An Efficient and Sustainable Synthesis of the Antimalarial Drug Tafenoquine

Kavthe, Rahul D.; Kincaid, Joseph R. A.; Lipshutz, Bruce H.

doi:10.1021/acssuschemeng.2c05628

Cited by 7 publications

(7 citation statements)

References 46 publications

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“…It is also plausible that the more polar Savie is better able to clean the surface of the iron, thereby increasing the reactive surface area. The yield in the nitro reduction to afford aniline 17 , a precursor to the antimalarial drug tafenoquine, nearly doubled using a micellar medium composed of Savie instead of TPGS-750-M.…”

Section: Resultsmentioning

confidence: 99%

Introducing Savie: A Biodegradable Surfactant Enabling Chemo- and Biocatalysis and Related Reactions in Recyclable Water

et al. 2023

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Savie is a biodegradable surfactant derived from vitamin E and polysarcosine (PSar) developed for use in organic synthesis in recyclable water. This includes homogeneous catalysis (including examples employing only ppm levels of catalyst), heterogeneous catalysis, and biocatalytic transformations, including a multistep chemoenzymatic sequence. Use of Savie frequently leads to significantly higher yields than do conventional surfactants, while obviating the need for wastegenerating organic solvents.

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Section: Resultsmentioning

confidence: 99%

Introducing Savie: A Biodegradable Surfactant Enabling Chemo- and Biocatalysis and Related Reactions in Recyclable Water

et al. 2023

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“…The diaryl ether unit is present in various drug molecules and natural products [1] . For example, lenvatinib is used as an anticancer drug, [2] and tefenoquine is an antimalarial drug (Scheme 1a) [3] . Additionally, they serve as the basic framework for bidentate phosphine ligands in catalysis [4] .…”

Section: Methodsmentioning

confidence: 99%

“…[1] For example, lenvatinib is used as an anticancer drug, [2] and tefenoquine is an antimalarial drug (Scheme 1a). [3] Additionally, they serve as the basic framework for bidentate phosphine ligands in catalysis. [4] More importantly, two diaryl ether chiral axes exist in the cyclic peptide aglycone of antibiotic vancomycin (Scheme 1b).…”

mentioning

confidence: 99%

Enantioselective Synthesis of C−O Axially Chiral Diaryl Ethers by NHC‐Catalyzed Atroposelective Desymmetrization**

Shee,

Shree Ranganathappa,

Gadhave

et al. 2023

Angew Chem Int Ed

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Axially chiral diaryl ethers, a distinguished class of atropisomers possessing unique dual C−O axis, hold immense potential for diverse research domains. In contrast to the catalytic enantioselective synthesis of conventional single axis bearing atropisomers, the atroposelective synthesis of axially chiral ethers containing flexible C−O axis remains a significant challenge. Herein, we demonstrate the first N‐heterocyclic carbene (NHC)‐catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde‐containing diaryl ethers. Mechanistically, the reaction proceeds via NHC‐catalyzed desymmetrization strategy to afford the corresponding axially chiral diaryl ether atropisomers in good yields and high enantioselectivities under mild conditions. The derivatization of the synthesized product expands the utility of present strategy via access to a library of C−O axially chiral compounds. The temperature dependency and preliminary investigations on the racemization barrier of C−O bonds are also presented.

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“…Differently from the previous synthetic routes, where many steps and toxic reagents represented big limitations, Lipshutz's team successfully managed to develop a green and economically attractive synthesis of tafenoquine succinate (1, Scheme 1). 28 Specifically, N-(4-methoxyphenyl)-3-oxobutanamide 2 has been obtained in a two-step one-pot synthesis starting from 4- 25 Atom economy (AE) refers to the enhancement of the reaction efficiency by reducing the depletion of raw materials. The AE metric 26 is a useful tool for rapid evaluation of different routes, as it is calculated by dividing the molecular weight of the product by the total of the molecular weights of all substances formed in the stoichiometric equation for the reaction involved.…”

Section: Drug Development For Vbpdsmentioning

confidence: 99%

Harnessing the 12 Green Chemistry Principles for Sustainable Antiparasitic Drugs: Toward the One Health Approach

Martinengo,

Diamanti,

Uliassi

et al. 2024

ACS Infect. Dis.

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Antiparasitic drug development stands as a critical endeavor in combating infectious diseases which, by affecting the well-being of humans, animals, and the environment, pose significant global health challenges. In a scenario where conventional pharmacological interventions have proven inadequate, the One Health approach, which emphasizes interdisciplinary collaboration and holistic solutions, emerges as a vital strategy. By advocating for the integration of One Health principles into the R&D pharmaceutical pipeline, this Perspective promotes green chemistry methodologies to foster the development of environmentally friendly antiparasitic drugs for both human and animal health. Moreover, it highlights the urgent need to address vector-borne parasitic diseases (VBPDs) within the context of One Health-driven sustainable development, underscoring the pivotal role of medicinal chemists in driving transformative change. Aligned with the Sustainable Development Goals (SDGs) and the European Green Deal, this Perspective explores the application of the 12 Principles of Green Chemistry as a systematic framework to guide drug discovery and production efforts in the context of VBPD. Through interdisciplinary collaboration and a constant commitment to sustainability, the field can overcome the challenges posed by VBPD while promoting global and environmental responsibility. Serving as a call to action, scientists are urged to integrate One Health concepts and green chemistry principles into routine drug development practices, thereby paving the way for a more sustainable R&D pharmaceutical pipeline for antiparasitic drugs.

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An Efficient and Sustainable Synthesis of the Antimalarial Drug Tafenoquine

Cited by 7 publications

References 46 publications

Introducing Savie: A Biodegradable Surfactant Enabling Chemo- and Biocatalysis and Related Reactions in Recyclable Water

Introducing Savie: A Biodegradable Surfactant Enabling Chemo- and Biocatalysis and Related Reactions in Recyclable Water

Enantioselective Synthesis of C−O Axially Chiral Diaryl Ethers by NHC‐Catalyzed Atroposelective Desymmetrization**

Harnessing the 12 Green Chemistry Principles for Sustainable Antiparasitic Drugs: Toward the One Health Approach

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