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Synthesis of new p-quinone methide containing morpholine fragment: access to (diarylmethyl)phosphonamidates with antitumor activity

El'mira Mingaleevna Gibadullina 1
El'mira Mingaleevna Gibadullina
, 
Tran H.B. Nguyen 2
Tran H.B. Nguyen
, 
Thu Thi Nguyen 2
Thu Thi Nguyen
, 
Anna Georgievna Strelnik 1
Anna Georgievna Strelnik
, 
Alexandra Dmitrievna Voloshina 1
Alexandra Dmitrievna Voloshina
, 
Anna Pavlovna Lyubina 1
Anna Pavlovna Lyubina
, 
Syumbel Kamilevna Amerhanova 1
Syumbel Kamilevna Amerhanova
, 
Alexander Romanovich Burilov 1
Alexander Romanovich Burilov
1 A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
2 Kazan National Research Technological University, Kazan, Russian Federation
10.1016/j.mencom.2023.02.027
Published 2023-02-13
Communication , Volume 33, Issue 2, 234-236
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Gibadullina E. M. et al. Synthesis of new p-quinone methide containing morpholine fragment: access to (diarylmethyl)phosphonamidates with antitumor activity // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 234-236.
GOST all authors (up to 50) Copy
Gibadullina E. M., Nguyen T. H., Nguyen T. T., Strelnik A. G., Voloshina A. D., Lyubina A. P., Amerhanova S. K., Burilov A. R. Synthesis of new p-quinone methide containing morpholine fragment: access to (diarylmethyl)phosphonamidates with antitumor activity // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 234-236.
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TY - JOUR
DO - 10.1016/j.mencom.2023.02.027
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.027
TI - Synthesis of new p-quinone methide containing morpholine fragment: access to (diarylmethyl)phosphonamidates with antitumor activity
T2 - Mendeleev Communications
AU - Gibadullina, El'mira Mingaleevna
AU - Nguyen, Tran H.B.
AU - Nguyen, Thu Thi
AU - Strelnik, Anna Georgievna
AU - Voloshina, Alexandra Dmitrievna
AU - Lyubina, Anna Pavlovna
AU - Amerhanova, Syumbel Kamilevna
AU - Burilov, Alexander Romanovich
PY - 2023
DA - 2023/02/13
PB - Mendeleev Communications
SP - 234-236
IS - 2
VL - 33
ER -
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@article{2023_Gibadullina,
author = {El'mira Mingaleevna Gibadullina and Tran H.B. Nguyen and Thu Thi Nguyen and Anna Georgievna Strelnik and Alexandra Dmitrievna Voloshina and Anna Pavlovna Lyubina and Syumbel Kamilevna Amerhanova and Alexander Romanovich Burilov},
title = {Synthesis of new p-quinone methide containing morpholine fragment: access to (diarylmethyl)phosphonamidates with antitumor activity},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.027},
number = {2},
pages = {234--236},
doi = {10.1016/j.mencom.2023.02.027}
}
MLA
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MLA Copy
Gibadullina, El'mira Mingaleevna, et al. “Synthesis of new p-quinone methide containing morpholine fragment: access to (diarylmethyl)phosphonamidates with antitumor activity.” Mendeleev Communications, vol. 33, no. 2, Feb. 2023, pp. 234-236. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.027.

Keywords

(diarylmethyl)phosphonamidates
1 2-benzoxaphospholes
1 6-conjugate addition
antitumour activity.
cytotoxicity
p-quinone methides
phosphonamidates

Abstract

Novel (diarylmethyl)phosphonamidates containing 2,6-di-tert-butylphenol and heterocycle moieties were synthesized by 1,6-conjugate addition of phosphorylated p-quinone methide with morpholine fragment to 2,6-diaminopyridine or 1,3-diaminobenzene. In the case of an acid-catalyzed reaction of p-quinone methide with sesamol, morpholine was cleaved to form 1,2-benzoxaphosphole substituent. Cytotoxic effects of starting compounds and obtained products were evaluated towards human cancer and normal cells.

