Bioisosteres of the phenyl ring: recent strategic applications in lead optimization and drug design

MAM Subbaiah, NA Meanwell - Journal of Medicinal Chemistry, 2021 - ACS Publications
The benzene moiety is the most prevalent ring system in marketed drugs, underscoring its
historic popularity in drug design either as a pharmacophore or as a scaffold that projects …

Opportunities for tapping into three-dimensional chemical space through a quaternary carbon

TT Talele - Journal of Medicinal Chemistry, 2020 - ACS Publications
A quaternary carbon bears four other carbon substituents or combination of four non-
hydrogen substituents at four vertices of a tetrahedron. The spirocyclic quaternary carbon …

Catalytic Asymmetric Construction of Chiral Polysubstituted 3-Azabicyclo [3.1. 1] heptanes by Copper-Catalyzed Stereoselective Formal [4π+ 2σ] Cycloaddition

X Wang, R Gao, X Li - Journal of the American Chemical Society, 2024 - ACS Publications
The direct construction of bioisosteric compounds enriched in Csp3 content represents an
attractive and dependable approach to imbuing biologically active molecules with enhanced …

Pyrrolidine in drug discovery: a versatile scaffold for novel biologically active compounds

G Li Petri, MV Raimondi, V Spanò, R Holl… - Topics in Current …, 2021 - Springer
The five-membered pyrrolidine ring is one of the nitrogen heterocycles used widely by
medicinal chemists to obtain compounds for the treatment of human diseases. The great …

Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among US FDA approved pharmaceuticals: miniperspective

E Vitaku, DT Smith, JT Njardarson - Journal of medicinal chemistry, 2014 - ACS Publications
Nitrogen heterocycles are among the most significant structural components of
pharmaceuticals. Analysis of our database of US FDA approved drugs reveals that 59% of …

[HTML][HTML] The use of spirocyclic scaffolds in drug discovery

Y Zheng, CM Tice, SB Singh - Bioorganic & Medicinal Chemistry Letters, 2014 - Elsevier
Owing to their inherent three-dimensionality and structural novelty, spiro scaffolds have
been increasingly utilized in drug discovery. In this brief review, we highlight selected …

Synthesis of polysubstituted azepanes by dearomative ring expansion of nitroarenes

R Mykura, R Sánchez-Bento, E Matador, VK Duong… - Nature Chemistry, 2024 - nature.com
The synthesis of functionalized nitrogen heterocycles is integral to discovering,
manufacturing and evolving high-value materials. The availability of effective strategies for …

Facile access to fused 2D/3D rings via intermolecular cascade dearomative [2+ 2] cycloaddition/rearrangement reactions of quinolines with alkenes

J Ma, S Chen, P Bellotti, T Wagener, C Daniliuc… - Nature Catalysis, 2022 - nature.com
Hybrid fused two-dimensional/three-dimensional (2D/3D) rings are important
pharmacophores in drugs owing to their unique structural and physicochemical properties …

A Photochemical Strategy for the Conversion of Nitroarenes into Rigidified Pyrrolidine Analogues

E Matador, MJ Tilby, I Saridakis, M Pedrón… - Journal of the …, 2023 - ACS Publications
Bicyclic amines are important motifs for the preparation of bioactive materials. These species
have well-defined exit vectors that enable accurate disposition of substituents toward …

Modular access to substituted cyclohexanes with kinetic stereocontrol

Y Li, Y Li, H Shi, H Wei, H Li, I Funes-Ardoiz, G Yin - Science, 2022 - science.org
Substituted six-membered cyclic hydrocarbons are common constituents of biologically
active compounds. Although methods for the synthesis of thermodynamically favored …