An efficient synthesis of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-one:a new ring system of pharmaceutical interest

Paola Barraja; Anna Carbone; Virginia Spano'; Barbara Parrino; Girolamo Cirrincione; Patrizia Diana; Alessandra Montalbano

An efficient synthesis of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-one:a new ring system of pharmaceutical interest

Paola Barraja, Anna Carbone, Virginia Spano', Barbara Parrino, Girolamo Cirrincione, Patrizia Diana, Alessandra Montalbano

Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche

Risultato della ricerca: Article

24 Citazioni (Scopus)

Abstract

A series of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-ones 4 was prepared in good yields by reactingenaminoketones with cyanomethylene active compounds such as phenylsulfonylacetonitrile, benzoylacetonitrile,and malononitrile. Derivatives of the title ring system were tested by the National CancerInstitute of Bethesda against a panel of about 60 human tumor cell lines, and one of them showed inhibitoryactivity against all cancer cell lines reaching on 48% of them GI50 values at submicromolar leveland on the majority of the remaining ones in the low micromolar concentration

Lingua originale	English
pagine (da-a)	5087-5094
Numero di pagine	9
Rivista	Tetrahedron
Volume	68
Stato di pubblicazione	Published - 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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Cita questo

Barraja, P., Carbone, A., Spano', V., Parrino, B., Cirrincione, G., Diana, P., & Montalbano, A. (2012). An efficient synthesis of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-one:a new ring system of pharmaceutical interest. Tetrahedron, 68, 5087-5094.

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title = "An efficient synthesis of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-one:a new ring system of pharmaceutical interest",

abstract = "A series of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-ones 4 was prepared in good yields by reactingenaminoketones with cyanomethylene active compounds such as phenylsulfonylacetonitrile, benzoylacetonitrile,and malononitrile. Derivatives of the title ring system were tested by the National CancerInstitute of Bethesda against a panel of about 60 human tumor cell lines, and one of them showed inhibitoryactivity against all cancer cell lines reaching on 48% of them GI50 values at submicromolar leveland on the majority of the remaining ones in the low micromolar concentration",

keywords = "2':4, 2-b]pyridin-2-one, 5]thiopyrano[3, Angelicin, Antiproliferative activity, Enaminoketones, Pyrrolo[3', 2':4, 2-b]pyridin-2-one, 5]thiopyrano[3, Angelicin, Antiproliferative activity, Enaminoketones, Pyrrolo[3'",

author = "Paola Barraja and Anna Carbone and Virginia Spano' and Barbara Parrino and Girolamo Cirrincione and Patrizia Diana and Alessandra Montalbano",

year = "2012",

language = "English",

volume = "68",

pages = "5087--5094",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - An efficient synthesis of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-one:a new ring system of pharmaceutical interest

AU - Barraja, Paola

AU - Carbone, Anna

AU - Spano', Virginia

AU - Parrino, Barbara

AU - Cirrincione, Girolamo

AU - Diana, Patrizia

AU - Montalbano, Alessandra

PY - 2012

Y1 - 2012

N2 - A series of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-ones 4 was prepared in good yields by reactingenaminoketones with cyanomethylene active compounds such as phenylsulfonylacetonitrile, benzoylacetonitrile,and malononitrile. Derivatives of the title ring system were tested by the National CancerInstitute of Bethesda against a panel of about 60 human tumor cell lines, and one of them showed inhibitoryactivity against all cancer cell lines reaching on 48% of them GI50 values at submicromolar leveland on the majority of the remaining ones in the low micromolar concentration

AB - A series of pyrrolo[3',2':4,5]thiopyrano[3,2-b]pyridin-2-ones 4 was prepared in good yields by reactingenaminoketones with cyanomethylene active compounds such as phenylsulfonylacetonitrile, benzoylacetonitrile,and malononitrile. Derivatives of the title ring system were tested by the National CancerInstitute of Bethesda against a panel of about 60 human tumor cell lines, and one of them showed inhibitoryactivity against all cancer cell lines reaching on 48% of them GI50 values at submicromolar leveland on the majority of the remaining ones in the low micromolar concentration

KW - 2':4

KW - 2-b]pyridin-2-one

KW - 5]thiopyrano[3

KW - Angelicin

KW - Antiproliferative activity

KW - Enaminoketones

KW - Pyrrolo[3'

KW - 2':4

KW - 2-b]pyridin-2-one

KW - 5]thiopyrano[3

KW - Angelicin

KW - Antiproliferative activity

KW - Enaminoketones

KW - Pyrrolo[3'

UR - http://hdl.handle.net/10447/63314

M3 - Article

VL - 68

SP - 5087

EP - 5094

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

ER -