Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group
Pierrik Lassalas
1
,
Killian Oukoloff
2
,
Vishruti Makani
3
,
Michael James
3
,
Van Tran
1
,
Yuemang Yao
3
,
Longchuan Huang
1
,
Krishna Vijayendran
1
,
Ludovica Monti
2
,
John Trojanowski
3
,
Virginia M.-Y. Lee
3
,
AMOS A. SMITH
1
,
K. R. Brunden
3
,
C. Ballatore
2
Publication type: Journal Article
Publication date: 2017-07-18
scimago Q1
wos Q2
SJR: 0.805
CiteScore: 5.8
Impact factor: 4.0
ISSN: 19485875
PubMed ID:
28835803
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The oxetane ring serves as an isostere of the carbonyl moiety, suggesting that oxetan-3-ol may be considered as a potential surrogate of the carboxylic acid functional group. To investigate this structural unit, as well as thietan-3-ol and the corresponding sulfoxide and sulfone derivatives, as potential carboxylic acid bioisosteres, a set of model compounds has been designed, synthesized, and evaluated for physicochemical properties. Similar derivatives of the cyclooxygenase inhibitor, ibuprofen, were also synthesized and evaluated for inhibition of eicosanoid biosynthesis in vitro. Collectively, the data suggest that oxetan-3-ol, thietan-3-ol, and related structures hold promise as isosteric replacements of the carboxylic acid moiety.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
4
5
|
|
|
Journal of Organic Chemistry
5 publications, 11.11%
|
|
|
Journal of Medicinal Chemistry
4 publications, 8.89%
|
|
|
European Journal of Medicinal Chemistry
3 publications, 6.67%
|
|
|
Bioorganic and Medicinal Chemistry Letters
2 publications, 4.44%
|
|
|
Chemistry - A European Journal
2 publications, 4.44%
|
|
|
Chemical Science
2 publications, 4.44%
|
|
|
RSC Medicinal Chemistry
2 publications, 4.44%
|
|
|
Advances in Heterocyclic Chemistry
2 publications, 4.44%
|
|
|
Beilstein Journal of Organic Chemistry
1 publication, 2.22%
|
|
|
Current Medicinal Chemistry
1 publication, 2.22%
|
|
|
Current Topics in Medicinal Chemistry
1 publication, 2.22%
|
|
|
Molecules
1 publication, 2.22%
|
|
|
Nature
1 publication, 2.22%
|
|
|
Journal of Cheminformatics
1 publication, 2.22%
|
|
|
Tetrahedron
1 publication, 2.22%
|
|
|
European Journal of Organic Chemistry
1 publication, 2.22%
|
|
|
ACS Catalysis
1 publication, 2.22%
|
|
|
ACS Medicinal Chemistry Letters
1 publication, 2.22%
|
|
|
Organic Letters
1 publication, 2.22%
|
|
|
Journal of Chemistry
1 publication, 2.22%
|
|
|
Bioorganic Chemistry
1 publication, 2.22%
|
|
|
Organic and Biomolecular Chemistry
1 publication, 2.22%
|
|
|
Progress in Heterocyclic Chemistry
1 publication, 2.22%
|
|
|
Synthesis
1 publication, 2.22%
|
|
|
ACS Omega
1 publication, 2.22%
|
|
|
Journal of the American Chemical Society
1 publication, 2.22%
|
|
|
Expert Opinion on Drug Discovery
1 publication, 2.22%
|
|
|
1
2
3
4
5
|
Publishers
|
2
4
6
8
10
12
14
|
|
|
American Chemical Society (ACS)
14 publications, 31.11%
|
|
|
Elsevier
12 publications, 26.67%
|
|
|
Wiley
5 publications, 11.11%
|
|
|
Royal Society of Chemistry (RSC)
5 publications, 11.11%
|
|
|
Bentham Science Publishers Ltd.
2 publications, 4.44%
|
|
|
Springer Nature
2 publications, 4.44%
|
|
|
Beilstein-Institut
1 publication, 2.22%
|
|
|
MDPI
1 publication, 2.22%
|
|
|
Hindawi Limited
1 publication, 2.22%
|
|
|
Georg Thieme Verlag KG
1 publication, 2.22%
|
|
|
Taylor & Francis
1 publication, 2.22%
|
|
|
2
4
6
8
10
12
14
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
45
Total citations:
45
Citations from 2025:
9
(20%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Lassalas P. et al. Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group // ACS Medicinal Chemistry Letters. 2017. Vol. 8. No. 8. pp. 864-868.
GOST all authors (up to 50)
Copy
Lassalas P., Oukoloff K., Makani V., James M., Tran V., Yao Y., Huang L., Vijayendran K., Monti L., Trojanowski J., Lee V. M., Kozlowski M. C., SMITH A. A., Brunden K. R., Ballatore C. Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group // ACS Medicinal Chemistry Letters. 2017. Vol. 8. No. 8. pp. 864-868.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acsmedchemlett.7b00212
UR - https://doi.org/10.1021/acsmedchemlett.7b00212
TI - Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group
T2 - ACS Medicinal Chemistry Letters
AU - Lassalas, Pierrik
AU - Oukoloff, Killian
AU - Makani, Vishruti
AU - James, Michael
AU - Tran, Van
AU - Yao, Yuemang
AU - Huang, Longchuan
AU - Vijayendran, Krishna
AU - Monti, Ludovica
AU - Trojanowski, John
AU - Lee, Virginia M.-Y.
AU - Kozlowski, Marisa C
AU - SMITH, AMOS A.
AU - Brunden, K. R.
AU - Ballatore, C.
PY - 2017
DA - 2017/07/18
PB - American Chemical Society (ACS)
SP - 864-868
IS - 8
VL - 8
PMID - 28835803
SN - 1948-5875
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Lassalas,
author = {Pierrik Lassalas and Killian Oukoloff and Vishruti Makani and Michael James and Van Tran and Yuemang Yao and Longchuan Huang and Krishna Vijayendran and Ludovica Monti and John Trojanowski and Virginia M.-Y. Lee and Marisa C Kozlowski and AMOS A. SMITH and K. R. Brunden and C. Ballatore},
title = {Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group},
journal = {ACS Medicinal Chemistry Letters},
year = {2017},
volume = {8},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acsmedchemlett.7b00212},
number = {8},
pages = {864--868},
doi = {10.1021/acsmedchemlett.7b00212}
}
Cite this
MLA
Copy
Lassalas, Pierrik, et al. “Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group.” ACS Medicinal Chemistry Letters, vol. 8, no. 8, Jul. 2017, pp. 864-868. https://doi.org/10.1021/acsmedchemlett.7b00212.