Home / Publications / Diazo chemistry in the access to novel fatty acids linked to spiro-fused oxetane-pyrazolone scaffold

Diazo chemistry in the access to novel fatty acids linked to spiro-fused oxetane-pyrazolone scaffold

Igor Vladimirovich Solovyev 1
Igor Vladimirovich Solovyev
, 
Dmitry Viktorovich Dar’in 1
Dmitry Viktorovich Dar’in
, 
Mikhail Yur'evich Krasavin 1, 2
Mikhail Yur'evich Krasavin
1 Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
2 Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation
10.1016/j.mencom.2023.01.006
Published 2022-12-26
Communication , Volume 33, Issue 1, 21-23
1
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Solovyev I. V., Dar’in D. V., Krasavin M. Y. Diazo chemistry in the access to novel fatty acids linked to spiro-fused oxetane-pyrazolone scaffold // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 21-23.
GOST all authors (up to 50) Copy
Solovyev I. V., Dar’in D. V., Krasavin M. Y. Diazo chemistry in the access to novel fatty acids linked to spiro-fused oxetane-pyrazolone scaffold // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 21-23.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2023.01.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.006
TI - Diazo chemistry in the access to novel fatty acids linked to spiro-fused oxetane-pyrazolone scaffold
T2 - Mendeleev Communications
AU - Solovyev, Igor Vladimirovich
AU - Dar’in, Dmitry Viktorovich
AU - Krasavin, Mikhail Yur'evich
PY - 2022
DA - 2022/12/26
PB - Mendeleev Communications
SP - 21-23
IS - 1
VL - 33
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Solovyev,
author = {Igor Vladimirovich Solovyev and Dmitry Viktorovich Dar’in and Mikhail Yur'evich Krasavin},
title = {Diazo chemistry in the access to novel fatty acids linked to spiro-fused oxetane-pyrazolone scaffold},
journal = {Mendeleev Communications},
year = {2022},
volume = {33},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.006},
number = {1},
pages = {21--23},
doi = {10.1016/j.mencom.2023.01.006}
}
MLA
Cite this
MLA Copy
Solovyev, Igor Vladimirovich, et al. “Diazo chemistry in the access to novel fatty acids linked to spiro-fused oxetane-pyrazolone scaffold.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 21-23. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.006.
Views / Downloads
1 / 10

Keywords

fatty acid mimetics
free fatty acid receptor 1
GPR40
intramolecular SN2 reaction.
oxetanes
pyrazolone
rhodium(II)-catalyzed O–H insertion
spiro compounds

Abstract

A novel free fatty acid mimetic based on the spirocyclic oxetane pyrazolone 1-oxa-6,7-diazaspiro[3.4]oct-7-en-5-one scaffold has been obtained in seven steps. The key stages are based upon the toolbox of diazo chemistry, including the F SAFE diazo transfer and RhII-catalyzed O-H insertion followed by base-triggered oxetane closing.

References

.
Spirocyclic Scaffolds in Medicinal Chemistry
Hiesinger K., Dar’in D., Proschak E., Krasavin M.
Journal of Medicinal Chemistry, 2020
.
Molecular Properties That Influence the Oral Bioavailability of Drug Candidates
Veber D.F., Johnson S.R., Cheng H., Smith B.R., Ward K.W., Kopple K.D.
Journal of Medicinal Chemistry, 2002
.
Expanding the scope of C-H amination through catalyst design.
Espino C.G., Fiori K.W., Kim M., Du Bois J.
Journal of the American Chemical Society, 2004
.
Spirocyclic Motifs in Natural Products
Chupakhin E., Babich O., Prosekov A., Asyakina L., Krasavin M.
Molecules, 2019
.
Lead-like Drugs: A Perspective
Raymer B., Bhattacharya S.K.
Journal of Medicinal Chemistry, 2018
.
Synthesis of Tetrasubstituted Pyrazoles from Substituted Hydrazines and β-Keto Esters
Bakanas I.J., Moura-Letts G.
European Journal of Organic Chemistry, 2016
.
A selective GPR40 (FFAR1) agonist LY2881835 provides immediate and durable glucose control in rodent models of type 2 diabetes
Chen Y., Song M., Riley J.P., Hu C.C., Peng X., Scheuner D., Bokvist K., Maiti P., Kahl S.D., Montrose‐Rafizadeh C., Hamdouchi C., Miller A.R.
Pharmacology Research and Perspectives, 2016
.
Fasiglifam (TAK-875): Mechanistic Investigation and Retrospective Identification of Hazards for Drug Induced Liver Injury
Otieno M.A., Snoeys J., Lam W., Ghosh A., Player M.R., Pocai A., Salter R., Simic D., Skaggs H., Singh B., Lim H.
Toxicological Sciences, 2017
.
Evaluation of the hepatotoxicity of the novel GPR40 (FFAR1) agonist CPL207280 in the rat and monkey
Bazydlo-Guzenda K., Buda P., Mach M., Pieczykolan J., Kozlowska I., Janiszewski M., Drzazga E., Dominowski J., Ziolkowski H., Wieczorek M., Gad S.C.
PLoS ONE, 2021
.
Spirocyclic Oxetanes: Synthesis and Properties
Wuitschik G., Rogers-Evans M., Buckl A., Bernasconi M., Märki M., Godel T., Fischer H., Wagner B., Parrilla I., Schuler F., Schneider J., Alker A., Schweizer W. ., Müller K., Carreira E., et. al.
Angewandte Chemie - International Edition, 2008
.
Polar aromatic periphery increases agonist potency of spirocyclic free fatty acid receptor (GPR40) agonists inspired by LY2881835
Krasavin M., Lukin A., Bagnyukova D., Zhurilo N., Golovanov A., Zozulya S., Zahanich I., Moore D., Tikhonova I.G.
European Journal of Medicinal Chemistry, 2017
.
The Orphan G Protein-coupled Receptor GPR40 Is Activated by Medium and Long Chain Fatty Acids
Briscoe C.P., Tadayyon M., Andrews J.L., Benson W.G., Chambers J.K., Eilert M.M., Ellis C., Elshourbagy N.A., Goetz A.S., Minnick D.T., Murdock P.R., Sauls H.R., Shabon U., Spinage L.D., Strum J.C., et. al.
Journal of Biological Chemistry, 2003
.
Chupakhin E., Kantin G., Dar'in D., Krasavin M.
Mendeleev Communications, 2022