Citation: KONG Du-Lin, JIANG Jie, WU Lu-Yong, WANG Xiang-Hui, SHI Zai-Feng, WU Ming-Shu, WANG Xin, LIN Qiang. Synthesis, Structure and Antimicrobial Activity of 9,9-Dimethyl-9,10-dihydrospiro[benzo[a]-xanthene-12,3'-indoline]-2',11(8H)-dione[J]. Chinese Journal of Structural Chemistry, ;2016, 35(12): 1849-1854. doi: 10.14102/j.cnki.0254-5861.2011-1249 shu

Synthesis, Structure and Antimicrobial Activity of 9,9-Dimethyl-9,10-dihydrospiro[benzo[a]-xanthene-12,3'-indoline]-2',11(8H)-dione

  • Corresponding author: WU Ming-Shu, wmsh@hainuu.edu.cn WANG Xin, wangx@njust.edu.cn LIN Qiang, linqianggroup@163.com
  • Received Date: 15 April 2016

    Fund Project: Natural Science Foundation of Hainan Province 20162033Cultivation Research Foundation of Hainan Medical University HY2015-02

Figures(4)

  • One novel spiro-compound (C26H21NO3) has been synthesized and characterized by means of NMR spectroscopy, elemental analyses and X-ray diffraction. The single crystal belongs to the monoclinic system, space group P21/c with a=8.8039(7), b=24.123(2), c=10.0751(9)Å, β=108.403(3)°, Mr=395.44, V=2030.3(3)Å3, Z=4, Dc=1.294 g/cm3, F(000)=832.0, μ=0.085 mm-1, R=0.0801 and wR=0.2228. The title compound shows good activities against Micrococcus tetragenus, Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, S. albus and Escherichia coli.
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    1. [1]

      Hilton S. T, Ho T. C, Pljevaljcic G, Jones K. A new route to spirooxindoles[J]. Org. Lett, 2000,2:2639-2641. doi: 10.1021/ol0061642

    2. [2]

      Kornet M. J, Thio A. P. Oxindole-3-spiropyrrolidines and -piperidines[J]. Synthesis and local anesthetic activity. J. Med. Chem, 1976,19:892-898.

    3. [3]

      Cui C. B, Kakeya H, Okada G, Onose R, Ubukata M, Takahashi I, Isono K, Osada H. Tryprostatins A and B, novel mammalian cell cycle inhibitors produced by Aspergillus fumigatus[J]. J. Antibiot, 1995,48:1382-1384. doi: 10.7164/antibiotics.48.1382

    4. [4]

      Yu N, Aramini J. M, Germann M. W, Huang Z. Reactions of salicylaldehydes with alkyl cyanoacetates on the surface of solid catalysts: syntheses of 4H-chromene derivatives[J]. Tetra. Lett, 2000,41:6993-6996. doi: 10.1016/S0040-4039(00)01195-3

    5. [5]

      Chen H, Shi D. Efficient one-pot synthesis of novel spirooxindole derivatives via three-component reaction in aqueous medium[J]. J. Comb. Chem, 2010,12:571-576. doi: 10.1021/cc100056p

    6. [6]

      Abdel-Rahman A. H, Keshk E. M, Hanna M. A, El-Bady S. M. Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents[J]. Biorg. Med. Chem, 2004,12:2483-2488. doi: 10.1016/j.bmc.2003.10.063

    7. [7]

      Wang L. M, Jiao N, Qiu J, Yu J. J, Liu J. Q, Guo F. L, Liu Y. Sodium stearate-catalyzed multicomponent reactions for efficient synthesis of spirooxindoles in aqueous micellar media[J]. Cheminform, 2010,66:339-343.  

    8. [8]

      Bazgir A, Hosseini G, Ghahremanzadeh R. Copper ferrite nanoparticles: an efficient and reusable nanocatalyst for a green one-pot, three-component synthesis of spirooxindoles in water[J]. ACS Comb. Sci, 2013,15:530-534. doi: 10.1021/co400057h

    9. [9]

      Chen Q, Liang J, Wang S, Wang D, Wang R. An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst[J]. Chem. Commun, 2013,44:1657-1659.

    10. [10]

      Galliford C. V, Prof K. A. S. Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents[J]. Angew. Chem. Int. Ed, 2007,46:8748-8758. doi: 10.1002/(ISSN)1521-3773

    11. [11]

      Guo R. Y, An Z. M, Mo L. P, Wang R. Z, Liu H. X, Wang S. X, Zhang Z. H. Meglumine: a novel and efficient catalyst for one-pot, three-component combinatorial synthesis of functionalized 2-amino-4H-pyrans[J]. ACS Comb. Sci, 2013,15:557-563. doi: 10.1021/co400107j

    12. [12]

      Jin S. S, Wang H, Guo H. Y. Ionic liquid catalyzed one-pot synthesis of novel spiro-2-amino-3-phenylsulfonyl-4 H -pyran derivatives[J]. Tetra. Lett, 2013,54:2353-2356. doi: 10.1016/j.tetlet.2013.02.073

