The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB1 Receptor Positive Allosteric Modulators (PAMs)

Tseng, Chih-ChungBaillie, GemmaDonvito, GiuliaMustafa, Mohammed A.Juola, Sophie E.Zanato, ChiaraMassarenti, ChiaraDall'angelo, SergioHarrison, William T. A.Lichtman, Aron H.Ross, Ruth A.Zanda, MatteoGreig, Iain R.2020-05-022020-05-022019Tseng, C-C, Baillie, G, Donvito, G, Mustafa, M A, Juola, S E, Zanato, C, Massarenti, C, Dall'angelo, S, Harrison, W T A, Lichtman, A H, Ross, R A, Zanda, M & Greig, I R 2019, 'The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB1 Receptor Positive Allosteric Modulators (PAMs)', Journal of Medicinal Chemistry, vol. 62, no. 10, pp. 5049-5062. https://doi.org/10.1021/acs.jmedchem.9b002520022-2623Mendeley: ef82582c-c645-34af-8958-ad8b3c81b71cORCID: /0000-0003-0338-8664/work/58936582ORCID: /0000-0003-0603-3383/work/65549949ORCID: /0000-0001-9377-0474/work/176747545https://hdl.handle.net/2164/14228The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jmedchem.9b00252. Experimental procedures, characterization of all intermediates and target compounds, and copies of NMR spectra of compounds 1, 39-57. Molecular formula strings of target compounds are available. ACKNOWLEDGEMENTS. We gratefully thank Signal Pharma and the Canadian Institutes of Health Research Proof of Principle grants PPP-125784 and PP2-139101 for financial support and fellowship (C.C.T), NIH grants R01DA039942, P30DA033934 and VCU School of Pharmacy start-up funds (A.H.L.). We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collection. We are grateful to Dr Monica Sani (CNR-ICRM, Milan, Italy) and Mr Massimo Frigerio (Politecnico di Milano, Italy) for the synthesis of two tetrazole-substituted indoles (Het-1 and Het-2)14494691engQD ChemistryR Medicine (General)Drug DiscoveryMolecular MedicineOtherPPP-125784PP2-139101R01DA039942P30DA033934Supplementary DataQDR1The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB1 Receptor Positive Allosteric Modulators (PAMs)Journal article10.1021/acs.jmedchem.9b00252http://www.mendeley.com/research/trifluoromethyl-group-bioisosteric-replacement-aliphatic-nitro-group-cb1-receptor-positive-allosterihttp://www.scopus.com/inward/record.url?scp=85066022827&partnerID=8YFLogxKhttps://abdn.pure.elsevier.com/en/en/researchoutput/the-trifluoromethyl-group-as-a-bioisosteric-replacement-of-the-aliphatic-nitro-group-in-cb1-receptor-positive-allosteric-modulators-pams(be1c59c4-139f-40c4-8183-31a797b12efb).html6210