Synthesis and Cytotoxic Activity of Pentacyclic Triterpenoid Sulfamates

被引:23
|
作者
Sommerwerk, Sven [1 ]
Heller, Lucie [1 ]
Csuk, Rene [1 ]
机构
[1] Univ Halle Wittenberg, Bereich Organ Chem, D-06120 Halle, Saale, Germany
关键词
Carbamoylsulfamates; Cytotoxic activity; Triterpenoids; Sulfamates; CARBONIC-ANHYDRASE INHIBITORS; EPITHELIAL-CELL LINE; ANTICANCER AGENTS; STEROID SULFATASE; ANTIPROLIFERATIVE SAR; ANTITUMOR AGENTS; MASLINIC ACID; ISOZYME-IX; APOPTOSIS; 2-METHOXYESTRADIOL-BIS-SULFAMATE;
D O I
10.1002/ardp.201400297
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Methyl triterpenoates derived from oleanolic, ursolic, betulinic, glycyrrhetinic, platanic, or maslinic acid were converted into their corresponding sulfamates and carbamoylsulfamates. The sulfamates were screened in photometric sulforhodamine assays for cytotoxic activity employing several human tumor cell lines. Many of the compounds showed EC50 values in one-digit mu M concentration. Of special interest seems methyl (3 beta) 3-(aminosulfonyloxy)-11-oxo-oleanoate (18) showing good cytotoxicity for the human adenocarcinomic alveolar basal epithelial cell line A549 while being less toxic for non-malignant NIH 3T3 mouse fibroblasts.
引用
收藏
页码:46 / 54
页数:9
相关论文
共 50 条
  • [41] Synthesis and Biological Activity of a Novel Pentacyclic Heterocycle
    Das, Biswanath
    Satyakumar, Avula
    Ravikanth, Bommena
    Rao, Bommena Vittal
    Raju, Tuniki Venugopal
    Siddhardha, Busi
    Murty, Upadyayula Suryanaryana
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (02) : 430 - 434
  • [42] THE CONSTITUTION OF ALNUSENONE (GLUTINONE), A NEW TYPE OF PENTACYCLIC TRITERPENOID
    SPRING, FS
    BEATON, JM
    STEVENSON, R
    STEWART, JL
    CHEMISTRY & INDUSTRY, 1956, (39) : 1054 - 1056
  • [43] Synthesis of New C-2 Triazole-Linked Analogs of Triterpenoid Pentacyclic Saponins
    A. Yu. Spivak
    Z. R. Galimshina
    D. A. Nedopekina
    V. N. Odinokov
    Chemistry of Natural Compounds, 2018, 54 : 315 - 323
  • [44] Biodegradation of lantadene a, the pentacyclic triterpenoid hepatotoxin by Pseudomonas pickettii
    Biochemistry Laboratory, Indian Veterinary Research Institute, Regional Station, Palampur, India
    不详
    不详
    不详
    LETT. APPL. MICROBIOL., 4 (229-232):
  • [45] CHOLESTEROL INHIBITION OF PENTACYCLIC TRITERPENOID BIOSYNTHESIS IN TETRAHYMENA PYRIFORMIS
    CONNER, RL
    LANDREY, JR
    BURNS, CH
    MALLORY, FB
    JOURNAL OF PROTOZOOLOGY, 1968, 15 (03): : 600 - &
  • [46] Pentacyclic triterpenoid esters from the fruits of Bruguiera cylindrica
    Laphookhieo, S
    Karalai, C
    Ponglimanont, C
    Chantrapromma, K
    JOURNAL OF NATURAL PRODUCTS, 2004, 67 (05): : 886 - 888
  • [47] Pentacyclic triterpenoid glycosyl esters from Rubus pileatus
    Wang, BG
    Shen, XM
    Yang, L
    Jia, ZJ
    PHYTOCHEMISTRY, 1997, 46 (03) : 559 - 563
  • [48] Biodegradation of lantadene A, the pentacyclic triterpenoid hepatotoxin by Pseudomonas pickettii
    Sharma, OP
    Dawra, RK
    Datta, AK
    Kanwar, SS
    LETTERS IN APPLIED MICROBIOLOGY, 1997, 24 (04) : 229 - 232
  • [50] ZIZYBERANALIC ACID, A PENTACYCLIC TRITERPENOID OF ZIZYPHUS-JUJUBA
    KUNDU, AB
    BARIK, BR
    MONDAL, DN
    DEY, AK
    BANERJI, A
    PHYTOCHEMISTRY, 1989, 28 (11) : 3155 - 3158