The Synthesis of Functionalized Dimethylphosphinoyl Cyclopropanes and Cyclobutanes-Reference-Cited by-同舟云学术

The Synthesis of Functionalized Dimethylphosphinoyl Cyclopropanes and Cyclobutanes

Published:2023-12-10 Issue:4 Volume:21 Page:36-42
ISSN:2518-1548
Container-title:Journal of Organic and Pharmaceutical Chemistry
language:
Short-container-title:J. Org. Pharm. Chem.

Author:

Aleksandrova Anastasiia M.¹^ORCID,Cherednichenko Alona S.¹^ORCID,Rassukana Yuliya V.^ORCID

Affiliation:

1. Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Ukraine

Abstract

A simple preparative approach to a series of functionalized dimethylphosphinoyl-containing cyclopropanes and cyclobutanes has been developed; it is based on cyclocondensation of dimethylphosphinoyl acetonitrile with 1,2- and 1,3-dibromoalkanes. Synthetic procedures for obtaining nitriles, amines and carboxylic acids containing in their structure small saturated cyclic rings of cyclopropane or cyclobutane and a dimethylphosphine oxide fragment, which are popular in drug design, have been developed.

Publisher

National University of Pharmacy

Reference20 articles.

1. Bauer, M. R.; Di Fruscia, P.; Lucas, S. C. C.; Michaelides, I. N.; Nelson, J. E.; Storer, R. I.; Whitehurst, B. C. Put a ring on it: application of small aliphatic rings in medicinal chemistry. RSC Med. Chem. 2021, 12, 448 - 471. https://doi.org/10.1039/D0MD00370K.

2. Talele, T. T. The “Cyclopropyl Fragment” is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules. J. Med. Chem. 2016, 59, 8712 - 8756. https://doi.org/10.1021/acs.jmedchem.6b00472.

3. Meanwell, N. A. Synopsis of Some Recent Tactical Application of Bioisosteres in Drug Design. J. Med. Chem. 2011, 54, 2529 - 2591. https://doi.org/10.1021/jm1013693.

4. Reichelt, A.; Gaul, C.; Frey, R. R.; Kennedy, A.; Martin, S. F. Design, Synthesis, and Evaluation of Matrix Metalloprotease Inhibitors Bearing Cyclopropane-Derived Peptidomimetics as P1′ and P2′ Replacements. J. Am. Chem. Soc. 2002, 124, 205 - 215. https://doi.org/10.1021/jo0110698.

5. Wipf, P.; Xiao, J. Convergent Approach to (E)-Alkene and Cyclopropane Peptide Isosteres. Org. Lett. 2005, 7, 103 - 106. https://doi.org/10.1021/ol0477529.