Design, synthesis, antibacterial and antifungal activity of novel spiro-isoxazolyl bis-[5,5']thiazolidin-4-ones and spiro-isoxazolyl thiazolidin-4-one-[5,5']-1,2-4 oxdiazolines

被引：16
|
作者：
Rajanarendar, Eligeti [1 ]
Rao, Enugala Kalyan [1 ]
Shaik, Firoz Pasha [1 ]
Reddy, Modugu Nagi [1 ]
Srinivas, Manda [1 ]
机构：
[1] Kakatiya Univ, Dept Chem, Warangal 506009, Andhra Pradesh, India
来源：
JOURNAL OF SULFUR CHEMISTRY | 2010年 / 31卷 / 04期
关键词：
cyclocondensation reaction; spirothiazolidinones; cycloaddition reaction; antibacterial activity; antifungal activity; INHIBITORS; AGENTS;
D O I：
10.1080/17415993.2010.492474
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of novel isoxazolyl 1,6-dithia-4,9-diazaspiro[4.4]nonane-3,8-diones (4a-h) and isoxazolyl 1-oxa-6-thia-2,4,9-triazaspiro[4.4]non-2-ene-8-ones (5a-h) analogs is described. Reaction of N-1-\{3-methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl}-2-chloroacetamide (2) with aryl isothiocyanates yielded 3,3-methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl-2-(arylimino)-1,3-thiazolan-4-ones (3). Cyclocondensation of 3 with mercaptoacetic acid furnished novel isoxazolyl-1,6-dithia-4,9-diazaspiro[4.4]nonane-3,8-diones (4a-h). Cycloaddition of 3 with benzonitrile oxides afforded novel isoxazolyl 1-oxa-6-thia-2,4,9-triazaspiro[4.4]non-2-ene-8-ones (5a-h). Compounds 4a-h and 5a-h showed significant biological activity against all the standard strains.
引用
收藏
页码：263 / 274
页数：12
相关论文
共 50 条
  • [41] Synthesis of heterocycles from arylation products of unsaturated compounds:: XIII.: 5-R1-benzyl-2-(R2-2-pyridylimino)thiazolidin-4-ones
    Matiichuk, VS
    Obushak, NA
    Tsyalkovskii, VM
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 41 (07) : 1050 - 1054
  • [42] Synthesis, Antimicrobial Activity, Drug-likeness, and Molecular Docking Studies of Novel 3-((2-(Benzylthio)-5-(phenylselanyl) pyrimidin-4-yl)amino)-2-(4-substituted phenyl)thiazolidin-4-ones
    Basha, N. Jeelan
    Akshay, K. T.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2024, 56 (06) : 626 - 632
  • [43] Synthesis of novel cyclopentenone derivatives and crystal structure determination of 3,4-bis(4-chlorophenyl)-5,5-dimethyl-4-hydroxy-2-cyclopenten-1-one
    Marjani, Katayoun
    Mousavi, Mohsen
    Ashouri, Akram
    Arazi, Omid
    Bourghani, Samira
    Asgari, Maryam
    JOURNAL OF CHEMICAL RESEARCH, 2008, (07) : 398 - 401
  • [44] DESIGN, SYNTHESIS, DOCKING STUDY AND PHARMACOLOGICAL EVALUATION OF NOVEL -2- (5-(1H-INDOL-3-YL)- 1, 3, 4-THIADIAZOL -2 -YLIMINO) -5 -(SUBSTITUTED BENZYLIDENE) THIAZOLIDIN-4-ONE ANALOGUES
    Taya, Poonam
    Mehta, Dinesh Kumar
    Das, Rina
    INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2019, 10 (02): : 701 - 711
  • [45] Synthesis of 3′,4′-Diaryl-4′H-spiro[indoline-3,5′-[1′,2′,4′]-oxadiazol]-2-ones via DMAP-catalyzed Domino Reactions and Their Antibacterial Activity
    Shi, Guanghao
    He, Xinwei
    Shang, Yongjia
    Xiang, Liwei
    Yang, Cheng
    Han, Guang
    Du, Bing
    CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (09) : 901 - 909
  • [46] Synthesis of some cyclopentenones and crystal structure of 4-hydroxy-3,4-bis(4-methoxyphenyl)-5,5-dimethyl-2-cyclopenten-1-one
    Marjani, Katayoun
    Mousavi, Mohsen
    Arazi, Omid
    Ashouri, Akram
    Bourghani, Samira
    Rajabi, Mohammad
    MONATSHEFTE FUR CHEMIE, 2009, 140 (11): : 1331 - 1336
  • [47] Synthesis of some cyclopentenones and crystal structure of 4-hydroxy-3,4-bis(4-methoxyphenyl)-5,5-dimethyl-2-cyclopenten-1-one
    Katayoun Marjani
    Mohsen Mousavi
    Omid Arazi
    Akram Ashouri
    Samira Bourghani
    Mohammad Rajabi
    Monatshefte für Chemie - Chemical Monthly, 2009, 140 : 1331 - 1336
  • [48] New novel synthesis and antibacterial activity of 1-(substituted phenyl)-2-phenyl-4-(3′-halo, 4′-hydroxy 5′-methoxy benzylidene)-imidazole-5-ones
    Siddiqui, SA
    Bhusare, SR
    Jarikote, DV
    Pawar, RP
    Vibhute, YB
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2001, 22 (09) : 1033 - 1036
  • [49] Design, Synthesis, and Insecticidal Activity of 5,5-Disubstituted 4,5-Dihydropyrazolo[1,5-a]quinazolines as Novel Antagonists of GABA Receptors
    Jiang, Xunyuan
    Yang, Shuai
    Yan, Ying
    Lin, Fei
    Zhang, Ling
    Zhao, Weijing
    Zhao, Chen
    Xu, Hanhong
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2020, 68 (50) : 15005 - 15014
  • [50] Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Iminoethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one
    Zhao, Yu
    Liu, Xinlei
    Li, Yihao
    Xu, Leichuan
    Su, Yanhao
    Jiang, Jiazhen
    Wang, Ming'an
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (08) : 2547 - 2554
12345