Stereochemistry of Knoevenagel Condensation Products from Cyanoacetates and Aromatic Aldehydes

Hidetsura Cho; Takashi Iwashita; Mikiko Hamaguchi; Yoshiaki Oyama

doi:10.1248/cpb.39.3341

Stereochemistry of Knoevenagel Condensation Products from Cyanoacetates and Aromatic Aldehydes

Hidetsura Cho, Takashi Iwashita, Mikiko Hamaguchi, Yoshiaki Oyama

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

The C-13 long-range selective proton decoupling method and X-ray crystallographic analysis were employed to determine the stereochemistry of the caffeic acid derivatives, extremely potent 12-lipoxygenase inhibitors, synthesized from cyanoacetates and aromatic aldehydes. The ester group of 1 and 2 was found to be trans to the phenyl group.

Original language	English
Pages (from-to)	3341-3342
Number of pages	2
Journal	Chemical and Pharmaceutical Bulletin
Volume	39
Issue number	12
DOIs	https://doi.org/10.1248/cpb.39.3341
Publication status	Published - 1991

Keywords

12-lipoxygenase
12-lipoxygenase inhibitor
C-13 NMR long-range selective proton decoupling (LSPD)
E-regioisomer
Keywords stereochemistry
Knoevenagel condensation
X-ray crystallographic analysis
Z-regioisomer
caffeic acid derivative
regioselectivity

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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abstract = "The C-13 long-range selective proton decoupling method and X-ray crystallographic analysis were employed to determine the stereochemistry of the caffeic acid derivatives, extremely potent 12-lipoxygenase inhibitors, synthesized from cyanoacetates and aromatic aldehydes. The ester group of 1 and 2 was found to be trans to the phenyl group.",

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author = "Hidetsura Cho and Takashi Iwashita and Mikiko Hamaguchi and Yoshiaki Oyama",

year = "1991",

doi = "10.1248/cpb.39.3341",

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T1 - Stereochemistry of Knoevenagel Condensation Products from Cyanoacetates and Aromatic Aldehydes

AU - Cho, Hidetsura

AU - Iwashita, Takashi

AU - Hamaguchi, Mikiko

AU - Oyama, Yoshiaki

PY - 1991

Y1 - 1991

N2 - The C-13 long-range selective proton decoupling method and X-ray crystallographic analysis were employed to determine the stereochemistry of the caffeic acid derivatives, extremely potent 12-lipoxygenase inhibitors, synthesized from cyanoacetates and aromatic aldehydes. The ester group of 1 and 2 was found to be trans to the phenyl group.

AB - The C-13 long-range selective proton decoupling method and X-ray crystallographic analysis were employed to determine the stereochemistry of the caffeic acid derivatives, extremely potent 12-lipoxygenase inhibitors, synthesized from cyanoacetates and aromatic aldehydes. The ester group of 1 and 2 was found to be trans to the phenyl group.

KW - 12-lipoxygenase

KW - 12-lipoxygenase inhibitor

KW - C-13 NMR long-range selective proton decoupling (LSPD)

KW - E-regioisomer

KW - Keywords stereochemistry

KW - Knoevenagel condensation

KW - X-ray crystallographic analysis

KW - Z-regioisomer

KW - caffeic acid derivative

KW - regioselectivity

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VL - 39

SP - 3341

EP - 3342

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 12

ER -

Stereochemistry of Knoevenagel Condensation Products from Cyanoacetates and Aromatic Aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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