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Photochemistry in Flow for Drug Discovery

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Flow Chemistry in Drug Discovery

Part of the book series: Topics in Medicinal Chemistry ((TMC,volume 38))

Abstract

The discovery of new drug candidates and the development of new lead structures for future active pharmaceutical ingredients are continuous processes, which combine the expertise of many scientific disciplines. The race for novel molecular building blocks with potent biological activity triggered the development of new synthesis methodologies and forced the scientific communities to interact even stronger with each other. The result of one very fruitful interaction is the application of continuous flow chemistry and micro reaction technology to photochemistry and photocatalysis. The synergy of those research fields combined is an environment for mild and controlled reaction conditions, which allows new synthesis routes with higher conversion and selectivity, straightforward scale-up and possible integration in multi-step syntheses. In this chapter, several examples for molecular transformations are highlighted, which are important for the synthesis of complex molecular structures or for the integration of pharmaceutically active functional groups. This snapshot gives an overview of a vivid research field for drug discovery and illustrates the benefits for synthetic organic photochemistry by going to flow.

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Abbreviations

2-MeTHF:

2-Methyltetrahydrofuran

4CzIPN:

1,2,3,5-Tetrakis(carbazol-9-yl)-4,6-dicyanobenzene

4-DPA-IPN:

2,4,5,6-Tetrakis(diphenylamino)isophthalonitrile

4-HTP:

4-Hydroxythiophenol

acac:

Acetylacetonate

ADP:

Adenosine diphosphate

API:

Active pharmaceutical ingredient

B2pin2:

Bis(pinacolato)diboron

Boc:

Tert-butyloxycarbonyl

bpy:

Bipyridine

CFD:

Computational fluid dynamics

CFL:

Compact fluorescent lamp

cod:

1,5-Cyclooctadien

Cp:

Cyclopentadienyl

DABCO:

1,4-Diazabicyclo[2.2.2]octane

dba:

Dibenzylideneacetone

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCE:

Dichloroethane

dF(CF3)ppy3:

3,5-Difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C

DIPEA:

Diisopropylethylamine

DMA:

N,N-dimethylacetamide

DMAP:

4-Dimethylaminopyridine

dme:

Dimethoxyethane

DMF:

N,N-dimethylformamide

dmppy:

Dimethylphenylpyridine

DMSO:

Dimethylsulfoxid

dtbbpy:

4,4′-Di-tert-butyl-2,2′-dipyridyl

eq:

Equivalent

FEP:

Fluorinated ethylene propylene

GABA:

γ-Aminobutyric acid

HALEX:

HALogen EXchange (reaction)

HAT:

Hydrogen atom transfer (reaction)

HFIP:

1,1,1,3,3,3-Hexafluoro-propan-2-ol

hν :

Photon energy

I.D.:

Inner diameter

JohnPhos:

(2-Biphenyl)di-tert-butylphosphine

KRED:

Keto reductase

LC-MS:

Liquid chromatography-mass spectrometry

LED:

Light emitting diode

MAO:

Monoamine oxidase

m-CPBA:

Meta-chloroperbenzoic acid

Mes-Acr-4:

9-Mesityl-10-methylacridinium tetrafluoroborate

NADPH/NADP+:

Nicotinamide adenine dinucleotide

NaDT:

Sodium decatungstate

NFSI:

N-fluorobenzenesulfonimide

NHC:

N-heterocyclic carbenes

NMR:

Nuclear magnetic resonance

PDMS:

Polydimethylsiloxane

PET:

Positron emission tomography

PFA:

Perfluoroalkoxy alkane

ppy:

2-Phenylpyridine

r.t.:

Room temperature

rAaeUPO:

A. Aegerita unspecified peroxygenase

RCY:

Radiochemical yield

SCE:

Saturated calomel electrode

SLAP:

Silicone amine protocol

sppy:

Sulphonated 2-phenylpyridine

TBADT:

Tetrabutylammonium decatungstate

TBAF:

Tetrabutylammonium fluoride

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

TMDAM:

N,N,N′,N′-tetramethyldiaminomethane

TMS:

Trimethylsilyl

TMSCN:

Trimethylsilyl cyanide

TMSOTf:

Trimethylsilyl trifluoromethanesulfonate

TPP:

2,4,6-triphenylpyrylium tetrafluoroborate

UPO:

Unspecific peroxygenase

UV:

Ultraviolet

W:

Watt

Xphos:

2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

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Authors and Affiliations

  1. Division Chemistry, Sustainable Chemical Syntheses Group, Fraunhofer Institute for Microengineering and Microsystems IMM, Mainz, Germany

    Thomas H. Rehm

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  1. Thomas H. Rehm
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Correspondence to Thomas H. Rehm .

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Editors and Affiliations

  1. Discovery Chemistry, Janssen Pharmaceutical Companies of J&J, Janssen-Cilag, S.A., Toledo, Spain

    Jesus Alcazar

  2. Faculty of Chemistry, University of Castilla-La Mancha, Ciudad Real, Ciudad Real, Spain

    Antonio de la Hoz

  3. Faculty of Chemistry, University of Castilla-La Mancha, Ciudad Real, Spain

    Angel Díaz-Ortiz

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Informed Consent: No patients were studied in this chapter.

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Rehm, T.H. (2021). Photochemistry in Flow for Drug Discovery. In: Alcazar, J., de la Hoz, A., Díaz-Ortiz, A. (eds) Flow Chemistry in Drug Discovery. Topics in Medicinal Chemistry, vol 38. Springer, Cham. https://doi.org/10.1007/7355_2021_112

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