Synthesis 2018; 50(10): 2099-2105
DOI: 10.1055/s-0036-1591952
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis, Structure, and Biological Activity of 2,6-Disubstituted 2,3a,4a,6,7a,8a-Hexaazaperhydrocyclopenta[def]fluorene-4-thioxo­-8-ones

Yana A. Barsegyan
a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation   Email: ase1313@mail.ru
b   D. Mendeleev University of Chemical Technology of Russia, Miusskaya Sq., 9, Moscow 125047, Russian Federation
,
a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation   Email: ase1313@mail.ru
,
Angelina N. Kravchenko
a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation   Email: ase1313@mail.ru
,
Yuri A. Strelenko
a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation   Email: ase1313@mail.ru
,
Lada V. Anikina
c   Institute of Physiologically Active Substances, Russian Academy of Sciences, Chernogolovka, Moscow oblast, Russia
,
Valentina A. Karnoukhova
d   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation
,
Natalya G. Kolotyrkina
a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation   Email: ase1313@mail.ru
› Author Affiliations
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.

Supporting Information

 
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