- Synthesis of amide and ester derivatives of cinnamic acid and its analogs: Evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities
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A series of cinnamic acid derivatives, amides (1–12) and esters (13–22), were synthesized, and structure–activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1–10, 12–18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxy-indole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9–11, 15, 17–22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer’s disease.
- Takao, Koichi,Toda, Kazuhiro,Saito, Takayuki,Sugita, Yoshiaki
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p. 1020 - 1027
(2017/11/17)
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- Novel c-Met inhibitory olive secoiridoid semisynthetic analogs for the control of invasive breast cancer
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Dysregulated receptor tyrosine kinase c-Met and its ligand HGF is valid and attractive molecular target for therapeutic blockade in cancer. Inspired by the chemical structure of the naturally occurring olive secoiridoid (-)-oleocanthal (1) and its documen
- Mohyeldin, Mohamed M.,Busnena, Belnaser A.,Akl, Mohamed R.,Dragoi, Ana Maria,Cardelli, James A.,El Sayed, Khalid A.
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supporting information
p. 299 - 315
(2016/06/09)
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- Inhibition of mammalian carbonic anhydrase isoforms I-XIV with a series of phenolic acid esters
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A series of phenolic acid esters incorporating caffeic, ferulic, and p-coumaric acid, and benzyl, m/p-hydroxyphenethyl- as well as p-hydroxy-phenethoxy-phenethyl moieties were investigated for their inhibitory effects against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Many of the mammalian isozymes of human (h) or murine (m) origin, hCA I-hCA XII, mCA XIII and hCA XIV, were inhibited in the submicromolar range by these derivatives (with KIs of 0.31-1.03 μM against hCA VA, VB, VI, VII, IX and XIV). The off-target, highly abundant isoforms hCA I and II, as well as hCA III, IV and XII were poorly inhibited by many of these esters, although the original phenolic acids were micromolar inhibitors. These phenols, like others investigated earlier, possess a CA inhibition mechanism distinct of the sulfonamides/sulfamates, clinically used drugs for the treatment of a multitude of pathologies, but with severe side effects due to hCA I/II inhibition. Unlike the sulfonamides, which bind to the catalytic zinc ion, phenols are anchored at the Zn(II)-coordinated water molecule, binding more externally within the active site cavity, and making contacts with amino acid residues at the entrance of the active site. As this is the region with the highest variability between the many CA isozymes found in mammals, this class of compounds shows isoform-selective inhibitory profiles, which may be exploited for obtaining pharmacological agents with less side effects compared to other classes of inhibitors.
- Maresca, Alfonso,Akyuz, Gulay,Osman, Sameh M.,Alothman, Zeid,Supuran, Claudiu T.
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p. 7181 - 7188
(2015/11/16)
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- PARA-COUMARIC ACID OR PARA-HYDROXYCINNAMIC ACID DERIVATIVES AND THEIR USE IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS
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The invention relates to the use of para-coumaric acid or para-hydroxycinnamic acid derivatives in cosmetic or derma-tological compositions, specifically to the use of at least one compound derived from para-coumaric acid having a general formula (I) below: in which, especially, Z represents an oxygen or an -NH- group; X and Y are identical and each represent a CH or CH2 group, as an active principle with depigmenting, free-radical- scavenging and/or antiinflammatory activity. The invention also relates to the use of the above compounds for cosmetic care or for the preparation of a pharmaceutical composition, especially for depigmenting an area of skin, having antiradi-cal and/or antiinflammatory activity
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Page/Page column 7
(2010/11/28)
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