Synthesis, biological assessment, and molecular modeling of racemic 7-aryl-9,10,11,12-tetrahydro-7H-benzo[7,8]chromeno[2,3-b]quinolin-8-amines as potential drugs for the treatment of Alzheimer's disease

Maalej, Emna; Chabchoub, Fakher; Oset-Gasque, María Jesús; Esquivias-Pérez, Mario; González, M.P.; Monjas, Leticia; Pérez, Concepción; Rı́os, Cristóbal de los; Rodríguez‐Franco, María Isabel; Iriepa, Isabel; Moraleda, Ignacio; Chioua, Mourad; Romero, Alejandro; Marco‐Contelles, José; Samadi, Abdelouahid

doi:10.1016/j.ejmech.2012.06.038

Cited by 68 publications

(19 citation statements)

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“…The microwave‐assisted reactions were performed in a synthetic microwave: Monowave 300 apparatus with a maximum power of 300 W. All tested compounds were found to be ≥95 % pure by HPLC analysis by using a Hitachi Lachrom Elite series instrument. 3‐Amino‐1‐phenyl‐1 H ‐benzo[ f ]chromene‐2‐carbonitrile ( 1 a ), 3‐amino‐1‐(3‐methoxyphenyl)‐1 H ‐benzo[ f ]chromene‐2‐carbonitrile ( 1 b ), 2‐amino‐4‐phenyl‐4 H ‐benzo[ h ]chromene‐3‐carbonitrile ( 2 a ), and 2‐amino‐4‐(3‐methoxyphenyl)‐4 H ‐benzo[ h ]chromene‐3‐carbonitrile ( 2 b ) were previously described.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ₁₋₄₂ Aggregation Inhibitors for Alzheimer's Disease Therapy

et al. 2016

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Given the complex nature of Alzheimer's disease (AD), compounds that are able to simultaneously address two or more AD-associated targets show greater promise for development into drugs for AD therapy. Herein we report an efficient two-step synthesis and biological evaluation of new racemic benzochromene derivatives as antioxidants, inhibitors of cholinesterase and β-amyloid (Aβ1-42 ) aggregation. Based on the results of the primary screening, we identified 15-(3-methoxyphenyl)-9,11,12,15-tetrahydro-10H,14H-benzo[5,6]chromeno[2,3-d]pyrido[1,2-a]pyrimidin-14-imine (3 e) and 16-(3-methoxyphenyl)-9,10,11,12,13,16-hexahydro-15H-benzo[5',6']chromeno[2',3':4,5]pyrimido[1,2-a]azepin-15-imine (3 f) as new potential multitarget-directed ligands for AD therapy. Further in-depth biological analysis showed that compound 3 f is a good human acetylcholinesterase inhibitor [IC50 =(0.36±0.02) μm], has strong antioxidant activity (3.61 μmol Trolox equivalents), and moderate Aβ1-42 antiaggregating power (40.3 %).

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Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ₁₋₄₂ Aggregation Inhibitors for Alzheimer's Disease Therapy

et al. 2016

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“…To solve this problem, recently in situ generated ortho ‐quinone methides were extensively employed in different asymmetric transformations (Scheme ). Few of these strategies had been found to be successful for the construction of important structural frameworks including natural products and necessary precursors of pharmaceutically active drug molecules such as ( S )‐4‐methoxydalbergione, ( R )‐tolterodine, SB‐209670, SB‐217242, sideroxylonal B, carpanone, tacrine analogue etc. (Figure ).…”

Section: Brief History Of Ortho‐quinone Methides and Its Synthetic Utmentioning

confidence: 99%

“…Operationally simple procedure and broad substrate scope are the main merits of this work. Also the authors transformed product 16 a to biologically important drug molecule 16′a having anti‐Alzheimer activities …”

Section: Asymmetric Reactions With O‐qmsmentioning

confidence: 99%

Applications of Bifunctional Organocatalysts on ortho‐Quinone Methides

2019

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ortho-Quinone methides are important structures, having a cyclohexadiene core bearing an exocyclic alkylidiene and carbonyl functionality at the ortho-position, and are widely used as essential intermediates in organic synthesis. These reactive intermediates are also used as important building blocks for the construction of a variety of heterocycles by hetero Diels-Alder, electrocyclization reactions. Moreover, ortho-quinone methides are a class of electrophiles, serving as Michael acceptors leading to conjugate additions with various nucleophiles. In general, ortho-Quinone methides have transient existence and are highly reactive in nature. ortho-Quinone methides have been generated in situ from stable precursors using either Brønsted acids or Brønsted bases. In the last few years, ortho-quinone methides have been explored as imperative class of substrates in various bifunctional organocatalysts mediated asymmetric conjugate additions, cycloannulation, acyl-transfer reaction, thiolation and hydrophosphination reactions. This review illustrates recent advancements of asymmetric transformations of ortho-quinone methides with bifunctional H-bonding organocatalysts.[a] S.

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“…27,28 Peroxyl radicals were thermally generated from 2,2-azobis-(amidinopropane) dihydrochloride and reacted with fluorescein to form nonfluorescent products at 535 nm. The antioxidant capacity of compounds 20-50 was determined by their competition with fluorescein in the radical capture, using a fluorescence microplate reader.…”

Section: Antioxidant Activitymentioning

confidence: 99%

Design, synthesis and evaluation of chromone-2-carboxamido-alkylbenzylamines as multifunctional agents for the treatment of Alzheimer’s disease

Liu

Qiang

et al. 2015

Bioorganic & Medicinal Chemistry

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Synthesis, biological assessment, and molecular modeling of racemic 7-aryl-9,10,11,12-tetrahydro-7H-benzo[7,8]chromeno[2,3-b]quinolin-8-amines as potential drugs for the treatment of Alzheimer's disease

Cited by 68 publications

References 62 publications

Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ₁₋₄₂ Aggregation Inhibitors for Alzheimer's Disease Therapy

Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ₁₋₄₂ Aggregation Inhibitors for Alzheimer's Disease Therapy

Applications of Bifunctional Organocatalysts on ortho‐Quinone Methides

Design, synthesis and evaluation of chromone-2-carboxamido-alkylbenzylamines as multifunctional agents for the treatment of Alzheimer’s disease

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Synthesis, biological assessment, and molecular modeling of racemic 7-aryl-9,10,11,12-tetrahydro-7H-benzo[7,8]chromeno[2,3-b]quinolin-8-amines as potential drugs for the treatment of Alzheimer's disease

Cited by 68 publications

References 62 publications

Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ1−42 Aggregation Inhibitors for Alzheimer's Disease Therapy

Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ1−42 Aggregation Inhibitors for Alzheimer's Disease Therapy

Applications of Bifunctional Organocatalysts on ortho‐Quinone Methides

Design, synthesis and evaluation of chromone-2-carboxamido-alkylbenzylamines as multifunctional agents for the treatment of Alzheimer’s disease

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Product

Resources

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Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ₁₋₄₂ Aggregation Inhibitors for Alzheimer's Disease Therapy

Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ₁₋₄₂ Aggregation Inhibitors for Alzheimer's Disease Therapy