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Synthesis of Guanidines and Some of Their Biological Applications

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Guanidines as Reagents and Catalysts I

Part of the book series: Topics in Heterocyclic Chemistry ((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.

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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

References

  1. Menor-Salvan C, Marin-Yaseli MR (2012) Chem Soc Rev 41:5404–5415

    Article  CAS  Google Scholar 

  2. Haas DJ, Harris DR, Mills HH (1965) Acta Crystallogr 19:676–679

    Article  CAS  Google Scholar 

  3. Yamada T, Liu X, Englert U, Yamane H, Dronskowski R (2009) Chem Eur J 15:5651–5655

    Article  CAS  Google Scholar 

  4. Parker EJ, Pratt AJ (2010) In: Hughes AB (ed) Amino acids, peptides, proteins in organic chemistry. Wiley-VCH, Weinheim, pp 1–82

    Google Scholar 

  5. Sokalingam S, Raghunathan G, Soundrarajan N, Lee SG (2012) PLoS One 7:e40410

    Article  CAS  Google Scholar 

  6. Dougherty DA (2013) Acc Chem Res 46:885–893

    Article  CAS  Google Scholar 

  7. Crowley PB, Golovin A (2005) Proteins 59:231–239

    Article  CAS  Google Scholar 

  8. Blanco F, Kelly B, Sanchez-Sanz G, Trujillo C, Alkorta I, Elguero J, Rozas I (2013) J Phys Chem B 11:11608–11616

    Article  CAS  Google Scholar 

  9. Kelly B, Sanchez-Sanz G, Blanco F, Rozas I (2012) Comput Theor Chem 998:64–73

    Article  CAS  Google Scholar 

  10. Gund P (1972) J Chem Ed 49:100–103

    Article  CAS  Google Scholar 

  11. Blanco F, Kelly B, Alkorta I, Rozas I, Elguero J (2011) Chem Phys Lett 511:129–134

    Article  CAS  Google Scholar 

  12. Rozas I, Sanchez-Sanz G, Alkorta I, Elguero J (2013) J Phys Org Chem 26:378–385

    Article  CAS  Google Scholar 

  13. Sączewski F, Balewski Ł (2013) Expert Opin Ther Pat 23:965–995

    Article  CAS  Google Scholar 

  14. Berlinck RG, Trindade-Silva AE, Santos MF (2012) Nat Prod Rep 29:1382–1406

    Article  CAS  Google Scholar 

  15. Kishi Y, Aratani M, Fukuyama T, Nakatsubo F, Goto T, Inoue S, Tanino H, Sugiura S, Kakoi H (1972) J Am Chem Soc 94:9217–9219

