Thenoyltrifluoroacetone

Thenoyltrifluoroacetone[1]
Names
Preferred IUPAC name
4,4,4-Trifluoro-1-(thiophen-2-yl)butane-1,3-dione
Other names
2-thenoyltrifluoroacetone
Identifiers
3D model (JSmol)
Abbreviations TTFA
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.743 Edit this at Wikidata
EC Number
  • 206-316-7
UNII
  • InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2 checkY
    Key: TXBBUSUXYMIVOS-UHFFFAOYSA-N checkY
  • InChI=1/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2
    Key: TXBBUSUXYMIVOS-UHFFFAOYAR
  • O=C(c1sccc1)CC(=O)C(F)(F)F
Properties
C8H5F3O2S
Molar mass 222.18 g mol−1
Appearance fine, slightly yellow crystals
Melting point 40 to 44 °C (104 to 111 °F; 313 to 317 K)
Boiling point 96 to 98 °C (205 to 208 °F; 369 to 371 K) 8 mmHg
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
Flash point 12 °C (54 °F; 285 K) (closed cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Thenoyltrifluoroacetone, C8H5F3O2S, is a chemical compound used pharmacologically as a chelating agent. It is an inhibitor of cellular respiration by blocking the respiratory chain at complex II.

Perhaps the first report of TTFA as an inhibitor of respiration was by A. L. Tappel in 1960.[2] Tappel had the (erroneous) idea that inhibitors like antimycin and alkyl hydroxyquinoline-N-oxide might work by chelating iron in the hydrophobic milieu of respiratory membrane proteins, so he tested a series of hydrophobic chelating agents. TTFA was a potent inhibitor, but not because of its chelating ability. TTFA binds at the quinone reduction site in Complex II, preventing ubiquinone from binding. The first x-ray structure of Complex II showing how TTFA binds, 1ZP0, was published in 2005 .[3]

Thenoyltrifluoroacetone can be made in a Claisen condensation of ethyl trifluoroacetate and 2-acetylthiophene.[4][5]

References

  1. ^ Sigma-Aldrich product page
  2. ^ Tappel (July 1960). "Inhibition of electron transport by antimycin A, alkyl hydroxy naphthoquinones and metal coordination compounds". Biochem. Pharmacol. 3 (4): 289–96. doi:10.1016/0006-2952(60)90094-0. PMID 13836892.
  3. ^ Sun, Fei; Huo, Xia; Zhai, Yujia; Wang, Aojin; Xu, Jianxing; Su, Dan; Bartlam, Mark; Rao, Zihe (2005). "Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II". Cell. 121 (7): 1043–1047. doi:10.1016/j.cell.2005.05.025. PMID 15989954. S2CID 16697879.
  4. ^ Gergel, Max G. (March 1977). Excuse me sir, would you like to buy a kilo of isopropyl bromide?. Pierce Chemical. p. 130.
  5. ^ Taydakov, Ilya V; Kreshchenova, Yuliya M; Dolotova, Ekaterina P (27 December 2018). "A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety". Beilstein Journal of Organic Chemistry. 14: 3106–3111. doi:10.3762/bjoc.14.290. PMC 6317410. PMID 30643588.
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