Synlett 2021; 32(09): 858-874
DOI: 10.1055/s-0040-1707324
account

Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications

Claire Fleurisson
,
Erica Benedetti
,
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques – UMR8601 CNRS Université de Paris, 45 rue des Saints Pères, 75006 Paris, France   eMail: [email protected]   eMail: [email protected]
› Institutsangaben


Part of the work conducted in our lab and reported in this account has been financed by MESR (ACI 2003), ANR (TrigerRNA), Université Paris Descartes and Satt IDFInnov.


Abstract

Cyclic cis-1,3-diamines are versatile building blocks frequently found in natural molecules or biologically active compounds. In comparison with widely studied 1,2-diamines, and despite their chemical similarity, 1,3-diamines have been investigated less intensively probably because of a lack of general synthetic procedures giving access to these compounds with good levels of chemo-, regio-, and stereocontrol. In this Account we will give a general overview of the biological interest of cyclic cis-1,3-diamines. We will then describe the synthesis and potential applications of these compounds with a particular focus on the work realized in our laboratory.

1 Introduction

2 Biological Relevance of the cis-1,3-Diamine Motif

3 Classical Synthetic Strategies towards cis-1,3-Diamines

4 N–N Bond Cleavage of Bicyclic Hydrazines: A Versatile Method to Access cis-1,3-Diamines

4.1 Preparation of Five-Membered Cyclic cis-1,3-Diamino Alcohols

4.2 Access to Fluorinated 1,3-cis-Diaminocyclopentanes

4.3 Synthesis of cis-1,3-Diaminocyclohexitols

4.4 Formation of Cyclic cis-3,5-Diaminopiperidines

5 Applications of Cyclic cis-1,3-Diamines

5.1 Small-Molecular RNA Binders

5.2 Fluorinated 1,3-Diamino Cyclopentanes as NMR Probes

6 Concluding Remarks



Publikationsverlauf

Eingereicht: 28. August 2020

Angenommen nach Revision: 11. September 2020

Publikationsdatum:
19. Oktober 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Lucet D, Le Gall T, Mioskowski C. Angew. Chem. Int. Ed. 1998; 37: 2580
    • 1b Zhu Y, Cornwall RG, Du H, Zhao B, Shi Y. Acc. Chem. Res. 2014; 47: 3665
    • 1c Erik T, Michalson ET, Szmuszkoviczin J. In Progress in Drug Research . Jucker E. Birkhäuser; Basel: 1989: 135
    • 1d González-Sabín J, Rebolledo F, Goto V. Chem. Soc. Rev. 2009; 38: 1916
  • 2 For a selected review on the synthesis of 1,3-diamines, see: Ji X, Huang H. Org. Biomol. Chem. 2016; 14: 10557
    • 3a Guillon J, Hebert G, Dallemagne P, Leger J.-M, Vidaillac C, The C, Lisowski V, Rault S, Demotes-Mainard J, Jarry C. J. Enzyme Inhib. Med. Chem. 2003; 18: 147
    • 3b Hurley C, Kulagowski J, Zak M. WO2013007768A1, 2013
    • 3c Jia ZJ, Kane B, Xu Q, Bauer SM, Song Y, Pandey A, Dick R. WO2013078468A1, 2013
    • 3d Dorsch D, Hoelzemann G, Calderini M, Wegener A, Poeschke O. WO2014135244A1, 2014
    • 3e Tsaklakidis C, Staehle W, Leuthner B, Czodrowski P, Fuchss T. WO2014202168A1, 2014
  • 4 Mittendorf J, Kunisch F, Matzke M, Militzer H.-C, Schmidt A, Schonfeld W. Bioorg. Med. Chem. Lett. 2003; 13: 433
  • 5 Jarvis MF, Yu H, McGaraughty S, Wismer CT, Mikusa J, Zhu C, Chu K, Kohlhaas K, Cowart M, Lee C.-H, Stewart AO, Cox BF, Polakowski J, Kowaluk EA. Pain 2002; 96: 107
  • 6 Qian Y, Conde-Knape K, Erickson SD, Falcioni F, Gillespie P, Hakimi I, Mennona F, Ren Y, Salari H, So S.-S, Tilley JW. Bioorg. Med. Chem. Lett. 2013; 23: 4216
