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Synthesis 2018; 50(10): 2099-2105
DOI: 10.1055/s-0036-1591952
DOI: 10.1055/s-0036-1591952
paper
Synthesis, Structure, and Biological Activity of 2,6-Disubstituted 2,3a,4a,6,7a,8a-Hexaazaperhydrocyclopenta[def]fluorene-4-thioxo-8-ones
This work was supported by the Russian Science Foundation (Project RNF 17-73-10415)Further Information
Publication History
Received: 11 December 2017
Accepted after revision: 12 February 2018
Publication Date:
20 March 2018 (online)
Abstract
A two-step one-pot condensation for the synthesis of previously inaccessible 2,6-disubstituted 2,3a,4a,6,7a,8a-hexaazaperhydrocyclopenta[def]fluorene-4-thioxo-8-ones from simple reagents [5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one, paraformaldehyde and amines] was developed. The structure, antimicrobial, and anticancer activity of a number of synthesized compounds were studied.
Key words
multicomponent reaction - one-pot condensation - thioglycolurils - polyheterocyclic compounds - antifungal activitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591952.Included are copies of 1H and 13C NMR spectra, HSQC, NOESY and X-ray data and the results of anticancer activities for selected compounds.
- Supporting Information
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References
- 1a Cong H. Ni XL. Xiao X. Huang Y. Zhu QJ. Xue SF. Tao J. Lindoy LF. Wei G. Org. Biomol. Chem. 2016; 14: 4335
- 1b Lagona J. Mukhopadhyay P. Chakrabarti S. Isaacs L. Angew. Chem. Int. Ed. 2005; 44: 4844
- 2a Yawer MA. Havel V. Sindelar V. Angew. Chem. Int. Ed. 2015; 54: 276
- 2b Fiala T. Ludvíková L. Heger D. Švec J. Slanina T. Vetráková LU. Babiak M. Nečas M. Kulhánec P. Klán P. Sindelar V. J. Am. Chem. Soc. 2017; 139: 2597
- 2c Torti E. Havel V. Yawer M. Ludvíkova L. Babiak M. Klán P. Sindelar V. Chem. Eur. J. 2017; 23: 16768
- 3a Liu Q. Wang J. Zhao G. J. Chem. Crystallogr. 2012; 42: 727
- 3b Lizal T. Ustrnul L. Necas M. Sindelar V. J. Org. Chem. 2016; 81: 8906
- 3c She N. Moncelet D. Gilberg L. Lu X. Sindelar V. Briken V. Isaacs L. Chem. Eur. J. 2016; 22: 15270
- 4a Rebek J. Acc. Chem. Res. 1999; 32: 278
- 4b Rowan AE. Elemans JA. A. W. Nolte RJ. M. Acc. Chem. Res. 1999; 32: 995
- 4c Barsegyan YA. Baranov VV. Kravchenko AN. Chem. Heterocycl. Compd. 2017; 53: 116
- 4d Johnson DW. Hof F. Palmer LC. Martín T. Obst U. Rebek JJr. Chem. Commun. 2003; 1638
- 4e She NF. Meng XG. Gao M. Wu AX. Isaacs L. Chem. Commun. 2008; 3133
- 4f Zhang M. Sigwalt D. Isaacs L. Chem. Commun. 2015; 51: 14620
- 5a Singh M. Parvari G. Botoshansky M. Keinan E. Reany O. Eur. J. Org. Chem. 2014; 933
- 5b Wingard LA. Johnson EC. Sabatini JJ. Tetrahedron Lett. 2016; 57: 1681
- 5c Wang Z. Xi H. Acta Crystallogr., Sect. E 2009; 65: o1426
- 5d Wu Y. Sun Y. Acta Crystallogr., Sect. E 2009; 65: o1715
- 5e Deng C. Shu W. Zhang D. Acta Crystallogr., Sect. E 2010; 66: o1524
- 5f Singh M. Solel E. Keinan E. Reany O. Chem. Eur. J. 2015; 21: 536
- 5g Lang C. Mohite A. Deng X. Yang F. Dong Z. Xu J. Liu J. Keinan E. Reany O. Chem. Commun. 2017; 53: 7557
- 6a Gazieva GA. Anikina LV. Pukhov SA. Karpova TB. Nelyubina YuV. Kravchenko AN. Mol. Divers. 2016; 20: 837
- 6b Gazieva GA. Anikina LV. Nechaeva TV. Pukhov SA. Karpova TB. Popkov SV. Nelyubina YuV. Kolotyrkina NG. Kravchenko AN. Eur. J. Med. Chem. 2017; 140: 141
- 6c Seprődi J. Sarkadi B. Hegedűs T. Kéri G. Őrfi L. Idei M. Hollósy F. Teplán I. Okada Y. WO Patent 0220527, 2002 ; Chem. Abstr. 2005, 136, 232309
- 7 Mock WL. Manimaran T. Freeman WA. Kuksuk RM. Maggio JE. Williams DH. J. Org. Chem. 1985; 50: 60
- 8a Chikunov IE. Kravchenko AN. Makhova NN. Mendeleev Commun. 2007; 17: 321
- 8b Kravchenko AN. Chikunov IE. Lyssenko KA. Baranov VV. Chem. Heterocycl. Compd. 2014; 50: 1322
- 9a Ahameethunisa AR. Hopper W. BMC Complement. Altern. Med. 2010; 10: 2
- 9b Nasrin F. Bulbul IJ. Begum Y. Khanum S. Agric. Biol. J. N. Am. 2012; 3: 43
- 10 Mosmann T. J. Immunol Methods 1983; 65: 55
- 11 http://dtp.nci.nih.gov/.
- 12 Baranov VV. Nelyubina YuV. Kravchenko AN. Kolotyrkina NG. Biriukova KA. Tetrahedron Lett. 2015; 56: 6085
- 13 Bruker SAINT V8.34A . Bruker AXS Inc; Madison, WI: 2013
- 14 Sheldrick GM. SADABS v2014/5, TWINABS v2012/1, Bruker/Siemens Area Detector Absorption Correction Programs. University of Göttingen; Göttingen: 2014
- 15 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
- 16 CCDC numbers 1588002–1588005 contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.