1609627-89-5

Basic information

• Product Name: (2E)-1-(4-chlorophenyl)-3-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenyl]prop-2-en-1-one
• Synonyms: (2E)-1-(4-chlorophenyl)-3-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenyl]prop-2-en-1-one
• CAS NO: 1609627-89-5
• Molecular Weight: 328.795
• Mol File: 1609627-89-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2E)-1-(4-chlorophenyl)-3-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenyl]prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-chlorophenyl)-3-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenyl]prop-2-en-1-one(1609627-89-5)
• EPA Substance Registry System: (2E)-1-(4-chlorophenyl)-3-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenyl]prop-2-en-1-one(1609627-89-5)

Safety Data

• Hazardous Substances Data: 1609627-89-5(Hazardous Substances Data)

Upstream product

• 20240-58-8 3-allyl-4-hydroxy-5-methoxybenzaldehyde 
• 99-91-2 para-chloroacetophenone 
• 22280-95-1 4-allyloxy-3-methoxybenzaldehyde 
• 121-33-5 vanillin 

Relevant articles and documents

Design, economical synthesis and antiplasmodial evaluation of vanillin derived allylated chalcones and their marked synergism with artemisinin against chloroquine resistant strains of Plasmodium falciparum

The in vitro blood stage antiplasmodial activity of a series of allylated chalcones based on the licochalcone A as lead molecule was investigated against chloroquine (CQ) sensitive Pf3D7 and CQ resistant PfINDO strains of Plasmodium falciparum using SYBR Green I assay. Of the forty two chalcones tested, eight showed IC50 ≥ 5 μM. Structure-activity relationship (SAR) studies revealed 9 {1-(4-Chlorophenyl)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl] -prop-2-en-1-one} as the most potent (IC∑: 2.5 μM) against Pf3D7 with resistance indices of 1.2 and 6.6 against PfDd2 and PfINDO strains, respectively. Later on, the synergistic effects 9 with standard antimalarials {artemisinin (ART) and chloroquine (CQ)} were studied in order to provide the basis for the selection of the best partner drug. In vitro combinations of 9 with ART showed strong synergy against PfINDO (ΣFIC∑: 0.31-0.72) but additive to slight antagonistic effects (ΣFIC∑: 1.97-2.64) against Pf3D7. ΣFIC∑ 0.31 of ART+9 combination corresponded to a 320 fold and 3 fold reduction in IC∑ of 9 and ART, respectively. Similar combinations of 9 with CQ showed synergy to additivity to mild antagonism against the two strains {ΣFIC∑: 0.668-2.269 (PfINDO); 1.45-2.83 (Pf3D7)}. Drug exposure followed by drug withdrawal indicated that 9 taken alone at IC∑ killed rings, trophozoites and schizonts of P. falciparum. The combination of ART and 9 (1X ΣFIC∑) selectively inhibited the growth of rings while the 2X ΣFIC∑ combination of the same caused killing of rings without affecting trophozoites and schizonts. In contrast, the 1X combination of CQ and 9 (ΣFIC ∑: 0.5) killed rings and trophozoites. DNA fragmentation and loss of mitochondrial membrane potential (ΔΨm) in the 9 treated P. falciparum culture indicated apoptotic death in malaria parasites. Prediction of ADME properties revealed that most of the molecules did not violate Lipinski's parameters and have low TPSA value suggesting good absorption. The results suggest the promising drug-like properties of 9 against CQ resistant Pf and propensity for synergy with classical antimalarial drugs together with easy and economical synthesis.