91963-08-5

Usage

InChI:InChI=1/C12H12O3/c1-2-9-15-11-6-4-3-5-10(11)7-8-12(13)14/h2-8H,1,9H2,(H,13,14)/b8-7+

Upstream product

• 91-64-5 coumarin 
• 106-95-6 allyl bromide 
• 28752-82-1 2-(allyloxy)benzaldehyde 
• 141-82-2 malonic acid 
• 614-60-8 o-Coumaric acid 

Downstream Products

• 1350704-73-2 C₁₂H₁₄Br₂O₂ 
• 1350704-57-2 C₁₁H₁₂Br₂O₂ 
• 928214-88-4 2'-(2-allyloxycinnamoyloxy)-4',6'-dimethoxyacetophenone 

Relevant academic research and scientific papers

A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines

A photocatalytic method for the α-selective hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of α-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the α-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group at the β-position. Simple scale-up is demonstrated under continuous flow conditions, highlighting the practicality of the method.

Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases

The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel acetylcholinesterase (EeAChE) and horse serum butyrylcholinesterase (hBChE) and some of the compounds appeared as moderately potent inhibitors of EeAChE and hBChE. The compound 3-(2-(Benzyloxy)phenyl)-N- (3,4,5-trimethoxyphenyl)acrylamide (3i) showed maximum activity against EeAChE with an IC50 0.29 ± 0.21 μM whereas 3-(2-chloro-6- nitrophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide (3k) was proved to be the most potent inhibitor of hBChE having IC50 1.18 ± 1.31 μM. To better understand the enzyme-inhibitor interaction of the most active compounds toward cholinesterases, molecular modelling studies were carried out on high-resolution crystallographic structures. The anticancer effects of synthesized compounds were also evaluated against cancer cell line (lung carcinoma). The compounds may be useful leads for the design of a new class of anticancer drugs for the treatment of cancer and cholinesterase inhibitors for Alzheimer's disease (AD).

Synthesis of n′-allyl-2-styrylchromones by a Baker Venkataraman transformation

n′-allyl-2-styrylchromones have been prepared by the Baker-Venkataraman method, by two different synthetic routes, both of them involving a Claisen rearrangement. The two synthetic routes were compared in terms of yields and practical execution. All compo