Читать книгу Spiro Compounds - Группа авторов - Страница 19

1 1 Moss, G. (1999). Extension and revision of the nomenclature for spiro compounds. Pure Appl. Chem. 71 (3): 531–558.

2 2 Knox, C., Law, V., Jewison, T. et al. (2011). DrugBank 3.0: a comprehensive resource for “omics” research on drugs. Nucleic Acids Res. 39: D1035–D1041.

3 3 Krebs, A., Schafer, B., and Kochner, A. (2010). Method for producing azoniaspironortropine esters and nortropan‐3‐one compounds, US2010048903.

4 4 Smith, L.K. and Baxendale, I.R. (2015). Total syntheses of natural products containing spirocarbocycles. Org. Biomol. Chem. 13 (39): 9907–9933.

5 5 Zhang, F.‐M., Zhang, S.‐Y., and Tu, Y.‐Q. (2018). Recent progress in the isolation, bioactivity, biosynthesis, and total synthesis of natural spiroketals. Nat. Prod. Rep. 35 (1): 75–104.

6 6 Perron, F. and Albizati, K.F. (1989). Chemistry of spiroketals. Chem. Rev. 89 (7): 1617–1661.

7 7 Quintavalla, A. (2018). Spirolactones: recent advances in natural products, bioactive compounds and synthetic strategies. Curr. Med. Chem. 25 (8): 917–962.

8 8 Anthoni, U., Chevolot, L., Larsen, C. et al. (1987). Marine alkaloids. 12. chartellines, halogenated beta‐lactam alkaloids from the marine bryozoan Chartella papyracea. J. Org. Chem. 52 (21): 4709–4712.

9 9 Manam, R.R., Teisan, S., White, D.J. et al. (2005). Lajollamycin, a nitro‐tetraene spiro‐β‐lactone‐γ‐lactam antibiotic from the marine actinomycete Streptomyces nodosus. J. Nat. Prod. 68 (2): 240–243.

10 10 Arulananda Babu, S., Padmavathi, R., Ahmad Aslam, N., and Rajkumar, V. (2015). Chapter 8 ‐ recent developments on the synthesis and applications of natural products‐inspired spirooxindole frameworks. In: Studies in Natural Products Chemistry, vol. 46 (ed. R. Attaur), 227–339. Elsevier.

11 11 Hong, L. and Wang, R. (2013). Recent advances in asymmetric organocatalytic construction of 3,3′‐spirocyclic oxindoles. Adv. Synth. Catal. 355 (6): 1023–1052.

12 12 Singh, G.S. and Desta, Z.Y. (2012). Isatins as privileged molecules in design and synthesis of spiro‐fused cyclic frameworks. Chem. Rev. 112 (11): 6104–6155.

13 13 Wang, J., Soisson, S.M., Young, K. et al. (2006). Platensimycin is a selective FabF inhibitor with potent antibiotic properties. Nature 441 (7091): 358–361.

14 14 Häbich, D. and von Nussbaum, F. (2006). Platensimycin, a new antibiotic and “superbug challenger” from nature. ChemMedChem 1 (9): 951–954.

15 15 Nicolaou, K.C., Li, A., and Edmonds, D.J. (2006). Total synthesis of platensimycin. Angew. Chem. Int. Ed. 45 (42): 7086–7090.

16 16 Trost, B.M., Surivet, J.‐P., and Toste, F.D. (2004). Ruthenium‐catalyzed enyne cycloisomerizations. Effect of allylic silyl ether on regioselectivity. J. Am. Chem. Soc. 126 (47): 15592–15602.

17 17 Nicolaou, K.C., Li, A., Edmonds, D.J. et al. (2009). Total synthesis of platensimycin and related natural products. J. Am. Chem. Soc. 131 (46): 16905–16918.

18 18 Trajkovic, M., Ferjancic, Z., Saicic, R.N., and Bihelovic, F. (2019). Enantioselective synthesis of the platensimycin core by silver(I)‐promoted cyclization of Δ6‐α‐iodoketone. Chem. Eur. J. 25 (17): 4340–4344.

