2017
DOI: 10.1016/j.tet.2017.05.057
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Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism

Abstract: We here report the preparation of a new 2,6,8-trisubstituted bicyclic tripeptidomimetic scaffold through TFAmediated cyclization of a linear precursor containing three side chains. The introduction of a triphenylmethyl-protected thiol into carboxylic acid containing building blocks through sulfa Michael additions onto a,b-unsaturated hexafluoroisopropyl esters is described. The stereoselectivity of the bicycle

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Cited by 4 publications
(3 citation statements)
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“… The electron-poor hexafluoroisopropyl ester increased the electrophilicity of the unsaturated esters as SMA acceptors and led to improved yields and enantioselectivities compared to TFE and ethanol esters. Similar SMA reaction of trityl mercaptan with α,β-unsaturated HFIP esters was reported in the presence of Et 3 N in DCM . In another report, trifluoroethyl- and hexafluoroisopropyl-containing α,β-unsaturated sulfonic esters were more reactive toward a palladium-catalyzed asymmetric addition of diarylphosphines, leading to the preparation of chiral phosphine sulfonates …”
Section: Hfip As An Active Estermentioning
confidence: 99%
“… The electron-poor hexafluoroisopropyl ester increased the electrophilicity of the unsaturated esters as SMA acceptors and led to improved yields and enantioselectivities compared to TFE and ethanol esters. Similar SMA reaction of trityl mercaptan with α,β-unsaturated HFIP esters was reported in the presence of Et 3 N in DCM . In another report, trifluoroethyl- and hexafluoroisopropyl-containing α,β-unsaturated sulfonic esters were more reactive toward a palladium-catalyzed asymmetric addition of diarylphosphines, leading to the preparation of chiral phosphine sulfonates …”
Section: Hfip As An Active Estermentioning
confidence: 99%
“…In chemistry similar to Scheme 128, treatment of compounds 419 with TFA, thioanisole, and water (90:5:5) gave cyclized compounds 420 (Scheme 129). 7,228,229 The same reaction had earlier been used to make peptide-heterocycle hybrids. 230,231 Scheme 129 T3P 159 in DIPEA has been used to prepare b-fused compounds 422 starting from either 3sulfanylpropanoic acid (190) or from N-acetylcysteine (187, R = NHAc) (Scheme 130).…”
Section: Scheme 128mentioning
confidence: 97%
“…Compounds with the 1,3-thiazin-4-one ring (Figure 1) have shown bioactivity in many areas, for example muscle relaxant, 1 antitubercular, 2,3 anticancer, [4][5][6] CXC chemokine receptor 4 (CXCR4) antagonism, 7 antimalarial, 3 antibacterial, 3,8 HIV-RT inhibition, 9 antifungal, 8 antiinflammatory, 10 antioxidant, 11 antihyperglycemic, 12 and cardioprotection. 13…”
Section: Introductionmentioning
confidence: 99%