Keywords
1
2
4-triazole-3-carboxamides
4-triazole-3-carboxylic acid derivatives
5-(ω-aminoalkyl)-1
acute lymphoblastic leukemia
acyloxalamidrazones
antimicrobial properties.
antiviral
agents
chronic myeloid leukemia
Abstract
New homologues of 5-amino-1,2,4-triazole-3-carboxamide, viz., 5-(ω-aminoalkyl)-1,2,4-triazole-3-carboxamides have been synthesized. The intermediate acyloxalamidrazones undergo thermal cyclization to 1,2,4-triazoles with the better yield in the absence of catalyst while in the presence of 10 mol% TsOH the main product is the corresponding 1,3,4-oxadiazole derivative. The obtained compounds have demonstrated various biological properties comparable to those of the nucleoside drug ribavirin.
Funders
Russian Science Foundation
23-25-00382
References
.
Xia Y., Li W., Qu F., Fan Z., Liu X., Berro C., Rauzy E., Peng L.
Organic and Biomolecular Chemistry,
2007
.
Liu Y., Xia Y., Fan Y., Maggiani A., Rocchi P., Qu F., Iovanna J.L., Peng L.
Bioorganic and Medicinal Chemistry Letters,
2010
.
Zhurilo N.I., Chudinov M.V., Matveev A.V., Smirnova O.S., Konstantinova I.D., Miroshnikov A.I., Prutkov A.N., Grebenkina L.E., Pulkova N.V., Shvets V.I.
Bioorganic and Medicinal Chemistry Letters,
2018
.
Fan Y., Xia Y., Tang J., Rocchi P., Qu F., Iovanna J., Peng L.
Organic Letters,
2010
.
Borg S., Estenne-Bouhtou G., Luthman K., Csoeregh I., Hesselink W., Hacksell U.
Journal of Organic Chemistry,
1995
.
Francis J.E., Gorczyca L.A., Mazzenga G.C., Meckler H.
Tetrahedron Letters,
1987
.
Chudinov M.V., Matveev A.V., Zhurilo N.I., Prutkov A.N., Shvets V.I.
Journal of Heterocyclic Chemistry,
2014
.
Naik S.R., Witkowski J.T., Robins R.K.
Journal of Heterocyclic Chemistry,
1974
.
Kukuljan L., Kranjc K.
Tetrahedron Letters,
2019
.
Wang M., Zhu R., Fan Z., Fu Y., Feng L., Yao J., Maggiani A., Xia Y., Qu F., Peng L.
Bioorganic and Medicinal Chemistry Letters,
2011
.
McDowell M., Gonzales S.R., Kumarapperuma S.C., Jeselnik M., Arterburn J.B., Hanley K.A.
Antiviral Research,
2010
.
Xia Y., Fan Z., Yao J., Liao Q., Li W., Qu F., Peng L.
Bioorganic and Medicinal Chemistry Letters,
2006
.
Xia Y., Qu F., Peng L.
Mini-Reviews in Medicinal Chemistry,
2010
.
Xia Y., Wang M., Beraldi E., Cong M., Zoubeidi A., Gleave M., Peng L.
Anti-Cancer Agents in Medicinal Chemistry,
2015
.
Chudinov M.V.
Fine Chemical Technologies,
2019
.
Dost J., Stein J., Heschel M.
Zeitschrift für Chemie,
2010
.
Guan Q., Xing S., Wang L., Zhu J., Guo C., Xu C., Zhao Q., Wu Y., Chen Y., Sun H.
Journal of Medicinal Chemistry,
2024
.
Mikhina E.A., Stepanycheva D.V., Maksimova V.P., Sineva O.N., Markelova N.N., Grebenkina L.E., Lesovaya E.A., Yakubovskaya M.G., Matveev A.V., Zhidkova E.M.
Molecules,
2024