N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

被引：0
|
作者：
Langer, Peter [1 ]
机构：
[1] Univ Rostock, Inst Chem, Albert Einstein Str 3a, D-18059 Rostock, Germany
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 20卷
关键词：
cancerostatic activity; carbohydrates; heterocycles; N; -glycosides; indirubin; KINASE INHIBITORY POTENCIES; OXYGEN SPECIES ROS; ANTIPROLIFERATIVE ACTIVITY; 1ST SYNTHESIS; STREPTOMYCES SP; CELL-CULTURE; DERIVATIVES; MELANOMA; AKASHIN; DEATH;
D O I：
10.3762/bjoc.20.240
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Indigo, indirubin, and isoindigo derivatives have been used for centuries as pigments. Since the 1990s, a new aspect of the chemistry of this type of compounds is their activity against various types of cancer. N-Glycosides of indigo, indirubin, and isoindigo, blue, red, and yellow sugars, turned out to be of special interest because of their high cancerostatic activity and structural novelty. The present article provides an account on the synthesis and anticancer activity of these compounds.
引用
收藏
页码：2840 / 2869
页数：30
相关论文
共 30 条
  • [1] First synthesis of indirubin N-glycosides (red sugars)
    Libnow, Stefanie
    Hein, Martin
    Michalik, Dirk
    Langer, Peter
    TETRAHEDRON LETTERS, 2006, 47 (38) : 6907 - 6909
  • [2] Synthesis of the first deprotected indigo N-glycosides (blue sugars) by reductive glycosylation of dehydroindigo
    Hein, Martin
    Bich Phuong, Nguyen Thi
    Michalik, Dirk
    Goerls, Helmar
    Lalk, Michael
    Langer, Peter
    TETRAHEDRON LETTERS, 2006, 47 (32) : 5741 - 5745
  • [3] Indirubin N-glycosides inhibit important intracellular signalling pathways in malignant melanoma
    Schoenherr, M.
    Bhattacharya, A.
    Langer, P.
    Kunz, M.
    EXPERIMENTAL DERMATOLOGY, 2012, 21 (03) : e45 - e45
  • [4] Ferrier-Type N-Glycosylation: Synthesis of N-Glycosides of Enone Sugars
    Ding, Feiqing
    William, Ronny
    Liu, Xue-Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03): : 1293 - 1299
  • [5] Synthesis of Thia-Analogous Indirubin N-Glycosides and their Influence on Melanoma Cell Growth and Apoptosis
    Kunz, Manfred
    Driller, Katrin M.
    Hein, Martin
    Libnow, Stephanie
    Hohensee, Ina
    Ramer, Robert
    Hinz, Burkhard
    Berger, Anja
    Eberle, Juergen
    Langer, Peter
    CHEMMEDCHEM, 2010, 5 (04) : 534 - 539
  • [6] The First N-Glycosylated Indoxyls and Their Application to the Synthesis of Indirubin-N-glycosides (Purple Sugars)
    Libnow, Stefanie
    Hein, Martin
    Langer, Peter
    SYNLETT, 2009, (02) : 221 - 224
  • [7] Synthesis and biological activity of high-molecular N-glycosides
    Shul'tsev, A. L.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2015, 85 (10) : 2361 - 2365
  • [8] Synthesis and biological activity of high-molecular N-glycosides
    A. L. Shul’tsev
    Russian Journal of General Chemistry, 2015, 85 : 2361 - 2365
  • [9] Synthesis of nonionic surfactants with azole ring bearing N-glycosides and their antibacterial activity
    Brahimi, Fawzia Taieb
    Belkadi, Mohamed
    Othman, Adil A.
    ARABIAN JOURNAL OF CHEMISTRY, 2017, 10 : S1690 - S1698
  • [10] A Sensitive LC-MS/MS Method for the Simultaneous Determination of Two Thia-Analogous Indirubin N-Glycosides and Indirubin-3′-Monoxime in Plasma and Cell Culture Medium
    Fischle, Alica
    Schwarz, Rico
    Wendt, Franziska
    Kordt, Marcel
    Ramer, Robert
    Boeckmann, Lars
    Hein, Martin
    Langer, Peter
    Emmert, Steffen
    Vollmar, Brigitte
    Hinz, Burkhard
    MOLECULES, 2022, 27 (09):
123