Investigations on the 4-quinolone-3-carboxylic acid motif. 6. Synthesis and pharmacological evaluation of 7-substituted quinolone-3-carboxamide derivatives as high affinity ligands for cannabinoid receptors

Pasquini, Serena; Rosa, Maria de Lurdes Pereira; Ligresti, Alessia; Mugnaini, Claudia; Brizzi, Antonella; Caradonna, Nicola P.; Cascio, Maria Grazia; Bolognini, Daniele; Pertwee, Roger G.; Marzo, Vincenzo Di; Corelli, Federico

doi:10.1016/j.ejmech.2012.09.035

Cited by 24 publications

(23 citation statements)

References 32 publications

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“…The 4-quinolone-3-carboxylic acid derivatives are widely known for their use as antibacterial agents. Additionally, these types of compounds are an attractive scaffold in medicinal chemistry to obtain many quinolone derivatives, as amides which are a promising class of compounds displaying interesting biological activity as anti- HIV agents [24] or as cannabinoid ligands, [25] among others [26].…”

Section: Resultsmentioning

confidence: 99%

Microwave Assisted Synthesis of ethyl-quinolon-4-one-3-carboxylates and Hydrolysis to quinolon-4-one-3-carboxylic Acids

Malvacio¹,

Vera²,

Moyano³

2014

CMIC

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A fast and efficient microwave assisted synthesis of several ethyl-quinolon-4-one-3-carboxylates and quinolon-4-one-3-carboxylic acids has been developed. The 3-carboethoxy quinolones are easily obtained in a one-pot procedure through the cyclization of aminomethylenemalonate intermediates obtained by reaction of different p-substituted anilines and diethyl-ethoxymethylenmalonate. These quinolones are then irradiated under base hydrolysis conditions to get the carboxylic acids through a very fast and clean approach.

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Section: Resultsmentioning

confidence: 99%

Microwave Assisted Synthesis of ethyl-quinolon-4-one-3-carboxylates and Hydrolysis to quinolon-4-one-3-carboxylic Acids

Malvacio¹,

Vera²,

Moyano³

2014

CMIC

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“…Several substituents on the 4-oxoquinoline structure have been investigated [ 89 , 90 , 91 , 92 ]. High CB receptor affinities may be attributed mainly to the alkyl linear chains at C-(1) position with the n -pentyl group leading to the highest relative affinity to CB2.…”

Section: Discussionmentioning

confidence: 99%

Structure-Activity Relationship of Cannabis Derived Compounds for the Treatment of Neuronal Activity-Related Diseases

et al. 2018

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Cannabis sativa active compounds are extensively studied for their therapeutic effects, beyond the well-known psychotropic activity. C. Sativa is used to treat different medical indications, such as multiple sclerosis, spasticity, epilepsy, ulcerative colitis and pain. Simultaneously, basic research is discovering new constituents of cannabis-derived compounds and their receptors capable of neuroprotection and neuronal activity modulation. The function of the various phytochemicals in different therapeutic processes is not fully understood, but their significant role is starting to emerge and be appreciated. In this review, we will consider the structure-activity relationship (SAR) of cannabinoid compounds able to bind to cannabinoid receptors and act as therapeutic agents in neuronal diseases, e.g., Parkinson’s disease.

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“…The presence of OH or CO groups in the 2- or 4-position of the core increases the affinity vs the target via H-bonds formation . On the core scaffold, R 1 can be (i) a linear alkyl chain (four to six carbon atoms) often formed by five methylene units (that proved to be optimal for receptor affinity − due to their ability to maximize the interactions with a hydrophobic region of the receptor), (ii) cycloalkyl or aromatic alkyl groups, (iii) heterocycloalkyl ring such as alkylmorpholine or piperidine …”

Section: Cb2r Agonists: the Proposed Pharmacophorementioning

confidence: 99%

Cannabinoid Receptor Subtype 2 (CB2R) in a Multitarget Approach: Perspective of an Innovative Strategy in Cancer and Neurodegeneration

et al. 2020

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The cannabinoid receptor subtype 2 (CB2R) represents an interesting and new therapeutic target for its involvement in the first steps of neurodegeneration as well as in cancer onset and progression. Several studies, focused on different types of tumors, report a promising anticancer activity induced by CB2R agonists due to their ability to reduce inflammation and cell proliferation. Moreover, in neuroinflammation, the stimulation of CB2R, overexpressed in microglial cells, exerts beneficial effects in neurodegenerative disorders. With the aim to overcome current treatment limitations, new drugs can be developed by specifically modulating, together with CB2R, other targets involved in such multifactorial disorders. Building on successful case studies of already developed multitarget strategies involving CB2R, in this Perspective we aim at prompting the scientific community to consider new promising target associations involving HDACs (histone deacetylases) and σ receptors by employing modern approaches based on molecular hybridization, computational polypharmacology, and machine learning algorithms.

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Investigations on the 4-quinolone-3-carboxylic acid motif. 6. Synthesis and pharmacological evaluation of 7-substituted quinolone-3-carboxamide derivatives as high affinity ligands for cannabinoid receptors

Cited by 24 publications

References 32 publications

Microwave Assisted Synthesis of ethyl-quinolon-4-one-3-carboxylates and Hydrolysis to quinolon-4-one-3-carboxylic Acids

Microwave Assisted Synthesis of ethyl-quinolon-4-one-3-carboxylates and Hydrolysis to quinolon-4-one-3-carboxylic Acids

Structure-Activity Relationship of Cannabis Derived Compounds for the Treatment of Neuronal Activity-Related Diseases

Cannabinoid Receptor Subtype 2 (CB2R) in a Multitarget Approach: Perspective of an Innovative Strategy in Cancer and Neurodegeneration

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