    Article  CAS  Google Scholar 

  16. Suhs T, Konig B (2006) Mini Rev Org Chem 3:315–331

    Article  CAS  Google Scholar 

  17. Kim KS, Qian LG (1993) Tetrahedron Lett 34:7677–7680

    Article  CAS  Google Scholar 

  18. Chen H-M, Li G, Cao L-H (2008) J Chin Chem Soc 55:474–478

    Article  CAS  Google Scholar 

  19. Diez-Cecilia E, Kelly B, Perez C, Zisterer DM, Nevin DK, Lloyd DG, Rozas I (2014) Eur J Med Chem 81:427–441

    Article  CAS  Google Scholar 

  20. Kelly B, McMullan M, Muguruza C, Ortega JE, Meana JJ, Callado LF, Rozas I (2015) J Med Chem 58:963–977

    Article  CAS  Google Scholar 

  21. Cunha S, Rodrigues MT, da Silva CC, Napolitano HB, Vencato I, Lariucci C (2005) Tetrahedron 61:10536–10540

    Article  CAS  Google Scholar 

  22. O’Donovan DH, Rozas I (2011) Tetrahedron Lett 52:4117–4119

    Article  CAS  Google Scholar 

  23. Cunha S, Rodrigues MT (2006) Tetrahedron Lett 47:6955–6956

    Article  CAS  Google Scholar 

  24. Kelly B, Rozas I (2013) Tetrahedron Lett 54:3982–3984

    Article  CAS  Google Scholar 

  25. Ramadas K, Srinivasan N (1995) Tetrahedron Lett 36:2841–2844

    Article  CAS  Google Scholar 

  26. Shibanuma T, Shiono M, Mukaiyama T (1977) Chem Lett 575–576

    Google Scholar 

  27. Ohara K, Vasseur JJ, Smietana M (2009) Tetrahedron Lett 50:1463–1465

    Article  CAS  Google Scholar 

  28. Porcheddu A, De Luca L, Giacomelli G (2009) Synlett 3368–3372

    Google Scholar 

  29. Maryanoff CA, Stanzione RC, Plampin JN, Mills JE (1986) J Org Chem 51:1882–1884

    Article  CAS  Google Scholar 

  30. Isidro-Llobet A, Alvarez M, Albericio F (2009) Chem Rev 109:2455–2504

    Article  CAS  Google Scholar 

  31. Manimala JC, Anslyn EV (2002) Tetrahedron Lett 43:565–567

    Article  CAS  Google Scholar 

  32. Madalengoitia J, Flemer S (2007) Synthesis 1848–1860

    Google Scholar 

  33. Alonso-Moreno C, Antinolo A, Carrillo-Hermosilla F, Otero A (2014) Chem Soc Rev 43:3406–3425

    Article  CAS  Google Scholar 

  34. Kantam ML, Priyadarshini S, Joseph PJA, Srinivas P, Vinu A, Klabunde KJ, Nishina Y (2012) Tetrahedron 68:5730–5737

    Article  CAS  Google Scholar 

  35. Pottabathula S, Royo B (2012) Tetrahedron Lett 53:5156–5158

    Article  CAS  Google Scholar 

  36. Toy PH, Lam Y (eds) (2012) Solid-phase organic synthesis: concepts, strategies, applications. Wiley, Hoboken

    Google Scholar 

  37. Drewry DH, Gerritz SW, Linn JA (1997) Tetrahedron Lett 38:3377–3380

    Article  CAS  Google Scholar 

  38. Josey JA, Tarlton CA, Payne CE (1998) Tetrahedron Lett 39:5899–5902

    Article  CAS  Google Scholar 

  39. Ube H, Uraguchi D, Terada M (2007) J Organomet Chem 692:545–549

    Article  CAS  Google Scholar 

  40. Powell DA, Ramsden PD, Batey RA (2003) J Org Chem 68:2300–2309

    Article  CAS  Google Scholar 

  41. Ma D, Xia C, Jiang J, Zhang J, Tang W (2003) J Org Chem 68:442–451

    Article  CAS  Google Scholar 

  42. Kim M, Mulcahy JV, Espino CG, Bois JD (2006) Org Lett 8:1073–1076

    Article  CAS  Google Scholar 

  43. Roizen JL, Zalatan DN, Bois JD (2013) Angew Chem Int Ed Engl 52:11343–11346

    Article  CAS  Google Scholar 

  44. Wang S, Romo D (2008) Angew Chem Int Ed Engl 47:1284–1286

    Article  CAS  Google Scholar 

  45. Feichtinger K, Zapf C, Sings HL, Goodman M (1998) J Org Chem 63:3804–3805

