Synthesis of Guanidines and Some of Their Biological Applications

Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 50)

Abstract

Guanidine is one of the most versatile functional groups in chemistry; compounds containing this system have found application in a diversity of biological activities, and in this chapter, the advances in the field of the synthesis of guanidines are presented. First, the preparation of acyclic guanidines involving the reaction of an amine with an activated guanidine precursor followed by the deprotection to yield the corresponding free guanidine is discussed. Thiourea derivatives as guanidylating agents have been widely used as guanidine precursors using coupling reagents or metal-catalysed guanidylation. Alternatively, S-methylisothiourea has shown to be a very efficient guanidylating agent, and N,N′,N″-trisubstituted guanidines have also been used to install the guanidine functionality. Despite the similarity between urea and thiourea, the former has received much less attention; however, its application in guanidine synthesis has also been proved. Examples of the preparation of guanidines using cyanamides that react with derivatised amines as well as the use of copper-catalysed cross-coupling chemistry are also presented. Moreover, cyclic guanidines such as 2-aminoimidazolines (five-membered rings), 2-amino-1,4,5,6-tetrahydropyrimidines (six-membered rings) and 2-amino-4,5,6,7-tetrahydro-1H-1,3-diazepines (seven-membered rings) are present in many natural products and compounds of medicinal interest. Accordingly, an overview of the methods found in the literature for the preparation of these cyclic guanidines is presented. Finally, some biological applications of guanidines as DNA minor groove binders, kinase inhibitors and α2-noradrenaline receptors antagonists are discussed.

Keywords

Guanidine Synthesis 

Abbreviations

α2-AR

α2-Adrenoceptor

Boc

tert-Butyloxycarbonyl

Cbz

Carboxybenzyl

CSA

Camphor sulfonic acid

Dba

Dibenzylideneacetone

DCC

Dicyclohexylcarbodiimide

DDQ

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DEAD

Diethylazodicarboxylate

DIPEA

Diisopropylethylamine

DMAP

4-Dimethylaminopyridine

DME

Dimethoxyethane

DMF

Dimethylformamide

DMP

Dess–Martin periodinane

DMSO

Dimethyl sulfoxide

DNA

Deoxyribonucleic acid

DtBPF

1,1′-Bis(di-tert-butylphosphino)ferrocene

EDCI

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

Fmoc

Fluorenylmethoxycarbonyl

Gua

Guanidine

HB

Hydrogen bond

LDA

Lithium diisopropylamine

LiHMDS

Lithium hexamethyldisilazide

MBH

Morita–Baylis–Hillman

MGB

Minor groove binder

mIBG

meta-Iodobenzylguanidine

Mtr

2,3,6-Trimethyl-4-methoxybenzenesulfonyl

NBS

N-Bromosuccinimide

NIS

N-Iodosuccinimide

NMM

N-Methylmorpholine

PET

Positron emission tomography

Ph

Phenyl

PhNO

Nitrosobenzene

Piv

Pivaloyl

PMB

p-Methoxybenzyl

Pmc

2,2,5,7,8-Pentamethylchroman-6-sulfonyl

Py

Pyridine

PyHBr3

Pyridinium tribromide

RNA

Ribonucleic acid

RSM

Recovered starting material

TBAB

tetra-Butylammonium bromide

TBD

1,5,7-Triazabicyclo[4.4.0]dec-5-ene

Tces

2,2,2-Trichloroethoxysulfonyl

TCT

2,4,6-Trichloro-1,3,5-triazine

TFA

Trifluoroacetic acid

TFAA

Trifluoroacetic anhydride

THF

Tetrahydrofuran

TIPS

Triisopropylsilyl

TMEDA

Tetramethylenediamine

TMG

1,1,3,3-Tetramethylguanidine

TON

Turnover number

Tosyl

4-Toluenesulfonyl

Trifyl

Trifluoromethylsulfonyl

Troc

2,2,2-Trichloroethoxycarbonyl

TsCl

4-Toluenesulfonyl chloride

Xantphos

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  • Julian W. Shaw
    • 1
  • David H. Grayson
    • 1
  • Isabel Rozas
    • 1
  1. 1.School of Chemistry, Trinity Biomedical Sciences InstituteTrinity College DublinDublin 2Ireland

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