Cytotoxic 1,3-Thiazole and 1,2,4-Thiadiazole Alkaloids from Penicillium oxalicum: Structural Elucidation and Total Synthesis

被引:22
|
作者
Yang, Zheng [1 ]
Huang, Nianyu [1 ]
Xu, Bang [1 ,2 ,3 ]
Huang, Wenfeng [4 ]
Xie, Tianpeng [1 ]
Cheng, Fan [1 ]
Zou, Kun [1 ]
机构
[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China
[2] China Three Gorges Univ Peoples Hosp, Yichang 443000, Peoples R China
[3] Yichang First Peoples Hosp, Yichang 443000, Peoples R China
[4] China Three Gorges Univ, Coll Med, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China
基金
中国国家自然科学基金;
关键词
Penicillium oxalicum; alkaloids; total synthesis; structure elucidation; cytotoxicity; IMMUNOSUPPRESSIVE POLYKETIDES; DALDINIA-ESCHSCHOLZII; MYXOCOCCUS-FULVUS; FUNGUS; 1,3,4-THIADIAZOLE; INHIBITORS; GLUCOSIDE; CANCER; ANALOG;
D O I
10.3390/molecules21030232
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Two new thiazole and thiadiazole alkaloids, penicilliumthiamine A and B (2 and 3), were isolated from the culture broth of Penicillium oxalicum, a fungus found in Acrida cinerea. Their structures were elucidated mainly by spectroscopic analysis, total synthesis and X-ray crystallographic analysis. Biological evaluations indicated that compound 1, 3a and 3 exhibit potent cytotoxicity against different cancer cell lines through inhibiting the phosphorylation of AKT/PKB (Ser 473), one of important cancer drugs target.
引用
收藏
页数:12
相关论文
共 50 条
  • [31] Advances in the synthesis and recent therapeutic applications of 1,2,4-thiadiazole heterocycles
    Castro, A
    Castaño, T
    Encinas, A
    Porcal, W
    Gil, C
    BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) : 1644 - 1652
  • [32] Design, Synthesis and Anticancer Activity of 1,2,4-Thiadiazole Derivatives Bearing 1,2,4-Oxadiazole
    Sudhakar, D. G. S.
    Rao, A. Srinivasa
    Reddy, Ch Venkata Ramana
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (08) : 1696 - 1701
  • [33] Synthesis of Some Novel 1,3,4- and 1,2,4-Thiadiazole Derivatives
    Durust, Yasar
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (11) : 2923 - 2935
  • [34] SYNTHESIS OF NEW 1,2,4-THIADIAZOLE AND 1,3,4-THIADIAZOLE BASED ACYCLIC NUCLEOSIDE ANALOGS WITH POTENTIAL ANTICANCER AND ANTIVIRAL ACTIVITY
    PARKANYI, C
    YUAN, HL
    CHO, NS
    JAW, JHJ
    WOODHOUSE, TE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 279 - ORGN
  • [35] Synthesis and antimicrobial evaluation of some 1,3-thiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazine derivatives including a 5-(benzofuran-2-yl)-1-phenylpyrazole moiety
    Bakr F. Abdel-Wahab
    Hatem A. Abdel-Aziz
    Essam M. Ahmed
    Monatshefte für Chemie - Chemical Monthly, 2009, 140 : 601 - 605
  • [36] Synthesis and antimicrobial evaluation of some 1,3-thiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazine derivatives including a 5-(benzofuran-2-yl)-1-phenylpyrazole moiety
    Abdel-Wahab, Bakr F.
    Abdel-Aziz, Hatem A.
    Ahmed, Essam M.
    MONATSHEFTE FUR CHEMIE, 2009, 140 (06): : 601 - 605
  • [37] Chromatographic and electrophoretic determination of thioamides based on thiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and tetrazole
    Chernov'yants, M. S.
    Aleshina, N. V.
    Burykin, I. V.
    JOURNAL OF ANALYTICAL CHEMISTRY, 2011, 66 (03) : 280 - 284
  • [38] Chromatographic and electrophoretic determination of thioamides based on thiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and tetrazole
    M. S. Chernov’yants
    N. V. Aleshina
    I. V. Burykin
    Journal of Analytical Chemistry, 2011, 66
  • [39] Synthesis of polyazaheterocycles containing linearly bound 1,2,4-thiadiazole using enaminones
    Shikhaliev, Kh S.
    Romanov, P. S.
    Shestakov, A. S.
    Stolpovskaya, N. V.
    Krysin, M. Yu.
    Potapov, A. Yu.
    Proshin, A. N.
    RUSSIAN CHEMICAL BULLETIN, 2016, 65 (04) : 1008 - 1012
  • [40] Synthesis and cytotoxicity studies of new 1,2,4-thiadiazole derivatives and their zinc complexes
    Trofimova, Tatiana P.
    Chikunov, Fedor S.
    Proshin, Alexey N.
    Borodkov, Alexey S.
    Orlova, Marina A.
    MENDELEEV COMMUNICATIONS, 2023, 33 (02) : 201 - 202