By Valentine Nenajdenko
This two-volume paintings combines finished details at the chemistry of the fluorinated heterocycles. the cloth has been divided such that the 1st quantity is devoted to five-membered fluorinated heterocycles and macrocycles, whereas the second one quantity combines facts hooked up with the chemistry of fluorine containing six-membered heterocycles. either volumes might be of curiosity to artificial natural chemists as a rule, and especially for these colleagues operating within the fields of heterocyclic-compound chemistry, fabrics chemistry, medicinal chemistry, and fluorine chemistry. All info is gifted and categorised sincerely to be potent resource for huge auditory of chemists. it will likely be attention-grabbing for scientists operating within the box of inorganic and coordination chemistry. Fluorinated heterocycles have gotten more and more vital in lots of parts together with the pharmaceutical undefined, fabrics technological know-how and agriculture. The presence of fluorine may end up in mammoth practical adjustments within the organic in addition to physicochemical homes of natural compounds. Incorporation of fluorine into drug molecules can drastically have an effect on their physicochemical houses, comparable to bond power, lipophilicity, bioavailability, conformation, electrostatic capability, dipole second, pKa and so forth. in addition to pharmacokinetic houses, similar to tissue distribution, cost of metabolism and pharmacological homes, similar to pharmacodynamics and toxicology.
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Additional info for Fluorine in Heterocyclic Chemistry Volume 1: 5-Membered Heterocycles and Macrocycles
A O O H N H3C N O N H3C N H H F favored b H O CN disfavored H N H3C N F H O O F H F CN CN Fig. 18 (a) Allylic 1,3-like strain between the fluorine and the nitrogen lone pair disfavors the endo-conformation of the mono-fluorinated arene. 7 560 >1000 55 Fig. , the electrostatic interaction between the C-F dipole and the nitrogen lone pair . In all cases the decrease in pKa corresponded to a decrease in binding affinity (Ki). Although the change in binding affinity is likely complex in origin, linear free energy relationships correlating pKa and binding free enthalpies (−ΔG) calculated for inhibition of thrombin and trypsin demonstrated a relationship between affinity and pKa.
However, it has been suggested that the volume of the SF5 group is slightly less than that of a tert-butyl group but larger than the CF3 group . In addition to differences in size, the geometries of these two groups are quite different. The SF5 group displays a pyramid of electron density whereas the CF3 group is associated with a cone shape of electron density . The subtle differences in properties between these two groups provides opportunity for deployment of the SF5 group in a fashion that allows optimization of many of the PK and PD properties discussed in this chapter, including potency.
Chem Soc Rev 37:320–330 19. Shah P, Westwell AD (2007) The role of fluorine in medicinal chemistry. J Enzym Inhib Med Chem 22:527–540 20. O’Hagan D (2008) Understanding organofluorine chemistry: an introduction to the C-F bond. Chem Soc Rev 37:308–319 21. Hunter L (2010) The C-F bond as a conformational tool in organic and biological chemistry. Belistein J Org Chem 6. 38 22. Zimmer LE, Sparr C, Gilmour R (2011) Fluorine conformational effects in organocatalysis: an emerging strategy for molecular design.