Synthesis of Primary Amines by One-Pot Reductive Amination of Aldehydes

Ayedi, Mohamed Ali; Bigot, Y. Le; Ammar, Houcine; Abid, Souhir; Gharbi, Rachid El; Delmas, M.

doi:10.1080/00397911.2012.714830

Cited by 26 publications

(30 citation statements)

References 23 publications

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“…The reductive alkylation of amines using nitriles was also used to obtain 51 and 74 in Schemes 3 and 7. The isonipecotic acid derivatization was achieved via Fischer esterification using the reagent-solvents propanol (37) and EtOH (38), respectively; methyl isonipecotate (36) and piperidine (39) were purchased from Sigma (Scheme 2).…”

Section: Synthesis Of Pteridine Derivatives With High Yieldmentioning

confidence: 99%

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Multitarget, Selective Compound Design Yields Potent Inhibitors of a Kinetoplastid Pteridine Reductase 1

Pöhner

Quotadamo

Panecka-Hofman

et al. 2022

Preprint

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The optimization of compounds with multiple targets is a difficult multidimensional problem in the drug discovery cycle. Here, we present a systematic, multidisciplinary approach to the development of selective anti-parasitic compounds. Computational fragment-based design of novel pteridine derivatives along with iterations of crystallographic structure determination allowed for the derivation of a structure-activity relationship for multitarget inhibition. The approach yielded compounds showing subnanomolar inhibition of T. brucei pteridine reductase 1 (PTR1), nanomolar inhibition of L. major PTR1, and selective submicromolar inhibition of parasite dihydrofolate reductase (DHFR) versus human DHFR. Moreover, by combining design for polypharmacology with a property-based on-parasite optimization, we found three compounds that exhibited micromolar EC50 values against T. brucei brucei, whilst retaining their target inhibition. Our results provide a basis for the further development of pteridine-based compounds, and we expect our multitarget approach to be generally applicable to the design and optimization of anti-infective agents.

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Section: Synthesis Of Pteridine Derivatives With High Yieldmentioning

confidence: 99%

“…The phenoxyphenyl-methanamine derivative intermediates (Scheme 5) were synthesized starting from 4-fluorobenzaldehyde and the respective phenol derivates 60-62 by an SNAr reaction. Subsequently, the primary amines 66-68 36 , or functionalized amines 69-70…”

Section: Synthesis Of Pteridine Derivatives With High Yieldmentioning

confidence: 99%

Multitarget, Selective Compound Design Yields Potent Inhibitors of a Kinetoplastid Pteridine Reductase 1

Pöhner

Quotadamo

Panecka-Hofman

et al. 2022

Preprint

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“…34,35 The reductive alkylation of amines using nitriles was also used to obtain 51 and 74 in Schemes 3 and 7. The isonipecotic acid derivatization was achieved via Fischer esterification using the reagent-solvents propanol (37) and EtOH (38), respectively; methyl isonipecotate (36) and piperidine (39) were purchased from Sigma (Scheme 2).…”

Section: Synthesis Of Pteridine Derivatives With High Yieldmentioning

confidence: 99%

Multitarget, Selective Compound Design Yields Picomolar Inhibitors of a Kinetoplastid Pteridine Reductase 1

Pöhner¹,

Quotadamo²,

Panecka-Hofman³

et al. 2020

Preprint

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The optimization of compounds with multiple targets in the drug discovery cycle is a difficult multidimensional problem. Here, we present a systematic, multidisciplinary approach to the development of selective anti-parasitic compounds. Efficient microwave-assisted synthesis of pteridines along with iterations of crystallographic structure determination were used to validate computational docking predictions and support derivation of a structure-activity relationship for multitarget inhibition. This approach yielded compounds showing picomolar inhibition of T. brucei pteridine reductase 1 (PTR1), nanomolar inhibition of L. major PTR1, along with selective submicromolar inhibition of parasitic dihydrofolate reductase (DHFR). Moreover, by combining design for polypharmacology with a property-based on-parasite optimization, we found three compounds that exhibited micromolar EC50 values against T. brucei brucei, whilst retaining their target inhibition. Our results provide a basis for the further development of pteridine-based compounds and we expect our multitarget approach to be generally applicable to the design and optimization of anti-infective agents.

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“…However, such processes often require the use of protecting groups, numerous chemical steps, and toxic reductive agents [30,31] . To circumvent these issues, several chemocatalytic pathways have been recently developed; [30,31,32] however, these are not ideal for the synthesis of furfurylamines deriving from HMF, owing to the sensitivity of the furan ring to reductive conditions and the tendency of these compounds to form secondary and tertiary amines [17,32g,33] . An efficient alternative to perform reductive amination of HMF derivatives is the use of transaminases, already largely described for carbonyl group amination, [34] for the efficient conversion of carbonyl moieties to primary amines in water at low temperatures.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Conversion of 5‐Hydroxymethylfurfural to 5‐Aminomethyl‐2‐furancarboxylic acid: Toward New Bio‐sourced Polymers

Lancien

Wojcieszak²,

Cuvelier³

et al. 2020

ChemCatChem

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Hybrid catalysis, which combines chemo‐ and biocatalytic benefits, is an efficient way to address green chemistry principles. 5‐Hydroxymethylfurfural (HMF) is a versatile building block in numerous industrial applications. To date, few studies have described the production of its amine derivatives and their polymers. Finding a good methodology to directly transform HMF to 5‐aminomethyl‐2‐furancarboxylic acid (AMFC) therefore represents an important challenge. After selecting the best oxidation catalyst for HMF conversion to 5‐aldehyde‐2‐furancarboxylic acid and immobilizing a transaminase onto a solid carrier, we implemented the first one‐pot/two‐steps hybrid catalytic process to produce AMFC (77 % yield); this is the most efficient AMFC catalytic production method from HMF reported to date. This process also produced 2,5‐furandicarboxylic acid (21 % yield) as a major secondary product that can be applied to polymer syntheses such as polyethylene furanoate. Herein, we report a novel way to access new biosourced polymers based on HMF oxidized and aminated derivatives.

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Synthesis of Primary Amines by One-Pot Reductive Amination of Aldehydes

Abstract: OATAO is an open access repository that collects the work of Toulouse researchers and makes it freely available over the web where possible.

Cited by 26 publications

References 23 publications

Multitarget, Selective Compound Design Yields Potent Inhibitors of a Kinetoplastid Pteridine Reductase 1

Multitarget, Selective Compound Design Yields Potent Inhibitors of a Kinetoplastid Pteridine Reductase 1

Multitarget, Selective Compound Design Yields Picomolar Inhibitors of a Kinetoplastid Pteridine Reductase 1

Hybrid Conversion of 5‐Hydroxymethylfurfural to 5‐Aminomethyl‐2‐furancarboxylic acid: Toward New Bio‐sourced Polymers

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