Fluorine in medicinal chemistry: A century of progress and a 60-year retrospective of selected highlights

Future Medicinal Chemistry

Volumn 1, Issue 5, 2009, Pages 777-791

  Filler, Robert ^a   Saha, Rituparna ^a  

^a Illinois Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; ANESTHETIC AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; CHLOROQUINE; CLEVUDINE; DIFLUNISAL; DOCETAXEL; EFAVIRENZ; FLUDARABINE; FLUFENISAL; FLUORINE; FLUORINE 18; FLUOROURACIL; FLUOXETINE; FLUPHENAZINE; FLUPREDNISOLONE; FLURAZEPAM; FLURBIPROFEN; FLUTICASONE PROPIONATE; GEMCITABINE; HALOPERIDOL; MEFLOQUINE; NONSTEROID ANTIINFLAMMATORY AGENT; PACLITAXEL; PENFLURIDOL; PHENOTHIAZINE; STEROID; TEGAFUR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALLERGIC RHINITIS; ARTHRITIS; ASTHMA; BREAST CANCER; CANCER CHEMOTHERAPY; COLORECTAL CANCER; DIGESTIVE SYSTEM CANCER; DRUG ACTIVITY; DRUG EFFICACY; DRUG SYNTHESIS; HEPATITIS B; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; ISOTOPE LABELING; LUNG NON SMALL CELL CANCER; LYMPHATIC LEUKEMIA; MALARIA; OSTEOARTHRITIS; OVARY CANCER; PANCREAS CANCER; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; REVIEW; SKIN CANCER;

ANTI-BACTERIAL AGENTS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CHEMISTRY, PHARMACEUTICAL; CHLOROQUINE; FLUORINE; HALOGENATION; HUMANS; INFLAMMATION; MENTAL DISORDERS; RADIOPHARMACEUTICALS; STEROIDS;

EID: 72049096999     PISSN: 17568919     EISSN: None     Source Type: Journal    
DOI: 10.4155/fmc.09.65     Document Type: Review

References (86)