19 19 Ghosh, A.K. and Xi, K. (2007). Enantioselective synthesis of (−)‐platensimycin oxatetracyclic core by using an intramolecular Diels−Alder reaction. Org. Lett. 9 (20): 4013–4016.

20 20 Taylor, F.F. and Faloon, W.W. (1959). The role of potassium in the natriuretic response to a steroidal lactone (SC‐9420). J. Clin. Endocrinol. Metab. 19 (12): 1683–1687.

21 21 Roughley, S.D. and Jordan, A.M. (2011). The medicinal chemist’s toolbox: an analysis of reactions used in the pursuit of drug candidates. J. Med. Chem. 54 (10): 3451–3479.

22 22 Clemons, P.A., Bodycombe, N.E., Carrinski, H.A. et al. (2010). Small molecules of different origins have distinct distributions of structural complexity that correlate with protein‐binding profiles. Proc. Natl. Acad. Sci. U. S. A. 107 (44): 18787–18792.

23 23 Brooks, W.H., Guida, W.C., and Daniel, K.G. (2011). The significance of chirality in drug design and development. Curr. Top. Med. Chem. 11 (7): 760–770.

24 24 Nguyen, L.A., He, H., and Pham‐Huy, C. (2006). Chiral drugs: an overview. Int. J. Biomed. Sci. 2 (2): 85–100.

25 25 Matthews, S.J. and McCoy, C. (2003). Thalidomide: a review of approved and investigational uses. Clin. Ther. 25 (2): 342–395.

26 26 Lovering, F., Bikker, J., and Humblet, C. (2009). Escape from flatland: increasing saturation as an approach to improving clinical success. J. Med. Chem. 52 (21): 6752–6756.

27 27 Lovering, F. (2013). Escape from flatland 2: complexity and promiscuity. Med. Chem. Commun. 4 (3): 515–519.

28 28 Wipf, P., Skoda, E.M., and Mann, A. (2015). Chapter 11 – conformational restriction and steric hindrance in medicinal chemistry. In: The Practice of Medicinal Chemistry, 4e (eds. C.G. Wermuth, D. Aldous, P. Raboisson and D. Rognan), 279–299. San Diego: Academic Press.

29 29 Leeson, P.D. and Springthorpe, B. (2007). The influence of drug‐like concepts on decision‐making in medicinal chemistry. Nat. Rev. Drug Discov. 6 (11): 881.

30 30 Aldeghi, M., Malhotra, S., Selwood, D.L., and Chan, A.W.E. (2014). Two‐ and three‐dimensional rings in drugs. Chem. Biol. Drug Des. 83 (4): 450–461.

31 31 Ritchie, T.J. and Macdonald, S.J.F. (2009). The impact of aromatic ring count on compound developability – are too many aromatic rings a liability in drug design? Drug Discov. Today 14 (21): 1011–1020.

32 32 Zheng, Y.‐J. and Tice, C.M. (2016). The utilization of spirocyclic scaffolds in novel drug discovery. Expert Opin. Drug Discov. 11 (9): 831–834.

33 33 Zheng, Y., Tice, C.M., and Singh, S.B. (2014). The use of spirocyclic scaffolds in drug discovery. Bioorg. Med. Chem. Lett. 24 (16): 3673–3682.

34 34 Zhao, Y., Aguilar, A., Bernard, D., and Wang, S. (2015). Small‐molecule inhibitors of the MDM2‐p53 protein‐protein interaction (MDM2 inhibitors) in clinical trials for cancer treatment. J. Med. Chem. 58 (3): 1038–1052.

35 35 Skalniak, L., Surmiak, E., and Holak, T.A. (2019). A therapeutic patent overview of MDM2/X‐targeted therapies (2014–2018). Expert Opin. Ther. Pat. 29 (3): 151–170.

