Synthesis of triterpenoid-based 1,2,4-trioxolanes and 1,2,4-dioxazolidines by ozonolysis of allobetulin derivatives

被引：38
|
作者：
Kazakova, Oxana B. [1 ]
Kazakov, Dmitri V. [1 ]
Yamansarov, Emil Yu. [1 ]
Medvedeva, Natal'ya I. [1 ]
Tolstikov, Genrikh A. [1 ]
Suponitsky, Kyrill Yu. [2 ]
Arkhipov, Dmitri E. [2 ]
机构：
[1] Russian Acad Sci, Ufa Res Ctr, Inst Organ Chem, Ufa 450054, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 09期
基金：
俄罗斯基础研究基金会;
关键词：
Natural products; Triterpenoids; Betulin; Antimalarials; Peroxides; 1,2,4-Trioxolanes; 1,2,4-Dioxazolidines; Ozonolysis; ANTIMALARIAL ACTIVITY; QINGHAOSU ARTEMISININ; HEME ALKYLATION; BETULINIC ACID; PEROXIDES; DRUG; TRIOXANES;
D O I：
10.1016/j.tetlet.2010.12.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxidation of allobetulin derivatives with ozone results in good isolated yields of 1,2,4-trioxolanes and stable 1,2,4-dioxazolidines. Individual 3R,5R and 3S,5S diastereoisomers of allobetulin secondary ozonides were isolated and their structures confirmed by X-ray crystallographic analysis. Remarkable diastereoselectivity with formation of only the (3S,5S)-configured peroxides was observed during the oxidation of 1,5-di-O-methoxyoximinoallobetulin to dioxazolidines. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：976 / 979
页数：4
相关论文
共 50 条
  • [31] Bridged 1,2,4-Trioxolanes: SnCl4-Catalyzed Synthesis and an In Vitro Study against S. mansoni
    Radulov, Peter S.
    Yaremenko, Ivan A.
    Keiser, Jennifer
    Terent'ev, Alexander O.
    MOLECULES, 2023, 28 (13):
  • [32] The structure of antimalarial dispiro-1,2,4-trioxolanes: A density functional approach
    Moroni, L
    Salvi, PR
    CHEMICAL PHYSICS LETTERS, 2006, 419 (1-3) : 75 - 80
  • [33] Weak base dispiro-1,2,4-trioxolanes: Potent antimalarial ozonides
    Tang, Yuanqing
    Dong, Yuxiang
    Wittlin, Sergio
    Charman, Susan A.
    Chollet, Jacques
    Chiu, Francis C. K.
    Charman, William N.
    Matile, Hugues
    Urwyler, Heinrich
    Dorn, Arnulf
    Bajpai, Saroj
    Wang, Xiaofang
    Padmanilayam, Maniyan
    Karle, Jean M.
    Brun, Reto
    Vennerstrom, Jonathan L.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (05) : 1260 - 1265
  • [34] Kinetic parameters for the reaction of 1,2,4-trioxolanes and artemisinin with iron(II): New evidence for the source of antimalarial activity
    Lopes, Nicolas S.
    Ciscato, Luiz Francisco M. L.
    CHEMICAL BIOLOGY & DRUG DESIGN, 2018, 91 (01) : 328 - 331
  • [35] Syntheses of O-methylated-1,2,4-dioxazolidines by ozonolyses of O-methylated dioximes
    Lee, KR
    Lee, SE
    Huh, TS
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2000, 21 (10) : 1039 - 1040
  • [36] Synthesis of 1,2,4-dioxazolidine derivatives by the ozonolysis of indenes in the presence of primary amines
    Ushigoe, Y
    Satake, S
    Masuyama, A
    Nojima, M
    McCullough, KJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (13): : 1939 - 1942
  • [37] REGIOSELECTIVE SYNTHESIS OF 1,2,4-TRIAZOLE AND 1,2,4-OXADIAZOLE DERIVATIVES
    PEREZ, MA
    DORADO, CA
    SOTO, JL
    SYNTHESIS-STUTTGART, 1983, (06): : 483 - 486
  • [38] Recent Developments in Natural Product Inspired Synthetic 1,2,4-Trioxolanes (Ozonides): An Unusual Entry into Antimalarial Chemotherapy
    Tiwari, Mohit K.
    Yadav, Dharmendra K.
    Chaudhary, Sandeep
    CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2019, 19 (10) : 831 - 846
  • [39] Synthesis and insecticidal activity of 1,2,4-oxadiazole and 1,2,4-thiadiazole derivatives
    Suzuki, Jun
    Okamura, Daigo
    Gushikawa, Toru
    Hirai, Kenji
    Ando, Tetsu
    JOURNAL OF PESTICIDE SCIENCE, 2011, 36 (03) : 392 - 401
  • [40] SYNTHESIS OF 1,2,4-TRIAZOLES DERIVATIVES
    AZARYAN, AS
    IRADYAN, NS
    AROYAN, AA
    ARMYANSKII KHIMICHESKII ZHURNAL, 1975, 28 (09): : 709 - 714
12345