Synthesis of novel isoxazolo[2",3":1′,2′]pyrimido[4′,5′:4,5]pyrimido[6,1-b]quinazoline-8-ones and their in vitro anticancer and antimicrobial activities

被引:0
|
作者
Rajanarendar, E. [1 ]
Kishore, B. [1 ]
Ramakrishna, S. [1 ]
Nagaraju, D. [1 ]
Venkateshwarlu, P. [1 ]
机构
[1] Kakatiya Univ, Dept Chem, Warangal 506009, Andhra Pradesh, India
来源
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 2014年 / 53卷 / 10期
关键词
Isoxazolo[2 '',3 '':1 ',2 ']pyrimido[4 ',5 ':4,5]pyrimido[6,1-b]quinazoline-8-ones; one-pot synthesis; three-component reaction; anticancer activity; antimicrobial activity; INHIBITORS; DERIVATIVES; ANALOGS; DESIGN;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of novel isoxazolo[2 '',3 '': 1',2']pyrimido[4',5':4,5]pyrimido[6,1-b]quinazoline-8-ones 6a-j, has been achieved by reaction of 5-amino-2-methyl-7-phenyl-7H-isoxazolo[2,3-a] pyrimidin-6-yl cyanides 4, with dimethyl formamide dimethylacetal followed by treatment with anthranilic acids in situ in one-pot. The key intermediate, viz., 5-amino-2-methyl-7-phenyl-7H-isoxazolo[2,3-a]pyrimidin-6-yl cyanide 4 is obtained by reaction of 3-amino-5-methyl isoxazole with aromatic aldehydes and malononitrile by a three-component one-pot process. The newly synthesized compounds 6a-j have been evaluated for their in vitro anticancer and antimicrobial activity. Compounds 6e and 6f exhibit potent anticancer and antimicrobial activity comparable to that of standard drugs.
引用
收藏
页码:1275 / 1283
页数:9
相关论文
共 50 条
  • [31] SYNTHESIS OF "PYRIMIDO[4,5-E][1,4]OXAZEPIN-5-ONES
    SANTILLI, AA
    WANSER, SV
    KIM, DH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (02) : 309 - &
  • [32] SYNTHESIS OF 6-ARYLPYRIDO-[2',3'-4,5]PYRIMIDO-[1,6-A]BENZIMIDAZOLES
    REDDY, KV
    MOGILAIAH, K
    SREENIVASULU, B
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1984, 23 (11): : 1106 - 1107
  • [33] Synthesis of Some Novel Fused Pyrimido[4",5":5′,6′]- [1,2,4]triazino[3′,4′:3,4] [1,2,4]triazino[5,6-b]indoles with Expected Anticancer Activity
    Ali, Rania S.
    Saad, Hosam A.
    MOLECULES, 2018, 23 (03):
  • [34] Dimroth rearrangement in the synthesis of substituted cyclopentaand cyclohexa[4,5]thieno[2',3':4,5]pyrimido[1,6-b][1,2,4]triazines
    Kolomieitsev, Dmitriy O.
    Markov, Victor I.
    Varenichenko, Svetlana A.
    Astakhina, Valeriya O.
    Kovalenko, Sergiy I.
    Kharchenko, Alexandr V.
    Mazepa, Alexandr V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (07) : 498 - 502
  • [35] Dimroth rearrangement in the synthesis of substituted cyclopentaand cyclohexa[4,5]thieno[2',3':4,5]pyrimido[1,6-b][1,2,4]triazines
    Dmitriy O. Kolomieitsev
    Victor I. Markov
    Svetlana A. Varenichenko
    Valeriya O. Astakhina
    Sergiy I. Kovalenko
    Alexandr V. Kharchenko
    Alexandr V. Mazepa
    Chemistry of Heterocyclic Compounds, 2016, 52 : 498 - 502
  • [36] Synthesis, Antimicrobial, Anticancer Activities and DNA Cleavage Study of 2-Substituted Pyrimido[4,5-a]carbazoles
    Tamilarasan, B.
    Sangeetha, V
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 28 (04) : 487 - 494
  • [37] SYNTHESIS OF SOME 4H-PYRIMIDO[2,1-B]BENZOTHIAZOL-4-ONES
    ALAIMO, RJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (05) : 769 - 772
  • [38] Synthesis of novel derivatives of (benz)imidazo[2,1-b]pyrimido[4,5-d][1,3] thiazine
    Akbarzadeh, Marzieh
    Bakavoli, Mehdi
    Eshghi, Hossein
    Shiri, Ali
    JOURNAL OF CHEMICAL RESEARCH, 2017, (12) : 730 - 733
  • [39] SYNTHESIS OF NOVEL 1H-IMIDAZO[5,1-B][3]BENZAZEPINE-1,3(2H)-DIONE AND PYRIMIDO[6,1-B][3]BENZAZEPINE-1,3,4(2H)-TRIONE
    GALLASCHUN, RJ
    SCHNUR, RC
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (04) : 963 - 966
  • [40] Synthesis of thieno[2,3-b][1,6]naphthyridines and pyrimido[4′,5′:4,5] thieno[2,3-b][1,6]naphthyridines
    Abdel-Wadood, Fatma K.
    Abdel-Monem, Maisa I.
    Fahmy, Atiat M.
    Geies, Ahmed A.
    JOURNAL OF CHEMICAL RESEARCH, 2008, (02) : 89 - 94