  • 7 Simov V, Deshmukh SV, Dinsmore CJ, Elwood F, Fernandez RB, Garcia Y, Gibeau C, Gunaydin H, Jung J, Katz JD, Kraybill B, Lapointe B, Patel SB, Siu T, Su HR, Young JR. Bioorg. Med. Chem. Lett. 2016; 26: 1803
  • 8 Ji H, Stanton BZ, Igarashi J, Li H, Martasek P, Roman LJ, Poulos TL, Silverman RB. J. Am. Chem. Soc. 2008; 130: 3900
    • 9a Ogawa A, Shuto S, Tanaka M, Sasaki T, Mori S, Shigeta S, Matsuda A. Chem. Pharm. Bull. 1999; 47: 1000
    • 9b Barnard DL, Stowell VD, Seley KL, Hegde VR, Das SR, Rajappan VP, Schneller SW, Smee DF, Sidwell RW. Antiviral Chem. Chemother. 2001; 12: 241
    • 10a Janssens FE, Lacrampe JF. A, Guillemont JE. G, Venet MG, Andries KJ. L. M. WO2001000615A1, 2001
    • 10b Beaton G, Moree WJ, Rueter JK, Dahl RS, McElligott DL, Goldman P, Demaggio AJ, Christenson E, Herendeen D, Fowler KW, Goldman P, Herendeen D, Huang D, Jiang Q, McElligott DL, Moree WJ, Reisch HA, Rueter JK, Song RH, Zhichkin PE. WO2003015785A1, 2003
    • 10c Ogawa A, Ujjainwalla F, Chu L, Li B, Wei L, Xu J, Ok HO, Lackner A, Kopka IE. WO2011005608A1, 2011
    • 10d Babu S, Bergeron P, Dragovich P, Dyke HJ, Gibbons P, Gradl S, Hanan E, Hurley C, Johnson T, Koehler M, Kulagowski JJ, Labadie SS, Lyssikatos JP, Mendonca R, Pulk R, Ward S, Waszkowycz B, Zak M. WO2011086053A1, 2011
    • 10e Wohlfahrt G, Rummakko P, Karjalainen A, Passiniemi M, Pietikainen P, Haikarainen A, Vaisanen E, Tiainen E. WO2014202827A1, 2014
    • 10f Burnett DA, Vacca J. WO2018119395A1, 2018
    • 11a Peng F, Chen Y, Chen C.-Y, Dormer PG, Kassim A, McLaughlin M, Reamer RA, Sherer EC, Song ZJ, Tan L, Tudge MT, Wan B, Chung JY. L. J. Org. Chem. 2017; 82: 9023
    • 11b Chung JY. L, Scott JP, Anderson C, Bishop B, Bremeyer N, Cao Y, Chen Q, Dunn R, Kassim A, Lieberman D, Moment AJ, Sheen F, Zacuto M. Org. Process Res. Dev. 2015; 19: 1760
    • 11c Chen P, Feng D, Qian X, Apgar J, Wilkening R, Kuethe JT, Gao Y.-D, Scapin G, Cox J, Doss G, Eiermann G, He H, Li X, Lyons KA, Metzger J, Petrov A, Wuc JK, Xu S, Weber AE, Yan Y, Sinha Roy R, Biftu T. Bioorg. Med. Chem. Lett. 2015; 25: 5767
    • 12a Van Eis M, Schuler W, Von Matt A, Soldermann N, Monovich LG, Gaul C. WO2008122614A1, 2008
    • 12b Burger M, Lan J. WO2010026122A1, 2010
    • 12c Pohlmann J, Stieger M, Reinelt S, Lane H. WO2016128465A1, 2016
  • 13 Padilla F, Bhagirath N, Chen S, Chiao E, Goldstein DM, Hermann JC, Hsu J, Kennedy-Smith JJ, Kuglstatter A, Liao C, Liu W, Lowrie LE, Luk KC, Lynch SM, Menke J, Niu L, Owens TD, O-Yang C, Railkar A, Schoenfeld RC, Slade M, Steiner S, Tan Y.-C, Villasñeor AG, Wang C, Wanner J, Xie W, Xu D, Zhang X, Zhou M, Lucas MC. J. Med. Chem. 2013; 56: 1677
  • 14 Takeuchi J, Ohkubo A, Yuasa H. Chem. Asian J. 2015; 10: 586
  • 15 Yoshizawa S, Fourmy D, Eason RG, Puglishi JD. Biochemistry 2002; 41: 6263
    • 16a Davis BD, Chen L, Tai PC. Proc. Natl. Acad. Sci. U.S.A. 1986; 83: 6164
    • 16b Moazed D, Noller HF. Nature 1987; 327: 389
    • 16c Brodersen DE, Clemons WM, Carter AP, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V. Cell 2000; 103: 1143
    • 16d Hermann T. Biopolymers 2003; 70: 4
    • 16e Carnevali M, Parsons J, Wyles DL, Hermann T. ChemBioChem 2010; 11: 1364
    • 17a Zhou Y, Chow C, Murphy DE, Sun Z, Bertolini T, Froelich JM, Webber SE, Hermann T, Wall D. Bioorg. Med. Chem. Lett. 2008; 18: 3369
    • 17b Cottin T, Pyrkotis C, Stathakis CI, Mavridis I, Katsoulis IA, Anastasopoulou P, Kythreoti G, Zografos AL, Nahmias VR, Papakyriakou A, Vourloumis D. ChemBioChem 2011; 12: 71

