Pyrazoles

Yet, Larry

doi:10.1016/b978-008044992-0.00401-6

Cited by 38 publications

(11 citation statements)

References 986 publications

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“…The spirocyclic oxindoles as an ubiquitous skeleton are widely found in both natural alkaloids and synthetic therapeutic agents. , Owing to the importance in modern organic synthetic and medicinal chemistry, numerous efficient synthetic strategies to construct these diverse spirocyclic oxindole derivatives have been developed over the past decades . Spiro[pyrazolin-3,3′-oxindoles] are not only a kind of heterocyclic compounds with biologically activities, but also important intermediates for the transformation to spiro[cyclopropyl-3,3′-oxindoles] and other compounds. 1,3-Dipolar cycloaddition of 3-ylidene-oxindoles and α-diazocarbonyl compounds is a straightforward approach for the construction of spiro[pyrazolin-3,3′-oxindoles] (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Spiro[pyrazolin-3,3′-oxindoles] and 3-Arylcarbonylmethyl Substituted Ylideneoxindoles by 1,3-Dipolar Cycloadditions of 3-Ylideneoxindoles and In-Situ-Generated α-Diazoketones

et al. 2017

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An efficient 1,3-dipolar cycloaddition of 3-ylideneoxindoles with in-situ-generated α-diazoketones to potentially biological active spiro[pyrazolin-3,3'-oxindoles] 4 with excellent regioselectivity and diastereoselectivity and synthetically useful building block 3-arylcarbonylmethyl substituted ylideneoxindoles 5 in different conditions has been developed. This method has advantages of mild conditions, simple workup, and wide substrate scopes as well as without using any transition metal catalyst.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Spiro[pyrazolin-3,3′-oxindoles] and 3-Arylcarbonylmethyl Substituted Ylideneoxindoles by 1,3-Dipolar Cycloadditions of 3-Ylideneoxindoles and In-Situ-Generated α-Diazoketones

et al. 2017

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“…The 7R allele, as a risk allele for executive dysfunction, flexibility, and cognitive shifting, can be correlated with low creativity [ 49 ]. In addition to ADHD, studies have shown that drugs target DRD4 for the treatment of schizophrenia, Parkinson’s disease, depression, and psychostimulant addiction [ 50 , 51 ]. In this study, aaptamine displayed an antagonistic activity on the dopaminergic system’s signals through DRD2-like subtypes: DRD2Long (L) (73.7% inhibition; IC 50 38.7 µM), DRD2Short (S) (74.4% inhibition; IC 50 25.7 µM), and particularly, DRD4 (94.5% inhibition; IC 50 6.9 µM).…”

Section: Resultsmentioning

confidence: 99%

GPCR Pharmacological Profiling of Aaptamine from the Philippine Sponge Stylissa sp. Extends Its Therapeutic Potential for Noncommunicable Diseases

Luyao

Luesch

2021

Molecules

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We report the first isolation of the alkaloid aaptamine from the Philippine marine sponge Stylissa sp. Aaptamine possessed weak antiproliferative activity against HCT116 colon cancer cells and inhibited the proteasome in vitro at 50 µM. These activities may be functionally linked. Due to its known, more potent activity on certain G-protein coupled receptors (GPCRs), including α-adrenergic and δ-opioid receptors, the compound was profiled more broadly at sub-growth inhibitory concentrations against a panel of 168 GPCRs to potentially reveal additional targets and therapeutic opportunities. GPCRs represent the largest class of drug targets. The primary screen at 20 µM using the β-arrestin functional assay identified the antagonist, agonist, and potentiators of agonist activity of aaptamine. Dose-response analysis validated the α-adrenoreceptor antagonist activity of aaptamine (ADRA2C, IC50 11.9 µM) and revealed the even more potent antagonism of the β-adrenoreceptor (ADRB2, IC50 0.20 µM) and dopamine receptor D4 (DRD4, IC50 6.9 µM). Additionally, aaptamine showed agonist activity on selected chemokine receptors, by itself (CXCR7, EC50 6.2 µM; CCR1, EC50 11.8 µM) or as a potentiator of agonist activity (CXCR3, EC50 31.8 µM; CCR3, EC50 16.2 µM). These GPCRs play a critical role in the treatment of cardiovascular disease, diabetes, cancer, and neurological disorders. The results of this study may thus provide novel preventive and therapeutic strategies for noncommunicable diseases (NCDs).

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“…Ethyl 5-((8-hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylate was synthesized by a classic azo coupling reaction between 4-(ethoxycarbonyl)-3-methyl-1Hpyrazole-5-diazonium chloride and 8-hydroxyquinoline. The diazotization and coupling were conducted following procedures from the literature [11][12][13][14], and the conditions were adapted in order to obtain the desired product. The synthesis followed the below Scheme 1: Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

5-((8-Hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylic Acid

Burcă

Badea

Deleanu

et al. 2021

Molbank

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A new azo compound was prepared via the azo coupling reaction between 4-(ethoxycarbonyl)-3-methyl-1H-pyrazole-5-diazonium chloride and 8-hydroxyquinoline (oxine). The ester functional group of the obtained compound was hydrolyzed and thus a new chemical structure with a carboxylic functional group resulted. The structures of the new compounds were fully characterized by: UV–Vis, FT-IR, 1D and 2D NMR spectroscopy, and HRMS spectrometry.

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Pyrazoles

Cited by 38 publications

References 986 publications

Synthesis of Spiro[pyrazolin-3,3′-oxindoles] and 3-Arylcarbonylmethyl Substituted Ylideneoxindoles by 1,3-Dipolar Cycloadditions of 3-Ylideneoxindoles and In-Situ-Generated α-Diazoketones

Synthesis of Spiro[pyrazolin-3,3′-oxindoles] and 3-Arylcarbonylmethyl Substituted Ylideneoxindoles by 1,3-Dipolar Cycloadditions of 3-Ylideneoxindoles and In-Situ-Generated α-Diazoketones

GPCR Pharmacological Profiling of Aaptamine from the Philippine Sponge Stylissa sp. Extends Its Therapeutic Potential for Noncommunicable Diseases

5-((8-Hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylic Acid

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