27676-31-9

Basic information

• Product Name: Benzenepropanoic acid, 4-cyclohexyl-b-hydroxy-b-methyl-, ethyl ester
• CAS NO: 27676-31-9
• Molecular Formula: C18H26O3
• Molecular Weight: 290.403
• Mol File: 27676-31-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, 4-cyclohexyl-b-hydroxy-b-methyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, 4-cyclohexyl-b-hydroxy-b-methyl-, ethyl ester(27676-31-9)
• EPA Substance Registry System: Benzenepropanoic acid, 4-cyclohexyl-b-hydroxy-b-methyl-, ethyl ester(27676-31-9)

Safety Data

• Hazardous Substances Data: 27676-31-9(Hazardous Substances Data)

Upstream product

• 18594-05-3 4-cyclohexylacetophenone 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 610781-37-8 3-(4-cyclohexylphenyl)-1-hydroxy-but-3-en-2-hydroperoxide 
• 610781-36-7 3-(4-cyclohexylphenyl)-2-butenol 
• 610781-35-6 ethyl 3-hydroxy-3-(4'-cyclohexylphenyl)-but-2-enoate 

Relevant articles and documents

Design, Synthesis, Structure-Activity Relationship and Docking Studies of Novel Functionalized Arylvinyl-1,2,4-Trioxanes as Potent Antiplasmodial as well as Anticancer Agents

A novel series of synthetic functionalized arylvinyl-1,2,4-trioxanes (8 a–p) has been prepared and assessed for their in vitro antiplasmodial activity against the chloroquine-resistant Pf INDO strain of Plasmodium falciparum by using a SYBR green-I fluorescence assay. Compounds 8 g (IC50=0.051 μM; SI=589.41) and 8 m (IC50=0.059 μM; SI=55.93) showed 11-fold and >9-fold more potent antiplasmodial activity, respectively, as compared to chloroquine (IC50=0.546 μM; SI=36.63). Different in silico docking studies performed on many target proteins revealed that the most active arylvinyl-1,2,4-trioxanes (8 g and 8 m) showed dihydrofolate reductase (DHFR) binding affinities on a par with those of chloroquine and artesunate. The in vitro cytotoxic potentials of 8 a–p were also evaluated against human lung (A549) and liver (HepG2) cancer cell lines along with immortalized normal lung (BEAS-2B) and liver (LO2) cell lines. Following screening, five derivatives viz. 8 a, 8 h, 8 l, 8 m and 8 o (IC50=1.65–31.7 μM; SI=1.08–10.96) were found to show potent cytotoxic activity against (A549) lung cancer cell lines, with selectivity superior to that of the reference compounds artemisinin (IC50=100 μM), chloroquine (IC50=100 μM) and artesunic acid (IC50=9.85 μM; SI=0.76). In fact, the most active 4-naphthyl-substituted analogue 8 l (IC50=1.65 μM; SI >10) exhibited >60 times more cytotoxicity than the standard reference, artemisinin, against A549 lung cancer cell lines. In silico docking studies of the most active anticancer compounds, 8 l and 8 m, against EGFR were found to validate the wet lab results. In summary, a new series of functionalized aryl-vinyl-1,2,4-trioxanes (8 a–p) has been shown to display dual potency as promising antiplasmodial and anticancer agents.

NOVEL SUBSTITUTED 1,2,4-TRIOXANES USEFUL AS ANTIMALARIAL AGENTS AND A PROCESS FOR THE PREPARATION THEREOF

In the present invention relates to a novel series of antimalarial 1,2,4-trioxanes analogues of general formula (7), wherein R represents cycloalkyl groups selected from the groups consisting of cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl or aryl