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
  • [21] New facile synthesis of 7-hydroxy-6-amino-4-substituted benzopyran-2-ones
    Evagelos, G
    Maria, PP
    Michael, K
    Andreast, V
    SYNTHETIC COMMUNICATIONS, 2004, 34 (22) : 4233 - 4242
  • [22] 7-Hydroxy-6-methoxy-3-[(2-oxo-2H-1-benzopyran-7-yl)oxy]-2H-1-benzopyran-2-one
    Zhang, TZ
    Wei, CY
    Xu, GH
    Park, SW
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2006, 62 : O86 - O88
  • [23] Synthesis of novel 2-amino-4-(5′-substituted 2′-phenyl-1H-indol-3′-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents
    Saundane, Anand R.
    Vijaykumar, Katkar
    Vaijinath, A. Verma
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (07) : 1978 - 1984
  • [24] Multicomponent one-pot synthesis, characterization and antimicrobial screening of 2 cyanoimino-6-aryl-4-(6-methoxynaphthalen-2-yl)-3,4-dihydro-1H-pyrimidines
    Sivagami, Swaminathan
    Kavitha, Rengarajan
    Satanathan, Sasikurba
    Rajesh, Jegathalaprathaban
    Narenkumar, Jayaraman
    Parthipan, Punniyakotti
    Muthusamy, Karnan
    Alfarhan, Ahmed
    Process Biochemistry, 2022, 123 : 63 - 69
  • [25] Synthesis of some 3,5-bis-1,4-dihydro-4-phenyl 2,6-dimethyl pyridino-2'-amino-6'-phenyl Pyrimidines
    Thore, S. N.
    ASIAN JOURNAL OF CHEMISTRY, 2007, 19 (06) : 4429 - 4432
  • [26] SYNTHESIS OF 4-SUBSTITUTED AND 6-SUBSTITUTED 2,2-DIMETHYL-2H-CHROMENES
    TALLEY, JJ
    SYNTHESIS-STUTTGART, 1983, (10): : 845 - 847
  • [27] Improved synthesis of 10-substituted-6a,7-dihydro-6H-6-phenyl-7(phenyl/4-substituted phenyl)-[1]benzopyrano[3,4-c][1,5]benzothiazepines
    Sharma, BS
    Bhatia, A
    Pant, UC
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 8 (02) : 157 - 158
  • [28] SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 2-{4′-[(5"-ARYL)-4"-5"-DIHYDRO-1-PHENYL PYRAZOL-3"-YL]-PHENYL AMINO}-6-[BIS (2′"-CHLORO ETHYL) AMINO]-4-METHOXY-1,3,5-TRIAZINES
    Kathiriya, P. J.
    Patolia, V. N.
    Purohit, D. M.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 20 (03) : 285 - 286
  • [29] SYNTHESIS OF POTENTIAL METABOLITES OF ETHYL (E)-4-[2-(3,4-DIHYDRO-4,4-DIMETHYL-2H-1-BENZOPYRAN-6-YL)-1-PROPENYL]BENZOATE
    SUNTHANKAR, PS
    BERLIN, KD
    NELSON, EC
    THORNE, RL
    GENO, PW
    ARCHER, JC
    ROLF, LL
    BARTELS, KE
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1993, 82 (05) : 543 - 545
  • [30] Studies on potassium channel openers .1. Synthesis and cardiovascular activity of substituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols
    Sun, HB
    Hua, WY
    Chen, L
    Peng, SX
    Wang, T
    Liu, GQ
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 1997, 18 (05): : 730 - 733