Resorcylic acid lactones as new lead structures for kinase inhibition

Hofmann, Ted J.; Altmann, Karl‐Heinz

doi:10.1016/j.crci.2008.06.010

Cited by 63 publications

(26 citation statements)

References 67 publications

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“…Unexpectedly, almost none of the compounds investigated with the solid-state CD/TDDFT approach did show any apparent effect of solid-state intermolecular interactions in their CD spectra. 52,53 This molecule was one of the first cases of application of the solid-state CD/ TDDFT approach 54 and also has a crystal lattice hold together by multiple hydrogen bonds. 48 Hydrogen bonding has a primary importance in determining organic crystal structures and may strongly affect electronic transitions.…”

Section: Introductionmentioning

confidence: 99%

Solid‐state Circular Dichroism and Hydrogen Bonding, Part 2: The Case of Hypothemycin Re‐investigated

Pescitelli

2012

Chirality

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The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and consisted in the isolated molecule, its cluster with five water molecules, and 20 different dimers (plus water molecules) representative of all the closest neighbors found in the crystal. The effects of solid-state intermolecular hydrogen bonds and through-space exciton couplings in determining the solid-state CD spectrum of hypothemycin were evaluated and compared.

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Section: Introductionmentioning

confidence: 99%

Solid‐state Circular Dichroism and Hydrogen Bonding, Part 2: The Case of Hypothemycin Re‐investigated

Pescitelli

2012

Chirality

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“…In 2004, a modular synthesis of pochonin C (20) was presented by the group of Winssinger [111] ; then, concise syntheses of pochonin A (18) [112] and radicicol analog A (11) [113] were reported by the same group. The Altmann group [114] reported the total syntheses of LL-Z1640-2 (3), hypothemycin (4), L-783277 (12), radicicol analog A (11), and aigialomycin D (16). Recently, the asymmetric total syntheses of paecilomycin E (32) [115] and cochliomycin A (37) [116] were achieved by the Nanda group.…”

Section: Chemical Synthesismentioning

confidence: 98%

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

Jiang

Zhang

et al. 2014

Acta Pharmacol Sin

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Macrolides, which comprise a family of lactones with different ring sizes, belong to the polyketide class of natural products. Resorcinolic macrolides, an important subgroup, possess interesting structures and exhibit a wide variety of bioactivities, such as anti-tumor, anti-bacteria, and anti-malaria activities, etc. This review summarizes progress in isolation, bioactivity studies, biosynthesis, and representative chemical syntheses of this group of macrolides in recent decades, encompassing 63 naturally occurring macrolides published in 120 articles.

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“…The more recent discovery that several members of this family are potent inhibitors of ATPases and kinases has revived interest in the resorcylides (see Fig. 1 for selected examples) [3,4]. RALs are secondary metabolites produced by the modular polyketide synthase (PKS) and a number of variations in the oxidation state of the macrocycle have already been isolated from various environments ranging from the Sonoran desert in Arizona [5] to mangroves in Thailand [6] and new members continue to be isolated [7].…”

Section: Introductionmentioning

confidence: 97%

Hsp90 Inhibition with Resorcylic Acid Lactones (RALs)

Winssinger¹,

Fontaine²,

Barluenga

2009

CTMC

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Heat shock protein 90 (Hsp90) is an ATP-dependent chaperone which is involved in the post-translational maturation and stabilization of over one hundred proteins ("its clients"). In the absence of Hsp90's chaperoning, its clients are misfolded and degraded via ubiquitin-proteasome pathway. It has become the focus of intense drug discovery efforts as its activity has been implicated in diverse pathologies ranging from oncology to neurodegenerative and infectious diseases. The most promising inhibitors reported to date inhibit the ATPase activity by binding to the N-terminal ATP pocket. Radicicol, a member of the resorcylic acid lactones (RALs), represents an important pharmacophore to this end. Efforts towards the development of this pharmacophore and its SAR are reviewed herein.

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Resorcylic acid lactones as new lead structures for kinase inhibition

Cited by 63 publications

References 67 publications

Solid‐state Circular Dichroism and Hydrogen Bonding, Part 2: The Case of Hypothemycin Re‐investigated

Solid‐state Circular Dichroism and Hydrogen Bonding, Part 2: The Case of Hypothemycin Re‐investigated

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

Hsp90 Inhibition with Resorcylic Acid Lactones (RALs)

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