Synthesis and characterization of new 2-amino-4-(3,4-dihydro-7-methoxy-2,2-dimethyl-2H-benzopyran-6-yl)-6-(substituted phenyl)pyrimidines and their bioevaluation

被引:1
|
作者
Murthy, Yellajyosula Lakshmi Narasimha [1 ]
Suhasini, Kilaru Padma [1 ]
Jha, Anjali [2 ]
机构
[1] Andhra Univ, Dept Organ Chem, Visakhapatnam, Andhra Pradesh, India
[2] GITAM Univ, Gitam Inst Sci, Dept Chem, Visakhapatnam, Andhra Pradesh, India
关键词
benzopyran; chalcones; Claisen-Schmidt condensation; 2-amino pyrimidine derivatives; antimicrobial activity; XYLOKETAL B PROTECTS; ACETYLENIC KETONES; NITROGEN; ANTIBACTERIAL; PYRIMIDINES; AGENTS;
D O I
10.2298/JSC110923008M
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of eight novel 2-amino-4-(3,4-dihydro-7-methoxy-2,2-dimethyl-2H-benzopyran-6-yl)-6-(substituted phenyl)pyrimidines were designed and synthesized by utilizing benzene-1,3-diol as the starting material. The structures of the isolated products (6a-h) were established through H-1-NMR, C-13-NMR, and FT-IR spectroscopic techniques and elemental analysis. The antimicrobial properties of the synthesized compounds were screened against gram positive (Bacillus pumilus, Bacillus subtilis and Streptococcus faecalis), gram negative bacteria (Enterococcus faecalis, Escherchia coli and Proteus vulgaris) and fungi (Pencillium expansum, Aspergillus niger and Candida albicans) using ampicillin and ketoconazole as reference compounds. Most of the compounds showed moderate to high antibacterial and antifungal activities against the studied strains, with inhibition zones between 8 and 30 mm.
引用
收藏
页码:859 / 866
页数:8
相关论文
共 50 条
  • [1] Synthesis and Characterization of Some New 2-Amino-4-(4′-substituted)-6-(4"-substituted)diphenyl Pyrimidines
    Hasan, Aurangzeb
    Khaleeq, Musfirah
    Riaz, Uzma
    ASIAN JOURNAL OF CHEMISTRY, 2010, 22 (07) : 5581 - 5587
  • [2] Synthesis and Antimicrobial Activity of Some 2-Amino-4-(7-Substituted/Unsubstituted Coumarin-3-yl)-6-(Chlorosubstitutedphenyl) Pyrimidines
    Imran, Mohd
    Abida
    Khan, Suroor Ahmad
    TROPICAL JOURNAL OF PHARMACEUTICAL RESEARCH, 2015, 14 (07) : 1265 - 1272
  • [3] Synthesis, Characterization, and Antimicrobial Evaluation of Some Novel 3′-(6-(Substituted Phenyl)-4-Phenyl-6H-1,3-Thiazine-2-yl)Spiro[Indoline-3,3′-Isothiazolidine]-2,4′-Dione Derivatives
    Srivastava, Krishna
    Singh, Raj Bahadur
    Srivastava, Abhishek
    Tiwari, Ram Prakash
    Srivastava, Jyoti
    Jahan, Asmat
    Bhargava, Prachi
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2023, 57 (7) : 992 - 1000
  • [4] Synthesis and antimicrobial screening of 5-(4,7-dimethyl-2-oxo-2H-benzopyran-6-ylazo)-2-methyl-6-morpholin-4-yl-2,3dihydro-3H-pyrimidin-4-oneand5-(4,7dimethyl-2-oxo-2H-benzopyran-6-ylazo)2-methyl-6-piperidin-1-yl-2,3-dihydro-3H-pyrimidin-4-one
    Mulwad, Vinata V.
    Mayekar, Sagar A.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2007, 46 (11): : 1873 - 1878
  • [5] Synthesis, Characterization, and Antimicrobial Evaluation of Some Novel 3′-(6-(Substituted Phenyl)-4-Phenyl-6H-1,3-Thiazine-2-yl)Spiro[Indoline-3,3′-Isothiazolidine]-2,4′-Dione Derivatives
    Krishna Srivastava
    Raj Bahadur Singh
    Abhishek Srivastava
    Ram Prakash Tiwari
    Jyoti Srivastava
    Asmat Jahan
    Prachi Bhargava
    Pharmaceutical Chemistry Journal, 2023, 57 : 992 - 1000
  • [6] A short synthesis of 5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid methyl ester
    Henry, GE
    Jacobs, H
    TETRAHEDRON, 2001, 57 (25) : 5335 - 5338
  • [7] Design, Synthesis and In Vitro Antimicrobial Activity of 6-(1H-Benzimidazol-2-yl)-3,5-dimethyl-4-oxo-2-thio-3,4-dihydrothieno[2,3-d]pyrimidines
    Vlasov, Sergiy V.
    Vlasova, Olena D.
    Severina, Hanna I.
    Krolenko, Konstantin Yu.
    Borysov, Oleksandr V.
    Abu Sharkh, Amjad Ibrahim M.
    Vlasov, Vitaliy S.
    Georgiyants, Victoriya A.
    SCIENTIA PHARMACEUTICA, 2021, 89 (04)
  • [8] SYNTHESIS AND BIOLOGICAL ACTIVITIES OF 3-{6-[3-(SUBSTITUTED PHENYL)1-PHENYL-1H-PYRAZOL-4-YL]-2-THIOXO-1,2,5,6-TETRAHYDROPYRIMIDIN-4YL}-2H-CHROMEN-2-ONES
    Goudgaon, N. M.
    Sheshikant, B. U.
    Dhage, Deepa
    HETEROCYCLIC LETTERS, 2012, 2 (02): : 154 - 161
  • [9] Synthesis and antimicrobial activity of some 2-Piperidinomethylamino-4-(7-H/substituted coumarin-3-yl)6-chlorosubstitutedphenyl pyrimidines
    Imran, Mohd
    Alam, Ozair
    Abida
    TROPICAL JOURNAL OF PHARMACEUTICAL RESEARCH, 2016, 15 (09) : 1955 - 1965
  • [10] (4R,7S)-2-Amino-4-(3,4-dimethoxyphenyl)-5-oxo-7-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile monohydrate
    Sun, Rong
    Wu, Dong-Dong
    Wang, Ke
    Huang, Wei
    Ou, Yang-Bing
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O409 - U698