References

.
Some insight into the mode of cytotoxic action of organotin compounds with protective 2,6-di-tert-butylphenol fragments
Milaeva E.R., Shpakovsky D.B., Gracheva Y.A., Antonenko T.A., Osolodkin D.I., Palyulin V.A., Shevtsov P.N., Neganova M.E., Vinogradova D.V., Shevtsova E.F.
Journal of Organometallic Chemistry, 2015
.
Global Cancer Statistics 2020: GLOBOCAN Estimates of Incidence and Mortality Worldwide for 36 Cancers in 185 Countries
Sung H., Ferlay J., Siegel R.L., Laversanne M., Soerjomataram I., Jemal A., Bray F.
Ca-A Cancer Journal for Clinicians, 2021
.
New 2,6-diaminopyridines containing a sterically hindered benzylphosphonate moiety in the aromatic core as potential antioxidant and anti-cancer drugs
Gibadullina E., Nguyen T.T., Strelnik A., Sapunova A., Voloshina A., Sudakov I., Vyshtakalyuk A., Voronina J., Pudovik M., Burilov A.
European Journal of Medicinal Chemistry, 2019
.
Reactions of [(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dien- 1-ylidene)methyl]phosphonates with Phenols
Gibadullina E.M., Shaekhov T.R., Voronina Y.K., Pudovik M.A., Burilov A.R.
Russian Journal of Organic Chemistry, 2018
.
Targeted inhibition of STAT/TET1 axis as a therapeutic strategy for acute myeloid leukemia
Jiang X., Hu C., Ferchen K., Nie J., Cui X., Chen C., Cheng L., Zuo Z., Seibel W., He C., Tang Y., Skibbe J.R., Wunderlich M., Reinhold W.C., Dong L., et. al.
Nature Communications, 2017
.
Preformulation, formulation, and in vivo efficacy of topically applied Apomine
Kuehl P.J., Stratton S.P., Powell M.B., Myrdal P.B.
International Journal of Pharmaceutics, 2009
.
Benzo[d]-1,2-oxaphospholes as Precursors of Stabilized C-Centered Radicals
Pérez-Prieto J., Galian R.E., Miranda M.A., Catalina F., Martín-Vargas N., López-Ortiz F.
Organic Letters, 2004
.
New Type of Metalloproteinase Inhibitor:  Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids
Sawa M., Kiyoi T., Kurokawa K., Kumihara H., Yamamoto M., Miyasaka T., Ito Y., Hirayama R., Inoue T., Kirii Y., Nishiwaki E., Ohmoto H., Maeda Y., Ishibushi E., Inoue Y., et. al.
Journal of Medicinal Chemistry, 2002
.
Phosphonamidate Prodrugs of a Butyrophilin Ligand Display Plasma Stability and Potent Vγ9 Vδ2 T Cell Stimulation
Lentini N.A., Foust B.J., Hsiao C.C., Wiemer A.J., Wiemer D.F.
Journal of Medicinal Chemistry, 2018
.
Silver-Catalyzed Regioselective Phosphorylation of para-Quinone Methides with P(III)-Nucleophiles
Xu S., Xie J., Liu Y., Xu W., Tang K., Xiong B., Wong W.
Journal of Organic Chemistry, 2021
.
Base-Catalyzed 1,6-Hydrophosphonylation of p -Quinone Methides with Diphenylphosphane Oxide/Phosphites
Zhang B., Liu L., Mao S., Zhou M., Wang H., Li L.
European Journal of Organic Chemistry, 2019
.
para -Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules
Lima C.G., Pauli F.P., Costa D.C., de Souza A.S., Forezi L.S., Ferreira V.F., de Carvalho da Silva F.
European Journal of Organic Chemistry, 2020
.
CF3 -Containing para -Quinone Methides for Organic Synthesis
Winter M., Schütz R., Eitzinger A., Ofial A.R., Waser M.
European Journal of Organic Chemistry, 2020
.
Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides
Eitzinger A., Winter M., Schörgenhumer J., Waser M.
Chemical Communications, 2020
.
Novel di-tertiary-butyl phenylhydrazones as dual cyclooxygenase-2/5-lipoxygenase inhibitors: Synthesis, COX/LOX inhibition, molecular modeling, and insights into their cytotoxicities
Ghatak S., Vyas A., Misra S., O’Brien P., Zambre A., Fresco V.M., Markwald R.R., Swamy K.V., Afrasiabi Z., Choudhury A., Khetmalas M., Padhye S.
Bioorganic and Medicinal Chemistry Letters, 2014
.
Phosphamide-containing diphenylpyrimidine analogues (PA-DPPYs) as potent focal adhesion kinase (FAK) inhibitors with enhanced activity against pancreatic cancer cell lines
Liu H., Wu B., Ge Y., Huang J., Song S., Wang C., Yao J., Liu K., Li Y., Li Y., Ma X.
Bioorganic and Medicinal Chemistry, 2017
.
Tham P.T., Chinh P.T., Tuyen N.V., Bang D.N., Van D.T., Kien V.T., Thanh H.T., Quynh D.H., Cuong V.D., Thanh N.H., Pérez-Encabo A.
Mendeleev Communications, 2021
.
Kibardina L.K., Trifonov A.V., Dobrynin A.B., Pudovik M.A., Burilov A.R., Voloshina A.D., Strelnik A.G., Gazizov A.S.
Mendeleev Communications, 2021
.
Chugunova E.A., Smolobochkin A.V., Gazizov A.S., Burilov A.R., Voloshina A.D., Lyubina A.P., Amerhanova S.K., Melnikova A.A., Tulesinova A.I., Akylbekov N.I., Akhatayev N.A., Syakaev V.V.
Mendeleev Communications, 2021