Bioisosterism in Medicinal Chemistry

Brown, Nathan

doi:10.1002/9783527654307.ch1

Cited by 36 publications

(52 citation statements)

References 13 publications

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“…In order to build a universal data set for future work, the tribological test method and conditions were kept in accordance with the previous tests mentioned in the published papers [16,18,20].…”

Section: Tribology Testsmentioning

confidence: 99%

“…In 1925, Grimm formulated the hydride displacement law [16]. In 1932, Erlenmeyer proposed a broadening of the term isosterism by defining isosteres as elements, molecules, or ions that have the same number of valence electrons [16]. In 1951, Friedman introduced the term bioisosterism for the similar or antagonistic biological activity of structurally related compounds [13,14,16].…”

Section: Introductionmentioning

confidence: 99%

“…In 1932, Erlenmeyer proposed a broadening of the term isosterism by defining isosteres as elements, molecules, or ions that have the same number of valence electrons [16]. In 1951, Friedman introduced the term bioisosterism for the similar or antagonistic biological activity of structurally related compounds [13,14,16]. In 1979, Thornber broadened the term bioisosteres to include subunits, groups, or molecules that possess physicochemical properties with similar biological effects [13,14,16].…”

Section: Introductionmentioning

confidence: 99%

“…In 1951, Friedman introduced the term bioisosterism for the similar or antagonistic biological activity of structurally related compounds [13,14,16]. In 1979, Thornber broadened the term bioisosteres to include subunits, groups, or molecules that possess physicochemical properties with similar biological effects [13,14,16]. In structure optimization research, bioisosterism is actively used for structural modification of drugs to replace isosteres with one another in the variable part of the basic molecular structure.…”

Section: Introductionmentioning

confidence: 99%

“…These similarities often occur for atoms that are in the same column in the periodic table-the column with atoms having the same number of outer electrons or having similar sizes and properties or behaviors. In 1925, Grimm formulated the hydride displacement law [16]. In 1932, Erlenmeyer proposed a broadening of the term isosterism by defining isosteres as elements, molecules, or ions that have the same number of valence electrons [16].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Isosteric design of friction-reduction and anti-wear lubricant additives with less sulfur content

et al. 2017

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Abstract:To reduce harmful sulfur content in lubricant additives, making use of isosterism has been shown to be an effective strategy. When thiobenzothiazole compounds were used as templates, the exchange of sulfur atoms in the thiazole ring with oxygen atoms and NH groups produced twelve isosteres. Similarly, 2-benzothiazole-S-carboxylic acid esters were used as template molecules to produce six isosteres. About 30% of the isosteres exhibited a satisfactory deviation of ±5% relative to the template, ignoring the specific changes in the base oils, the differences in molecular structure, and the friction or wear properties. The template molecules and isosteres in triisodecyl trimellitate exhibited better tribological properties than in trimethylolpropane trioleate or bis(2-ethylhexyl) adipate. Comparative molecular field analysis (CoMFA)-and comparative molecular similarity index analysis (CoMSIA)-quantitative structure tribo-ability relationship (QSTR) models were employed to study the correlation of molecular structures between the base oils and additives. The models indicate that the higher the structural similarities of the base oils and additives are, the more synergetic the molecular force fields of the lubricating system are; the molecular force fields creating synergistic effects will improve tribological performance.

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Section: Tribology Testsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Isosteric design of friction-reduction and anti-wear lubricant additives with less sulfur content

et al. 2017

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Rational Design in Photopharmacology with Molecular Photoswitches

et al. 2023

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Photopharmacology is an attractive approach for achieving targeted drug action with the use of light. In photopharmacology, molecular photoswitches are introduced into the structure of biologically active small molecules to allow for the optical control of their potency. Going beyond trial and error, photopharmacology has progressively applied rational drug design methodologies to devise light-controlled bioactive ligands. In this review, we categorize photopharmacological efforts from the standpoint of medicinal chemistry strategies, focusing on diffusible photochromic ligands modified with photoswitches that operate through E-Z bond isomerization. In the vast majority of cases, photoswitchable ligands are designed as analogs of existing compounds, through a variety of approaches. By analyzing in detail a comprehensive list of instructive examples, we describe the state of the art and discuss future opportunities for rational design in photopharmacology.

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Oxa‐TriQuinoline: A New Entry to Aza‐Oxa‐Crown Architectures**

Toi

Kumagai

2023

Angewandte Chemie

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A new 15‐membered‐macrocyclic molecular entity, oxa‐TriQuinoline (o‐TQ), was designed and synthesized. In o‐TQ, three oxygen atoms were joined onto three quinoline units at the 2‐ and 8‐positions in a head‐to‐tail fashion by three‐fold SNAr reactions, giving rise to the characteristic N3O3 aza‐oxa‐crown architecture. o‐TQ can serve as a new tridentate nitrogen ligand to capture a CuI cation and adopt a bowl shape, before supramolecular complexation with corannulene and [12]cycloparaphenylene (CPP) occurs through π–π and CH–π interactions. In the presence of the CuI cation, the non‐emissive o‐TQ becomes a highly emissive material in the solid state, whereby the emission wavelengths depend on the ancillary ligand on the CuI cation. The o‐TQ/CuI complex is able to promote carbene catalysis to provide a range of enamines with a gem‐difluorinated terminus.

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Bioisosterism in Medicinal Chemistry

Cited by 36 publications

References 13 publications

Isosteric design of friction-reduction and anti-wear lubricant additives with less sulfur content

Isosteric design of friction-reduction and anti-wear lubricant additives with less sulfur content

Rational Design in Photopharmacology with Molecular Photoswitches

Oxa‐TriQuinoline: A New Entry to Aza‐Oxa‐Crown Architectures**

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