36 36 de Jonge, M., de Weger, V.A., Dickson, M.A. et al. (2017). A phase I study of SAR405838, a novel human double minute 2 (HDM2) antagonist, in patients with solid tumours. Eur. J. Cancer 76: 144–151.

37 37 de Weger, V.A., de Jonge, M., Langenberg, M.H.G. et al. (2019). A phase I study of the HDM2 antagonist SAR405838 combined with the MEK inhibitor pimasertib in patients with advanced solid tumours. Br. J. Cancer 120 (3): 286–293.

38 38 Brown, Z.Z., Akula, K., Arzumanyan, A. et al. (2012). A spiroligomer α‐helix mimic that binds HDM2, penetrates human cells and stabilizes HDM2 in cell culture. PLoS One 7 (10): e45948.

39 39 Brown, Z.Z. and Schafmeister, C.E. (2010). Synthesis of hexa‐ and pentasubstituted diketopiperazines from sterically hindered amino acids. Org. Lett. 12 (7): 1436–1439.

40 40 Schafmeister, C.E., Brown, Z.Z., and Gupta, S. (2008). Shape‐programmable macromolecules. Acc. Chem. Res. 41 (10): 1387–1398.

41 41 MK‐1602 Clinical trials. https://clinicaltrials.gov/ct2/results?term=MK‐1602&age_v=&gndr=&type=&rslt=&phase=2&Search=Apply (accessed September 2019).

42 42 Bell, I.M. (2014). Calcitonin gene‐related peptide receptor antagonists: new therapeutic agents for migraine. J. Med. Chem. 57 (19): 7838–7858.

43 43 Johansson, A., Löfberg, C., Antonsson, M. et al. (2016). Discovery of (3‐(4‐(2‐Oxa‐6‐azaspiro[3.3]heptan‐6‐ylmethyl)phenoxy)azetidin‐1‐yl)(5‐(4‐methoxyphenyl)‐1,3,4‐oxadiazol‐2‐yl)methanone (AZD1979), a melanin concentrating hormone receptor 1 (MCHr1) antagonist with favorable physicochemical properties. J. Med. Chem. 59 (6): 2497–2511.

44 44 Högberg, T., Frimurer, T.M., and Sasmal, P.K. (2012). Melanin concentrating hormone receptor 1 (MCHR1) antagonists — still a viable approach for obesity treatment? Bioorg. Med. Chem. Lett. 22 (19): 6039–6047.

45 45 Bingham, M. and Rankovic, Z. (2012). Chapter 18 medicinal chemistry challenges in CNS drug discovery. In: Drug Discovery for Psychiatric Disorders (eds. Z. Rankovic, R. Hargreaves and M. Bingham), 465–509. The Royal Society of Chemistry.

46 46 Lavey, B.J., Kozlowski, J.A., Shankar, B.B. et al. (2007). Optimization of triaryl bis‐sulfones as cannabinoid‐2 receptor ligands. Bioorg. Med. Chem. Lett. 17 (13): 3760–3764.

47 47 Ishikawa, M. and Hashimoto, Y. (2011). Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry. J. Med. Chem. 54 (6): 1539–1554.

48 48 Carreira, E.M. and Fessard, T.C. (2014). Four‐membered ring‐containing spirocycles: synthetic strategies and opportunities. Chem. Rev. 114 (16): 8257–8322.

49 49 Baell, J.B. and Holloway, G.A. (2010). New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays. J. Med. Chem. 53 (7): 2718–2740.

50 50 Reboul, M. (1878). Oxyde de Propylene Normal et Polyoxypropylenes. Ann. Chim. (Paris) 14: 495–497.

51 51 Bull, J.A., Croft, R.A., Davis, O.A. et al. (2016). Oxetanes: recent advances in synthesis, reactivity, and medicinal chemistry. Chem. Rev. 116 (19): 12150–12233.

52 52 Ringnér, B., Sunner, S., and Watanabe, H. (1971). The enthalpies of combustion and formation of some 3,3‐disubstituted oxetanes. Acta Chem. Scand. 25: 141–146.

