• 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国中文核心期刊
  • 中国科学引文数据库核心期刊
Advanced Search
MOU Yi, CHEN Tong, HUANG Zhangjian, LAI Yisheng, PENG Sixun, JI Hui, ZHANG Yihua. Design, synthesis and anti-inflammatory evaluation of CDDO-Me ester prodrugs[J]. Journal of China Pharmaceutical University, 2016, 47(6): 661-665. DOI: 10.11665/j.issn.1000-5048.20160605
Citation: MOU Yi, CHEN Tong, HUANG Zhangjian, LAI Yisheng, PENG Sixun, JI Hui, ZHANG Yihua. Design, synthesis and anti-inflammatory evaluation of CDDO-Me ester prodrugs[J]. Journal of China Pharmaceutical University, 2016, 47(6): 661-665. DOI: 10.11665/j.issn.1000-5048.20160605
shu

Design, synthesis and anti-inflammatory evaluation of CDDO-Me ester prodrugs

More Information
    Graphical Abstract
    • Abstract
  • In order to search for new anti-inflammatory agents with strong activity and less toxicity relative to CDDO-Me, the ester prodrugs 2 - 8 of CDDO-Me were synthesized by treatment of oleanolic acid(OA)with DMF/K2CO3 to generate 1 , followed by esterification of 1 with various aliphatic and aromatic carboxylic acids, respectively. All the target compounds showed strong inhibitory effects on LPS-induced NO production in RAW 264. 7 cells. Among them, compounds 2 and 7 possessed the most potent inhibitory effects with IC50=(2. 34±0. 67)and(3. 83±0. 97)nmol/L, respectively. Moreover, MTT assay indicated that all the target compounds( 2 - 8 )displayed much weaker anti-proliferative activity against RAW 264. 7 cell lines than CDDO-Me, suggesting that they may be less toxic than CDDO-Me.
    • FullText(HTML)
    • References (8)
  • [1]
    Johansson MH.Reversible michael additions:covalent inhibitors and prodrugs[J].Mini Rev Med Chem,2012,12(13):1330-1344.
    [2]
    Shi BL,Greaney MF.Reversible Michael addition of thiols as a new tool for dynamic combinatorial chemistry[J].Chem Commun,2005(7):886-888.
    [3]
    You R,Long W,Lai Z,et al.Discovery of a potential anti-inflammatory agent:3-oxo-29-noroleana-1,9(11),12-trien-2,20-dicarbonitrile[J].J Med Chem,2013,56(5):1984-1995.
    [4]
    Liby KT,Sporn MB.Synthetic oleanane triterpenoids:multifunctional drugs with a broad range of applications for prevention and treatment of chronic disease[J].Pharmacol Rev,2012,64(4):972-1003.
    [5]
    Sporn MB,Liby KT,Yore MM,et al.New synthetic triterpenoids:potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress[J].J Nat Prod,2011,74(3):537-545.
    [6]
    Ding Y,Huang ZJ,Yin J,et al.DDQ-promoted dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones by a radical ion mechanism[J].Chem Commun,2011,47(33):9495-9497.
    [7]
    de Zeeuw D,Akizawa T,Audhya P,et al.Bardoxolone methyl in type 2 diabetes and stage 4 chronic kidney disease[J].N Engl J Med,2013,369(26):2492-2503.
    [8]
    Honda T, Rounds BV, Bore L, et al. Synthetic oleanane and ursane triterpenoids with modified rings A and C:a series of highly active inhibitors of nitric oxide production in mouse macrophages[J].J Med Chem,2000,43(22):4233-4246.
    • Related Articles

  • Related Articles

    [1]LI Linzhen, WEI Xi, LIU Lu, LI Yongjun, LIANG Jingyu. Chemical constituents from the stems of Clerodendrum trichotomum Thunb.[J]. Journal of China Pharmaceutical University, 2019, 50(5): 544-548. DOI: 10.11665/j.issn.1000-5048.20190506
    [2]LIN Qinghua, XU Jian, FENG Feng. Chemical constituents from the stems of Picrasma quassioides Bennet[J]. Journal of China Pharmaceutical University, 2017, 48(6): 675-679. DOI: 10.11665/j.issn.1000-5048.20170607
    [3]XU Yunhui, JIANG Xueyang, XU Jian, JIANG Renwang, ZHANG Jie, XIE Zijian, FENG Feng. Chemical constituents from Callicarpa kwangtungensis Chun[J]. Journal of China Pharmaceutical University, 2016, 47(3): 299-302. DOI: 10.11665/j.issn.1000-5048.20160309
    [4]MA Lin, ZHANG Rongfei, YU Shule, WU Zhengfeng, ZHAO Shouxun, Wang Lei, YE Wencai, ZHANG Jian, YIN Zhiqi. Chemical constituents of Fructus Gleditsiae Abnormalis[J]. Journal of China Pharmaceutical University, 2015, 46(2): 188-193. DOI: 10.11665/j.issn.1000-5048.20150209
    [5]LI Linzhen, WANG Menghua, SUN Jianbo, LIANG Jingyu. Chemical constituents from Aletris spicata[J]. Journal of China Pharmaceutical University, 2014, 45(2): 175-177. DOI: 10.11665/j.issn.1000-5048.20140208
    [6]CHANG Bo, XIAO Linjing, ZHANG Jian, ZHAO Shouxun, YE Wencai, YIN Zhiqi. Chemical constituents from Abies ernestii var.salouenensis[J]. Journal of China Pharmaceutical University, 2014, 45(1): 43-47. DOI: 10.11665/j.issn.1000-5048.20140107
    [7]LI Jiu-hui, CHEN Guang-ying, HAN Chang-ri, MO Zheng-rong, SONG Xiao-ping. Chemical constituents from the stems of Vatica mangachpoi Blanco[J]. Journal of China Pharmaceutical University, 2012, 43(1): 25-27.
    [8]SUN Jing, YIN Zhi-qi, ZHANG Qing-wen, YE Wen-cai, WANG Yi-ta, ZHAO Shou-xun. Chemical constituents from ethyl acetate extract of Ganoderma lucidum[J]. Journal of China Pharmaceutical University, 2011, 42(3): 220-222.
    [9]Chemical constituents from n-butanol extract of the stems of Lonicera japonica[J]. Journal of China Pharmaceutical University, 2010, 41(4): 333-336.
    [10]Chemical constituents from Senecio nemorensis.[J]. Journal of China Pharmaceutical University, 2010, 41(1): 26-28.

Catalog

    Get Citation
    PDF
    XML
    Article views (969) PDF downloads (1267) Cited by()
    Turn off MathJax
    Article Contents
    Abstract
    References
    Related Articles

    Copyright © Journal of China Pharmaceutical University苏ICP备12050101号-2

    Address：24 Tongjia Lane, Nanjing City, Jiangsu Province （210009）Tel: 025-83271566E-mail: xuebao@cpu.edu.cn

    Supported by: Beijing Renhe Information Technology Co., Ltd.  Baidu Analytics

    Total visits：292644

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return