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Applications of MCR-Derived Heterocycles in Drug Discovery

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Synthesis of Heterocycles via Multicomponent Reactions II

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 25))

Abstract

Heterocyclic structures are an integral part of numerous drugs and natural products and there is a considerable interest in efficient methods for their synthesis. A variety of multicomponent reactions (MCRs) provide access to heterocyclic structures such as isocyanide based MCRs, dicarbonyl derivative and cycloaddition MCRs. MCR-derived heterocycles are typically prepared in few, versatile and atom efficient synthetic steps and exhibit anticancer, antioxidant and antimicrobial properties.

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Abbreviations

ATP:

Adenosine 5′-triphosphate

BACE:

β-Secretase

Boc:

t-Butoxy carbonyl

Cdc:

Cyclin-dependent kinase

cGMP:

Cyclic guanosine monophosphate

DBP:

Diastolic blood pressure

DDQ:

2,3-Dichloro-5,6-dicyano-p-benzoquinone

DEAD:

Diethyl azodicarboxylate

DIC:

N,N′-Diisopropylcarbodiimide

DIEA:

Diisopropylethylamine

DMAP:

4-Di(methylamino)pyridine

DMF:

Dimethylformamide

DOS:

Diversity-oriented synthesis

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

EDCI:

N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide

EDDA:

Ethylenediammonium diacetate

F:

Bioavailability

HOBt:

1-Hydroxybenzotriazole

Hsp:

Heat shock protein

HTS:

High-throughput screening

MCR:

Multicomponent reaction

MDR:

Multidrug resistance

MIC:

Minimum inhibitory concentration

MMP:

Matrix metalloproteinase

MSO:

l-Methionine-SR-sulfoximine

MtGS:

Mycobacterium tuberculosis glutamine synthase

NMP:

1-Methyl-2-pyrrolidinone

PDE:

Phosphodiesterase

Pgp:

P-glycoprotein

PPT:

Phospinothricin

PTSA:

p-Toluenesulfonic acid

RCM:

Ring-closing metathesis

Red-Al:

Sodium bis(2-methoxyethoxy)aluminum hydride

ROC:

Ring-opening metathesis

ROS:

Reactive oxygen species

RSA:

Radical scavenging activity

SBP:

Systolic blood pressure

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

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Authors and Affiliations

  1. Medicinal Chemistry Technologies, Abbott Laboratories, Abbott Park, IL, 60064, USA

    Irini Akritopoulou-Zanze & Stevan W. Djuric

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  1. Irini Akritopoulou-Zanze
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  2. Stevan W. Djuric
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Correspondence to Irini Akritopoulou-Zanze .

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Editors and Affiliations

  1. Fac. Sciences, Dept. Chemistry &, VU University Amsterdam, De Boelelaan 1083, Amsterdam, 1081 HV, Netherlands

    Romano V. A. Orru

  2. Faculty of Sciences, Section of Synthetic &, VU University Amsterdam, Amsterdam, 1081 HV, Netherlands

    Eelco Ruijter

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Akritopoulou-Zanze, I., Djuric, S.W. (2010). Applications of MCR-Derived Heterocycles in Drug Discovery. In: Orru, R., Ruijter, E. (eds) Synthesis of Heterocycles via Multicomponent Reactions II. Topics in Heterocyclic Chemistry, vol 25. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_46

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