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

KONG Du-Lin ^a,b ,
JIANG Jie ^c ,
WU Lu-Yong ^c ,
WANG Xiang-Hui ^c ,
SHI Zai-Feng ^c ,
WU Ming-Shu ^c,*,, ,
WANG Xin ^a,*,, ,
LIN Qiang ^a,c,*,,

a.
College of Chemical Engineering, Nanjing University of Science & Technology, 200 Xiaolingwei, Nanjing 210094, China
b.
School of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, China
c.
Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, China

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
Accepted Date: 9 August 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)°, M_r=395.44, V=2030.3(3)Å³, Z=4, D_c=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.
- synthesis,
- crystal structure,
- spirooxindole ring,
- heterocycle,
- antimicrobial activity
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.
1. [1]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
2. [2]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
3. [3]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
4. [4]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
5. [5]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
6. [6]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
7. [7]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
8. [8]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
9. [9]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
10. [10]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
11. [11]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
12. [12]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
13. [13]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
14. [14]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
15. [15]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
16. [16]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
17. [17]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
18. [18]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
19. [19]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
20. [20]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(7304)
HTML views(263)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142