Synthesis of the New Ring System Bispyrido[4',3':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine and Its Deaza Analogue

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Abstract

Derivatives of the new ring systems bispyrido[4',3':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine-6,13-dione and its deaza analogue pyrido[4'',3'':4',5']pyrrolo-[1',2':4,5]pyrazino[1,2-a]indole-6,13-dione were conveniently synthesized through a four-step sequence.Symmetrical derivatives of the former ring system were obtained through selfcondensation. On the other hand, condensation of 6-azaindole carboxylic acid with indole2-carboxylic acid afforded the deaza analogue ring system. Derivatives of the title ringsystem were tested by the National Cancer Institute (Bethesda, MD, USA) and four ofthem exhibited modest activity against MCF7 (a breast cancer cell line) and/or UO-31(a renal cancer cell line).
Lingua originaleEnglish
pagine (da-a)13342-13357
Numero di pagine16
RivistaMolecules
Volume19
Stato di pubblicazionePublished - 2014

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Pyrazines
pyrazines
Carboxylic Acids
cancer
Dione
analogs
Derivatives
cultured cells
carboxylic acids
Cell Line
National Cancer Institute (U.S.)
Kidney Neoplasms
rings
synthesis
Cells
indoles
Breast Neoplasms
breast
Condensation
condensation

All Science Journal Classification (ASJC) codes

  • Medicine(all)
  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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@article{d39fefe566614c8589b29c2fc5152ac9,
title = "Synthesis of the New Ring System Bispyrido[4',3':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine and Its Deaza Analogue",
abstract = "Derivatives of the new ring systems bispyrido[4',3':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine-6,13-dione and its deaza analogue pyrido[4'',3'':4',5']pyrrolo-[1',2':4,5]pyrazino[1,2-a]indole-6,13-dione were conveniently synthesized through a four-step sequence.Symmetrical derivatives of the former ring system were obtained through selfcondensation. On the other hand, condensation of 6-azaindole carboxylic acid with indole2-carboxylic acid afforded the deaza analogue ring system. Derivatives of the title ringsystem were tested by the National Cancer Institute (Bethesda, MD, USA) and four ofthem exhibited modest activity against MCF7 (a breast cancer cell line) and/or UO-31(a renal cancer cell line).",
keywords = "antiproliferative activity, bispyrido-pyrrolo-pyrazine, diketopiperazines, plinabulin A, pyrido-pyrrolopyrazino- indole",
author = "Girolamo Cirrincione and Alessandra Montalbano and Patrizia Diana and Anna Carbone and Paola Barraja and Virginia Spano' and Barbara Parrino",
year = "2014",
language = "English",
volume = "19",
pages = "13342--13357",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

}

TY - JOUR

T1 - Synthesis of the New Ring System Bispyrido[4',3':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine and Its Deaza Analogue

AU - Cirrincione, Girolamo

AU - Montalbano, Alessandra

AU - Diana, Patrizia

AU - Carbone, Anna

AU - Barraja, Paola

AU - Spano', Virginia

AU - Parrino, Barbara

PY - 2014

Y1 - 2014

N2 - Derivatives of the new ring systems bispyrido[4',3':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine-6,13-dione and its deaza analogue pyrido[4'',3'':4',5']pyrrolo-[1',2':4,5]pyrazino[1,2-a]indole-6,13-dione were conveniently synthesized through a four-step sequence.Symmetrical derivatives of the former ring system were obtained through selfcondensation. On the other hand, condensation of 6-azaindole carboxylic acid with indole2-carboxylic acid afforded the deaza analogue ring system. Derivatives of the title ringsystem were tested by the National Cancer Institute (Bethesda, MD, USA) and four ofthem exhibited modest activity against MCF7 (a breast cancer cell line) and/or UO-31(a renal cancer cell line).

AB - Derivatives of the new ring systems bispyrido[4',3':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine-6,13-dione and its deaza analogue pyrido[4'',3'':4',5']pyrrolo-[1',2':4,5]pyrazino[1,2-a]indole-6,13-dione were conveniently synthesized through a four-step sequence.Symmetrical derivatives of the former ring system were obtained through selfcondensation. On the other hand, condensation of 6-azaindole carboxylic acid with indole2-carboxylic acid afforded the deaza analogue ring system. Derivatives of the title ringsystem were tested by the National Cancer Institute (Bethesda, MD, USA) and four ofthem exhibited modest activity against MCF7 (a breast cancer cell line) and/or UO-31(a renal cancer cell line).

KW - antiproliferative activity

KW - bispyrido-pyrrolo-pyrazine

KW - diketopiperazines

KW - plinabulin A

KW - pyrido-pyrrolopyrazino- indole

UR - http://hdl.handle.net/10447/97043

M3 - Article

VL - 19

SP - 13342

EP - 13357

JO - Molecules

JF - Molecules

SN - 1420-3049

ER -