Keywords
abietane diterpenes
amino imides
anticancer activity.
azido-Ugi reaction
isocyanides
methyl maleopimarate
tetrazoles
Abstract
The azido-Ugi reaction of methyl maleopimarate N-(2- aminoethyl) imide with isocyanides, paraformaldehyde and trimethylsilyl azide in one step leads to 1,5-disubstituted diterpene bis-tetrazoles. The compounds demonstrate selective cytotoxicity against NCI-60 cancer cell panel.
References
.
Tretyakova E.V., Smirnova I.E., Salimova E.V., Odinokov V.N.
Bioorganic and Medicinal Chemistry,
2015
.
Herr R.J.
Bioorganic and Medicinal Chemistry,
2002
.
Sarvary A., Maleki A.
Molecular Diversity,
2014
.
Dömling A.
Chemical Reviews,
2005
.
Ugi I.
Pure and Applied Chemistry,
2001
.
Ugi I., Werner B., Dömling A.
Molecules,
2003
.
Ugi I., Meyr R.
Angewandte Chemie,
1958
.
Malik M.A., Wani M.Y., Al-Thabaiti S.A., Shiekh R.A.
Journal of Inclusion Phenomena and Macrocyclic Chemistry,
2013
.
Ostrovskii V.A., Trifonov R.E., Popova E.A.
Russian Chemical Bulletin,
2012
.
Tretyakova E.V., Ma X., Kazakova O.B., Shtro A.A., Petukhova G.D., Smirnova A.A., Xu H., Xiao S.
Natural Product Research,
2022
.
Váradi A., Palmer T., Notis Dardashti R., Majumdar S.
Molecules,
2015
.
Pseudo-Seven-Component Double Azido-Ugi Reaction: an Efficient Synthesis of Bistetrazole Derivatives
Kutovaya I.V., Zarezin D.P., Shmatova O.I., Nenajdenko V.G.
European Journal of Organic Chemistry,
2019
.
Yuskaitis C.J., Rossitto L., Groff K.J., Dhamne S.C., Zhang B., Lalani L.K., Singh A.K., Rotenberg A., Sahin M.
Annals of Clinical and Translational Neurology,
2021
.
Sadjadi S., Heravi M.M., Nazari N.
RSC Advances,
2016
.
Schror K.
Diabetes, Obesity and Metabolism,
2002
.
Gorbacheva A.M., Krutov I.A., Vorozhtsov N.I., Khrustalev V.N., Nenajdenko V.G.
Mendeleev Communications,
2021
.
Elliott W.J., Calhoun D.A., DeLucca P.T., Gazdick L.P., Kerns D.E., Zeldin R.K.
Clinical Therapeutics,
2001
.
Tret’yakova E.V., Ma X., Kazakova O.B., Shtro A.A., Petukhova G.D., Klabukov A.M., Dyatlov D.S., Smirnova A.A., Xu H., Xiao S.
Phytochemistry Letters,
2022
.
Barkhatova D., Zhukovsky D., Heim C., Maiwald S., Hartmann M.D., Krasavin M.
Mendeleev Communications,
2022
.
Smirnova A.A., Zakirova L.M., Smirnova I.E., Tretyakova E.V.
MolBank,
2023
.
Smirnova A.A., Tret’yakova E.V.
Russian Chemical Bulletin,
2023