Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.

Katalin Prokai-Tatrai; John A. Zoltewicz; William R. Kem

doi:10.1016/S0040-4020(01)89606-X

Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.

Katalin Prokai-Tatrai, John A. Zoltewicz, William R. Kem

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

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Abstract

The synthesis and conformational analysis of a "bridged" anabasine, 5,8,9,10,11,11a-hexahydro-6H-pyrido[2,1-f][1,6] naphthyridine (5), and related compounds are reported. Conformational assignments were made using NMR data (including coupling constants, homonuclear Overhauser effects, and 2D correlations) and the results of molecular mechanics (MM2) calculations. The tricyclic compounds have trans-quinolizidine ring fusion with a chair-shaped piperidine ring. The center ring shows a half-chair conformation for the title compound, and a half-boat shape for its 6-oxo derivative. Calculated vicinal coupling constants are in good agreement with those obtained experimentally.

Original language	English
Pages (from-to)	9909-9918
Number of pages	10
Journal	Tetrahedron
Volume	50
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4020(01)89606-X
State	Published - 1994

Keywords

Bridged anabasine
Conformational analysis
Molecular mechanics.
Nuclear Overhauser enhancement

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10.1016/S0040-4020(01)89606-X

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@article{236050f003094c2c860eecd83605a2e9,

title = "Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.",

abstract = "The synthesis and conformational analysis of a {"}bridged{"} anabasine, 5,8,9,10,11,11a-hexahydro-6H-pyrido[2,1-f][1,6] naphthyridine (5), and related compounds are reported. Conformational assignments were made using NMR data (including coupling constants, homonuclear Overhauser effects, and 2D correlations) and the results of molecular mechanics (MM2) calculations. The tricyclic compounds have trans-quinolizidine ring fusion with a chair-shaped piperidine ring. The center ring shows a half-chair conformation for the title compound, and a half-boat shape for its 6-oxo derivative. Calculated vicinal coupling constants are in good agreement with those obtained experimentally.",

keywords = "Bridged anabasine, Conformational analysis, Molecular mechanics., Nuclear Overhauser enhancement",

author = "Katalin Prokai-Tatrai and Zoltewicz, {John A.} and Kem, {William R.}",

note = "Funding Information: This work was supported by Taiho Pharmacetical Co., Tokyo, Japan. The authors thank Mr. Craig Porter for his assistance with the CaCheTM Worksystem, and for obtaining the 500 MHz NMR spectra.",

year = "1994",

doi = "10.1016/S0040-4020(01)89606-X",

language = "English",

volume = "50",

pages = "9909--9918",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "33",

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TY - JOUR

T1 - Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.

AU - Prokai-Tatrai, Katalin

AU - Zoltewicz, John A.

AU - Kem, William R.

N1 - Funding Information: This work was supported by Taiho Pharmacetical Co., Tokyo, Japan. The authors thank Mr. Craig Porter for his assistance with the CaCheTM Worksystem, and for obtaining the 500 MHz NMR spectra.

PY - 1994

Y1 - 1994

N2 - The synthesis and conformational analysis of a "bridged" anabasine, 5,8,9,10,11,11a-hexahydro-6H-pyrido[2,1-f][1,6] naphthyridine (5), and related compounds are reported. Conformational assignments were made using NMR data (including coupling constants, homonuclear Overhauser effects, and 2D correlations) and the results of molecular mechanics (MM2) calculations. The tricyclic compounds have trans-quinolizidine ring fusion with a chair-shaped piperidine ring. The center ring shows a half-chair conformation for the title compound, and a half-boat shape for its 6-oxo derivative. Calculated vicinal coupling constants are in good agreement with those obtained experimentally.

AB - The synthesis and conformational analysis of a "bridged" anabasine, 5,8,9,10,11,11a-hexahydro-6H-pyrido[2,1-f][1,6] naphthyridine (5), and related compounds are reported. Conformational assignments were made using NMR data (including coupling constants, homonuclear Overhauser effects, and 2D correlations) and the results of molecular mechanics (MM2) calculations. The tricyclic compounds have trans-quinolizidine ring fusion with a chair-shaped piperidine ring. The center ring shows a half-chair conformation for the title compound, and a half-boat shape for its 6-oxo derivative. Calculated vicinal coupling constants are in good agreement with those obtained experimentally.

KW - Bridged anabasine

KW - Conformational analysis

KW - Molecular mechanics.

KW - Nuclear Overhauser enhancement

UR - http://www.scopus.com/inward/record.url?scp=0028001571&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)89606-X

DO - 10.1016/S0040-4020(01)89606-X

M3 - Article

AN - SCOPUS:0028001571

SN - 0040-4020

VL - 50

SP - 9909

EP - 9918

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.

Abstract

Keywords

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