Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations
1
Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University, Sugitani 2630, Toyama 930-01, Japan
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Publication type: Journal Article
Publication date: 1996-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
2-Ethenylpyrrolidine derivative 8b was prepared from N-protected proline ethyl ester 6b. Bromofluorination of 8b with NBS-Bu4NF/2HF gave a 1:1 regioisomeric mixture, 9b and 10b (X = Br). Dehydrobromination of 9b and 10b with t-BuOK produced a fluoroolefin 11 and a proline amide isostere model 12, respectively. Deprotection of the Z group in 12 was attempted by treatment with CF3COOH. Although formation of the useful molecule in pseudopeptide synthesis, 13, was observed as checked by NMR spectra, it seemed to decompose slowly during purification procedure to give a mixture of fluorine-free compounds.
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Total citations:
18
Citations from 2025:
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(5.56%)
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MLA
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GOST
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Takeuchi Y. et al. Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations // Tetrahedron. 1996. Vol. 52. No. 1. pp. 225-232.
GOST all authors (up to 50)
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Takeuchi Y., Yamada A., Suzuki T., Koizumi T. Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations // Tetrahedron. 1996. Vol. 52. No. 1. pp. 225-232.
Cite this
RIS
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TY - JOUR
DO - 10.1016/0040-4020(95)00910-z
UR - https://doi.org/10.1016/0040-4020(95)00910-z
TI - Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations
T2 - Tetrahedron
AU - Takeuchi, Yoshio
AU - Yamada, Asuka
AU - Suzuki, Takanori
AU - Koizumi, Toru
PY - 1996
DA - 1996/01/01
PB - Elsevier
SP - 225-232
IS - 1
VL - 52
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1996_Takeuchi,
author = {Yoshio Takeuchi and Asuka Yamada and Takanori Suzuki and Toru Koizumi},
title = {Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations},
journal = {Tetrahedron},
year = {1996},
volume = {52},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/0040-4020(95)00910-z},
number = {1},
pages = {225--232},
doi = {10.1016/0040-4020(95)00910-z}
}
Cite this
MLA
Copy
Takeuchi, Yoshio, et al. “Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations.” Tetrahedron, vol. 52, no. 1, Jan. 1996, pp. 225-232. https://doi.org/10.1016/0040-4020(95)00910-z.