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Phosphonium and arsonium salts based on alantolactone

Mariya Eduardovna Shemakhina 1
Mariya Eduardovna Shemakhina
,  , 
Denis Vladimirovich Chachkov 3
Denis Vladimirovich Chachkov
, 
Sergei Aleksandrovich Pukhov 4
Sergei Aleksandrovich Pukhov
, 
1 Alexander Butlerov Institute of Chemistry, Kazan Federal University, Kazan, Russian Federation
2 A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
3 Kazan Department of Joint Supercomputer Center, Scientific Research Institute for System Analysis, Russian Academy of Sciences, Kazan, Russian Federation
4 Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation
10.1016/j.mencom.2023.10.006
Published 2023-10-18
Communication , Volume 33, Issue 6, 759-761
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Shemakhina M. E. et al. Phosphonium and arsonium salts based on alantolactone // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 759-761.
GOST all authors (up to 50) Copy
Shemakhina M. E., Nemtarev A. V., Chachkov D. V., Pukhov S. A., Mironov V. F. Phosphonium and arsonium salts based on alantolactone // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 759-761.
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TY - JOUR
DO - 10.1016/j.mencom.2023.10.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.006
TI - Phosphonium and arsonium salts based on alantolactone
T2 - Mendeleev Communications
AU - Shemakhina, Mariya Eduardovna
AU - Nemtarev, Andrey Vladimirovich
AU - Chachkov, Denis Vladimirovich
AU - Pukhov, Sergei Aleksandrovich
AU - Mironov, Vladimir Fedorovich
PY - 2023
DA - 2023/10/18
PB - Mendeleev Communications
SP - 759-761
IS - 6
VL - 33
ER -
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@article{2023_Shemakhina,
author = {Mariya Eduardovna Shemakhina and Andrey Vladimirovich Nemtarev and Denis Vladimirovich Chachkov and Sergei Aleksandrovich Pukhov and Vladimir Fedorovich Mironov},
title = {Phosphonium and arsonium salts based on alantolactone},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.006},
number = {6},
pages = {759--761},
doi = {10.1016/j.mencom.2023.10.006}
}
MLA
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MLA Copy
Shemakhina, Mariya Eduardovna, et al. “Phosphonium and arsonium salts based on alantolactone.” Mendeleev Communications, vol. 33, no. 6, Oct. 2023, pp. 759-761. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.006.

Keywords

addition reaction
alantolactone
arsonium salts
lactone
phosphonium salts
quantum chemical calculations.
sesquiterpenes

Abstract

The reaction of alantolactone, a sesquiterpene α,β-unsaturated lactone, with H-phosphonium or H-arsonium triflates proceeds as P-H or As-H addition at the terminal =CH2 moiety to afford novel triphenyl(sesquiterpenyl)phosponium or -arsonium triflates. Their diastereoisomerism at the formed C11 chiral center has been simulated by quantum chemical calculations.

