Roggen, Heidi; Bohlin, Lars; Burman, Robert; Charnock, Colin; Felth, Jenny; Gorbitz, Carl Henrik; Larsson, Rolf; Tamm, Toomas; Gundersen, Lise-Lotte; IUPAC Commission published the artcile< 2-substituted agelasine analogs: synthesis and biological activity, and structure and reactivity of synthetic intermediates>, Formula: C6H4Cl2N4, the main research area is purine agelasine analog synthesis tautomerization antimicrobial activity; anticancer cytotoxicity purine agelasine analog synthesis; protozoacide activity purine agelasine analog synthesis; fungicide activity purine agelasine analog synthesis; DFT B3LYP calculation tautomer structure purine agelasine analog synthesis; hydrogen bonding purine agelasine analog synthesis; antibacterial activity purine agelasine analog synthesis; antimycobacterial activity purine agelasine analog synthesis; crystal structure purine agelasine analog synthesis.
2-Substituted N-methoxy-9-methyl-9H-purin-6-amines, such as I [R2 = H, Me, NHMe, NMe2, OEt, OMe, CF3, Cl, NO2, R7 = CH2Ph; R2 = H, Me, NHMe, NMe2, OEt, OMe, CF3, Cl, NO2, OH, R7 = geranylgeranyl], were synthesized either from their corresponding 6-chloro-9-methyl-9H-purines or 2-chloro-N-methoxy-9-methyl-9H-purin-6-amine. Great diversity in the amino/imino tautomeric ratios was observed and calculated based on 1H NMR. The tautomers were identified by 1D and 2D 1H, 13C, and 15N NMR techniques, and showed significant variation both in 13C and 15N shift values. Comparison of the tautomeric ratios with Hammett F values revealed that as the field/inductive withdrawing abilities of the 2-substituent increased, the ratio of amino:imino tautomers was shifted toward the amino tautomer. Computational chem. exposed the significance of hydrogen bonding between solvent and the compound in question to reach accurate predictions for tautomeric ratios. B3LYP/def2-TZVP d. functional theory (DFT) calculations resulted in quant. more accurate predictions than when employing the less expensive BP86 functional. N-7-Alkylation of the 2-substituted N-methoxy-9-methyl-9H-purin-6-amines showed that when the field/inductive withdrawing ability of the 2-substituent reached a certain point the reactivity drastically dropped. This correlated with the at. charges on N-7 calculated using a natural bond orbital (NBO) anal. Biol. screening of the 2-substituted agelasine geranylgeralyl analogs indicated that the introduction of a Me group in the 2-position is advantageous for antimycobacterial and antiprotozoal activity, and that an amino function may improve activity against several cancer cell lines.
Pure and Applied Chemistry published new progress about Antibacterial agents. 2382-10-7 belongs to class chlorides-buliding-blocks, and the molecular formula is C6H4Cl2N4, Formula: C6H4Cl2N4.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics