse M,Karthikeyan C,Deora G S,et al.Design, Synthesis and Molecular Modelling Studies of Novel 3-Acetamido-4-Methyl Benzoic Acid Derivatives as Inhibitors of Protein Tyrosine Phosphatase 1B[J]. Euro J Med Chem,2013,70:469-476.
[16]	Zinatossadat H. Solvent-free Synthesis of Substituted Five Membered Heterocycles:One-pot Reaction of Primary Amine and Alkyl Propiolate or Isothiocyanate in the Presence of Oxalyl Chloride[J]. Chinese Chem Lett,2014,25(1):159-162.
[17]	Park Y H,Jeon Y H,Kim I Y. Selenoprotein W Promotes Cell Cycle Recovery from G2 Arrest Throgh the Activation of CDC25B[J]. Biochim Biophys Acta,Mol Cell Res,2012,1823(12):2217-2226.
[18]	Jeffrey J,Anderson S,Wingard B,et al.Uptake of Cyantraniliprole into Tomato Fruit and Foliage under Hydroponic Conditions:Application to Calibration of a Plant/Soil Uptake Model[J]. Agric Food Chem,2013,61(38):9027-9035.
[19]	ZHANG Chenglu, ZHU Chang'an,WU Feiyu, et al. Synthesis, Biological Activity and Electrochenical Properties of Ferrocenyl 1,3,4-Triazoles Derivatives[J]. Chinese J Appl Chem,2014,31(4):455-461(in Chinese). 张成路,朱长安,武飞宇,等. 二茂铁基1,3,4-三唑席夫碱衍生物合成及生物活性和电化学性质[J]. 应用化学,2014,31(4):455-461.
[20]	Mobinikhaledi A,Foroughifar N,Bayat M. Synthesis of Some Novel 3-(4-Pyridinyl)-6-ary-1,2,4-triaz-olo[3,4-b]-1,3,4 -thiadiazoles[J]. Org Prep Proced Int,2011,43(4):368-371.
[21]	Tu G G,Li S H,Huang H M,et al.Novel Aminopeptidase N Inhibitors Derived from 1,3,4-Thiazole Scaffold[J]. Bioorg Med Chem,2008,16:6663-6668.
[22]	Lindqvist A, Källström H, Lundgren A,et al.Cdc25B Cooperates With Cdc25A to Induce Mitosis but Has a Unique Role in Activating Cyclin B1 Cdk1 at the Centrosome[J]. J Cell Biol,2005,171(1):35-45.
[23]	Sun L P,Shen Q,Piao H H,et al.Synthese and Biological Evaluation of (±)-3-(2-(2-Fluorobenzyloxy) Napthalen-6-yl)-2-Aminopropanoic Acid Derivatives as Novel PTP1B Inhibitors[J]. Eur J Med Chem,2011,46(9):3630-3638.
[24]	He X P,Li C,Jin X P,et al.Microwave-assisted Construction of Triazole-linked Amino Acid-Glucoside Conjugates as Novel PTP1B Inhibitors[J]. New J Chem,2011,35(3): 622-631.

Synthesis and Bioactivity of Novel Bis-heterocyclic Amide Modified Sulfide Derivatives

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