789
Views
0
CrossRef citations to date
0
Altmetric
Perspective

Fluorine in Medicinal Chemistry: A Century of Progress and a 60-Year Retrospective of Selected Highlights

&
Pages 777-791 | Published online: 19 Aug 2009

Bibliography

  • Banks RE , TatlowJC. In: Fluorine: The First Hundred Years (1886–1986). BanksRE, SharpDWA, TatlowJC (Eds). Elsevier Science Publishing Co., Inc., NY, USA, 93–97 (1986).
  • Midgley T , HenneAL. Organic fluorides as refrigerants.Ind. Eng. Chem.22, 542 (1930).
  • Banks RE , TatlowJC. In: Fluorine: The First Hundred Years (1886–1986). Banks RE, Sharp DWA, Tatlow JC (Eds). Elsevier Science Publishing Co., Inc., NY, USA, 101–103 (1986).
  • Schmitt R , von Gehren H. J. Prakt. Chem.1, 394 (1870).
  • Balz G , SchiemannG. Über aromatische fluorverbindungen, I: ein neues verfahren zu ihrer darstellung.Chem. Ber.1186 (1927).
  • Swarts F . Fluorine derivatives of toluene.Bull. Acad. Roy. Belg.35, 375 (1898).
  • McBee ET . Fluorine chemistry.Ind. Eng. Chem.39, 236–237__ (1947).
  • Peters RA . Croonian lecture: lethal synthesis.Proc. Roy. Soc. Series B139, 143 (1952).
  • Goldman P . The carbon-fluorine bond in compounds of biological interest.Science164, 1123–1130 (1969).
  • Smith F . Carbon-Fluorine Compounds. Chemistry, Biochemistry and Biological Activities. A Ciba Foundation Symposium, Elsevier, London, UK (1972).
  • Biochemistry Involving Carbon-Fluorine Bonds . ACS Symposium Series 28, FillerR (Ed.) 1976.
  • Biochemistry of the Elemental Halogens and Inorganic Halides . KirkKL, Plenum Press, NY, USA (1991).
  • Biochemistry of Halogenated Organic Compounds . KirkKL, Plenum Press, NY, USA (1991).
  • Kirk KL . Fluorine in biomedicinal chemistry.J. Fluorine Chem.129(9), 725–887 (2008).
  • Molecular Modification in Drug Design: Advances in Chemistry Series 45 , American Chemical Society (1964).
  • Simons JH . Production of fluorocarbons.J. Electrochem. Soc.95, 47 (1949).
  • Yale HL . The trifluoromethyl group in medicinal chemistry.J. Med. Pharm. Chem.1(2), 121–133 (1959).
  • Robbins BH . Preliminary studies of the anesthetic activity of fluorinated hydrocarbons.J. Pharmacol. Exptl Therapeutics86, 197–204 (1946).
  • McBee ET , FillerR. The reaction of 1,2-dichloro-1,1,3,3,3-pentafluoropropane with ethanolic alkali.J. Org. Chem.21(3), 370–371 (1956).
  • Suckling CW . Some chemical and physical factors in the development of fluothane.Brit. J. Anesthesia29, 466 (1957).
  • Raventós J . The action of fluothane; a new volatile anaesthetic.Brit. J. Pharmacol.11, 394–410 (1956).
  • Halpern DF . Recent developments in fluorine substituted volatile anesthetics. In: Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications. Filler R, Kobayashi Y, Yagupolskii LM (Eds). Elsevier, Amsterdam, The Netherlands, 101–133 (1993).
  • Ferstandig LL . Fluorinated anesthetics. Chemistry of Organic Fluorine Compounds II. A Critical Review. Hudlicky M, Pavlath AE (Eds). American Chemical Society Monograph 187, American Chemical Society, Washington DC, USA, 1133–1137 (1995).