      For the preparation of five-membered rings, see:
    • 18a Clark MA, Goering BK, Li J, Ganem B. J. Org. Chem. 2000; 65: 4058
    • 18b Kiss L, Forro E, Sillanpaeae R, Fueloep F. J. Org. Chem. 2007; 72: 8786
    • 18c Kiss L, Forro E, Sillanpaeae R, Fueloep F. Synthesis 2010; 153

    • For the synthesis of six-membered rings, see:
    • 18d Schuerrle K, Beier B, Piepersberg W. J. Chem. Soc., Perkin Trans. 1 1991; 2407
    • 18e Tan Q, Hayashi M. Org. Lett. 2009; 3314
    • 18f Busscher GF, Groothuys S, De Gelder R, Rutjes FP. J. T, Van Delft FL. J. Org. Chem. 2004; 69: 4477
    • 19a Monn JA, Valli MJ, Massey SM, Hao J, Reinhard MR, Bures MG, Heinz BA, Wang X, Carter JH, Getman BG, Stephenson GA, Herin M, Catlow JT, Swanson S, Johnson BG, McKinzie DL, Henry SS. J. Med. Chem. 2013; 56: 4442
    • 19b Baer HH, Arai I, Radatus B, Rodwell J, Nguyen C. J. Can. Chem. 1987; 65: 1443
    • 19c Bauder C. Org. Biomol. Chem. 2008; 6: 2952
    • 20a Verhelst SH. L, Martinez BP, Timmer MS. M, Lodder G, Van der Marel GA, Overkleeft HS, Van Boom JH. J. Org. Chem. 2003; 68: 9598
    • 20b Verhelst SH. L, Magnee L, Wennekes T, Wiedenhof W, Van Der Marel GA, Overkleeft HS, Van Boeckel CA. A, Van Boom JH. Eur. J. Org. Chem. 2004; 2404
    • 20c Verhelst SH. L, Wiedenhof W, Ovaa H, van der Marel GA, Overkleeft HS, van Boeckel CA. A, van Boom JH. Tetrahedron Lett. 2002; 43: 6451
    • 20d Verhelst SH. L, Wennekes T, van der Marel GA, Overkleeft HS, van Boeckel CA. A, van Boom JH. Tetrahedron 2004; 60: 2813
    • 21a Couladouros EA, Constantinou K, Georgiadis MP, Kokotos G. Carbohydr. Res. 1994; 254: 317
    • 21b Trost BM, Malhotra S. Chem. Eur. J. 2014; 20: 8288
    • 21c De Almeida MV, Da Silva ET, Le Hyaric M, Machado AS, De Souza MV. N, Santiago RM. J. Carbohydr. Synth. 2003; 22: 733
    • 21d Nakajima M, Kurihara N, Hasegawa A, Kurokawa T. Justus Liebigs Ann. Chem. 2006; 689: 243
    • 21e Da Silva ET, Le Hyaric M, Machado AS, De Almeida MV. Tetrahedron Lett. 1998; 39: 6659
  • 22 Zhou H, Topiol SW, Grenon M, Jimenez HN, Uberti MA, Smith DG, Brodbeck RM, Chandrasena G, Pedersen H, Madsen JC, Doller D, Li G. Bioorg. Med. Chem. Lett. 2013; 23: 1398
    • 23a Kitagawa I, Kadota A, Yoshikawa M. Chem. Pharm. Bull. 1978; 26: 3825
    • 23b Yoshikawa M, Kamigauchi T, Ikeda Y, Kitagawa I. Chem. Pharm. Bull. 1981; 29: 2582
    • 23c Yoshikawa M, Ikeda Y, Takenaka K, Torihara M, Kitagawa I. Chem. Lett. 1984; 12: 2097
    • 23d Yoshikawa M, Ikeda Y, Kayakiri H, Kitagawa I. Heterocycles 1982; 17: 209
