Investigations of regio- and stereoselectivities in the synthesis of cytotoxic isoxazolidines through 1,3-dipolar cycloadditions of nitrones to dipolarophiles bearing an allylic oxygen

被引：30
|
作者：
Singh, Rajinder
Bhella, Surinderjit Singh
Sexana, A. K.
Shanmugavel, M.
Faruk, Abdul
Ishar, M. P. S. [1 ]
机构：
[1] Guru Nanak Dev Univ, Dept Pharmaceut Sci, Bioorgan & Photochem Lab, Amritsar 143005, Punjab, India
[2] Reg Res Lab, Div Pharmacol, Jammu 184001, Jammu & Kashmir, India
来源：
TETRAHEDRON | 2007年 / 63卷 / 10期
关键词：
cycloadditions; nitrone; stereoselectivities; secondary interactions; isoxazolidines; anticancer activity;
D O I：
10.1016/j.tet.2006.12.076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regio- and stereoselectivities in cycloadditions of nitrones to dipolarophiles bearing an allylic oxygen, which furnishes substituted-isoxazolidine analogs of the furanose ring of nucleosides, have been investigated. Although the obtained regioselectivities are anticipated, a rationalization of the preferred formation of endo-cycloadducts necessitates the involvement of an allylic oxygen in secondary interaction. The obtained isoxazolidines display cytotoxic activities against a number of human cancer cell lines. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2283 / 2291
页数：9
相关论文
共 50 条
  • [21] Regio- and stereoselective synthesis of isoxazolidine derivatives by asymmetric 1,3-dipolar cycloaddition reaction of chiral nitrones with 1-propene-1,3-sultone
    Zhang, Hong-Kui
    Chan, Wing-Hong
    Lee, Albert W. M.
    Wong, Wai-Yeung
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (04) : 957 - 962
  • [22] Regio- and facial-selective effects of allylic heteroatoms in 1,3-dipolar cycloaddition of a nitrile oxide
    Kakisawa, Hiroshi, 1600, Chemical Society of Japan (63):
  • [23] SYNTHESIS OF TRIFLUOROMETHYL-SUBSTITUTED ISOXAZOLIDINES AND 4,5-DIHYDROISOXAZOLES BY 1,3-DIPOLAR CYCLOADDITIONS
    BRAVO, P
    BRUCHE, L
    MELE, A
    ZECCHI, G
    JOURNAL OF CHEMICAL RESEARCH-S, 1991, (04): : 81 - 81
  • [24] Chemo-, regio-, and stereoselectivity in 1,3-dipolar cycloaddition of piperine with nitrones. A cycloadditive route to aminoalcohols
    Wojtowicz-Rajchel, Hanna
    Kazmierczak, Marcin
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (15) : 6015 - 6025
  • [25] A theoretical investigation of the regio- and stereoselectivities of the 1,3-dipolar cycloaddition of C-diethoxyphosphoryl-N-methylnitrone with substituted alkenes
    Nacereddine, Abdelmalek Khorief
    Yahia, Wassila
    Bouacha, Samir
    Djerourou, Abdelhafid
    TETRAHEDRON LETTERS, 2010, 51 (19) : 2617 - 2621
  • [26] Regio- and enantioselective synthesis of novel functionalized pyranopyrrolidines by 1,3-dipolar cycloaddition of carbohydrates
    Bashiardes, G
    Cano, C
    Mauzé, B
    SYNLETT, 2005, (04) : 587 - 590
  • [27] Regio- and Stereoselectivity in 1,3-Dipolar Cycloadditions: Activation Strain Analyses for Reactions of Hydrazoic Acid with Substituted Alkenes
    Vilhena, Felipe S.
    Bickelhaupt, F. Matthias
    Carneiro, Jose W. M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (29) : 4313 - 4318
  • [28] Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Nitrones to Alkylidene Malonates: Highly Enantioselective Synthesis of Multisubstituted Isoxazolidines
    Chen, Donghui
    Wang, Zhen
    Li, Jiangting
    Yang, Zhigang
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (19) : 5226 - 5229
  • [29] THE REGIOSELECTIVE EFFECT OF THE ALLYLIC SILICON OR OXYGEN ATOM IN 1,3-DIPOLAR CYCLO-ADDITION OF NITRONES
    NIWAYAMA, S
    DAN, S
    INOUYE, Y
    KAKISAWA, H
    CHEMISTRY LETTERS, 1985, (07) : 957 - 960
  • [30] Enantioselective Synthesis of 4-Isoxazolines by 1,3-Dipolar Cycloadditions of Nitrones to Alkynals Catalyzed by Fluorodiphenylmethylpyrrolidines
    Aleman, Jose
    Fraile, Alberto
    Marzo, Leyre
    Ruano, Jose Luis Garcia
    Izquierdo, Cristina
    Diaz-Tendero, Sergio
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) : 1665 - 1671
12345