异长叶烯基噻唑类化合物的合成及其抑菌、抗肿瘤活性研究

doi:10.3969/j.issn.0253-2417.2016.06.007

Abstract

Abstract: Eleven new kinds of isolongifolanyl thiazole compounds were synthesized by condensation, nucleophilic substitution and cyclization from isolongifolenone. The structures of the target compounds were characterized by ¹H NMR, ¹³C NMR, LC-MS and FT-IR, respectively. Antibacterial evaluation of the compounds was carried out by minimum inhibitory concentrations assay (MIC). The results showed that the antibacterial activities of (E)-4-(4-methoxyphenyl)-2-(2-(1,1,5,5-tetramethyl-3,4,5,6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)thiazole(2e) and (E)-2-(2-(1,1,5,5-tetramethyl-3,4,5,6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)-4-(p-tolyl) thiazole (2g) were better than those of others against Escherichia coli and Staphylococcus aureus. Their MIC were 7.8 mg/L. The antibacterial activity of (E)-4-(4-chlorophenyl)-2-(2-(1,1,5,5-tetramethyl-3,4,5,6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)thiazole (2b) was better than those of others against fungus. Its MIC value aganist Candida albicans and Candida tropicalis was 15.6 mg/L. Their antitumor activities against HepG2 were evaluated by thiazole blue test(MTT). Compound 2g (IC₅₀=43.9±0.9 mg/L) was found to be the most potent derivative overall the tested compounds against HepG2.

Key words: isolongifolenone, thiazole compounds, antibacterial activity, antitumor activity

CLC Number:

TQ35

RUI Jian, YANG Jin-lai, CAI Tao, XU Xu, WANG Shi-fa. Synthesis of Isolongifolanyl Thiazole Compounds and Their Antibacterial and Antitumor Activities[J]. Chemistry and Industry of Forest Products, 2016, 36(6): 41-48.

References

[1] 彭晗,杨丽娟,徐徐,等.异长叶烯酮的绿色合成研究[J].林产化学与工业,2015,35(3):97-103. PENG Han,YANG Li-juan,XU Xu,et al.Green synthesis of isolongifolenone[J].Chemistry and Industry of Forest Products,2015,35(3):97-103.
[2] THIRUMURUGAN R,SRIRAM D,SAXENA A,et al.2,4-Dimethoxyphenylsemicarbazones with anticonvulsant activity against three animal models of seizures:Synthesis and pharmacological evaluation[J].Bioorganic & Medicinal Chemistry,2006,14(9):3106-3112.
[3] KHAN S A,KUMAR P,JOSHI R,et al.Synthesis and in vitro antibacterial activity of new steroidal thiosemicarbazone derivatives[J].European Journal of Medicinal Chemistry,2008,43(9):2029-2034.
[4] PANDYA D H,SHARMA J A,JALANI H B,et al.Novel thiazole-thiophene conjugates as adenosine receptor antagonists:Synthesis,biological evaluation and docking studies[J].Bioorganic & Medicinal Chemistry Letters,2015,25(6):1306-1309.
[5] 张静,康卓,李淼,等.具有生物活性的异噻唑类化合物研究进展[J].农药,2011,50(3):157-164. ZHANG Jing,KANG Zhuo,LI Miao,et al.The research progress of isothiazole compounds with bioactivities[J].Agrochemicals,2011,50(3):157-164.
[6] GHASEMI B,SANJARANI G,SANJARANI Z,et al.Evaluation of anti-bacterial effects of some novel thiazole and imidazole derivatives against some pathogenic bacteria[J].Iranian Journal of Microbiology,2015,7(5):281-286.
[7] DAWOOD K M,ELDEBSS T M A,EL-ZAHABI H S A,et al.Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents[J].European Journal of Medicinal Chemistry,2013,70:740-749.
[8] ALI A R,El-BENDARY E R,GHHALY M A,et al.Synthesis,in vitro anticancer evaluation and in silico studies of novel imidazo[2,1-b] thiazole derivatives bearing pyrazole moieties[J].European Journal of Medicinal Chemistry,2014,75:492-500.
[9] HELAL M H M,SALEM M A,EL-GABY M S A,et al.Synthesis and biological evaluation of some novel thiazole compounds as potential anti-inflammatory agents[J].European Journal of Medicinal Chemistry,2013,65:517-526.
[10] HOLLA B S,MALINI K V,RAO B S,et al.Synthesis of some new 2,4-disubstituted thiazoles as possible antibacterial and anti-inflammatory agents[J].European Journal of Medicinal Chemistry,2003,38(3):313-318.
[11] WANG Ning-yu,XU Ying,ZUO Wei-xiong,et al.Discovery of imidazo[2,1-b] thiazole HCV NS4B inhibitors exhibiting synergistic effect with other direct-acting antiviral agents[J].Journal of Medicinal Chemistry,2015,58(6):2764-2778.
[12] EL-SABBAGH O I,BARAKA M M,IBRAHIM S M,et al.Synthesis and antiviral activity of new pyrazole and thiazole derivatives[J].European Journal of Medicinal Chemistry,2009,44(9):3746-3753.
[13] 严曼,石德清,肖琳霞.新型N-(4,6-二取代嘧啶-2-基)-1-[取代吡啶(噻唑)甲基]-5-甲基-1H-1,2,3-三唑基-4-甲酰胺的合成与除草活性[J].有机化学,2008,28(6):1012-1015. YAN Man,SHI De-qing,XIAO Lin-xia.Synthesis and herbicidal activity of novel N-(4,6-disubstituted pyrimidin-2-yl)-1-[substitutedpyridyl(thiazolyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides[J].Chinese Journal of Organic Chemistry,2008,28(06):1012-1015.
[14] DAI H,XIAO Y S,LI Z,et al.The thiazoylmethoxy modification on pyrazole oximes:Synthesis and insecticidal biological evaluation beyond acaricidal activity[J].Chinese Chemical Letters,2014,25(7):1014-1016.
[15] O'HALLORAN D M,BURNELL A M.An investigation of chemotaxis in the insect parasitic nematode Heterorhabditis bacteriophora[J].Parasitology,2003,127(04):375-385.
[16] YU Hai-bo,QIN Zhen-feng,DAI Hong,et al.Synthesis and insecticidal activity of N-substituted (1,3-thiazole) alkyl sulfoximine derivatives[J].Journal of Agricultural and Food Chemistry,2008,56(23):11356-11360.

Synthesis of Isolongifolanyl Thiazole Compounds and Their Antibacterial and Antitumor Activities

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