    • 23e Wolfrom ML, Olin SM, Polglase WJ. J. Am. Chem. Soc. 1950; 72: 1724
    • 23f Suami T, Ogawa S, Tanno N, Suguro M, Rinehart KL. Jr. J. Am. Chem. Soc. 1973; 95: 8734
    • 23g Ogawa S, Rinehart KL. Jr, Kimura G, Johnson RP. J. Org. Chem. 1974; 39: 812
    • 23h Hasegawa A, Sable HZ. Tetrahedron 1969; 25: 3567
    • 23i Yoshikawa M, Ikeda Y, Kayakiri H, Takenaka K, Kitagawa I. Tetrahedron Lett. 1982; 23: 4717
    • 24a Garsi J.-B, Vece V, Sernissi L, Auger-Morin C, Hanessian S, McCracken AN, Selwan E, Ramirez C, Dahal A, Ben Romdhane N, Finicle BT, Edinger AL. Bioorg. Med. Chem. Lett. 2019; 29: 2681
    • 24b Busscher GF, Rutjes FP. J. T, Van Delft FL. Tetrahedron Lett. 2004; 45: 3629
    • 24c Ohlmeyer M, Kastrinsky D. WO2017044572A1, 2017
    • 25a Tomkins P, Muller TE. ChemCatChem 2018; 10: 1438
    • 25b Merten GJ, Neis C, Stucky S, Huch V, Rentschler E, Natter H, Hempelmann R, Stoewe K, Hegetschweiler K. Eur. J. Inorg. Chem. 2012; 31
    • 25c Hegetschweiler K, Erni I, Schneider W, Schmalle H. Helv. Chim. Acta 1990; 73: 97
    • 25d Parker D, Senanayake K, Vepsailainen J, Williams S, Batsanov AS, Howard JA. K. J. Chem. Soc., Perkin Trans. 2 1997; 8: 1445
    • 25e Dijkstra D. Recl. Trav. Chim. Pays-Bas 1968; 87: 161
    • 25f Baer HH, Yu RJ. Tetrahedron Lett. 1967; 9: 807
    • 26a Schwesinger R, Prinzbach H. Angew. Chem., Int. Ed. Engl. 1975; 14: 630
    • 26b Prinzbach H, Kefier R, Schwesinger R. Angew. Chem., Int. Ed. Engl. 1975; 14: 632
    • 26c Jiao G.-S, Cregar L, Goldman ME, Millis SZ, Tang C. Bioorg. Med. Chem. Lett. 2006; 16: 1527
    • 26d Kavadias G, Velkof S, Belleau B. Can. J. Chem. 1978; 56: 404
    • 26e Suami T, Ogawa S, Uchino H, Funaki Y. J. Org. Chem. 1975; 40: 456
    • 26f Ogawa S, Ueda T, Funaki Y, Hongo Y, Kasuga A, Suami T. J. Org. Chem. 1977; 42: 3083
    • 26g Rattray NJ. W, Zalloum WA, Mansell D, Latimer J, Jaffar M, Bichenkova EV, Freeman S. Tetrahedron 2013; 69: 2758
  • 27 Chenevert R, Jacques F. Tetrahedron: Asymmetry 2006; 17: 1017
    • 28a Haviv F, Belleau B. Can. J. Chem. 1978; 56: 2677
    • 28b Vourloumis D, Winters GC, Simonsen KB, Takahashi M, Ayida BK, Shandrick S, Zhao Q, Han Q, Hermann T. ChemBioChem 2005; 6: 58
    • 29a Hasegawa A, Sable HZ. Tetrahedron 1969; 25: 3567
    • 29b Qiao J.-BaoZ, Yu-Ming Z, Gu P. Org. Lett. 2016; 18: 1984
    • 30a Suami T, Ogawa S, Naito S, Sano H. J. Org. Chem. 1968; 33: 2831
    • 30b Ogawa S, Ueda T, Funaki Y, Hongo Y, Kasuga A, Suami T. J. Org. Chem. 1977; 42: 3083
