Iodine (III)-mediated synthesis of some 2-aryl/hetarylbenzoxazoles as antibacterial/antifungal agents

被引:7
|
作者
Kumar, Ravi [1 ]
Nair, Reshmi R. [1 ]
Dhiman, Saurabh Sudha [2 ]
Sharma, Jitender [2 ]
Prakash, Om [1 ]
机构
[1] Kurukshetra Univ, Dept Chem, Kurukshetra 136119, Haryana, India
[2] Kurukshetra Univ, Dept Biotechnol, Kurukshetra 136119, Haryana, India
关键词
Iodobenzene diacetate; Schiff bases; 2-hetarylbenzoxazoles; Antibacterial activity; Antifungal activity; HETEROCYCLIC-COMPOUNDS; OXIDATIVE CYCLIZATION; SCHIFFS BASES; ORGANIC-SYNTHESIS; 2-ARYLBENZOXAZOLES; REAGENTS; <HYDROXY(TOSYLOXY)IODO>BENZENE; BENZOXAZOLES; INHIBITORS;
D O I
10.1007/s00044-009-9211-y
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Ten 2-aryl/hetarylbenzoxazoles (5a, 5b, and 6a-h) were synthesized via oxidative cyclization of Schiff bases (3a, 3b, and 4a-h) with 1.1 equivalent of iodobenzene diacetate (IBD) in methanol. All of these 2-aryl/hetarylbenzoxazoles (5a, 5b, and 6a-h) were tested in vitro for their antibacterial and antifungal activities against Bacillus subtilis, Bacillus stearothermophilus, Escherichia coli, and Pseudomonas putida. These compounds also were screened for their antifungal activity against Aspergillus flavus and Aspergillus niger. Biological activity of these compounds was compared with those of commercially available antibiotics, chloramphenicol and antifungal agent cycloheximide. Most of these compounds, 5a, 5b, 6a, 6b, 6d, 6e, 6g, 6h, were equipotent or more potent than these commercial drugs at concentration 100 mu g/ml.
引用
收藏
页码:541 / 550
页数:10
相关论文
共 50 条
  • [11] KOtBu Mediated Alcohol Dehydrogenation Strategy: Synthesis of 2-Aryl Quinazolinones
    Hima, P.
    Tomasini, Michele
    Poater, Albert
    Dey, Raju
    [J]. CHEMISTRYSELECT, 2024, 9 (11):
  • [12] Synthesis of some thiazolyl aminobenzothiazole derivatives as potential antibacterial, antifungal and anthelmintic agents
    Amnerkar, Nikhil D.
    Bhusari, Kishore P.
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2011, 26 (01) : 22 - 28
  • [13] SYNTHESIS OF SOME ARYLTHIAZOLYL MERCURY-COMPOUNDS AS POTENTIAL ANTIFUNGAL AND ANTIBACTERIAL AGENTS
    AHLUWALIA, VK
    ARORA, KK
    MEHTA, B
    [J]. SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1987, 17 (06): : 607 - 616
  • [14] Iodine-mediated 1,2-aryl migration of primary benzhydryl amines
    Du, Yangxu
    Hou, Jiao
    Lu, Qing
    Hao, Wei
    Yu, Wenquan
    Chang, Junbiao
    [J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (35) : 16223 - 16226
  • [15] Synthesis and antibacterial activity of alkyl-tris[2-aryl(hetaryl)vinyl]phosphonium iodides
    S. F. Malysheva
    E. E. Kuznetsova
    N. A. Belogorlova
    G. V. Kozlova
    T. N. Rakhmatulina
    M. L. Al’pert
    N. K. Gusarova
    B. A. Trofimiov
    N. S. Zefirov
    [J]. Pharmaceutical Chemistry Journal, 1998, 32 (11) : 591 - 592
  • [16] Efficient synthesis of a chiral 2-aryl Pyrrolidine
    Piper, Jared L.
    Kolis, Stanley P.
    Xie, Chaoyu
    Bertrand, Martial
    Boquel, Pascal
    [J]. CHIMICA OGGI-CHEMISTRY TODAY, 2012, 30 (04) : 38 - 40
  • [17] A Rapid Synthesis of 2-Aryl Polyhydroxylated Pyrrolidines
    Su, Jia-Kun
    Jia, Yue-Mei
    He, Ruirui
    Rui, Pei-Xin
    Han, Nanyin
    He, Xihui
    Xiang, Junfeng
    Chen, Xin
    Zhu, Jinghua
    Yu, Chu-Yi
    [J]. SYNLETT, 2010, (11) : 1609 - 1616
  • [18] Synthesis of novel 2-aryl AICAR derivatives
    Kohyama, N
    Katashima, T
    Yamamoto, Y
    [J]. SYNTHESIS-STUTTGART, 2004, (17): : 2799 - 2804
  • [19] Synthesis of 2-trifluoromethyl-phenothiazinoazetidin-2-ones as antibacterial and antifungal agents
    Havaldar, Freddy H.
    Khatri, Navinchandra K.
    [J]. INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 16 (01) : 87 - 88
  • [20] SYNTHESIS OF 2-ARYL DERIVATIVES OF PENTABORANE(9)
    HEPPERT, JA
    GAINES, DF
    [J]. INORGANIC CHEMISTRY, 1982, 21 (12) : 4117 - 4121