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 language | English |
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Pages (from-to) | 799-803 |
Number of pages | 5 |
Journal | Synlett |
Volume | 30 |
Issue number | 7 |
DOIs | |
Publication status | Published - Jan 1 2019 |
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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 journal › Article
}
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 -