Synthesis of hybrid phosphorated indenoquinolines and biological evaluation as topoisomerase I inhibitors and antiproliferative agents

María Fuertes; Asier Selas; Angela Trejo; Birgitta R. Knudsen; Francisco Palacios; Concepción Alonso

doi:10.1016/j.bmcl.2021.128517

Synthesis of hybrid phosphorated indenoquinolines and biological evaluation as topoisomerase I inhibitors and antiproliferative agents

María Fuertes, Asier Selas, Angela Trejo, Birgitta R. Knudsen, Francisco Palacios, Concepción Alonso^*

^*Corresponding author for this work

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

8 Citations (Scopus)

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Abstract

This work describes the first synthesis of diethyl 6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinolinylphosphonates 5, diethyl 7H-indeno[2,1-c]quinolinylphosphonates 6 and diethyl 7-oxo-7H-indeno[2,1-c]quinolinylphosphonates 7, which were prepared in good to high overall yields. The synthetic route involves a multicomponent reaction of 2-phosphonateaniline, aldehydes and indene as olefin and allows the selective generation of three stereogenic centres in a short, efficient and reliable manner. The selective dehydrogenation of 1,2,3,4-tetrahydroindenoquinolines leads to the formation of corresponding indenoquinolines, and subsequent oxidation of methylene group of the indenoquinolines allows the access to indenoquinolinones.

Original language	English
Article number	128517
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	57
ISSN	0960-894X
DOIs	https://doi.org/10.1016/j.bmcl.2021.128517
Publication status	Published - 1 Feb 2022

Keywords

Antiproliferative effect
Enzyme inhibition
Indenoquinolinyl phosphonates
Topoisomerase I

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1-s2.0-S0960894X21007447-mainFinal published version, 813 KBLicence: CC BY-NC-ND

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title = "Synthesis of hybrid phosphorated indenoquinolines and biological evaluation as topoisomerase I inhibitors and antiproliferative agents",

abstract = "This work describes the first synthesis of diethyl 6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinolinylphosphonates 5, diethyl 7H-indeno[2,1-c]quinolinylphosphonates 6 and diethyl 7-oxo-7H-indeno[2,1-c]quinolinylphosphonates 7, which were prepared in good to high overall yields. The synthetic route involves a multicomponent reaction of 2-phosphonateaniline, aldehydes and indene as olefin and allows the selective generation of three stereogenic centres in a short, efficient and reliable manner. The selective dehydrogenation of 1,2,3,4-tetrahydroindenoquinolines leads to the formation of corresponding indenoquinolines, and subsequent oxidation of methylene group of the indenoquinolines allows the access to indenoquinolinones.",

keywords = "Antiproliferative effect, Enzyme inhibition, Indenoquinolinyl phosphonates, Topoisomerase I",

author = "Mar{\'i}a Fuertes and Asier Selas and Angela Trejo and Knudsen, {Birgitta R.} and Francisco Palacios and Concepci{\'o}n Alonso",

note = "Publisher Copyright: {\textcopyright} 2021 The Author(s)",

year = "2022",

month = feb,

day = "1",

doi = "10.1016/j.bmcl.2021.128517",

language = "English",

volume = "57",

journal = "Bioorganic and Medicinal Chemistry Letters",

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Synthesis of hybrid phosphorated indenoquinolines and biological evaluation as topoisomerase I inhibitors and antiproliferative agents. / Fuertes, María; Selas, Asier; Trejo, Angela et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 57, 128517, 01.02.2022.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Synthesis of hybrid phosphorated indenoquinolines and biological evaluation as topoisomerase I inhibitors and antiproliferative agents

AU - Fuertes, María

AU - Selas, Asier

AU - Trejo, Angela

AU - Knudsen, Birgitta R.

AU - Palacios, Francisco

AU - Alonso, Concepción

PY - 2022/2/1

Y1 - 2022/2/1

N2 - This work describes the first synthesis of diethyl 6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinolinylphosphonates 5, diethyl 7H-indeno[2,1-c]quinolinylphosphonates 6 and diethyl 7-oxo-7H-indeno[2,1-c]quinolinylphosphonates 7, which were prepared in good to high overall yields. The synthetic route involves a multicomponent reaction of 2-phosphonateaniline, aldehydes and indene as olefin and allows the selective generation of three stereogenic centres in a short, efficient and reliable manner. The selective dehydrogenation of 1,2,3,4-tetrahydroindenoquinolines leads to the formation of corresponding indenoquinolines, and subsequent oxidation of methylene group of the indenoquinolines allows the access to indenoquinolinones.

AB - This work describes the first synthesis of diethyl 6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinolinylphosphonates 5, diethyl 7H-indeno[2,1-c]quinolinylphosphonates 6 and diethyl 7-oxo-7H-indeno[2,1-c]quinolinylphosphonates 7, which were prepared in good to high overall yields. The synthetic route involves a multicomponent reaction of 2-phosphonateaniline, aldehydes and indene as olefin and allows the selective generation of three stereogenic centres in a short, efficient and reliable manner. The selective dehydrogenation of 1,2,3,4-tetrahydroindenoquinolines leads to the formation of corresponding indenoquinolines, and subsequent oxidation of methylene group of the indenoquinolines allows the access to indenoquinolinones.

KW - Antiproliferative effect

KW - Enzyme inhibition

KW - Indenoquinolinyl phosphonates

KW - Topoisomerase I

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U2 - 10.1016/j.bmcl.2021.128517

DO - 10.1016/j.bmcl.2021.128517

M3 - Journal article

C2 - 34952177

AN - SCOPUS:85121980236

SN - 0960-894X

VL - 57

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

M1 - 128517

ER -

Synthesis of hybrid phosphorated indenoquinolines and biological evaluation as topoisomerase I inhibitors and antiproliferative agents

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