Spiro Compounds - Группа авторов

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that a carbonyl to oxetane switch can be a viable approach to mitigate epimerization at adjacent stereocenters.

      Source: Based on Wuitschik et al. [55].

Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound.
Solubility (μg ml−1) 4000 1400 220 4100 730 40 n.d. 24 000 290
Lipophilicity logD (logP) 1.2 (1.6) 1.0 (2.0) 2.3 (4.4) −0.1 (−0.1) 0.7 (1.5) 1.4 (3.7) n.d. 0.5 (1.2) 0.8 (3.1)
hCLint (min−1 mg−1 μl) 120 6 23 100 2 10 n.d. 3 0
mCLint (min−1 mg−1 μl) 88 22 31 580 27 39 n.d. 7 16
pK a amine 7.5 8.3 9.5 6.1 8.1 9.7 n.d. 8.0 9.6
Schematic illustration of a chemical reaction depicting spiro-oxetane as a morpholine bioisostere.

      Sources: Based on Carreira and Fessard [48]; Burkhard et al. [56];

      (b) comparison of exit vectors in the piperidine motif and its spiro counterpart; (c) spirocyclic oxetane based on mimics of morpholine.

      Source: Adapted from Carreira Wuitschik et al. [55].

Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound. Schematic illustration of the chemical structure of a compound.
Solubility (μg ml−1) 730 8000 24 000
Lipophilicity logD (logP) 0.7 (1.5) 1.5 (1.6) 0.5 (1.2)
hCLint (min−1 mg−1 μl) 2 9 3
mCLint (min−1 mg−1 μl) 27 8 7
pK a amine 8.1 7.0 8.0

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