    • 30c Pang L.-J, Wang D, Zhou J, Zhang L.-H, Ye X.-S. Org. Biomol. Chem. 2009; 7: 4252
    • 30d Fielden J, Sprott J, Cronin L. New J. Chem. 2005; 29: 1152
    • 30e Suami T, Ogawa S. Bull. Chem. Soc. Jpn 1965; 38: 2026
  • 31 Duan JJ.-W, Lu Z, Jiang B, Yang BV, Doweyko LM, Nirschl DS, Haque LE, Lin S, Brown G, Hynes JJr, Tokarski JS, Sack JS, Khan J, Lippy JS, Zhang RF, Pitt S, Shen G, Pitts WJ, Carter PH, Barrish JC, Nadler SG, Salter-Cid LM, McKinnon M, Fura A, Schieven GL, Wrobleski ST. Bioorg. Med. Chem. Lett. 2014; 24: 5721
    • 32a Jaramillo D, Buck DP, Collins JG, Fenton RR, Stootman FH, Wheate NJ, Aldrich-Wright JR. Eur. J. Inorg. Chem. 2006; 839
    • 32b Gillard RD, Newman PD, Vagg RS, Williams PA. Inorg. Chim. Acta 1995; 233: 79
    • 32c Zhou Z, Li Z, Li K, Yang Z, Zhao G, Wang L, Zhou Q, Tang C. Phosphorus, Sulfur Silicon Relat. Elem. 2003; 178: 1771
    • 32d Yang Z.-H, Wang L.-X, Zhou Z.-H, Zhou Q.-L, Tang C.-C. Tetrahedron: Asymmetry 2001; 12: 1579
    • 32e Menger FM, Bian J, Azov VA. Angew. Chem. Int. Ed. 2002; 41: 2581
    • 32f Bowen T, Planalp RP, Brechbiel MW. Bioorg. Med. Chem. Lett. 1996; 6: 807
  • 33 Ghisletta M, Jalett HP, Gerfin T, Gramlich V, Hegetschweiler K. Helv. Chim. Acta 1992; 75: 2233
    • 34a Mellor JM, Smith NM. J. Chem. Soc., Perkin Trans. 1 1984; 2921
    • 34b Grabowski S, Armbruster J, Prinzbach H. Tetrahedron Lett. 1997; 38: 5485
    • 34c Zaragoza Doerwald F, Hanselmann P, Zollinger D. EP2394982A1, 2011
    • 34d Dey RT, Sarkar TK. J. Org. Chem. 2010; 75: 4521
  • 35 MacKenzie JC. J, Rodgman A, Wright GF. J. Org. Chem. 1952; 17: 1666
  • 36 Bournaud C, Bonin M, Micouin L. Org. Lett. 2006; 8: 3041
    • 37a Perez Luna A, Ceschi M.-A, Bonin M, Micouin L, Husson H.-P, Gougeon S, Estenne-Bouhtou G, Marabout B, Sevrin M, George P. J. Org. Chem. 2002; 67: 3522
    • 37b Perez Luna A, Bonin M, Micouin L, Husson H.-P. J. Am. Chem Soc. 2002; 124: 12098
  • 38 Bunlaksananusorn T, Perez Luna A, Bonin M, Micouin L, Knochel P. Synlett 2003; 2240
  • 39 Pasco M, Moumné R, Lecourt T, Micouin L. J. Org. Chem. 2011; 76: 5137
    • 40a Smart BE. J. Fluorine Chem. 2001; 109
    • 40b Purser S, Moore PR, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
    • 40c Morgenthaler M, Schweizer E, Hoffmann-Roder A, Benini F, Martin RE, Jaeschke G, Wagner B, Fischer H, Bendels S, Zimmerli D, Schneider J, Diederich F, Kansy M, Muller K. ChemMedChem 2007; 2: 1100
    • 40d Muller K, Faeh C, Diederich F. Science 2007; 317: 1881
  • 41 Blond A, Turcaud S, Lecourt T, Micouin L. ACS Omega 2018; 3: 15302