    Article  CAS  Google Scholar 

  46. Baker TJ, Rew Y, Goodman M (2000) Pure Appl Chem 72:347–354

    Article  CAS  Google Scholar 

  47. Wu YQ, Hamilton SK, Wilkinson DE, Hamilton GS (2002) J Org Chem 67:7553–7556

    Article  CAS  Google Scholar 

  48. Bernatowicz MS, Wu YL, Matsueda GR (1992) J Org Chem 57:2497–2502

    Article  CAS  Google Scholar 

  49. Yong YF, Kowalski JA, Thoen JC, Lipton MA (1999) Tetrahedron Lett 40:53–56

    Article  CAS  Google Scholar 

  50. Musiol HJ, Moroder L (2001) Org Lett 3:3859–3861

    Article  CAS  Google Scholar 

  51. Gagnon PE, Boivin JL, Dickson JH (1959) Can J Chem 37:520–524

    Article  CAS  Google Scholar 

  52. Rachlin S, Bramm E, Ahnfelt-Ronne I, Arrigoni-Martelli E (1980) J Med Chem 23:13–20

    Article  CAS  Google Scholar 

  53. Wang Z (2010) Comprehensive organic name reactions, reagents. Wiley, Hoboken

    Book  Google Scholar 

  54. Elliott AJ, Morris PE Jr, Petty SL, Williams CH (1997) J Org Chem 62:8071–8075

    Article  CAS  Google Scholar 

  55. Atwal KS, Ferrara FN, Ahmed SZ (1994) Tetrahedron Lett 35:8085–8088

    Article  CAS  Google Scholar 

  56. Mitsunobu O, Yamada Y (1967) Bull Chem Soc (Japan) 40:2380–2382

    Article  CAS  Google Scholar 

  57. Dembinski R (2004) Eur J Org Chem 2004:2763–2772

    Article  CAS  Google Scholar 

  58. Feichtinger K, Sings HL, Baker TJ, Matthews K, Goodman M (1998) J Org Chem 63:8432–8439

    Article  CAS  Google Scholar 

  59. Fishlock D, Guillemette JG, Lajoie GA (2002) J Org Chem 67:2352–2354

    Article  CAS  Google Scholar 

  60. Olivier KS, Van Nieuwenhze MS (2010) Org Lett 12:1680–1683

    Article  CAS  Google Scholar 

  61. Jacobson GB, Westerberg G, Markides KE, Långström B (1996) J Am Chem Soc 118:6868–6872

    Article  CAS  Google Scholar 

  62. Ha HH, Kim JS, Kim BM (2008) Bioorg Med Chem Lett 18:653–656

    Article  CAS  Google Scholar 

  63. Looper RE, Haussener TJ, Mack JB (2011) J Org Chem 76:6967–6971

    Article  CAS  Google Scholar 

  64. Beletskaya IP, Cheprakov AV (2004) Coord Chem Rev 248:2337–2364

    Article  CAS  Google Scholar 

  65. Sambiagio C, Marsden SP, Blacker AJ, McGowan PC (2014) Chem Soc Rev 43:3525–3550

    Article  CAS  Google Scholar 

  66. Zhang H, Cai Q, Ma D (2005) J Org Chem 70:5164–5173

    Article  CAS  Google Scholar 

  67. Cohen T, Wood J, Dietz AG (1974) Tetrahedron Lett 15:3555–3558

    Article  Google Scholar 

  68. Paine AJ (1987) J Am Chem Soc 109:1496–1502

    Article  CAS  Google Scholar 

  69. Deng X, McAllister H, Mani NS (2009) J Org Chem 74:5742–5745

    Article  CAS  Google Scholar 

  70. Cortes-Salva M, Nguyen BL, Cuevas J, Pennypacker KR, Antilla JC (2010) Org Lett 12:1316–1319

    Article  CAS  Google Scholar 

  71. Hammoud H, Schmitt M, Bihel F, Antheaume C, Bourguignon JJ (2012) J Org Chem 77:417–423

    Article  CAS  Google Scholar 

  72. Beletskaya IP, Cheprakov AV (2012) Organometallics 31:7753–7808

    Article  CAS  Google Scholar 

  73. Xing H, Zhang Y, Lai Y, Jiang Y, Ma D (2012) J Org Chem 77:5449–5453

    Article  CAS  Google Scholar 

  74. Li J, Neuville L (2013) Org Lett 15:6124–6127

    Article  CAS  Google Scholar 

  75. Miyabe H, Yoshida K, Reddy VK, Takemoto Y (2009) J Org Chem 74:305–311

    Article  CAS  Google Scholar 

