Flow Chemistry Opportunities for Drug Discovery

Linares, María Lourdes; López, Enol; Palao, Eduardo; Alcázar, Jesús

doi:10.1002/9783527824595.ch3

Cited by 2 publications

(4 citation statements)

References 111 publications

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“…All reactions took place in a conventional flow coil reactor (CFC) with a volume of 10 mL. Therefore, a straightforward coupling between 5-pentenoic acid (21), activated in situ with carbonyldiimidazole (CDI), and (±)-serine methyl ester (22) in the presence of triethylamine took place, followed by successive cyclodehydration with diethylaminosulfur trifluoride (DAST) to form oxazoline (23). It was necessary to quench the excess of DAST and to capture the generated HF, improving the safety profile by using a CaCO 3 /SiO 2 scavenger.…”

Section: Scheme 3 Retrosynthetic Study Of (−)-Hennoxazole a (15)mentioning

confidence: 99%

“…Derivative ( 27) was also achieved on the multigram scale (<5 g). and (±)-serine methyl ester (22) in the presence of triethylamine took place, followed by successive cyclodehydration with diethylaminosulfur trifluoride (DAST) to form oxazoline (23). It was necessary to quench the excess of DAST and to capture the generated HF, improving the safety profile by using a CaCO3/SiO2 scavenger.…”

Section: Scheme 3 Retrosynthetic Study Of (−)-Hennoxazole a (15)mentioning

confidence: 99%

“…Although some of these methodologies have been reported in international journal articles (preparation of abemaciclib [15] and nevirapine [16]), most of them are covered by patents with few details of the chemical transformation [17]-for instance, the synthesis of brivaracetam [18], valacyclovir [19], or crizotinib as an intermediate [20]. Regarding drug discovery, the benefits of flow technology have also been considered but not significantly explored [21,22]. On the other hand, the ocean is still an underexplored environment which can be explored by scientists to identify new chemical analogs.…”

Section: Introductionmentioning

confidence: 99%

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Continuous Flow Chemistry: A Novel Technology for the Synthesis of Marine Drugs

Peña,

González-Andrés,

Parte

et al. 2023

Marine Drugs

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In this perspective, we showcase the benefits of continuous flow chemistry and photochemistry and how these valuable tools have contributed to the synthesis of organic scaffolds from the marine environment. These technologies have not only facilitated previously described synthetic pathways, but also opened new opportunities in the preparation of novel organic molecules with remarkable pharmacological properties which can be used in drug discovery programs.

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Section: Scheme 3 Retrosynthetic Study Of (−)-Hennoxazole a (15)mentioning

confidence: 99%

Section: Scheme 3 Retrosynthetic Study Of (−)-Hennoxazole a (15)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Continuous Flow Chemistry: A Novel Technology for the Synthesis of Marine Drugs

Peña,

González-Andrés,

Parte

et al. 2023

Marine Drugs

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“…However, flow chemistry is playing an increasingly important role in drug discovery at the small scale, in chemical process development, and in manufacturing in the pharmaceutical and agrochemical industries . The improved temperature and mass transfer that the plug flow reactors possess make them a safe and reproducible technology for scaling up high-temperature processes.…”

Section: Introductionmentioning

confidence: 99%

Multigram Synthesis of Chiral Cyclopropane Carboxylic Acids via Tandem Diastereoselective Wadsworth–Emmons Cyclopropanation-Hydrolysis in Continuous Flow

Mateos,

García-Cerrada,

García-Losada

et al. 2024

Org. Process Res. Dev.

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Here, we present a novel continuous flow approach for the Wadsworth−Emmons cyclopropanation of alkylsubstituted chiral epoxides into chiral cyclopropane carboxylic acids. The developed flow process circumvents the risks associated with the harsh conditions (high T/P) required, considering the highly volatile nature of the epoxide-SM. Additionally, the flow reactors offer increased efficiency, as their reduced headspace contributes to keeping a higher concentration of the low-boiling-point reactants in the liquid phase and thus enhanced reactivity, contrary to the use of sealed vessels in batch. The cyclopropane formation process is coupled with in-line workup and hydrolysis transformations to yield the desired enantiomerically pure cyclopropane carboxylic acids in good yields up to the 100 g scale.

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Flow Chemistry Opportunities for Drug Discovery

Cited by 2 publications

References 111 publications

Continuous Flow Chemistry: A Novel Technology for the Synthesis of Marine Drugs

Continuous Flow Chemistry: A Novel Technology for the Synthesis of Marine Drugs

Multigram Synthesis of Chiral Cyclopropane Carboxylic Acids via Tandem Diastereoselective Wadsworth–Emmons Cyclopropanation-Hydrolysis in Continuous Flow

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