The short way to chiral compounds with hexahydrofluoreno[9,1-bc]furan framework: synthesis and cytotoxic activity.
A simple and efficient method for synthesizing chiral heterocyclic compounds with the hexahydrofluoreno[9,1-bc]furan framework via interaction between trans-4-hydroxymethyl-2-carene and aromatic aldehydes containing methoxy and hydroxyl moieties in the presence of montmorillonite clay was found. One of the synthesized compounds exhibited a high cytotoxic activity against lymphoblastoid cell line MT-4 (CTD50 0.9μM), which was higher than that of the comparative drug Doxorubicin. Death of cancer cells in this case substantially occurs via induction of apoptosis.
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation.
Svetlana Yu
SY
Kurbakova
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation.
Irina V
IV
Il'ina
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation.
Oksana S
OS
Mikhalchenko
Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation.
Mikhail A
MA
Pokrovsky
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation.
Dina V
DV
Korchagina
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation. Electronic address: volcho@nioch.nsc.ru.
Konstantin P
KP
Volcho
Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation.
Andrey G
AG
Pokrovsky
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation.
Nariman F
NF
Salakhutdinov
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000633:toxicity*; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D005449:Fluorenes / Q000138:chemical synthesis / Q000633:toxicity; D005663:Furans / Q000138:chemical synthesis* / Q000633:toxicity*; D006801:Humans; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D005449:Fluorenes; D005663:Furans; C039281:furan
Antitumor activity; Apoptosis; Carene; Clay; Cytotoxicity; Heterocycle; Terpene