  76. Dardonville C, Goya P, Rozas I, Alsasua A, Martin I, Borrego J (2000) Bioorg Med Chem 8:1567–1577

    Article  CAS  Google Scholar 

  77. Rodriguez F, Rozas I, Ortega JE, Meana JJ, Callado LF (2007) J Med Chem 50:4516–4527

    Article  CAS  Google Scholar 

  78. Kan WM, Lin SH, Chern CY (2005) Synth Commun 35:2633–2639

    Article  CAS  Google Scholar 

  79. Hensler ME, Bernstein G, Nizet V, Nefzi A (2006) Bioorg Med Chem Lett 16:5073–5079

    Article  CAS  Google Scholar 

  80. McKay AF, Kreling ME (1957) Can J Chem 35:1438–1445

    Article  CAS  Google Scholar 

  81. European Patent, EP01986801990

    Google Scholar 

  82. Ye WP, Leow DS, Goh SLM, Tan CT, Chian CH, Tan CH (2006) Tetrahedron Lett 47:1007–1010

    Article  CAS  Google Scholar 

  83. Corey EJ, Grogan MJ (1999) Org Lett 1:157–160

    Article  CAS  Google Scholar 

  84. Yamamoto Y, Mizuno H, Tsuritani T, Mase T (2009) Tetrahedron Lett 50:5813–5815

    Article  CAS  Google Scholar 

  85. Li J (2009) Name reactions. Springer, Berlin, pp 332–333

    Book  Google Scholar 

  86. González-Rosende ME, Castillo E, Asíns B, Mamouni R, Sepúlveda-Arques J (2007) Tetrahedron 63:8709–8714

    Article  CAS  Google Scholar 

  87. Schroif-Gregoire C, Travert N, Zaparucha A, Al-Mourabit A (2006) Org Lett 8:2961–2964

    Article  CAS  Google Scholar 

  88. Zhou L, Chen J, Zhou J, Yeung YY (2011) Org Lett 13:5804–5807

    Article  CAS  Google Scholar 

  89. Bera S, Wallimann T, Ray S, Ray M (2008) FEBS J 275:5899–5909

    Article  CAS  Google Scholar 

  90. Guiheneuf S, Paquin L, Carreaux F, Durieu E, Meijer L, Bazureau JP (2012) Org Biomol Chem 10:978–987

    Article  CAS  Google Scholar 

  91. Li CM, Danishefsky SJ (2006) Tetrahedron Lett 47:385–387

    Article  CAS  Google Scholar 

  92. Olson DE, Roberts DA, Du Bois J (2012) Org Lett 14:6174–6177

    Article  CAS  Google Scholar 

  93. Hinman A, Du Bois J (2003) J Am Chem Soc 125:11510–11511

    Article  CAS  Google Scholar 

  94. Mulcahy JV, Du Bois J (2008) J Am Chem Soc 130:12630–12631

    Article  CAS  Google Scholar 

  95. Zhao B, Du H, Shi Y (2008) Org Lett 10:1087–1090

    Article  CAS  Google Scholar 

  96. Butler DCD, Inman GA, Alper H (2000) J Org Chem 65:5887–5890

    Article  CAS  Google Scholar 

  97. Godleski SA (1991) In: Trost BM, Fleming I, Semmelhack MF (eds) Comprehensive organic synthesis, vol 4. Pergamon, Oxford, pp 585–662, Chapter 3.3

    Chapter  Google Scholar 

  98. Craig RA 2nd, O’Connor NR, Goldberg AF, Stoltz BM (2014) Chem Eur J 20:4806–4813

    Article  CAS  Google Scholar 

  99. Hovelmann CH, Streuff J, Brelot L, Muniz K (2008) Chem Commun 2334–2336

    Google Scholar 

  100. Gainer MJ, Bennett NR, Takahashi Y, Looper RE (2011) Angew Chem Int Ed Engl 50:684–687

    Article  CAS  Google Scholar 

  101. Ritter S, Horino Y, Lex J, Schmalz HG (2006) Synlett 3309–3313

    Google Scholar 

  102. Bhonde VR, Looper RE (2011) J Am Chem Soc 133:20172–20174

    Article  CAS  Google Scholar 

  103. Pereshivko OP, Peshkov VA, Ermolatev DS, van Hove S, Van Hecke K, Van Meervelt L, van der Eycken EV (2011) Synthesis 1587–1594

    Google Scholar 

  104. Ishikawa M, Tsushima M, Kubota D, Yanagisawa Y, Hiraiwa Y, Kojima Y, Ajito K, Anzai N (2008) Org Proc Res Dev 12:596–602