  • Fried J , SaboEF. Synthesis of 17α -hydroxycorticosterone and its 9α-halo derivatives from 11-epi-17α –hydroxycorticosterone.J. Am. Chem. Soc.75, 2273–2274 (1953).
  • Fried J , SaboEF. 9α-Fluoro derivatives of cortisone and hydrocortisone.J. Am. Chem. Soc.76, 1455–1456 (1954).
  • Wettstein A . Chemistry of fluorosteroids and their hormonal properties.Reference10, 281–301 (1972).
  • Elliott AJ . The role of fluorine in the chemistry of central nervous system agents.Reference22, 209–239 (1993).
  • Duschinsky R , PlevenE, HeidelbergerC. The synthesis of 5-fluoropyrimidines.J. Am. Chem. Soc.79, 4559 (1957).
  • Heidelberger C , ChaudhuriNK, DannebergPet al. Fluorinated pyrimidines, a new class of tumour-inhibitory compounds. Nature 179, 663–666 (1957).
  • Filler R . Fluorinated compounds of medicinal interest.Chem. Tech.4, 752–757 (1974).
  • Edwards PN . Uses of fluorine in chemotherapy. In: Organofluorine Chemistry, Principles and Commercial Applications. Banks RE, Smart BE, Tatlow JC (Eds). Plenum Press, NY, USA, 501–541 (1994).
  • Hagmann WK . The many roles for fluorine in medicinal chemistry.J. Med. Chem.51(15), 4359–4369 (2008).
  • Bergstrom DE , SwartlingDJ. Fluorine substituted analogs of nucleic acid components. In: Fluorine-Containing Molecules, Structure, Reactivity, Synthesis, and Applications. Liebman JF, Greenberg A, Dolbier WR Jr (Eds). VCH Publishers, Inc. NY, USA, 259–308 (1988).
  • Hertel LW , TernanskyRJ. Fluorine-containing antiviral and anticancer compounds.Reference22, 23–71 (1993).
  • Meng W -D, Qing F-L. fluorinated nucleosides as antiviral and anti-tumor agents. Curr. Top. Med. Chem.6, 1499–1528 (2006).
  • Isanbor C , O‘HaganD. Fluorine in medicinal chemistry: a review of anticancer agents.J. Fluorine Chem.127, 303–319 (2006).
  • Grever MR et al. Long-term results of the CHOP regimen in stage C chronic lymphocytic leukaemia. Nouv. Rev. Fr. Hematol. 30, 457 (1988).
  • Montgomery JA . Has the well gone dry? The first Cain memorial award lecture.Cancer Res.42, 3911 (1982).
  • Grindey GB , BoderGB, HertelLWet al. Antitumor activity of 2´,2´-difluorodeoxycytidine (LY188011). Presented at: American Assn. Cancer. Res. 27, Los Angeles, CA, USA, 7–10 May 1986.
  • Purser S , MoorePR, SwallowS, GouverneurV. Fluorine in medicinal chemistry.Chem. Soc. Rev.37, 320–330 (2008).
  • Iseki K , KobayashiY. Fluorinated vitamin D3 analog with in vivo anticancer activity. In: Biomedical Frontiers of Fluorine Chemistry, Ojima I, McCarthy JR, Welch JT (Eds.). ACS Symposium Series 639, 214–227 (1996).
  • Ojima I et al. Synthesis, biological activity and conformational analysis of fluorine-containing taxoids. Reference 42, 228–243 (1996).
  • Ojima I , KudukSD, SlaterJCet al. Use of fluorine in medicinal chemistry and chemical biology of bioactive compounds – a case study on fluorinated taxane anticancer agents. ChemBioChem, Wiley–VCH Verlag, Weinheim, Germany, 5, 628–635 (2004).
  • Kuznetsova L , PepeA, UngureanuIM, PeraP, BernackiRJ, OjimaI. Synthesis and structure–activity relationships of novel 3´-difluoromethyl and 3´-trifluoromethyl-taxoids.J. Fluorine Chem.129, 817–828 (2008).
