(S)-5-Hexyl-1-[(S)-2-hydroxy-1-phenylethyl]-4-methoxy-1H-pyrrol-2(5H)-one
نویسندگان
چکیده
The title compound, C(19)H(27)NO(3), was obtained by the reaction of (3S,7aR)-7a-hexyl-7-meth-oxy-3-phenyl-2,3-dihydro-pyrrolo[2,1-b]oxazol-5(7aH)-one and triethyl-silane using titanium(IV) chloride as catalyst. In the mol-ecule, the phenyl and dihydro-pyrrolone rings form a dihedral angle of 83.8 (1)°. O-H⋯O hydrogen-bonding inter-actions lead to the formation of a chain parallel to the a axis.
منابع مشابه
Antitumor Activity of a 5-Hydroxy-1H-Pyrrol-2-(5H)-One-Based Synthetic Small Molecule In Vitro and In Vivo
Alternative chemo-reagents are in great demand because chemotherapy resistance is one of the major challenges in current cancer treatment. 5-hydoxy-1H-pyrrol-2-(5H)-one is an important N-heterocyclic scaffold that is present in natural products and medicinal chemistry. However, its antitumor activity has not been systematically explored. In this study, we screened a panel of 5-hydoxy-1H-pyrrol-...
متن کاملDiaryl- and triaryl-pyrrole derivatives: inhibitors of the MDM2–p53 and MDMX–p53 protein–protein interactions† †Electronic supplementary information (ESI) available: Experimental details for compound synthesis, analytical data for all compounds and intermediates. Details for the biological evaluation. Further details for the modeling. Table of combustion analysis data. See DOI: 10.1039/c3md00161jClick here for additional data file.
Screening identified 2-(3-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl)-2,5-dimethyl-1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile as an MDM2-p53 inhibitor (IC50 = 12.3 μM). MDM2-p53 and MDMX-p53 activity was seen for 5-((1-(4-chlorophenyl)-2,5-diphenyl-1H-pyrrol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (MDM2 IC50 = 0.11 μM; MDMX IC50 = 4.2...
متن کاملDesign, Synthesis, and Structure−Activity Relationship Exploration of 1-Substituted 4-Aroyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-one Analogues as Inhibitors of the Annexin A2−S100A10 Protein Interaction
S100 proteins are small adaptors that regulate the activity of partner proteins by virtue of direct protein interactions. Here, we describe the first small molecule blockers of the interaction between S100A10 and annexin A2. Molecular docking yielded candidate blockers that were screened for competition of the binding of an annexin A2 peptide to S100A10. Several inhibitory clusters were identif...
متن کاملPreparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol- 2(5H)-one derivatives using 1-methylpiperidinium hydrogen sulfate as an efficient catalyst
A highly efficient and environmentally friendly synthesis of various 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones catalyzed by 1-methylpiperidinium hydrogen sulfate via one-pot cyclo-condensation reaction ofaldehydes, amines and ethyl 2-oxopropanoate under ambient conditions has been explored. The presentmethodology offers several advantages such as good yields, simple procedure, shorter react...
متن کامل(5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one
The title compound, C(18)H(26)ClNO(3), was obtained via a tandem asymmetric Michael addition-elimination reaction of 3,4-dichloro-5-(S)-(l-menth-yloxy)furan-2(5H)-one and 2,5-di-hydro-1H-pyrrole in the presence of potassium fluoride. In the mol-ecule, the nearly planar dihydro-pyrrole ring [maximum atomic deviation = 0.019 (3) Å] is oriented at a dihedral angle of 10.73 (8)° to the the nearly p...
متن کامل