    Article  CAS  Google Scholar 

  105. Baskaran S, Hanan E, Byun D, Shen W (2004) Tetrahedron Lett 45:2107–2111

    Article  CAS  Google Scholar 

  106. Looper RE, Runnegar MTC, Williams RM (2006) Tetrahedron 62:4549–4562

    Article  CAS  Google Scholar 

  107. Larraufie MH, Ollivier C, Fensterbank L, Malacria M, Lacote E (2010) Angew Chem Int Ed Engl 49:2178–2181

    Article  CAS  Google Scholar 

  108. Nilsson BL, Overman LE (2006) J Org Chem 71:7706–7714

    Article  CAS  Google Scholar 

  109. Nagasawa K, Georgieva A, Takahashi H, Nakata T (2001) Tetrahedron 57:8959–8964

    Article  CAS  Google Scholar 

  110. Perl NR, Ide ND, Prajapati S, Perfect HH, Duron SG, Gin DY (2010) J Am Chem Soc 132:1802–1803

    Article  CAS  Google Scholar 

  111. Nishikawa T, Asai M, Isobe M (2002) J Am Chem Soc 124:7847–7852

    Article  CAS  Google Scholar 

  112. Aranha Potter R, Bowser AM, Yang Y, Madalengoitia JS, Ziller JW (2013) J Org Chem 78:11772–11782

    Article  CAS  Google Scholar 

  113. Ding H, Roberts AG, Harran PG (2012) Angew Chem Int Ed Engl 51:4340–4343

    Article  CAS  Google Scholar 

  114. Buchi G, Rodriguez AD, Yakushijin K (1989) J Org Chem 54:4494–4496

    Article  CAS  Google Scholar 

  115. Yu M, Pochapsky SS, Snider BB (2008) J Org Chem 73:9065–9074

    Article  CAS  Google Scholar 

  116. Sawayama Y, Nishikawa T (2011) Angew Chem Int Ed Engl 50:7176–7178

    Article  CAS  Google Scholar 

  117. Shaw JW, Grayson DH, Rozas I (2014) Eur J Org Chem 161–174

    Google Scholar 

  118. Shaw JW, Grayson DH, Rozas I (2014) Arkivoc 3565–3569

    Google Scholar 

  119. Zaed AM, Sutherland A (2010) Org Biomol Chem 8:4394–4399

    Article  CAS  Google Scholar 

  120. Zhou HB, Alper H (2004) Tetrahedron 60:73–79

    Article  CAS  Google Scholar 

  121. Sączewski F, Balewski Ł (2009) Expert Opin Ther Pat 19:1417–1448

    Article  CAS  Google Scholar 

  122. Dardonville C, Barrett MP, Brun R, Kaiser M, Tanious F, Wilson WD (2006) J Med Chem 49:3748–3752

    Article  CAS  Google Scholar 

  123. Nagle PS, Rodriguez F, Kahvedzic A, Quinn SJ, Rozas I (2009) J Med Chem 52:7113–7121

    Article  CAS  Google Scholar 

  124. McKeever C, Kaiser M, Rozas I (2013) J Med Chem 56:700–711

    Article  CAS  Google Scholar 

  125. O’Sullivan P, Rozas I (2014) ChemMedChem 9:2063–2073

    Google Scholar 

  126. Goonan Á, Kahvedzic A, Rodriguez F, Nagle PS, McCabe T, Rozas I, Erdozain AM, Meana JJ, Callado LF (2008) Bioorg Med Chem 16:8210–8217

    Article  CAS  Google Scholar 

  127. Kahvedzic A, Nathwani S-M, Zisterer D, Rozas I (2013) J Med Chem 56:451–459

    Article  CAS  Google Scholar 

  128. Nagle PS, Rodriguez F, Quinn SJ, O’Donovan DH, Kelly JM, Nguyen B, Wilson WD, Rozas I (2010) Org Biomol Chem 8:5558–5567

    Article  CAS  Google Scholar 

  129. Nagle PS, Rodriguez F, Nguyen B, Wilson WD, Rozas I (2012) J Med Chem 55:4397–4406

    Article  CAS  Google Scholar 

  130. Kahvedzic A, Nathwani S-M, Zisterer D, Rozas I (2015)

    Google Scholar 

  131. Diez-Cecilia E, Carson R, Kelly B, van Schaybroeck S, Murray JT, Rozas I (2015)

    Google Scholar 

  132. Rodriguez F, Rozas I, Ortega JE, Erdozain AM, Meana JJ, Callado LF (2008) J Med Chem 51:3304–3312

    Article  CAS  Google Scholar 

  133. Rodriguez F, Rozas I, Erdozain AM, Meana JJ, Callado LF (2009) J Med Chem 52:601–609

    Article  CAS  Google Scholar 

  134. Nakamura S (2012) Antidepressants and morphological plasticity of monoamine neurons. In: Lu R-B (ed) Effects of antidepressants. InTech, Rijeka. ISBN 978-953-51-0663-0

    Google Scholar 

  135. Muguruza C, Rodriguez F, Rozas I, Meana JJ, Uriguen L, Callado LF (2013) Neuropharmacology 65:13–19

    Article  CAS  Google Scholar 

  136. O’Donovan DH, Muguruza C, Callado LF, Rozas I (2014) Eur J Med Chem 82:242–254

    Article  CAS  Google Scholar 

  137. McMullan M, Kelly B, Erdozain AM, Callado LF, Rozas I (2015)

    Google Scholar 

  138. Nagle PS, McKeever C, Rodriguez F, Nguyen B, Wilson WD, Rozas I (2014) J Med Chem 57:4397–4406

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. School of Chemistry, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland

    Julian W. Shaw, David H. Grayson & Isabel Rozas

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  1. Julian W. Shaw
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  2. David H. Grayson
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Correspondence to Isabel Rozas .

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  1. Patheon Inc. , Linz, Austria

    Philipp Selig

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Shaw, J.W., Grayson, D.H., Rozas, I. (2015). Synthesis of Guanidines and Some of Their Biological Applications. In: Selig, P. (eds) Guanidines as Reagents and Catalysts I. Topics in Heterocyclic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/7081_2015_174

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