Synthesis and neurite growth evaluation of new analogues of honokiol, a neolignan with potent neurotrophic activity

Kumar, Vemula Praveen; Reddy, R. Gajendra; Vo, Duc Duy; Chakravarty, Sumana; Chandrasekhar, Srivari; Grée, René

doi:10.1016/j.bmcl.2011.12.015

Cited by 46 publications

(14 citation statements)

References 37 publications

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“…Encouraged by the broad applicability of this methodology, we further targeted the transformation of bioactive natural products, containing an acetyl functional group, to the corresponding α‐ketotriazole derivatives, which could for instance facilitate the structure–activity relationship studies of bioactive/drug‐like molecules (Scheme ). Accordingly, triazolization of acetovanillone with an excess of 2 led to the corresponding 1,2,3‐combretatriazole derivative 12 a after the methylation of the hydroxyl group . Applying this approach to the neuroactive endogenous steroid hormone, pregnenolone 11 b , provided the expected product 12 b furnished with an α‐ketotriazole heterocycle in 76 % yield Platanic acid 11 c is a naturally occurring pentacyclic triterpenoid and has gained much attention in natural product chemistry because of its potent anti‐HIV activity.…”

Section: Figurementioning

confidence: 99%

Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks

Thomas

Goyvaerts

Liekens

et al. 2016

Chemistry A European J

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Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.

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Section: Figurementioning

confidence: 99%

Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks

Thomas

Goyvaerts

Liekens

et al. 2016

Chemistry A European J

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“…Activation of TRP channels on afferent nerves in the bladder induces the release of neurokinins, which increase detrusor contractility. Drugs acting on neurotrophin receptors tyrosine kinase A, TrkA, TrkB and TrkC are another alternative to enhance the afferent input from bladder and neurotrophic activity 100–102 . Moreover, drugs activating TRP receptors are only likely to receive regulatory approval for topical use, as systemic administration of these agents is likely to induce pain.…”

Section: Expert Opinionmentioning

confidence: 99%

Advances in intravesical therapy for urinary tract disorders

Tyagi

Kashyap

Hensley

et al. 2015

Expert Opinion on Drug Delivery

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Introduction Intravesical therapy is a valuable option in the clinical management of urinary tract disorders such as interstitial cystitis/ painful bladder syndrome (IC/PBS) and refractory overactive bladder. This review will cover the latest advances in this field using polymer and liposomes as delivery platform for drugs, protein and nucleic acids. Areas covered This review summarizes the significance of intravesical therapy for lower urinary tract disorders. The recent advancement of liposomes as a drug delivery platform for botulinum toxin, tacrolimus and small interfering RNA is discussed. The importance of polymers forming indwelling devices and hydrogels are also discussed, where all preparations improved efficacy parameters in rodent models. Clinical experience of treating IC/PBS with indwelling devices and liposomes are summarized and preclinical evidence about the downregulation of target gene expression in rodent bladder with liposomes complexed with siRNA is also reviewed. Expert opinion There have been several advances in the field of intravesical therapy for improving clinical outcomes. One of the most promising research avenues is the repurposing of drugs, given previously by other routes of administration, such as tacrolimus. Intravesical therapy also opens up novel therapeutic targets with improved efficacy and safety for underactive bladder.

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“…Honokiol’s neuroprotective effects may be related to the promotion of healthy connections among nerve cells, as honokiol and its synthetic analogs have potent neurotrophic activity in vitro (37–39). Several putative pathways for neuroprotection have been investigated including inhibition of the immune system and oxidative stress pathways.…”

Section: Neuroprotectionmentioning

confidence: 99%

Neuro-Modulating Effects of Honokiol: A Review

Woodbury¹,

Yu²,

Wei³

et al. 2013

Front. Neurol.

117

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Honokiol is a poly-phenolic compound that exerts neuroprotective properties through a variety of mechanisms. It has therapeutic potential in anxiety, pain, cerebrovascular injury, epilepsy, and cognitive disorders including Alzheimer’s disease. It has been traditionally used in medical practices throughout much of Southeast Asia, but has now become more widely studied due to its pleiotropic effects. Most current research regarding this compound has focused on its chemotherapeutic properties. However, it has the potential to be an effective neuroprotective agent as well. This review summarizes what is currently known regarding the mechanisms involved in the neuroprotective and anesthetic effects of this compound and identifies potential areas for further research.

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Synthesis and neurite growth evaluation of new analogues of honokiol, a neolignan with potent neurotrophic activity

Cited by 46 publications

References 37 publications

Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks

Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks

Advances in intravesical therapy for urinary tract disorders

Neuro-Modulating Effects of Honokiol: A Review

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