Computational assessment of thioether isosteres

Barrows, Robert D.; Blacklock, Kristin; Rablen, Paul R.; Khare, Sagar D.; Knapp, Spencer

doi:10.1016/j.jmgm.2018.01.018

Cited by 2 publications

(1 citation statement)

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“…Sulfides may come in handy as bridging elements, since they exhibit favorable structural characteristics over conventional ethers. This was simply exemplified with calculated bond length, angle, and intermolecular distances between Ph‐S‐Ph and Ph‐O‐Ph: in general, sulfides featured longer bonds, narrow central bond angle and the phenyl rings were less co‐planar (Figure ) …”

Section: The Underestimated Element Sulfurmentioning

confidence: 99%

Interconnection of sulfides and sulfoxides in medicinal chemistry

Surur

Schulig

Link

2018

Arch. Pharm. Chem. Life Sci.

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Aromatic heterocycles with basic nitrogen atoms as well as carboxylic acid derivatives are the dominating chemical space in the universe of drug-like molecules. These established and exceedingly evaluated structural motifs have to be combined with elements of diversity in order to chart less well-explored galaxies of chemical space and to be able to tackle seemingly undruggable targets. Flat scaffolds should be replaced by shapely molecular cores. In this context, it has been unheeded that phenyl rings in diaryl sulfides are less co-planar than in ethers and that the metabolic interconnection of sulfides and sulfoxides offers advantages that are unalike from the chemistry of amines and N-oxides in the CHN-O world. Moreover, σ-hole potentials increase with the polarizability of the atom N < P < O < S and do not only play a role in long-time overlooked halogen bonds. Examples for λ 2 , λ 4 , and λ 6 S-based functionalities related to improved solubility, reduced drug resistance, linkers in drug conjugates, drugtargeting to parasites, and as basis for drug monitoring in sports are given and discussed. K E Y W O R D Santituberculosis activity, inhibitors, oxidation kinetics, rational drug design, sulfides, sulfoxides Arch Pharm Chem Life Sci. 2019;352:e1800248.wileyonlinelibrary.com/journal/ardp

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Section: The Underestimated Element Sulfurmentioning

confidence: 99%