A facile and convenient synthesis of novel imidazo[1,2-b] isoxazoles and their Mannich bases as potential biodynamic agents

被引:6
作者
Rajanarendar, E. [1 ]
Thirupathaiah, K. [1 ]
Ramakrishna, S. [1 ]
Nagaraju, D. [1 ]
机构
[1] Kakatiya Univ, Dept Chem, Warangal 506009, TS, India
关键词
Imidazo[1,2-b]isoxazoles; 2-Amines; Mannich bases; IN-VITRO; BINDING;
D O I
10.1016/j.cclet.2015.07.024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of novel imidazo[1,2-b]isoxazoles 3 and their Mannich bases 4-6 were synthesized via convenient reactions. The reaction of 3-aminoisoxazole 1 with substituted phenacyl bromides 2 in dry ethanol afforded the corresponding 6-methyl-3-aryl imidazo[1,2-b]isoxazoles 3 in good yields. Compounds 3 on treatment with 37% formaline and secondary amines furnished the corresponding novel Mannich bases viz., 6-methyl-3-aryl-2-(morpholine/pyrrolidin-1-yl/piperidin-1-yl)-methyl-imidazo[1,2-b]isoxazoles 4-6. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:1511 / 1513
页数:3
相关论文
共 27 条
  • [1] Batchelor T., 2000, LANCET, V355, P354
  • [2] Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin
    Bellina, Fabio
    Cauteruccio, Silvia
    Monti, Susanna
    Rossi, Renzo
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (22) : 5757 - 5762
  • [3] Synthesis of substituted aryloxy alkyl and aryloxy aryl alkyl imidazoles as antileishmanial agents
    Bhandari, Kalpana
    Srinivas, Nagarapu
    Marrapu, Vijay K.
    Verma, Aditya
    Srivastava, Saumya
    Gupta, Suman
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (01) : 291 - 293
  • [4] Parallel synthesis of substituted imidazoles from 1,2-aminoalcohols
    Bleicher, KH
    Gerber, F
    Wüthrich, Y
    Alanine, A
    Capretta, A
    [J]. TETRAHEDRON LETTERS, 2002, 43 (43) : 7687 - 7690
  • [5] Chemicals M. T., 1994, SEIYAKU KOGYOO, V6, P146
  • [6] A Fast and Highly Efficient Protocol for Reductive Amination of Aromatic Aldehydes Using NaBH4 and Isoxazole Amines in an Ionic Liquid Medium
    Eligeti, Rajanarendar
    Atthunuri, Siva Rami Reddy
    Samala, Raju
    Shaik, Firoz Pasha
    Kundur, Govardhan Reddy
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (04) : 769 - 772
  • [7] Eugster C.H., 1969, PROG CHEM ORG NAT PR, V27, P261
  • [8] Friedman HS, 2000, CLIN CANCER RES, V6, P2585
  • [9] CHARACTERIZATION OF THE PHYSICOCHEMICAL PROPERTIES OF THE IMIDAZOPYRIDINE DERIVATIVE ALPIDEM - COMPARISON WITH ZOLPIDEM
    GEORGES, GJ
    VERCAUTEREN, DP
    EVRARD, GH
    DURANT, FV
    GEORGE, PG
    WICK, AE
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (04) : 323 - 335
  • [10] Getal J, 1975, ANTIBIOTICS-BASEL, V28, P91