Theoretical conformational study of 1,2,4-trioxane molecule and its halogenated derivatives

被引：1
|
作者：
Jorge, N
Gómez-Vara, ME
Cafferata, LFR
Castro, EA
机构：
[1] Natl Univ La Plata, Fac Ciencias Exactas, Dept Quim, CEQUINOR, RA-1900 La Plata, Argentina
[2] UNNE, Fac Ciencias Exactas, FACENA, Area Fisicoquim, RA-3400 Corrientes, Argentina
[3] Natl Univ La Plata, Fac Ciencias Exactas, Dept Quim, Lab LADECOR, RA-1900 La Plata, Argentina
来源：
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2000年 / 530卷 / 1-2期
关键词：
1,2,4-trioxane; conformational study; molecular orbital method;
D O I：
10.1016/S0166-1280(00)00321-3
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A conformational study of 1,2,4-trioxane molecule and several halogenated derivatives was performed via the AM 1 and PM3 semiempirical molecular orbital methods. Results are analyzed in a comparative fashion and discussed considering available experimental data. Different factors determining molecular stability of preferred conformations are pointed out in order to explain their respective contributions. (C) 2000 Elsevier Science B.V. All rights reserved.
引用
收藏
页码：137 / 147
页数：11
相关论文
共 50 条
  • [31] Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore
    O'Neill, PM
    Mukhtar, A
    Ward, SA
    Bickley, JF
    Davies, J
    Bachi, MD
    Stocks, PA
    ORGANIC LETTERS, 2004, 6 (18) : 3035 - 3038
  • [32] An Asymmetric Synthesis of 1,2,4-Trioxane Anticancer Agents via Desymmetrization of Peroxyquinols through a Bronsted Acid Catalysis Cascade
    Rubush, David M.
    Morges, Michelle A.
    Rose, Barbara J.
    Thamm, Douglas H.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13554 - 13557
  • [33] Spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane pairs: Relationship between peroxide bond iron(II) reactivity, heme alkylation efficiency, and antimalarial activity
    Wang, Xiaofang
    Creek, Darren J.
    Schiaffo, Charles E.
    Dong, Yuxiang
    Chollet, Jacques
    Scheurer, Christian
    Wittlin, Sergio
    Charman, Susan A.
    Dussault, Patrick H.
    Wood, James K.
    Vennerstrom, Jonathan L.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (16) : 4542 - 4545
  • [34] Comparison between antimalarial spiroadmantyl 1,2,4-trioxane and 1,2,4-trioxolane pairs: Important balance between chemical reactivity and steric enviroment of the peroxide bond
    Wang, XF
    Dong, YX
    Wittlin, S
    Vennerstrom, JL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U2617 - U2617
  • [35] A technical note on the semi-empirical treatment of trans-3,6-dimethoxy-1,2,4-trioxane
    Jalbout, AF
    ACTA CHIMICA SLOVENICA, 2002, 49 (03) : 643 - 648
  • [36] Design, synthesis, derivatization, and structure-activity relationships of simplified, tricyclic, 1,2,4-trioxane alcohol analogues of the antimalarial artemisinin
    Cumming, JN
    Wang, DS
    Park, SB
    Shapiro, TA
    Posner, GH
    JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) : 952 - 964
  • [37] 1,2,3-Triazole tethered 1,2,4-trioxane trimer induces apoptosis in metastatic cancer cells and inhibits their proliferation, migration and invasion
    Khongsti, Kitboklang
    Pasupuleti, Bala Gangadhar
    Das, Bidyadhar
    Bez, Ghanashyam
    BIOORGANIC CHEMISTRY, 2021, 112
  • [38] Theoretical Study of Tautomeric Conformations for 1,2,4-Triazole Derivatives
    Mahboub, Radia
    ORBITAL-THE ELECTRONIC JOURNAL OF CHEMISTRY, 2021, 13 (01): : 33 - 38
  • [39] COMPUTATIONAL STUDIES OF THE STRUCTURES AND PROPERTIES OF POTENTIAL ANTIMALARIAL COMPOUNDS BASED ON THE 1,2,4-TRIOXANE RING STRUCTURE .1. ARTEMISININ-LIKE MOLECULES
    BERNARDINELLI, G
    JEFFORD, CW
    MARIC, D
    THOMSON, C
    WEBER, J
    INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 1994, : 117 - 131
  • [40] THEORETICAL CONFORMATIONAL STUDY OF ANISOLE MOLECULE
    BERGES, J
    PERRIN, H
    JOURNAL DE CHIMIE PHYSIQUE ET DE PHYSICO-CHIMIE BIOLOGIQUE, 1981, 78 (7-8) : 573 - 576
12345