    13. [13]

      Khalafi-Nezhad A, Shahidzadeh E. S, Sarikhani S, Panahi F. A new silica-supported organocatalyst based on L-proline: an efficient heterogeneous catalyst for one-pot synthesis of spiroindolones in water[J]. J. Mol. Catal. A-Chem, 2013,379:1-8. doi: 10.1016/j.molcata.2013.07.009

    14. [14]

      Lakshmi N. V, Sivakumar P. M, Muralidharan D, Doble M, Perumal P. T. Expeditious synthesis, antibacterial activity evaluation and GQSAR studies of 3-bisoxindoles, 2-oxindolyl-2-hydroxyindan-1,3-diones and 2-oxindolyl-2-hydroxyacenaphthylen-1-ones[J]. RSC Adv, 2013,3:496-507. doi: 10.1039/C2RA01215D

    15. [15]

      Yu F, Huang R, Ni H, Fan J, Yan S, Lin J. Three-component stereoselective synthesis of spirooxindole derivatives[J]. Green Chem, 2013,15:453-462. doi: 10.1039/C2GC36552A

    16. [16]

      Asadi S, Mohammadi Ziarani G, Rahimifard M, Abolhassani Soorki A. A green one-pot synthesis of spironaphthopyrano [1,2-b]indeno-7,3'-indolines[J]. Res. Chem. Intermed, 2014,41:6219-6227.  

    17. [17]

      Kong D, Liu R, Li G, Zhang P, Wu M. A rapid, convenient, solventless green approach for the synthesis of α-hydroxyphosphonates by grinding[J]. Asian J. Chem, 2014,26:1246-1248.  

    18. [18]

      Kong D, Li G, Liu R. Synthesis and crystal structure of diethyl tosyloxybenzylphosphonate[J]. Asian J. Chem, 2014,26:2138-2140.  

    19. [19]

      Li G, Wu M, Kong D, Liu R, Zhou X, Liu F. One-pot and highly regio-selective 1,3-dipole cycloaddition of azomethine ylide generated in situ to tetraethyl vinylidenebisphosphonate (VBP) catalyzed by cerium(IV) oxide[J]. New J. Chem, 2014,38:3350-3353. doi: 10.1039/C4NJ00558A

    20. [20]

      Kong D, Wu M, Hang C, Ma J, Wan D. Synthesis and characterization of α-aminophosphonic acids containing adenine[J]. Asian J. Chem, 2011,23:2871-2873.  

    21. [21]

      Kong D, Wu M, Li Q, Ma J. Stereospecific synthesis of cis-3-arylureido-2-phenyl-2-oxo- naphtho [1,2-d]-1,2-oxaphospholance[J]. Chin. J. Org. Chem, 2010,30:1911-1913.

    22. [22]

      Tsotinis A, Gerasimopoulou M, Vlachou M, Moreau D, Roussakis C. C5,C6-Disubstituted 1H-indole-2-carboxamides: synthesis and cytotoxic activity in the human non-small lung cancer cell line NSCLC-N16-L16[J]. Lett. Drug Des. Discovery, 2006,3:14-16. doi: 10.2174/157018006775240980

    23. [23]

      Kritsanida M, Magiatis P, Skaltsounis A. L, Peng Y, Li P, Wennogle L. P. Synthesis and antiproliferative activity of 7-azaindirubin-3?-oxime, a 7-aza isostere of the natural indirubin pharmacophore[J]. J. Nat. Prod, 2009,72:2199-2202. doi: 10.1021/np9003905

    24. [24]

      Bra?a M. F, Gradillas A, Ovalles A. G, López B, Acero N, Llinares F, Mingarro D. M. Synthesis and biological activity of N,N-dialkylaminoalkyl-substituted bisindolyl and diphenyl pyrazolone derivatives[J]. Biorg. Med. Chem, 2006,14:9-16. doi: 10.1016/j.bmc.2005.09.059

    25. [25]

      David M, Nichols C. J, Riley D. A, Simpkins N. S. The synthesis of bioactive indolocarbazoles related to K-252a[J]. Org. Biomol. Chem, 2005,3:2953-2975. doi: 10.1039/b506444a

    26. [26]

      Tsujii S, Rinehart K. L, Gunasekera S. P, Kashman Y, Cross S. S, Lui M. S, Pomponi S. A, Diaz M. C. Topsentin, bromotopsentin, and dihydrodeoxybromotopsentin: antiviral and antitumor bis(indolyl)imidazoles from Caribbean deep-sea sponges of the family Halichondriidae[J]. Structural and synthetic studies. J. Org. Chem, 2002,53:5446-5453.

    27. [27]

      Chen M, Wang Z, Hu C, Wu X, Wang P. Rapid evaluating of antimicrobial activity of vanillin with the microplate reader in 96-cell plate[J]. Food & Fermentation Industries, 2009,35:63-66.  

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