Synthesis and isomerization of acridine substituted 1,3-thiazolidin-4-ones and 4-oxo-1,3-thiazolidin-5-ylidene acetates. An experimental and computational study

Design, Synthesis, Biological Evaluation, and Computational Studies of Novel Fluorinated Candidates as PI3K Inhibitors: Targeting Fluorophilic Binding Sites

“…In the aromatic region, there are six protons morein comparison to 5a – e corresponding to five protons of the phenyl group at C4 and the proton at C5 of the thiazole ring that is originated from the methylene group of phenacyl bromide and has been noticed at δ H 6.0–8.0 ppm (Figures S10–S15). Stereochemistry of compounds 6a – e was recognized as Z for the imine bond at position 2 of the thiazole ring and E for the imine bond originated from the aldehyde moiety, which was also confirmed as E -configuration by X-ray of compound 5c (Figure ).…”

1H, 13C and 15N NMR of spiro acridines integrated with pyrrole scaffolds

“…Although the derivatives 2b-i are known (Scheme 2), their 15 N NMR chemical shifts and coupling constants 1 J C7/H7 had not been previously published. [19] The pairs of isomers of 2a-i differ in configuration of the amide C4─N5 bond ( Figure 1). The geometric configuration of N6═C7 double bond was resolved on the basis of heteronuclear coupling constants ( 1 J C7/H7 = 162.6-171.6 Hz, Table S8), [18] which indicated its E configuration in isomers 2a-i, as we previously reported.…”

“…Geometric configuration of the N6═C7 double bond in 5a,b,e was resolved by a heteronuclear coupling constant 1 J H7/C7 with values 166.2 Hz for 5b ( Figure S48), 165.6 Hz for 5c ( Figure S52), and 168.6 Hz for 5e and 5f, ( Figures S60 and S64), and by a value of 2 J H7/ N6~0 Hz (see 1 H, 15 N-HMBC spectra in SI), [18] which 13 C and 15 N NMR chemical shifts of the both isomers of derivative 2a together with numbering of atoms all indicated the N6═C7 double bond to be in the E configuration ( Figure 6). [19] 2.1 | Comparison of 1 H and 13 C chemical shifts of 5b,g with already published data The published NMR spectral data for derivatives 5b,g in de Almeida et al [15] contain partly an incorrect information. [19] 2.1 | Comparison of 1 H and 13 C chemical shifts of 5b,g with already published data The published NMR spectral data for derivatives 5b,g in de Almeida et al [15] contain partly an incorrect information.…”

“…However, the authors wrongly assigned the signal δ H = 6.89 ppm to the protons H-4′,5′ of the acridine core and that δ H = 6.99 ppm to the p-disubstituted phenyl ring. [19] 3 | EXPERIMENTAL Compounds 5a-i were prepared by reacting the appropriate cyanoacetohydrazide 2 and acridin-9-carbaldehyde (1a, see SI). Third, they interchanged resonances of aromatic phenyl carbons C-3″,5″ and C-4″ in the derivative AMTAC-01 (our 5b).…”

Synthesis, In Silico Prediction and In Vitro Evaluation of Antimicrobial Activity, DFT Calculation and Theoretical Investigation of Novel Xanthines and Uracil Containing Imidazolone Derivatives

“…All calculated bond distances, bond angles and dihedral angles between the atoms of the compound 13 are given in (Table S2). The C5-S8 bond length is 1.692 Å [53] and the C3-O7 bond length is 1.209 Å [50], while the C13-O17 bond length is 1.208 Å [50].…”