ACS Med. Chem. Lett. ASAP. Celeste Alverez Current Literature 8/5/2017. Celeste Wipf Group
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1 1 Evaluation of oxetan-3-ol, thietan-3-ol, and derivatives thereof as bioisosteres of the carboxylic acid functional group Lassalas, P.; Oukoloff, K.; Makani, V.; James, M.; Tran, V.; Yao, Y.; Huang, L.; Vijayendran, K.; Monti, L.; Trojanowski, J. Q.; Lee, V. M.-Y.; Kozlowski, M. C.; Smith, III, A. B.; Brunden, K. R.; Ballatore, C. ACS Med. Chem. Lett. ASAP Celeste Alverez Current Literature
2 Isosteres in Medicinal Chemistry u Recent definition: Similarities must exist between at least some of the properties of the isostere and those of the fragment being replaced, such that the new analogs retain the biological activities of the parent compound. At the same time, however, the isosteric replacement must produce changes in the physicochemical properties or susceptibility to metabolism compared to the parent compound in order to lead to improved derivatives. u Lassalas et al. J. Med. Chem. 2016, 59,
3 Carboxylic acid Isosteres u Many reported in literature 3 Lassalas et al. J. Med. Chem. 2016, 59,
4 Carboxylic acid Isosteres 4 Lassalas et al. J. Med. Chem. 2016, 59,
5 Carboxylic acid Isosteres 5 Lassalas et al. J. Med. Chem. 2016, 59,
6 Carboxylic acid Isosteres 6 Lassalas et al. J. Med. Chem. 2016, 59,
7 Oxetanes as Isosteres 7 # of Examples as Isoseter in Literature Lassalas et al. ACS Med. Chem. Lett. ASAP
8 Oxetanes in Medicinal Chemistry u Modulate lipophilicity u Improve solubility, stability Carreira et al. J. Med. Chem., 2010, 53, R logd Solubility (μm) Cl int (h/m) pk a CH / gem Me <4 16/ oxetane ,000 0/ Wipf et al. ACS Med. Chem. Lett. 2014, 5, 900. aq. solubility = 580 μm aq. solubility = 44,000 μm
9 Recent Uses of Oxetanes as non-classical Isosteres u Recently Carreria and Shipman groups have utilized oxetanes to mimic amides and esters 9 Möller et al. Org. Lett. 2017, 19,
10 Synthesis 10 Lassalas et al. ACS Med. Chem. Lett. ASAP
11 Properties of 4-membered Heterocycle Isosteres 11
12 Why modify Ibuprofen? 12 Martel-Pelletier et al. Ann. Rheum. Dis. 2003, 62,
13 Synthesis 13 Lassalas et al. ACS Med. Chem. Lett. ASAP
14 4-Membered Heterocycles in Ibuprofen Analogs Cmpd PGE 2 /D 2 Assay IC 50 ( M) LBT 4 Assay IC 50 ( M) > > > >
15 4-Membered Heterocycles in Ibuprofen Analogs 15 Concentration-response of inhibition of 5-LOX derived LTB 4 and COX-derived PGE 2 /PGD 2 by 2 (left) and 10 (right) Lassalas et al. ACS Med. Chem. Lett. ASAP
16 Proposed binding modes 16 COX-1 crystal structure (PDB: 1EQG) Lassalas et al. ACS Med. Chem. Lett. ASAP
17 Proposed binding modes 17 COX-1 crystal structure (PDB: 1EQG) Lassalas et al. ACS Med. Chem. Lett. ASAP
18 Isosteres of Carboxylic Acids 18 Lassalas et al. ACS Med. Chem. Lett. ASAP
19 Conclusions 19 u The 4-membered heterocyclic replacements of the carbonyl of carboxylic acids lead to improved lipophilicity and permeability u Decreased acidity u All replacements show weaker H-bonding interactions u Oxetan-3-ol and thietan-3-ol and related oxidized products can successfully act as bioisosteres of carboxylic acids u Potentially especially useful for CNS applications
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