Tetrahydroisoquinolines

doi:10.1002/9781118686263.ch10

Cited by 5 publications

(1 citation statement)

References 501 publications

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“…The tetrahydroisoquinoline contains a nitrogen heterocycle found in many approved drugs in clinical use for several diseases. Medicinal chemistry exploration of this scaffold has yielded analogues with antitubercular, antibacterial, antifungal, and antiviral action [ 19 ]. In a recent study of seventeen THIQs, six demonstrated a moderate but structure-related antibacterial activity against MDR S. Typhi strains comparable to some of the treatment antibiotics [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Synergistic Activity of Combinations of Tetrahydroisoquinolines and Treatment Antibiotics against Multidrug-Resistant Salmonella

Ndip,

Hanna,

Mbah

et al. 2023

Advances in Pharmacological and Pharmaceutical Sciences

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The global burden of Salmonella infections remains high due to the emergence of multidrug resistance to all recommended treatment antibiotics. Tetrahydroisoquinolines (THIQs) have demonstrated promising activity against multidrug-resistant (MDR) Salmonella Typhi. Hence, their interaction with treatment antibiotics was investigated for possible synergy. Twenty combinations of five THIQs (1, 2, 3, 4, and 5) and four antibiotics were tested against each of 7 Salmonella isolates by the checkerboard method giving a total of 140 assays performed. Fractional inhibitory concentration indices (FICIs) were calculated, and isobolograms were plotted. In terms of FICI, synergism ranged from 0.078 to 0.5 and the highest magnitude (0.078) was recorded for chloramphenicol-THIQ 1 combination. In a total of 140 antibiotics-THIQs combination assays, 27 were synergistic (17%), 42 were additive (30%), 11 were antagonistic (7.8%), and 60 were indifferent (42%). The synergistic activity recorded for each antibiotic class in combination based on the total of 7 bacterial isolates tested ranged from 14.29% to 71.43%; the highest percentage was recorded for two combinations (chloramphenicol or sulphamethoxazole with THIQ 1). Ciprofloxacin-THIQ 1 combination showed additivity on all bacteria isolates tested (100%). Overall, THIQ 1 was the most synergistic and most additive in combination with three antibiotics (ampicillin, chloramphenicol, or sulphamethoxazole-trimethoprim). Some combinations of the THIQs and treatment antibiotics have shown high synergism which could potentially be efficacious against multidrug-resistant S. Typhi, hence this interaction should be further studied in vivo.

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Section: Introductionmentioning

confidence: 99%

In Vitro Synergistic Activity of Combinations of Tetrahydroisoquinolines and Treatment Antibiotics against Multidrug-Resistant Salmonella

Ndip,

Hanna,

Mbah

et al. 2023

Advances in Pharmacological and Pharmaceutical Sciences

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Chemo‐Enzymatic One‐Pot Two‐Step Functionalization of 1,2,3,4‐Tetrahydroisoquinolines by Monoamine Oxidase‐Ugi‐Joullié Reaction Sequence

et al. 2022

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In memory of Ferenc FülöpA one-pot two-step chemo-enzymatic approach for the functionalization of substituted 1,2,3,4-tetrahydroisoquinolines (THIQs) was developed. The system combines monoamine oxidase (MAO)-catalyzed imine formation with Ugi-type threecomponent reaction in an aqueous buffer without intermediate isolation. The two steps were separately optimized for buffer and pH to obtain the expected products. MAOs enabled the functionalization of fifteen THIQs by oxidation to imines, while the Ugi-Joullié-reaction was successfully carried out with eight carboxylic acids and eight isonitriles. 41 products were isolated giving access to valuable building blocks for medicinal chemistry applications. Gram-scale transformation demonstrated the utility of the described protocol for organic synthesis.

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Metal‐Free Multicomponent Construction of Tetrahydroisoquinoline‐Indole Derivatives via In Situ Generated ortho‐Quinonoid Intermediate

Kaur

Gurjar²,

Kumar

et al. 2020

ChemistrySelect

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A metal‐ and ligand‐free multicomponent coupling of tetrahydroisoquinoline (THIQ), ortho‐hydroxybenzaldehydes and indoles under solvent‐free conditions is described. The developed protocol provided a waste‐free and concise access to C(1)‐functionalized THIQ‐indole derivatives under green conditions. The reactant molar ratio and neutral conditions were found crucial for controlling the selectivity of desired THIQ‐indole product over competitive by‐products i. e. oxazine and bis(indolyl)methane. The experimental and DFT study revealed the involvement of ortho‐quinonoid species which reacts with indoles in situ to form THIQ‐indole derivatives.

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Tetrahydroisoquinolines

Cited by 5 publications

References 501 publications

In Vitro Synergistic Activity of Combinations of Tetrahydroisoquinolines and Treatment Antibiotics against Multidrug-Resistant Salmonella

In Vitro Synergistic Activity of Combinations of Tetrahydroisoquinolines and Treatment Antibiotics against Multidrug-Resistant Salmonella

Chemo‐Enzymatic One‐Pot Two‐Step Functionalization of 1,2,3,4‐Tetrahydroisoquinolines by Monoamine Oxidase‐Ugi‐Joullié Reaction Sequence

Metal‐Free Multicomponent Construction of Tetrahydroisoquinoline‐Indole Derivatives via In Situ Generated ortho‐Quinonoid Intermediate

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