Novel fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety: design, synthesis, crystal structure and biological evaluation was written by Wang, Qing-Qing;Zhang, Shu-Guang;Jiao, Jian;Dai, Peng;Zhang, Wei-Hua. And the article was included in Molecules in 2021.Computed Properties of C6H5ClO2 The following contents are mentioned in the article:
A series of fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety I [R1 = H, F; R2 = Me, CF3; R3 = H, Cl; R4 = H, Me, Bn, etc.] was designed, synthesized and evaluated for their antifungal activity. All the target compounds were determined by 1H-NMR, 13C-NMR, FTIR and HR-MS spectra. The single-crystal structures of compounds I [R1 = H, F R2 = Me, CF3, R3 = H, R4 = Et, propargyl, butyl] were further confirmed using X-ray diffraction. The preliminary bioassays showed that some of the designed compounds I displayed the promising antifungal activities against Botrytis cinerea (B. cinerea), Alternariasolani (A. solani), Gibberella zeae (G. zeae), Rhizoctorzia solani (R. solani), Colletotrichum orbiculare (C. orbiculare) and Alternaria alternata (A. alternata) were evaluated in vitro. The target compounds I [R1 = H, F; R2 = Me, CF3, R3 = H, R4 = allyl, butyl] exhibited outstanding antifungal activity against B. cinerea at 100μg/mL, with the corresponding inhibition rates reached 90.1 and 85.0%, which were better than the pos. control Osthole (83.6%) and Azoxystrobin (46.5%). The compound I [R1 = H; R2 = CF3, R3 = Cl, R4 = allyl] was identified as the promising fungicide candidate against B. cinerea with the EC50 values of 5.75μg/mL, which was obviously better than Osthole (33.20μg/mL) and Azoxystrobin (64.95μg/mL). The compound I [R1 = H; R2 = CF3, R3 = Cl, R4 = allyl] showed remarkable antifungal activities against R. solani with the EC50 values of 28.96μg/mL, which was better than Osthole (67.18μg/mL) and equivalent to Azoxystrobin (21.34μg/mL). The results provided a significant foundation for the search of novel fluorinated 7-hydroxycoumarin derivatives I with good antifungal activity. This study involved multiple reactions and reactants, such as 4-Chlororesorcinol (cas: 95-88-5Computed Properties of C6H5ClO2).
4-Chlororesorcinol (cas: 95-88-5) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Computed Properties of C6H5ClO2
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics