Synthesis and characterization of novel bile-acid – heteroaryl conjugates with N-(2-aminoethyl)amido linker

Four novel bile acid conjugates N-[2-([2,2′]-bithiophen-5-ylmethyl)aminoethyl]-3α-hydroxy-5β-cholan-24-amide ( 1), N-[2-([2,2′]-bithiophen-5-ylmethyl)aminoethyl]-3α,7α,12α-trihydroxy-5β-cholan-24-amide ( 2), N-[2-(1 H-pyrrol-2-ylmethyl)aminoethyl]-3α-hydroxy-5β-cholan-24-amide ( 3), N-[2-(pyridin-2-...

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Bibliographic Details
Published in:Journal of molecular structure 2008-12, Vol.892 (1), p.53-57
Main Authors: Koivukorpi, Juha, Valkonen, Arto, Lahtinen, Manu, Kolehmainen, Erkki
Format: Article
Language:English
Subjects:
13C NMR chemical shifts
Bile acids
Conjugates
Crystal structure
Heteroaromatics
Mass spectrometry
Molecular structure
Molecular weight
Spectra
Synthesis
Thermal analysis
X-ray diffraction
Yttrium
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Summary:Four novel bile acid conjugates N-[2-([2,2′]-bithiophen-5-ylmethyl)aminoethyl]-3α-hydroxy-5β-cholan-24-amide ( 1), N-[2-([2,2′]-bithiophen-5-ylmethyl)aminoethyl]-3α,7α,12α-trihydroxy-5β-cholan-24-amide ( 2), N-[2-(1 H-pyrrol-2-ylmethyl)aminoethyl]-3α-hydroxy-5β-cholan-24-amide ( 3), N-[2-(pyridin-2-ylmethyl)aminoethyl]-3α-hydroxy-5β-cholan-24-amide ( 4) have been synthesized in moderate to good yields, and their structures have been characterized by 1H, 13C, 13C DEPT-135, PFG 1H, 13C HMQC, and PFG 1H, 13C HMBC NMR spectra. Their molecular weights and elemental compositions have been determined by ESI-TOF mass spectrometry and elemental analyses. Crystal structure of 1 characterized with orthorhombic P2 12 12 1 space group has also been determined.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2008.04.057