1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis

László Tóth, Attila Kiss-Szikszai, Gábor Vasvári, Ferenc Fenyvesi, M. Vecsernyés, P. Mátyus, S. Antus, Attila Mándi, T. Kurtán

Research output: Contribution to journalArticle

Abstract

Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.

Original languageEnglish
Pages (from-to)799-803
Number of pages5
JournalSynlett
Volume30
Issue number7
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Benzopyrans
Amination
Enantiomers
Isomerization
Cells
Derivatives

Keywords

  • 1,2-dihydrochromeno[2,3-c]pyrrol-3-one
  • antiproliferative
  • HPLC-ECD
  • isomerization
  • TDDFT-ECD

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives : Synthesis and HPLC-ECD Analysis. / Tóth, László; Kiss-Szikszai, Attila; Vasvári, Gábor; Fenyvesi, Ferenc; Vecsernyés, M.; Mátyus, P.; Antus, S.; Mándi, Attila; Kurtán, T.

In: Synlett, Vol. 30, No. 7, 01.01.2019, p. 799-803.

Research output: Contribution to journalArticle

Tóth, László ; Kiss-Szikszai, Attila ; Vasvári, Gábor ; Fenyvesi, Ferenc ; Vecsernyés, M. ; Mátyus, P. ; Antus, S. ; Mándi, Attila ; Kurtán, T. / 1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives : Synthesis and HPLC-ECD Analysis. In: Synlett. 2019 ; Vol. 30, No. 7. pp. 799-803.
@article{d16bf091e9a5420b9c3886c665dc641e,
title = "1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis",
abstract = "Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.",
keywords = "1,2-dihydrochromeno[2,3-c]pyrrol-3-one, antiproliferative, HPLC-ECD, isomerization, TDDFT-ECD",
author = "L{\'a}szl{\'o} T{\'o}th and Attila Kiss-Szikszai and G{\'a}bor Vasv{\'a}ri and Ferenc Fenyvesi and M. Vecserny{\'e}s and P. M{\'a}tyus and S. Antus and Attila M{\'a}ndi and T. Kurt{\'a}n",
year = "2019",
month = "1",
day = "1",
doi = "10.1055/s-0037-1612085",
language = "English",
volume = "30",
pages = "799--803",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "7",

}

TY - JOUR

T1 - 1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives

T2 - Synthesis and HPLC-ECD Analysis

AU - Tóth, László

AU - Kiss-Szikszai, Attila

AU - Vasvári, Gábor

AU - Fenyvesi, Ferenc

AU - Vecsernyés, M.

AU - Mátyus, P.

AU - Antus, S.

AU - Mándi, Attila

AU - Kurtán, T.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.

AB - Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.

KW - 1,2-dihydrochromeno[2,3-c]pyrrol-3-one

KW - antiproliferative

KW - HPLC-ECD

KW - isomerization

KW - TDDFT-ECD

UR - http://www.scopus.com/inward/record.url?scp=85064349277&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85064349277&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1612085

DO - 10.1055/s-0037-1612085

M3 - Article

AN - SCOPUS:85064349277

VL - 30

SP - 799

EP - 803

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 7

ER -