Synthesis, Characterization, Antioxidant, and Antibacterial Activities of 2-Aminochalcones and Crystal Structure of (2E)-1-(2-aminophenyl)-3-(4-ethoxyphenyl)-2-propen-1-one

被引:8
|
作者
Ruanwas, Pumsak [1 ,2 ]
Chantrapromma, Suchada [1 ,2 ]
Fun, Hoong-Kun [3 ,4 ]
机构
[1] Prince Songkla Univ, Fac Sci, Dept Chem, Hat Yai 90112, Songkhla, Thailand
[2] Prince Songkla Univ, Fac Sci, Ctr Excellence Innovat Chem, Hat Yai 90112, Songkhla, Thailand
[3] Univ Sains Malaysia, Sch Phys, Xray Crystallog Unit, George Town, Malaysia
[4] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
关键词
chalcones; heteroaryl; crystal structure; antibacterial; Antioxidant; CHALCONES;
D O I
10.1080/15421406.2014.950003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Five 2-aminochalcone derivatives [R = H(1), R = OCH2CH3(2), R = 2,4,5-OCH3(3), R = 3,4,5-OCH3(4), and R = thiophene(5)] were synthesized and characterized by H-1 NMR, FT-IR, and UV-Vis spectroscopy. Crystal structure of 2 was also determined by single crystal X-ray diffraction. Compound 2 crystallizes in a monoclinic P2(1)/n space group with the unit cell parameters a = 32.804(7) angstrom, b = 4.9972(11) angstrom, c = 21.7173(3) angstrom, beta = 128.440(4)degrees, V = 2788.4(10) angstrom(3), and Z = 8. There are two molecules in an asymmetric unit of 2, the molecular structure of 2 is twisted with the dihedral angle between the two phenyl rings being 13.6(3)degrees in one molecule and 7.1(3)degrees in the other. In the crystal packing, the molecules of 2 are linked into chains along the b-axis by C-H center dot center dot center dot O interactions. Antioxidant and antibacterial activities of 1-5 were also carried out.
引用
收藏
页码:126 / 139
页数:14
相关论文
共 50 条
  • [31] (2E)-1-(4-Aminophenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one
    Singh, Shailja
    Singh, Manavendra K.
    Agarwal, Alka
    Hussain, Firasat
    Awasthi, Satish K.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1616 - U2281
  • [32] Structural and spectroscopic investigation of the chalcones (E)-1-(4-aminophenyl)-3-(4′-ethoxyphenyl)-prop-2-en-1-one and (E)-1-(aminophenyl)-3-(4′-methoxyphenyl)-prop-2-en-1-one
    Campos Lima, Igor Kleber
    de Sousa, Filipe Dantas
    de Morais Bento, Ana Joyce
    Cruz, Beatriz Goncalves
    da Silva, Priscila Teixeira
    Bandeira, Paulo Nogueira
    dos Santos, Helcio Silva
    Saraiva, Gilberto Dantas
    Honorato Barreto, Antonio Cesar
    Cavalcante Freire, Paulo de Tarso
    Rodrigues Teixeira, Alexandre Magno
    VIBRATIONAL SPECTROSCOPY, 2020, 110
  • [33] COBALT(II), NICKEL(II) AND COPPER(II) COMPLEXES OF 1-(2-HYDROXYPHENYL)-3-(1-NAPHTHALENYL)-2-PROPEN-1-ONE AND 1-(1-HYDROXY-2-NAPHTHALENYL)-3-(1-NAPHTHALENYL)-2-PROPEN-1-ONE
    NATARAJAN, C
    THARMARAJ, P
    SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1990, 20 (02): : 151 - 166
  • [34] (2E)-1-(4-Aminophenyl)-3-(2-thienyl)prop-2-en-1-one ethanol hemisolvate
    Fun, Hoong-Kun
    Kobkeatthawin, Thawanrat
    Chantrapromma, Suchada
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2532 - +
  • [35] (E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinolyl)-3-(4-ethoxyphenyl)prop-2-en-1-one
    Shahani, Tara
    Fun, Hoong-Kun
    Sarveswari, S.
    Vijayakumar, V.
    Ragavan, R. Venkat
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O374 - U2585
  • [36] 3-(5-methyl-2-furyl)-1-(p-tolyl)-2-propen-1-one
    Guo, Huan-Mei
    Wang, Xian-Bing
    Jian, Fang-Fang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1951 - U4004
  • [38] 1-[4-(4-BROMOBENZYLIDENEAMINO)PHENYL]-3-(4-BROMOPHENYL)-2-PROPEN-1-ONE
    LI, ZD
    SU, GB
    HUANG, XY
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1994, 50 : 1788 - 1790
  • [39] PREPARATION AND PHOTOCHEMICAL PROPERTIES OF POLYMERS CONTAINING 1-(4-BENZYLPHENYL)-2-PROPEN-1-ONE OR 1-(4-BENZOYLPHENYL)-2-PROPEN-1-ONE STRUCTURAL UNITS
    LUKAC, I
    EVANS, CH
    SCAIANO, JC
    HRDLOVIC, P
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1990, 51 (03) : 411 - 427
  • [40] SYNTHESIS AND PHOTOCHEMICAL PROPERTIES OF POLY(1-(4-CARBOETHOXYPHENYL)-2-PROPEN-1-ONE)
    LUKAC, I
    HRDLOVIC, P
    GUILLET, JE
    POLYMER PHOTOCHEMISTRY, 1986, 7 (03): : 163 - 177