1. Banks RE, Tatlow JC. In: Fluorine: The First Hundred Years (1886-1986). Banks RE, Sharp DWA, Tatlow JC (Eds). Elsevier Science Publishing Co., Inc., NY, USA, 93-97 (1986).
2. Midgley T, Henne AL. Organic fluorides as refrigerants. Ind. Eng. Chem. 22, 542 (1930).
3. Banks RE, Tatlow JC. 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).
4. Schmitt R, von Gehren H. J. Prakt. Chem. 1, 394 (1870).
5. Balz G, Schiemann G. Über aromatische fluorverbindungen, I: ein neues verfahren zu ihrer darstellung. Chem. Ber. 1186 (1927).
6. Swarts F. Fluorine derivatives of toluene. Bull. Acad. Roy. Belg. 35, 375 (1898).
7. McBee ET. Fluorine chemistry. Ind. Eng. Chem. 39, 236-237-- (1947).
8. Peters RA. Croonian lecture: lethal synthesis. Proc. Roy. Soc. Series B 139, 143 (1952).
9. Goldman P. The carbon-fluorine bond in compounds of biological interest. Science 164, 1123-1130 (1969).
10. Smith F. Carbon-Fluorine Compounds. Chemistry, Biochemistry and Biological Activities. A Ciba Foundation Symposium, Elsevier, London, UK (1972).
11. Biochemistry Involving Carbon-Fluorine Bonds. ACS Symposium Series 28, Filler R (Ed.) 1976.
12. Biochemistry of the Elemental Halogens and Inorganic Halides. Kirk KL, Plenum Press, NY, USA (1991).
13. Biochemistry of Halogenated Organic Compounds. Kirk KL, Plenum Press, NY, USA (1991).
14. Kirk KL. Fluorine in biomedicinal chemistry. J. Fluorine Chem. 129 (9), 725-887 (2008).
15. Molecular Modification in Drug Design: Advances in Chemistry Series 45, American Chemical Society (1964).
16. Simons JH. Production of fluorocarbons. J. Electrochem. Soc., 95, 47 (1949).
17. Yale HL. The trifluoromethyl group in medicinal chemistry. J. Med. Pharm. Chem. 1(2), 121-133 (1959).
18. Robbins BH. Preliminary studies of the anesthetic activity of fluorinated hydrocarbons. J. Pharmacol. Exptl Therapeutics 86, 197-204 (1946).
19. McBee ET, Filler R. The reaction of 1,2-dichloro-1,1,3,3,3- pentafluoropropane with ethanolic alkali. J. Org. Chem. 21(3), 370-371 (1956).
20. Suckling CW. Some chemical and physical factors in the development of fluothane. Brit. J. Anesthesia 29, 466 (1957).
21. Raventós J. The action of fluothane; a new volatile anaesthetic. Brit. J. Pharmacol. 11, 394-410(1956).
22. 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).
23. 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).
24. Fried J, Sabo EF. Synthesis of 17 -hydroxycorticosterone and its 9-halo derivatives from 11-epi-17 - hydroxycorticosterone. J. Am. Chem. Soc. 75, 2273-2274 (1953).
25. Fried J, Sabo EF. 9-fluoro derivatives of cortisone and hydrocortisone. J. Am. Chem. Soc. 76, 1455-1456 (1954).
26. Wettstein A. Chemistry of fluorosteroids and their hormonal properties. Reference 10, 281-301 (1972).
27. Elliott AJ. The role of fluorine in the chemistry of central nervous system agents. Reference 22, 209-239 (1993).
28. Duschinsky R, Pleven E, Heidelberger C. The synthesis of 5-fluoropyrimidines. J. Am. Chem. Soc. 79, 4559 (1957).
29. Heidelberger C, Chaudhuri NK, Danneberg P et al. Fluorinated pyrimidines, a new class of tumour-inhibitory compounds. Nature 179, 663-666 (1957).
30. Filler R. Fluorinated compounds of medicinal interest. Chem. Tech. 4, 752-757 (1974).
31. 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).
32. Hagmann WK. The many roles for fluorine in medicinal chemistry. J. Med. Chem. 51(15), 4359-4369 (2008).
33. Bergstrom DE, Swartling DJ. 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).
34. Hertel LW, Ternansky RJ. Fluorinecontaining antiviral and anticancer compounds. Reference 22, 23-71 (1993).
35. Meng W-D, Qing F-L. fluorinated nucleosides as antiviral and anti-tumor agents. Curr. Top. Med. Chem. 6, 1499-1528 (2006).
36. Isanbor C, O'Hagan D. Fluorine in medicinal chemistry: a review of anticancer agents. J. Fluorine Chem. 127, 303-319 (2006).
37. Grever MR et al. Long-term results of the CHOP regimen in stage C chronic lymphocytic leukaemia. Nouv. Rev. Fr. Hematol. 30, 457 (1988).
38. Montgomery JA. Has the well gone dry? The first Cain memorial award lecture. Cancer Res. 42, 3911 (1982).
39. Grindey GB, Boder GB, Hertel LW et al. Antitumor activity of 2́,2́-difluorodeoxycytidine (LY188011). Presented at: American Assn. Cancer. Res. 27, Los Angeles, CA, USA, 7-10 May 1986.
40. Purser S, Moore PR, Swallow S, Gouverneur V. Fluorine in medicinal chemistry. Chem. Soc. Rev. 37, 320-330 (2008).
41. Iseki K, Kobayashi Y. 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).
42. Ojima I et al. Synthesis, biological activity and conformational analysis of fluorine-containing taxoids. Reference 42, 228-243 (1996).
43. Ojima I, Kuduk SD, Slater JC et 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).
44. Kuznetsova L, Pepe A, Ungureanu IM, Pera P, Bernacki RJ, Ojima I. Synthesis and structure- activity relationships of novel 3́-difluoromethyl and 3́-trifluoromethyl-taxoids. J. Fluorine Chem. 129, 817-828 (2008).
45. Walborsky HM, Baum ME. Chemical effects of the trifluoromethyl group: III. Synthesis of 2-amino-4,4,4-trifluorobutyric acid. J. Org. Chem. 21, 538 (1956).
46. Loncrini DF, Filler R. Aliphatic Fluoro Amino Acids. Advances in Fluorine Chemistry. Tatlow JC, Peacock RD, Hyman HH, Stacey M (Eds). Butterworths, London, UK, 6, 43-67 (1970).