  • Walborsky HM , BaumME. Chemical effects of the trifluoromethyl group: III. Synthesis of 2-amino-4,4,4-trifluorobutyric acid.J. Org. Chem.21, 538 (1956).
  • Loncrini DF , FillerR. Aliphatic Fluoro Amino Acids. Advances in Fluorine Chemistry. Tatlow JC, Peacock RD, Hyman HH, Stacey M (Eds). Butterworths, London, UK, 6, 43–67 (1970).
  • Ojima I . New developments in the synthesis and medicinal applications of fluoroamino acids and peptides.Reference22, 241–273 (1993).
  • Ojima I , KatoK, OkabeM, FuchikamiT. Hydroformylation of fluoro olefins, RfCH:CH2, catalyzed by group VIII transition-metal catalysts. Crucial factors for extremely high regioselectivity. J. Am. Chem. Soc.109, 7714 (1987).
  • Ojima I , HiraiK, FujitaM, FuchikamiT. New synthetic route to N-acyl-α-amino acids via amidocarbonylation by means of homogeneous binary catalyst systems. J. Organometal. Chem.279, 203 (1985).
  • Soloshonok VA . Practical synthesis of enantiopure fluoramino acids of biological interest by asymmetric aldol reactions.Reference42, 26–41 (1996).
  • Taguchi T , ShibuyaA, MorikawaT. Asymmetric synthesis of functionalized fluorinated cyclopropanes and its application to fluoromethano amino acids.Reference42, 73–82 (1996).
  • Kirk KL , Nie J-Y. Fluorinated amino acids in nerve systems. Reference42, 312–327 (1996).
  • Cieplak P , KollmanPA, RadomskiJP. Molecular design of fluorine-containing peptide mimetics.Reference42, 143–156 (1996).
  • Chu DTW . Fluoroquinolone carboxylic acids as antibacterial drugs.Reference22, 165–207 (1993).
  • Bonnet-Delpon D . Artemisinin, a target for fluorine chemists: challenging molecule, efficient antimalarial drug. Presented at: Abstracts, Division of Medicinal Chemistry, ACS National Meeting. Boston, MA, USA, 19–23 August 2007.
  • István ES , DeisenhoferJ. Structural mechanism for statin inhibition of HMG-CoA reductase.Science292, 1160–1164 (2001).
  • Annual Reports in Medicinal Chemistry, 33 . BristolJA (Ed.). 328 (1998).
  • Fowler JS . The synthesis and application of F-18 compounds in positron emission tomography.Reference22, 309–338 (1993).
  • Hamacher K , CoenenHH, StocklinG. Efficient stereospecific synthesis of no-carrier-added 2-[18F]-fluoro-2-deoxy-D-glucose using aminopolyether supported nucleophilic substitution. J. Nucl. Med.27, 235 (1986).
  • Arnett CD , Shiue C-Y, Wolf AP. Improved delineation of human dopamine receptors using [18F]-N-methylspiroperidol and PET. J. Neurochem.44, 835 (1985).
  • Shiue C -Y, Fowler JS, Wolf AP et al. No-carrier-added fluorine-18-labeled N-methylspiroperidol: synthesis and biodistribution in mice. J. Nucl. Med.27, 226 (1986).
  • Ding Y -S, Fowler JS. 18F labeled tracers for positron emission studies in the neurosciences. Reference42, 328–343 (1996).
  • Isanbor CI , O‘HaganD. Fluorine in medicinal chemistry: a review of anti-cancer agents.Reference37, 315–316 (2006).
  • Sun S , AdejareA. Fluorinated molecules as drugs and imaging agents in the CNS.Curr. Top. Med. Chem.6, 1457–1464 (2006).
  • Shah P , WestwellAD. The role of fluorine in medicinal chemistry.J. Enzyme Inhib. Med. Chem.22(5), 536–538 (2007).
