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
来源：
ARCHIV DER PHARMAZIE | 2015年 / 348卷 / 01期
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
  • [31] A pentacyclic triterpenoid possessing anti-inflammatory activity from the fruits of Dregea volubilis
    Biswas, M.
    Biswas, K.
    Ghosh, A. K.
    Haldar, P. K.
    PHARMACOGNOSY MAGAZINE, 2009, 5 (19) : 64 - 68
  • [32] ISOLATION OF A PENTACYCLIC TRITERPENOID ALCOHOL FROM A PROTOZOAN
    MALLORY, FB
    CONNER, RL
    GORDON, JT
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (09) : 1362 - &
  • [33] DUSTANIN - A NEW PENTACYCLIC TRITERPENOID AS A FUNGAL METABOLITE
    TSUDA, Y
    ISOBE, K
    TETRAHEDRON LETTERS, 1965, (37) : 3337 - &
  • [34] Design, synthesis and antitumor activity of pentacyclic triterpenoid ursolic acid derivatives and oleanolic acid derivatives based on multi-target
    Ma, Jun-Jiao
    Zhang, Liang-feng
    Xu, Dong-Ping
    Wang, Zan
    Meng, Yan-Qiu
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2025,
  • [35] THE FIRST EXAMPLES OF NONENZYMIC, BIOMIMETIC POLYENE PENTACYCLIZATIONS - TOTAL SYNTHESIS OF THE PENTACYCLIC TRITERPENOID SOPHORADIOL
    FISH, PV
    JOHNSON, WS
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09): : 2324 - 2335
  • [36] New Triterpenoid Saponins from Glochidion eriocarpum and Their Cytotoxic Activity
    Phan Van Kiem
    Vu Kim Thua
    Pham Hai Yen
    Nguyen Xuan Nhiem
    Nguyen Huu Tung
    Nguyen Xuan Cuong
    Chau Van Minh
    Hoang Thanh Huong
    Hyun, Jae-Hee
    Kang, Hee-Kyoung
    Kim, Young Ho
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (01) : 102 - 105
  • [37] Triterpenoid Saponins from the Roots of Clematis argentilucida and Their Cytotoxic Activity
    Zhao, Mei
    Ma, Ning
    Qiu, Feng
    Hai, Wen-Li
    Tang, Hai-Feng
    Zhang, Yan
    Wen, Ai-Dong
    PLANTA MEDICA, 2014, 80 (11) : 942 - 948
  • [38] A Pentacyclic Triterpene from Lippia origanoides HBK and its Cytotoxic Activity
    Kumar, Arvind
    Quintero Rueda, Elizabeth
    Rene Martinez, Jairo
    Elvira Ocazionez, Raquel
    Stashenko, Elena E.
    PHARMACOGNOSY MAGAZINE, 2020, 16 (05) : S513 - +
  • [39] 2-Hydroxydiplopterol, A New Cytotoxic Pentacyclic Triterpenoid from the Halotolerant Fungus Aspergillus variecolor B-17
    Wang, Wen-Liang
    Liu, Pei-Pei
    Zhang, Ya-Peng
    Li, Jing
    Tao, Hong-Wen
    Gu, Qian-Qun
    Zhu, Wei-Ming
    ARCHIVES OF PHARMACAL RESEARCH, 2009, 32 (09) : 1211 - 1214
  • [40] 2-Hydroxydiplopterol, a new cytotoxic pentacyclic triterpenoid from the halotolerant fungus Aspergillus variecolor B-17
    Wen-Liang Wang
    Pei-Pei Liu
    Ya-Peng Zhang
    Jing Li
    Hong-Wen Tao
    Qian-Qun Gu
    Wei-Ming Zhu
    Archives of Pharmacal Research, 2009, 32 : 1211 - 1214
12345