Synthesis and antihypertensive activity of 1-amino-3,4-dihydroisoquinolines

Diana, Guy D.; Hinshaw, William B.; Lape, Harlan E.

doi:10.1021/jm00213a025

Cited by 16 publications

(8 citation statements)

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“…Tested compounds dissolved in water or methanol (30 μL) were added at various concentrations (to final concentration of 2,4,8,16,32,64,128,256, 512 μg/mL) to freshly prepared 0.22 mM DPPH · in methanol (120 μL). The absorbance was measured against the control in the microplate reader at 517 nm after 30 min of incubation at room temperature (rt).…”

Section: Dpph Radical Scavenging Assaymentioning

confidence: 99%

“…Scavengers of · NO compete with oxygen leading to reduced production of nitric oxide. 10 mM sodium nitroprusside in 0.1 M phosphate buffer pH 7.4 (30 μL) was mixed with tested compounds dissolved in water or methanol (25 μL) at various concentrations (to final concentration of 2,4,8,16,32,64,128,256, 512 μg/mL) and incubated at 25 °C for 5 h. After incubation, Griess reagent (50 μL) was added. The absorbance was measured in the microplate reader at 546 nm against a control (without tested compounds) treated in the same way with Griess reagent.…”

Section: Nitric Oxide Radical Scavenging Assaymentioning

confidence: 99%

“…At least three concentrations of tested compounds were assayed. For each of these inhibitor concentrations, the percentage of inhibition was calculated using Equation (4). The difference in absorbance for the inhibitor at t = 10 min and t = 0 is denoted ΔAi.…”

Section: Ache Inhibitory Activitymentioning

confidence: 99%

“…Published activities include antimetastatic [1], anti-inflammatory and analgesic [2], antiarrhythmic, and antiaggregatory [3] antihypertensive [4], and antibacterial [5]. They also inhibit catechol O-methyltransferase [6] and kinase JNK3 [7].…”

Section: Introductionmentioning

confidence: 99%

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New Derivatives of 3,4-Dihydroisoquinoline-3-carboxylic Acid with Free-Radical Scavenging, D-Amino Acid Oxidase, Acetylcholinesterase and Butyrylcholinesterase Inhibitory Activity

et al. 2014

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A series of 3,4-dihydroisoquinoline-3-carboxylic acid derivatives were synthesised and tested for their free-radical scavenging activity using 2,2-diphenyl-1-picrylhydrazyl radical (DPPH · ), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical (ABTS ·+ ), superoxide anion radical (O2 ·− ) and nitric oxide radical ( · NO) assays. We also studied D-amino acid oxidase (DAAO), acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitory activity. Almost each of newly synthesised compounds exhibited radical scavenging capabilities. Moreover, several compounds showed moderate inhibitory activities against DAAO, AChE and BuChE. Compounds with significant free-radical scavenging activity may be potential candidates for therapeutics used in oxidative-stress-related diseases.

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Section: Dpph Radical Scavenging Assaymentioning

confidence: 99%

Section: Nitric Oxide Radical Scavenging Assaymentioning

confidence: 99%

Section: Ache Inhibitory Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New Derivatives of 3,4-Dihydroisoquinoline-3-carboxylic Acid with Free-Radical Scavenging, D-Amino Acid Oxidase, Acetylcholinesterase and Butyrylcholinesterase Inhibitory Activity

et al. 2014

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“…Hydrazones are one of the most important classes of organic compounds having a broad spectrum of pharmacological activities . Particularly, the anti‐inflammatory and analgesic, antimicrobial, antifungal, anticancer, antidepressant, anticonvulsant, antihypertensive and antiplatelet activities are important to mention (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis, crystal growth, characterization and computational study of new pyridine‐based halogenated hydrazones: Unveiling the stabilization behavior in terms of noncovalent interactions

Ali

Khalid

Abid

et al. 2019

Applied Organom Chemis

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The pyridine‐based halogenated hydrazone derivatives (E)‐N′‐benzylidene‐2‐[(6″‐chloroazin‐2″‐yl)oxy]acetohydrazide (6a), (E)‐N′‐(3′‐chlorobenzylidene)‐2‐[(6″‐chloroazin‐2″‐yl)oxy]acetohydrazide (6b) and (E)‐N′‐(3′‐bromobenzylidene)‐2‐[(6″‐chloroazin‐2″‐yl)oxy]acetohydrazide (6c) have been obtained using 6‐chloro‐2‐hydroxypyridine. The structure of the products (6a–c) has been verified using X‐ray crystallography and spectroscopic approaches. A single‐crystal X‐ray diffraction (SC‐XRD) investigation showed that the structures are stabilized by intermolecular attractive forces. Additionally, density functional theory (DFT) has been adopted to explore the structural properties, vibrational spectra, noncovalent interactions and frontier molecular orbitals using the B3LYP/6‐311 + G(d,p) level. The nonlinear optical properties of the title compounds were calculated using the CAM‐B3LYP/6‐311 + G(d,p) level. Frequency analysis confirmed the stability of the molecules, and an excellent correlation was observed between the DFT‐ and SC‐XRD‐based structural parameters. The SC‐XRD analysis confirmed that the dimers of 6a, 6b and 6c are linked by hydrogen‐bonding interactions. Natural bond orbital (NBO) analysis also reconfirmed the strength of intermolecular hydrogen‐bonding and hyperconjugative interactions. NBO investigation was also utilized to analyze the atomic charges. Moreover, Fourier transform infrared and natural population analyses endorsed that there are significant N&bond;H⋅⋅⋅O&dbond;C hydrogen‐bonding linkages in dimeric structures of the compounds. The hydrogen‐bonding network and different sorts of hyperconjugative interactions are the main reasons for the stability of the products in the solid state. The highest occupied and lowest unoccupied molecular orbital energies and first‐order nonlinear optical properties of these molecules are reported. The quantum chemical parameters were derived using frontier molecular orbital energies.

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