Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction

Angel Zamudio-Medina; Nury Pérez-Hernández; José Luis Castrejón-Flores; Susana Romero-García; Heriberto Prado-García; Angel Bañuelos-Hernández; Marco Franco-Pérez

doi:10.1080/10426507.2021.1878358

Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction

Angel Zamudio-Medina, Nury Pérez-Hernández, José Luis Castrejón-Flores, Susana Romero-García, Heriberto Prado-García, Angel Bañuelos-Hernández, Marco Franco-Pérez

Research output: Contribution to journal › Article › peer-review

Abstract

We present a new single-step multicomponent reaction strategy for the synthesis of symmetric and (novel) asymmetric bisphosphoramidate and bisphosphoramidothioate derivatives. Reactions proceed under routine experimental conditions, do not require the aid of any catalyst, and provide moderate yields after a short time. We synthesized 18 different compounds, 10 of them for the first time. The cytotoxic activity of our adducts was assessed by measuring their inhibitory capacity (IC₅₀) against two different cell lines, the A549 (lung cancer cells) and the SW1353 (chondrosarcoma cells).

Original language	English
Pages (from-to)	634-642
Number of pages	9
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	196
Issue number	7
DOIs	https://doi.org/10.1080/10426507.2021.1878358
State	Published - 2021

Keywords

Multicomponent reaction
bisphosphoramidates
bisphosphoramidothioates
cytotoxicity
double addition–elimination
symmetric and asymmetric derivatives

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1080/10426507.2021.1878358

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Zamudio-Medina, A., Pérez-Hernández, N., Castrejón-Flores, J. L., Romero-García, S., Prado-García, H., Bañuelos-Hernández, A., & Franco-Pérez, M. (2021). Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction. Phosphorus, Sulfur and Silicon and the Related Elements, 196(7), 634-642. https://doi.org/10.1080/10426507.2021.1878358

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title = "Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction",

abstract = "We present a new single-step multicomponent reaction strategy for the synthesis of symmetric and (novel) asymmetric bisphosphoramidate and bisphosphoramidothioate derivatives. Reactions proceed under routine experimental conditions, do not require the aid of any catalyst, and provide moderate yields after a short time. We synthesized 18 different compounds, 10 of them for the first time. The cytotoxic activity of our adducts was assessed by measuring their inhibitory capacity (IC50) against two different cell lines, the A549 (lung cancer cells) and the SW1353 (chondrosarcoma cells).",

keywords = "Multicomponent reaction, bisphosphoramidates, bisphosphoramidothioates, cytotoxicity, double addition–elimination, symmetric and asymmetric derivatives",

author = "Angel Zamudio-Medina and Nury P{\'e}rez-Hern{\'a}ndez and Castrej{\'o}n-Flores, {Jos{\'e} Luis} and Susana Romero-Garc{\'i}a and Heriberto Prado-Garc{\'i}a and Angel Ba{\~n}uelos-Hern{\'a}ndez and Marco Franco-P{\'e}rez",

note = "Publisher Copyright: {\textcopyright} 2021 Taylor & Francis Group, LLC.",

year = "2021",

doi = "10.1080/10426507.2021.1878358",

language = "Ingl{\'e}s",

volume = "196",

pages = "634--642",

journal = "Phosphorus, Sulfur and Silicon and the Related Elements",

issn = "1042-6507",

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Zamudio-Medina, A , Pérez-Hernández, N , Castrejón-Flores, JL, Romero-García, S, Prado-García, H, Bañuelos-Hernández, A & Franco-Pérez, M 2021, 'Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction', Phosphorus, Sulfur and Silicon and the Related Elements, vol. 196, no. 7, pp. 634-642. https://doi.org/10.1080/10426507.2021.1878358

Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction. / Zamudio-Medina, Angel ; Pérez-Hernández, Nury ; Castrejón-Flores, José Luis et al.
In: Phosphorus, Sulfur and Silicon and the Related Elements, Vol. 196, No. 7, 2021, p. 634-642.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction

AU - Zamudio-Medina, Angel

AU - Pérez-Hernández, Nury

AU - Castrejón-Flores, José Luis

AU - Romero-García, Susana

AU - Prado-García, Heriberto

AU - Bañuelos-Hernández, Angel

AU - Franco-Pérez, Marco

PY - 2021

Y1 - 2021

N2 - We present a new single-step multicomponent reaction strategy for the synthesis of symmetric and (novel) asymmetric bisphosphoramidate and bisphosphoramidothioate derivatives. Reactions proceed under routine experimental conditions, do not require the aid of any catalyst, and provide moderate yields after a short time. We synthesized 18 different compounds, 10 of them for the first time. The cytotoxic activity of our adducts was assessed by measuring their inhibitory capacity (IC50) against two different cell lines, the A549 (lung cancer cells) and the SW1353 (chondrosarcoma cells).

AB - We present a new single-step multicomponent reaction strategy for the synthesis of symmetric and (novel) asymmetric bisphosphoramidate and bisphosphoramidothioate derivatives. Reactions proceed under routine experimental conditions, do not require the aid of any catalyst, and provide moderate yields after a short time. We synthesized 18 different compounds, 10 of them for the first time. The cytotoxic activity of our adducts was assessed by measuring their inhibitory capacity (IC50) against two different cell lines, the A549 (lung cancer cells) and the SW1353 (chondrosarcoma cells).

KW - Multicomponent reaction

KW - bisphosphoramidates

KW - bisphosphoramidothioates

KW - cytotoxicity

KW - double addition–elimination

KW - symmetric and asymmetric derivatives

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U2 - 10.1080/10426507.2021.1878358

DO - 10.1080/10426507.2021.1878358

M3 - Artículo

AN - SCOPUS:85100571929

SN - 1042-6507

VL - 196

SP - 634

EP - 642

JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

IS - 7

ER -

Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction

Abstract

Keywords

UN SDGs

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