Synthesis 2019; 51(23): 4393-4400
DOI: 10.1055/s-0037-1611884
special topic
© Georg Thieme Verlag Stuttgart · New York

Improvements of C–H Radio-Iodination of N-Acylsulfonamides toward Implementation in Clinics

Emmanuelle Dubost
a  Normandie Univ, UNICAEN, Centre d’Etudes et de Recherche sur le Médicament de Normandie (CERMN), 14000 Caen, France
,
Victor Babin
a  Normandie Univ, UNICAEN, Centre d’Etudes et de Recherche sur le Médicament de Normandie (CERMN), 14000 Caen, France
,
Florian Benoist
a  Normandie Univ, UNICAEN, Centre d’Etudes et de Recherche sur le Médicament de Normandie (CERMN), 14000 Caen, France
,
Alexandra Hébert
a  Normandie Univ, UNICAEN, Centre d’Etudes et de Recherche sur le Médicament de Normandie (CERMN), 14000 Caen, France
,
Gilbert Pigrée
b  Normandie Univ, UNICAEN, IMOGERE, 14000 Caen, France
,
Jean-Philippe Bouillon
c  Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
,
Frédéric Fabis
a  Normandie Univ, UNICAEN, Centre d’Etudes et de Recherche sur le Médicament de Normandie (CERMN), 14000 Caen, France
,
a  Normandie Univ, UNICAEN, Centre d’Etudes et de Recherche sur le Médicament de Normandie (CERMN), 14000 Caen, France
b  Normandie Univ, UNICAEN, IMOGERE, 14000 Caen, France
d  Department of Nuclear Medicine, CHU Côte de Nacre, 14000 Caen, France   Email: thomas.cailly@unicaen.fr
› Author Affiliations
The authors are grateful for financial support provided by the Regional Council of Normandy, FEDER, Crunch Network, la Ligue Contre le Cancer, The ARC foundation, the University of Caen, Tremplin Carnot I2C and the French Ministry of Research.
Further Information

Publication History

Received: 29 May 2019

Accepted after revision: 18 June 2019

Publication Date:
09 July 2019 (online)

Published as part of the Special Topic Halogenation methods (with a view towards radioimaging applications)

Abstract

An improved protocol to perform C–H radio-iodination is described. These new conditions allow rapid and clean formation of radio-iodinated N-acylsulfonamides using [125I]NIS and catalytic amounts of palladium acetate and para-toluenesulfonic acid. No pre-functionalized precursors are required and the products are obtained with radiochemical conversions (RCC) of 27–84%.

Supporting Information

 
  • References

  • 1 Adam MJ, Wilbur DS. Chem. Soc. Rev. 2005; 34: 153
  • 2 Pimlott SL, Sutherland A. Chem. Soc. Rev. 2011; 40: 149
  • 3 Boyer IJ. Toxicology 1989; 55: 253
  • 4 Seevers RH, Counsell RE. Chem. Rev. 1982; 82: 575
  • 5 Wager KM, Jones GB. Curr. Radiopharm. 2010; 3: 37
  • 6 Cant AA, Champion S, Bhalla R, Pimlott SL, Sutherland A. Angew. Chem. Int. Ed. 2013; 52: 7829
  • 7 Wilson TC, McSweeney G, Preshlock S, Verhoog S, Tredwell M, Cailly T, Gouverneur V. Chem. Commun. 2016; 52: 13277
  • 8 Zhang P, Zhuang R, Guo Z, Su X, Chen X, Zhang X. Chem. Eur. J. 2016; 22: 16783
  • 9 Reilly SW, Makvandi M, Xu K, Mach RH. Org. Lett. 2018; 20: 1752
  • 10 Pimlott SL, Fletcher C, Sutherland A, Webster S, Lee A.-L, O’Rourke KM. Chem. Eur. J. 2017; 24: 937
  • 11 Sloan NL, Luthra SK, McRobbie G, Pimlott SL, Sutherland A. Chem. Commun. 2017; 53: 11008
  • 12 Dubost E, Babin V, Benoist F, Hébert A, Barbey P, Chollet C, Bouillon J.-P, Manrique A, Pieters G, Fabis F, Cailly T. Org. Lett. 2018; 20: 6302
  • 13 Corbett TH, White K, Polin L, Kushner J, Paluch J, Shih C, Grossman CS. Invest. New Drugs 2003; 21: 33
  • 14 Lobb KL, Hipskind PA, Aikins JA, Alvarez E, Cheung Y, Considine EL, De Dios A, Durst GL, Ferritto R, Grossman CS, Giera DD, Hollister BA, Huang Z, Iversen PW, Law KL, Li T, Lin H, Lopez B, Lopez JE, Cabrejas LM. M, McCann DJ, Molero V, Reilly JE, Richett ME, Shih C, Teicher B, Wikel JH, White WT, Mader MM. J. Med. Chem. 2004; 47: 5367
  • 15 Meier T, Uhlik M, Chintharlapalli S, Dowless M, Van Horn R, Stewart J, Blosser W, Cook J, Young D, Ye X, Evans G, Credille K, Ballard D, Huber L, Capen A, Chedid M, Ilaria R, Smith MC, Stancato L. Mol. Cancer Ther. 2011; 10: 2168
  • 16 Péron F, Fossey C, Cailly T, Fabis F. Org. Lett. 2012; 14: 1827
  • 17 Péron F, Fossey C, Sopkova-de Oliveira SantosJ, Cailly T, Fabis F. Chem. Eur. J. 2014; 20: 7507