  • 42 Carnevali M, Parsons J, Wyles DL, Hermann T. ChemBioChem 2010; 11: 1364
    • 43a Blond A, Dockerty P, Alvarez R, Turcaud S, Lecourt T, Micouin L. J. Org. Chem. 2013; 78: 12236
    • 43b Micouin L, Blond A, Calvez V, Marcellin A.-G, Soulie C, Corrot E. WO2015181387A1, 2015
    • 44a Mattick JS. Nat. Rev. Gen. 2004; 3: 316
    • 44b Mattick JS. Science 2005; 309: 1527
    • 44c Esteller M. Nat. Rev. Genet. 2011; 12: 861
    • 45a Zaman GJ. R, Michiels PJ. A, van Boeckel CA. A. Drug Discovery Today 2003; 8: 297
    • 45b Gallego J, Varani G. Acc. Chem. Res. 2001; 34: 836
    • 45c Thomas JR, Hergenrother PJ. Chem. Rev. 2008; 108: 1172
    • 45d Warner KD, Hajdin CE, Weeks KM. Nat. Rev. Drug Discov. 2018; 17: 547
    • 45e Costales MG, Childs-Disney JL, Haniff HS, Disney MD. J. Med. Chem. 2020; 63: 8880
  • 46 Luedtke NW, Tor Y. In Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes, Vol. 1 . Demeunynck M, Bailly C, Wilson WD. Wiley-VCH; Weinheim: 2003
  • 47 Marquet R, Isel C, Ehresmann B. Biochimie 1995; 77: 113
  • 48 Tisné C, Guillière F, Dardel F. Biochimie 2005; 87: 885
  • 49 Benas P, Bec G, Keith G, Marquet R, Ehresmann C, Ehresmann B, Dumas P. RNA 2000; 6: 1347
    • 50a Tisné C, Roques BP, Dardel F. J. Mol. Biol. 2001; 306: 443
    • 50b Tisné C, Roques BP, Dardel F. J. Biol. Chem. 2004; 279: 3588
    • 51a Rees DC, Congreve M, Murray C, Carr R. Nat. Rev. Drug Discov. 2004; 3: 660
    • 51b Jahnke W, Erlanson DA. Fragment-Based Approaches in Drug Discovery . Wiley-VCH; Weinheim: 2006: 34
    • 51c Murray CW, Rees DC. Nat. Chem. 2009; 1: 187
    • 51d Jhoti H, Williams G, Rees DC, Murray CW. Nat. Rev. Drug Discov. 2013; 12: 644
    • 52a Chung F, Tisne C, Lecourt T, Dardel F, Micouin L. Angew. Chem. Int. Ed. 2007; 46: 4489
    • 52b Chung F, Tisne C, Lecourt T, Seijo B, Dardel F, Micouin L. Chem. Eur. J. 2009; 15: 7109
    • 53a Zhang L, Chen X, Xue P, Sun HH. Y, Williams ID, Sharpless KB, Fokin VV, Jia G. J. Am. Chem. Soc. 2005; 127: 15998
    • 53b Boren BC, Narayazn S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G, Fokin VV. J. Am. Chem. Soc. 2008; 130: 8923
  • 54 Moumné R, Larue V, Seijo B, Lecourt T, Micouin L, Tisne C. Org. Biomol. Chem. 2010; 8: 1154
  • 55 Moumné R, Pasco M, Prost E, Lecourt T, Micouin L, Tisne C. J. Am. Chem. Soc. 2010; 132: 13111
  • 56 Dalvit C, Vulpetti A. J. Med. Chem. 2019; 62: 2218
  • 57 Lombès T, Moumné R, Larue V, Prost E, Catala M, Lecourt T, Dardel F, Micouin L, Tisné C. Angew. Chem. Int. Ed. 2012; 51: 9530