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 26 条
  • [1] Current drug development portfolio for antimalarial therapies
    Biagini, GA
    O'Neill, PM
    Bray, PG
    Ward, SA
    [J]. CURRENT OPINION IN PHARMACOLOGY, 2005, 5 (05) : 473 - 478
  • [2] Relationship between antimalarial activity and heme alkylation for spiro- and dispiro-1,2,4-trioxolane antimalarials
    Creek, Darren J.
    Charman, William N.
    Chiu, Francis C. K.
    Prankerd, Richard J.
    Dong, Yuxiang
    Vennerstrom, Jonathan L.
    Charman, Susan A.
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2008, 52 (04) : 1291 - 1296
  • [3] Antimalarial activity of betulinic acid and derivatives in vitro against Plasmodium falciparum and in vivo in P-berghei-infected mice
    de Sa, Matheus Santos
    Oliveira Costa, Jose Fernando
    Krettli, Antoniana Ursine
    Zalis, Mariano Gustavo
    de Azevedo Maia, Gabriela Lemos
    Fechine Sette, Ivana Maria
    Camara, Celso de Amorim
    Barbosa Filho, Jose Maria
    Giulietti-Harley, Ana Maria
    dos Santos, Ricardo Ribeiro
    Pereira Soares, Milena Botelho
    [J]. PARASITOLOGY RESEARCH, 2009, 105 (01) : 275 - 279
  • [4] Bioactive peroxides as potential therapeutic agents
    Dembitsky, Valery M.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (02) : 223 - 251
  • [5] The Structure-Activity Relationship of the Antimalarial Ozonide Arterolane (OZ277)
    Dong, Yuxiang
    Wittlin, Sergio
    Sriraghavan, Kamaraj
    Chollet, Jacques
    Charman, Susan A.
    Charman, William N.
    Scheurer, Christian
    Urwyler, Heinrich
    Tomas, Josefina Santo
    Snyder, Christopher
    Creek, Darren J.
    Morizzi, Julia
    Koltun, Maria
    Matile, Hugues
    Wang, Xiaofang
    Padmanilayam, Maniyan
    Tang, Yuanqing
    Dorn, Arnulf
    Brun, Reto
    Vennerstrom, Jonathan L.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (01) : 481 - 491
  • [6] Structure-Activity Relationship Study of Betulinic Acid, A Novel and Selective TGR5 Agonist, and Its Synthetic Derivatives: Potential Impact in Diabetes
    Genet, Cedric
    Strehle, Axelle
    Schmidt, Celine
    Boudjelal, Geoffrey
    Lobstein, Annelise
    Schoonjans, Kristina
    Souchet, Michel
    Auwerx, Johan
    Saladin, Regis
    Wagner, Alain
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (01) : 178 - 190
  • [7] N-methoxy-1,2,4-dioxazolidines by ozonolysis reactions
    Griesbaum, K
    Liu, XJ
    Henke, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) : 1086 - 1089
  • [8] Antitumour and antimalarial activity of artemisinin-acridine hybrids
    Jones, Michael
    Mercer, Amy E.
    Stocks, Paul A.
    La Pensee, Louise J. I.
    Cosstick, Rick
    Park, B. Kevin
    Kennedy, Miriam E.
    Piantanida, Ivo
    Ward, Stephen A.
    Davies, Jill
    Bray, Patrick G.
    Rawe, Sarah L.
    Baird, Jonathan
    Charidza, Tafadzwa
    Janneh, Omar
    O'Neill, Paul M.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (07) : 2033 - 2037
  • [9] Synthesis of new olean-18(19)-ene derivatives from allobetulin
    Kazakova, O. B.
    Khusnutdinova, E. F.
    Tolstikov, G. A.
    Suponitsky, K. Yu.
    [J]. RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2010, 36 (04) : 512 - 515
  • [10] A one-step approach to the synthesis of germanicane triterpenoids from allobetulin
    Kazakova, O. B.
    Tolstikov, G. A.
    Suponitskii, K. Yu.
    [J]. RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2010, 36 (01) : 133 - 135
123