47. Ojima I. New developments in the synthesis and medicinal applications of fluoroamino acids and peptides. Reference 22, 241-273 (1993).
48. Ojima I, Kato K, Okabe M, Fuchikami T. Hydroformylation of fluoro olefins, R fCH:CH2, catalyzed by group VIII transition-metal catalysts. Crucial factors for extremely high regioselectivity. J. Am. Chem. Soc. 109, 7714 (1987).
49. Ojima I, Hirai K, Fujita M, Fuchikami T. New synthetic route to N-acyl-?-amino acids via amidocarbonylation by means of homogeneous binary catalyst systems. J. Organometal. Chem. 279, 203 (1985).
50. Soloshonok VA. Practical synthesis of enantiopure fluoramino acids of biological interest by asymmetric aldol reactions. Reference 42, 26-41 (1996).
51. Taguchi T, Shibuya A, Morikawa T. Asymmetric synthesis of functionalized fluorinated cyclopropanes and its application to fluoromethano amino acids. Reference 42, 73-82 (1996).
52. Kirk KL, Nie J-Y. Fluorinated amino acids in nerve systems. Reference 42, 312-327 (1996).
53. Cieplak P, Kollman PA, Radomski JP. Molecular design of fluorine-containing peptide mimetics. Reference 42, 143-156 (1996).
54. Chu DTW. Fluoroquinolone carboxylic acids as antibacterial drugs. Reference 22, 165-207 (1993).
55. 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.
56. István ES, Deisenhofer J. Structural mechanism for statin inhibition of HMGCoA reductase. Science 292, 1160-1164 (2001).
57. Annual Reports in Medicinal Chemistry, 33. Bristol JA (Ed.). 328 (1998).
58. Fowler JS. The synthesis and application of F-18 compounds in positron emission tomography. Reference 22, 309-338 (1993).
59. Hamacher K, Coenen HH, Stocklin G. Efficient stereospecific synthesis of no-carrier-added 2-[18F]-fluoro-2-deoxy-dglucose using aminopolyether supported nucleophilic substitution. J. Nucl. Med. 27, 235 (1986).
60. Arnett CD, Shiue C-Y, Wolf AP. Improved delineation of human dopamine receptors using [18F]-N-methylspiroperidol and PET. J. Neurochem. 44, 835 (1985).
61. 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).
62. Ding Y-S, Fowler JS. 18F labeled tracers for positron emission studies in the neurosciences. Reference 42, 328-343 (1996).
63. Isanbor CI, O'Hagan D. Fluorine in medicinal chemistry: a review of anti-cancer agents. Reference 37, 315-316 (2006).
64. Sun S, Adejare A. Fluorinated molecules as drugs and imaging agents in the CNS. Curr. Top. Med. Chem. 6, 1457-1464 (2006).
65. Shah P, Westwell AD. The role of fluorine in medicinal chemistry. J. Enzyme Inhib. Med. Chem. 22(5), 536-538 (2007).
66. Purser S, Moore PR, Swallow S et al. Fluorine in medicinal chemistry. Chem. Soc. Rev. 37, 328-329 (2008).
67. Cobb SL, Murphy CD. 19F NMR applications in chemical biology. J. Fluorine Chem. 130, 132-143 (2009).
68. Stinson SC. Chiral drugs. Chem. Eng. News, 44, October 9, 1995.
69. Ramachandran PV. Asymmetric Fluoroorganic Chemistry: Synthesis, Applications, and Future Directions. ACS Symposium Series 746. American Chemical Society (2000).
70. Soloshonok VA. Biomimetic reductive amination of fluoro aldehydes and ketones via [1,3]-proton shift reaction. Reference 71, 26-41 (1996).
71. Soloshonok VA. Biominetic, redundancy agent - free reductions amination of fluorocarbonyl compounds: practical asymmetric synthesis of enantiopure fluoroamines and amino acids. Reference 71, 74-83 (2000).
72. Ojima I, Inoue T, Chakravarty S. Synthesis of enantiopure fluorine-containing taxoids and their use as anticancer agents as well as probes for biomedical problems. Reference 71, 158-181 (2000).
73. Kirk KL, Herbert B, Lu SF, Jayachandran B et al. Chemical and biochemical approaches to the enantiomers of chiral fluorinated catecholamines and amino acids. Reference 71, 194-209 (2000).
74. Ramig K. Chiral fluorinated anesthetics. Reference 71, 282-292 (2000).
75. Filler R. Fluorine-containing chiral compounds of biomedical interest. Reference 71, 1-20 (2000).
76. Olah GA, Nojima M, Kerekes I. Synthetic methods and reactions III. Halofluorination of alkenes in poly-hydrogen fluoride/pyridine solution. Synthesis 12, 780-783 (1973).
77. Olah GA, Shih JG, Prakash GKS in. Reference 1, 377-380 (1986).
78. Boswell GA Jr, Ripka WC, Scribner RM, Tullock CW. Fluorination by sulfur tetrafluoride. Organic Reactions 21, 1-124 (1974).
79. Filler R. Reactions of organic compounds with xenon fluorides. Israel J. Chem. 17, 71-79 (1978).
80. Rozen S. Selective fluorinations by reagents containing the OF group. Chem. Rev. 96, 1717-1736 (1996).
81. Lal GS, Pez GP, Syvret RG. Electrophilic NF fluorinating agents. Chem. Rev. 96, 1737-1755 (1996).
82. Resnati G, DesMarteau DD. N-fluorobis[(trifluoromethyl)sulfonyl]imide: an efficient reagent for the ?-fluorination of functionalized carbonyl compounds. J. Org. Chem. 56, 4925-4929 (1991).
83. Prakash GKS, Krishnamurti R, Olah GA. 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).
84. Ma J-A, Cahard D. Strategies for nucleophilic, electrophilic and radical trifluoromethylations. J. Fluorine Chem. 128, 975-996 (2007).
85. Umemoto T. Electrophilic perfluoroalkylating agents. Chem. Rev. 96, 1757-1777 (1996).
86. Iwai N, Sakái R, Tsuchida S, Kitazume M, Kitazume T. Screening of fluorinated materials degrading microbes. J. Fluorine Chem. 130, 434-437 (2009).