  • Purser S , MoorePR, SwallowSet al. Fluorine in medicinal chemistry. Chem. Soc. Rev. 37, 328–329 (2008).
  • Cobb SL , MurphyCD. 19F NMR applications in chemical biology. J. Fluorine Chem.130, 132–143 (2009).
  • Stinson SC . Chiral drugs.Chem. Eng. News44, October 9, 1995.
  • Ramachandran PV . Asymmetric Fluoroorganic Chemistry: Synthesis, Applications, and Future Directions. ACS Symposium Series 746. American Chemical Society (2000).
  • Soloshonok VA . Biomimetic reductive amination of fluoro aldehydes and ketones via [1,3]-proton shift reaction.Reference71, 26–41 (1996).
  • Soloshonok VA . Biominetic, redundancy agent – free reductions amination of fluorocarbonyl compounds: practical asymmetric synthesis of enantiopure fluoroamines and amino acids.Reference71, 74–83 (2000).
  • Ojima I , InoueT, ChakravartyS. Synthesis of enantiopure fluorine-containing taxoids and their use as anticancer agents as well as probes for biomedical problems.Reference71, 158–181 (2000).
  • Kirk KL , HerbertB, LuSF, JayachandranBet al. Chemical and biochemical approaches to the enantiomers of chiral fluorinated catecholamines and amino acids. Reference 71, 194–209 (2000).
  • Ramig K . Chiral fluorinated anesthetics.Reference71, 282–292 (2000).
  • Filler R . Fluorine-containing chiral compounds of biomedical interest.Reference71, 1–20 (2000).
  • Olah GA , NojimaM, KerekesI. Synthetic methods and reactions III. Halofluorination of alkenes in poly-hydrogen fluoride/pyridine solution.Synthesis12, 780–783 (1973).
  • Olah GA , ShihJG, PrakashGKS in. Reference1, 377–380 (1986).
  • Boswell GA Jr, Ripka WC, Scribner RM, Tullock CW. Fluorination by sulfur tetrafluoride. Organic Reactions21, 1–124 (1974).
  • Filler R . Reactions of organic compounds with xenon fluorides.Israel J. Chem.17, 71–79 (1978).
  • Rozen S . Selective fluorinations by reagents containing the OF group.Chem. Rev.96, 1717–1736 (1996).
  • Lal GS , PezGP, SyvretRG. Electrophilic NF fluorinating agents.Chem. Rev.96, 1737–1755 (1996).
  • Resnati G , DesMarteauDD. N-fluorobis[(trifluoromethyl)sulfonyl]imide: an efficient reagent for the α-fluorination of functionalized carbonyl compounds. J. Org. Chem.56, 4925–4929 (1991).
  • Prakash GKS , KrishnamurtiR, OlahGA. Synthetic methods and reactions. 141. Fluoride-induced trifluoromethylation of carbonyl compounds with trifluoromethyltrimethylsilane (TMS-CF3). A trifluoromethide equivalent. J. Am. Chem. Soc.111, 393–395 (1989).
  • Ma J -A, Cahard D. Strategies for nucleophilic, electrophilic and radical trifluoromethylations. J. Fluorine Chem.128, 975–996 (2007).
  • Umemoto T . Electrophilic perfluoroalkylating agents.Chem. Rev.96, 1757–1777 (1996).
  • Iwai N , SakáiR, TsuchidaS, KitazumeM, KitazumeT. Screening of fluorinated materials degrading microbes.J. Fluorine Chem.130, 434–437 (2009).

Patents

  • Schuman PD , TarrantP, WarnerDA, WestmorelandG. Process for fluorinating uracil and derivatives thereof. US Patent3954758 (1976).
  • Lontz JF , RaaschMS. α-Amino acids containing α-fluorinated-alkyl or cycloalkyl groups. US Patent 2,662,915 (1953).
  • Lal GS . Process for selectively ortho-fluorinating substituted aromatic compounds. US Patent5,233, 074 (1993).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.