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
  • [1] Synthesis and antimicrobial activity of novel spiro-isoxazolyl oxazolidin-4-one-[5,51]-1,2,4-oxadiazolines and thiazolidin-4-one-[5,51]-1,2,4-oxadiazolines
    Rajanarendar, E.
    Reddy, A. Siva Rami
    Reddy, K. Govardhan
    Raju, S.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2011, 50 (12): : 1800 - 1806
  • [2] Synthesis of 2-aryl- and 2-hetaryl derivatives of 2′-aminospiro[(1,3-dioxane)-5,5′-thiazolin]-4′-one and spiro[(1,3-dioxane)-5,5′-thiazolidin]-2′,4′-dione
    Ramsh, SM
    Ivanenko, AG
    Medvedskiy, NL
    Kushakova, PM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (07): : 1068 - 1075
  • [3] CYCLO-ADDITIONS .4. SYNTHESIS OF 2-ARYL-3-(3-METHYL-5-STYRYL-4-ISOXAZOLYL)THIAZOLIDIN-4-ONES
    RAJANARENDAR, E
    RAO, CJ
    MURTHY, AK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1982, 21 (09): : 878 - 880
  • [4] DESAMINATION NITREUSE DES SPIRO (4,5) DECANAMINE-1 1 ET SPIRO (5,5) UNDECANAMINE-1,2
    CHRISTOL, H
    BESSIERE, JM
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1966, (02): : 492 - &
  • [5] Studies on thiazolidin-4-ones .20. Synthesis and antimicrobial activity of 2-aryl-5H/methyl/carboxymethyl-3-[4-(3,4,5-trimethoxybenzamido)-benzoylamino]thiazolidin-4-ones
    Joshi, N
    Patel, P
    Parekh, H
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (08): : 867 - 870
  • [6] Synthesis of 2-aryl and 2-hetaryl derivatives of 2′-aminospiro[(1,3- dioxane)-5,5′-thiazolin]-4′-one and spiro[(1,3-dioxane)-5,5′- thiazolidine]2′,4′-dione
    Ramsh S.M.
    Ivanenko A.G.
    Shpilyovy V.A.
    Medvedskiy N.L.
    Kushakova P.M.
    Chemistry of Heterocyclic Compounds, 2004, 40 (7) : 919 - 926
  • [7] Design, Synthesis, Pharmacological Activities, Structure-Activity Relationship, and In Silico Studies of Novel 5-Substituted-2-(morpholinoimino)-thiazolidin-4-ones
    Sicak, Yusuf
    Aktar, Bedriye Seda Kursun
    Yilmaz, Gizem Tatar
    Ozturk, Fatma Aydogmus
    Ozturk, Mehmet
    Tok, Tugba Taskin
    Emre, Emine Elcin Oruc
    ACS OMEGA, 2023, 8 (41): : 38641 - 38657
  • [8] Spiro-bithiazole derivatives of amidinothiocarbamides: Novel utilization of the synthon 2-arylimino-5-carbethoxy-thiazolidin-4-one
    Chande, MS
    Carvalho, PVR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2004, 43 (04): : 876 - 879
  • [9] Synthesis, Characterization, Antibacterial and Antifungal Activity of 2-(Aryl)-3-(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl)thiazolidin-4-ones
    Chopde, Himani N.
    Pagadala, Ramakanth
    Meshram, Jyotsna S.
    Jetti, Venkateshwarlu
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (06) : 1323 - 1328
  • [10] Synthesis and fungicidal activity of 2-imino-3-(4-arylthiazol-2-yl)-thiazolidin-4-ones and their 5-arylidene derivatives
    Liu, HL
    Li, ZC
    Anthonsen, T
    MOLECULES, 2000, 5 (09) : 1055 - 1061
12345