References

.
Kinetics and mechanism of triphenylphosphine quarternization with unsaturated carboxylic acids in the medium of acetic acid
Galkin V.I., Salin A.V., Bakhtiyarova Y.V., Sobanov A.A.
Russian Journal of General Chemistry, 2009
.
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update
Hunter E.P., Lias S.G.
Journal of Physical and Chemical Reference Data, 1998
.
Reaction of methyl 2-methylidene-3-oxolup-20(29)-en-28-oate with triphenylphosphonium trifluoromethanesulfonate
Tsepaeva O.V., Nemtarev A.V., Mironov V.F.
Russian Journal of Organic Chemistry, 2017
.
Tsepaeva O.V., Nemtarev A.V., Kundina A.V., Grigor’eva L.R., Mironov V.F.
Mendeleev Communications, 2021
.
Shemakhina M.E., Nemtarev A.V., Fayzullin R.R., Khasiyatullina N.R., Grigor’eva L.R., Mironov V.F.
Mendeleev Communications, 2020
.
Synthesis of C-29-phosphonium derivatives of 3,28-diacetoxylup-20(29)-en-30-oic acid
Ponomaryov D.V., Grigor´eva L.R., Nemtarev A.V., Tsepaeva O.V., Mironov V.F., Antipin I.S.
Russian Chemical Bulletin, 2020
.
Some Features of Reaction of 2-Methyl-1,4-naphthoquinone with H-Phosphonium Salts Based on Diphenylphosphine
Khasiyatullina N.R., Islamov D.R., Mironov V.F.
Russian Journal of General Chemistry, 2019
.
Khasiyatullina N.R., Mironov V.F., Gumerova S.K., Voloshina A.D., Sapunova A.S.
Mendeleev Communications, 2019
.
Synthesis and Antimicrobial Properties of Novel Phosphonium Salts Bearing 1,4-Dihydroxyaryl Fragment
Khasiyatullina N.R., Mironov V.F., Voloshina A.D., Sapunova A.S.
Chemistry and Biodiversity, 2019
.
Convenient Synthesis of Polyfunctional Diphosphonium Salts Based on 2-Methyl-1,4-naphthoquinone
Khasiyatullina N.R., Mironov V.F.
Russian Journal of Organic Chemistry, 2019
.
A Novel Triphenylphosphonium Carrier to Target Mitochondria without Uncoupling Oxidative Phosphorylation
Kulkarni C.A., Fink B.D., Gibbs B.E., Chheda P.R., Wu M., Sivitz W.I., Kerns R.J.
Journal of Medicinal Chemistry, 2021
.
Applications of Sesquiterpene Lactones: A Review of Some Potential Success Cases
Moujir L., Callies O., Sousa P.M., Sharopov F., Seca A.M.
Applied Sciences (Switzerland), 2020
.
N-Alkylation of Anthracycline Antibiotics by Natural Sesquiterpene Lactones as a Way to Obtain Antitumor Agents with Reduced Side Effects
Neganova M., Semakov A., Aleksandrova Y., Yandulova E., Pukhov S., Anikina L., Klochkov S.
Biomedicines, 2021
.
Alantolactone: A sesquiterpene lactone with diverse pharmacological effects
Liu X., Bian L., Duan X., Zhuang X., Sui Y., Yang L.
Chemical Biology and Drug Design, 2021
.
The effect of isabelin, a sesquiterpene lactone from Ambrosia artemisiifolia on soil microorganisms and human pathogens
Molinaro F., Tyc O., Beekwilder J., Cankar K., Bertea C.M., Negre M., Garbeva P.
FEMS Microbiology Letters, 2018
.
Synthesis and Antiproliferative Activity of Conjugates of Anthracycline Antibiotics with Sesquiterpene Lactones of the Elecampane
Semakov A.V., Anikina L.V., Afanasyeva S.V., Pukhov S.A., Klochkov S.G.
Russian Journal of Bioorganic Chemistry, 2018
.
Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones
Salin A.V., Islamov D.R.
Organic and Biomolecular Chemistry, 2019
.
Selective delivery of remarkably high levels of gadolinium to tumour cells using an arsonium salt
Windsor M.S., Busse M., Morrison D.E., Baker R.W., Hill L.R., Rendina L.M.
Chemical Communications, 2021
.
Trypanocidal and Leishmanicidal Activities of Sesquiterpene Lactones from Ambrosia tenuifolia Sprengel (Asteraceae)
Sülsen V.P., Frank F.M., Cazorla S.I., Anesini C.A., Malchiodi E.L., Freixa B., Vila R., Muschietti L.V., Martino V.S.
Antimicrobial Agents and Chemotherapy, 2008
.
Design, synthesis and biological evaluation of alantolactone derivatives as potential anti-inflammatory agents
Kumar C., Kumar A., Nalli Y., Lone W.I., Satti N.K., Verma M.K., Ahmed Z., Ali A.
Medicinal Chemistry Research, 2019
.
Alantolactone selectively ablates acute myeloid leukemia stem and progenitor cells
Ding Y., Gao H., Zhang Y., Li Y., Vasdev N., Gao Y., Chen Y., Zhang Q.
Journal of Hematology and Oncology, 2016
.
What made sesquiterpene lactones reach cancer clinical trials?
Ghantous A., Gali-Muhtasib H., Vuorela H., Saliba N.A., Darwiche N.
Drug Discovery Today, 2010
.
Effect of Anchimeric Assistance in the Reaction of Triphenylphosphine with α,β-Unsaturated Carboxylic Acids
Salin A.V., Fatkhutdinov A.R., Il'in A.V., Galkin V.I.
International Journal of Chemical Kinetics, 2014
.
Natural sesquiterpene lactones induce programmed cell death in Trypanosoma cruzi: A new therapeutic target?
Jimenez V., Kemmerling U., Paredes R., Maya J.D., Sosa M.A., Galanti N.
Phytomedicine, 2014
.
Application Prospects of Triphenylphosphine-Based Mitochondria-Targeted Cancer Therapy
Cheng X., Feng D., Lv J., Cui X., Wang Y., Wang Q., Zhang L.
Cancers, 2023
.
Reynosin and santamarine: two sesquiterpene lactones fromAmbrosia confertiflorawith bactericidal activity against clinical strains ofMycobacterium tuberculosis
Coronado-Aceves E.W., Velázquez C., Robles-Zepeda R.E., Jiménez-Estrada M., Hernández-Martínez J., Gálvez-Ruiz J.C., Garibay-Escobar A.
Pharmaceutical Biology, 2016
.
Antimicrobial activity of Artemisia douglasiana and dehydroleucodine against Helicobacter pylori
Vega A.E., Wendel G.H., Maria A.O., Pelzer L.
Journal of Ethnopharmacology, 2009
.
Sesquiterpene lactones from the endemic Cape Verdean Artemisia gorgonum
Ortet R., Prado S., Mouray E., Thomas O.P.
Phytochemistry, 2008
.
Michael additions catalyzed by phosphines. An overlooked synthetic method
Gimbert C., Lumbierres M., Marchi C., Moreno-Mañas M., Sebastián R.M., Vallribera A.
Tetrahedron, 2005
.
Cynaropicrin: The First Plant Natural Product withIn VivoActivity againstTrypanosoma brucei
Zimmermann S., Kaiser M., Brun R., Hamburger M., Adams M.
Planta Medica, 2012
.
Lactones: Generic Inhibitors of Enzymes?
Konaklieva M., Plotkin B.
Mini-Reviews in Medicinal Chemistry, 2005
.
Structure-Activity Relationships of Sesquiterpene Lactones
Schmidt T.J.
Studies in Natural Products Chemistry, 2006
.
Recent Advances on Cytotoxic Sesquiterpene Lactones
Quintana J., Estévez F.
Current Pharmaceutical Design, 2019