53 53 Pritchard, J.G. and Long, F.A. (1958). The kinetics of the hydrolysis of trimethylene oxide in water, deuterium oxide and 40% aqueous dioxane1. J. Am. Chem. Soc. 80 (16): 4162–4165.

54 54 Rogers‐Evans, M., Knust, H., Plancher, J.‐M. et al. (2014). Adventures in drug‐like chemistry space: from oxetanes to spiroazetidines and beyond! CHIMIA Int. J. Chem. 68 (7‐8): 492–499.

55 55 Wuitschik, G., Rogers‐Evans, M., Buckl, A. et al. (2008). Spirocyclic oxetanes: synthesis and properties. Angew. Chem. Int. Ed. 47 (24): 4512–4515.

56 56 Burkhard, J.A., Wuitschik, G., Plancher, J.‐M. et al. (2013). Synthesis and stability of oxetane analogs of thalidomide and lenalidomide. Org. Lett. 15 (17): 4312–4315.

57 57 Dewdney, N.J., Kennedy‐Smith, J., Kondru, R.K., et al. (2009). Inhibitors of Bruton's tyrosine kinase ‐ Google patents. US Patent 20090306041A1.

58 58 Grue‐Sørensena, G., Liang, X., Högberga, T., et al. (2012). Ingenol‐3‐acylates iii and ingenol‐3‐carbamates ‐ Google patents. WO Patent 2012083953A1.

59 59 GmbH, G., Gruss, M., Kluge, S., and Pruehs, S. (2013). Crystalline (1R,4R)‐6'‐Fluoro‐N,N‐dimethyl‐4‐phenyl‐4',9'‐dihydro‐3'H‐spiro[cyclohexane‐1,1'‐pyrano[3,4,b]indolo]‐4‐amine ‐ Google patents. WO Patent 2013007361A8.

60 60 Mergelsberg, I., Scherer, D.H., Huttenloch, M.E., et al. (2013). Process and intermediates for the synthesis of 8‐[‐methyl]‐8‐phenyl‐1,7‐diazaspiro[4.5]decan‐2‐one compounds ‐ Google patents. US Patent 20140024834A1.

61 61 Li, X.‐Q., Hayes, M.A., Grönberg, G. et al. (2016). Discovery of a novel microsomal epoxide hydrolase–catalyzed hydration of a spiro oxetane. Drug Metab. Dispos. 44 (8): 1341–1348.

62 62 Kidd, S.L., Osberger, T.J., Mateu, N. et al. (2018). Recent applications of diversity‐oriented synthesis toward novel, 3‐dimensional fragment collections. Front. Chem 6 (460).

63 63 Sveiczer, A., North, A.J.P., Mateu, N. et al. (2019). Spirocycles as rigidified sp3‐rich scaffolds for a fragment collection. Org. Lett. 21 (12): 4600–4604.

64 64 King, T.A., Stewart, H.L., Mortensen, K.T. et al. (2019). Cycloaddition strategies for the synthesis of diverse heterocyclic spirocycles for fragment‐based drug discovery. Eur. J. Org. Chem. 2019 (31–32): 5219–5229.

65 65 Hung, A.W., Ramek, A., Wang, Y. et al. (2011). Route to three‐dimensional fragments using diversity‐oriented synthesis. Proc. Natl. Acad. Sci. 108 (17): 6799–6804.

66 66 Tan, W., Zhu, X.‐T., Zhang, S. et al. (2013). Diversity‐oriented synthesis of spiro‐oxindole‐based 2,5‐dihydropyrroles via three‐component cycloadditions and evaluation on their cytotoxicity. RSC Adv. 3 (27): 10875–10886.

67 67 Liu, Y., Wang, H., and Wan, J. (2013). Recent advances in diversity oriented synthesis through isatin‐based multicomponent reactions. Asian J. Org. Chem. 2 (5): 374–386.