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异长叶烷基噻唑类化合物的合成及其生物活性(PDF/HTML)

《南京林业大学学报(自然科学版)》[ISSN:1000-2006/CN:32-1161/S]

Issue:
2017年01期
Page:
149-155
Column:
研究论文
publishdate:
2017-01-31

Article Info:/Info

Title:
Synthesis and bioactivities evaluation of isolongifolanyl thiazole derivatives
Article ID:
1000-2006(2017)01-0149-07
Author(s):
RUI Jian1 CAI Tao1 YANG Jinlai1 YANG Yiqin2 XU Xu1 WANG Shifa1*
1.College of Chemical Engineering, Nanjing Forestry University, Jiangsu Co-Innovation Center of Efficient Process and Utilization of Forest Resources, Jiangsu Key Laboratory Biomass Green Fuels and Chemicals, Nanjing 210037, China;
2. College of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037, China
Keywords:
isolongifolanone isolongifolanyl thiosemicarbazide isolongifolanyl thiazole derivative antibacterial activity antitumor activity
Classification number :
TQ251
DOI:
10.3969/j.issn.1000-2006.2017.01.023
Document Code:
A
Abstract:
【Objective】This research is to construct the thiazole ring into the molecular skeleton of isolongifolanone for obtaining some new types of compounds with biological activity, developing the new application field and improving the utilization value of gum turpentine.【Method】Eleven novel isolongifolanyl thiazole derivatives(2a-2k)were synthesized by condensation and cyclization from isolongifolanone. Isolongifolanone was condensed with thiosemicarbazide to get the intermediate isolongifolanyl thiosemicarbazones, which was further cyclized with SymbolaA@-bromoacetophenone derivatives to obtain the compound 2a-2k. The structures of compound 2a-2k were characterized with FT-IR,1H NMR, 13C NMR, and HPLC-MS. The antimicrobial and antitumor activities of 2a-2k were investigated with minimum inhibitory concentrations assay(MIC)and MTT assay, respectively.【Result】The antibacterial activities of 4-(4-chlorophenyl)-2-(2-(1,1,5,5-tetramethyltetrahydro-1H-2,4SymbolaA@-methanonaphthalen-8-(2H,5H,8αH)-ylidene)hydrazinyl)thiazole(2b)and 4-(naphthalen-2-yl)-2-(2-(1,1,5,5-tetramethyl-tetrahydro-1H-2,4SymbolaA@-methanonaphthalen-8(2H,5H,8αH)-ylidene)hydrazinyl)thiazole(2j)were better than that of others against Bacillus subtilis and Pseudomonas fluorescens, and their MIC were 7.5 μg/mL. The antibacterial activity of compound 2b was better than that of others against fungus, and its MIC values against Candida albicans and Candida tropicalis was 15.6 μg/mL. It was also found that the antitumor activities of isolongifolanyl thiosemicarbazide against HepG2 was the best than that of its cyclized derivatives, and its IC50 was(34.5±0.8)μg/mL which was at the same level with that of the standard sample etoposide.【Conclusion】Isolongifolanyl thiosemicarbazide has the potential to be a new drug against HepG2 and deserves further research.

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Last Update: 2017-01-30