332079-42-2

Upstream product

• 15580-32-2 malonanilic acid 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 331-39-5 caffeic acid 
• 62-53-3 aniline 
• 121-33-5 vanillin 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 
• 331-39-5 caffeic acid 
• 861897-00-9 3,4-bis[(methoxycarbonyl)oxy]cinnamic acid 
• 5396-64-5 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 123019-93-2 (E)-[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]aminobenzene 

Relevant academic research and scientific papers

Evaluation of caffeic acid amide analogues as anti-platelet aggregation and anti-oxidative agents

A series of amides of caffeic acid were synthesized and evaluated for their anti-platelet and anti-oxidative activities. N-(2-Bromo-phenyl)-3-(3,4- dihydroxy-phenyl)-acrylamide (12) and N-(3-Bromo-phenyl)-3-(3,4-dihydroxy- phenyl)-acrylamide (13) exhibite

Synthesis of cinnamic amide derivatives and their anti-melanogenic effect in α-MSH-stimulated B16F10 melanoma cells

Of the three enzymes that regulate the biosynthesis of melanin, tyrosinase and its related proteins TYRP-1 and TYRP-2, tyrosinase is the most important because of its ability to limit the rate of melanin production in melanocytes. For treating skin pigmentation disorders caused by an excess of melanin, the inhibition of tyrosinase enzyme is by far the most established strategy. Cinnamic acid is a safe natural product with an (E)-β-phenyl-α,β-unsaturated carbonyl motif that we have previously shown to play an important role in high tyrosinase inhibition. Since cinnamic acid is relatively hydrophilic, which hinders its absorption on the skin, fifteen less hydrophilic cinnamic amide derivatives (1–15) were designed as safe and more potent tyrosinase inhibitors and were synthesized through a Horner-Wadsworth-Emmons reaction. The use of conc-HCl and acetic acid for debenzylation of the O-benzyl-protected cinnamic amides 40–54 produced the following three results. 1) Cinnamic amides 43, 48, and 53 with a 2,4-dibenzyloxyphenyl group, irrespective of the amine type of the amides, produced complex compounds with high polarity. 2) Cinnamic amides 40–42, 44, 50–52, and 54 with a benzylamino, or diethylamino group produced the desired debenzylated cinnamic amides 1–3, 5, 10–13, and 15. 3) Cinnamic amides 45–47, and 49 with an anilino moiety provided 3,4-dihydroquinolinones 16–19 through intramolecular Michael addition of the anilide group. Notably, the use of BBr3 as an alternative debenzylating agent for debenzylation of cinnamic amides 45–49 with the anilino moiety provided our desired cinnamic amides 6–10 without inducing the intramolecular Michael addition. Debenzylation of cinnamic amides 43, 48, and 53 with a 2,4-dibenzyloxyphenyl group was also successfully accomplished using BBr3 to give 4, 9, and 14. Among the nine compounds that inhibited mushroom tyrosinase more potently at 25 μM than kojic acid, four cinnamic amides 4, 5, 9, and 14 showed 3-fold greater tyrosinase inhibitory activity than kojic acid. The docking simulation using tyrosinase indicated that these four cinnamic amides (?6.2 to ?7.9 kcal/mol) bind to the active site of tyrosinase with stronger binding affinity than kojic acid (?5.7 kcal/mol). All four cinnamic amides inhibited melanogenesis and tyrosinase activity more potently than kojic acid in α-MSH-stimulated B16F10 melanoma cells in a dose-dependent manner without cytotoxicity. The strong correlation between tyrosinase activity and melanin content suggests that the anti-melanogenic effect of cinnamic amides is due to tyrosinase inhibitory activity. Considering that the cinnamic amides 4, 9, and 14, which exhibited strong inhibition on mushroom tyrosinase and potent anti-melanogenic effect in B16F10 cells, commonly have a 2,4-dihydroxyphenyl substituent, the 2,4-dihydroxyphenyl substituent appears to be essential for high anti-melanogenesis. These results support the potential of these four cinnamic amides as novel and potent tyrosinase inhibitors for use as therapeutic agents with safe skin-lightening efficiency.

Novel Chlorogenic Acid Derivatives and Composition for Treating Inflammatory Disease Comprising the Same

The present invention relates to a novel chlorogenic acid derivative compound having anti-inflammatory activities and an anti-inflammatory composition comprising the same as an active ingredient. The chlorogenic acid derivative compound of the present invention inhibits overproduction of nitrogen oxide (NO) induced by treating LPS in macrophage. The chlorogenic acid derivative compound of the present invention suppresses activation of NF-κB which is a signal transmission-mediated transcription factor significant in an oxidative stress and inflammation-promoting path. The chlorogenic acid derivative compound of the present invention can be developed as medicine for various inflammatory diseases by inhibiting overproduction of nitrogen oxide and activation of NF-κB.

Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis

We have disclosed our effort to develop caffeic acid derivatives as potent and non-toxic inhibitors of α-MSH-stimulated melanogenesis to treat pigmentation disorders and skin medication including a cosmetic skin-whitening agent. The SAR studies revealed t

Skin Whitening Composition Comprising Caffeic Acid Derivatives as the Active Ingredients

The present invention relates to a skin whitening composition containing a new caffeic acid derivative compound as an active ingredient. According to the present invention, the caffeic acid derivative compound can be developed for a skin whitening cosmetic product or for a medicine for the hyperpigmentation of melanin because having skin whitening activity by inhibiting the biosynthesis of melanin in melanocytes.

Novel Chlorogenic Acid Derivatives and Composition for Treating Inflammatory Disease Comprising the Same

The present invention relates to a novel chlorogenic acid derivative compound having anti-inflammatory activities and to an anti-inflammatory composition including the same as an active ingredient. The chlorogenic acid derivative compound of the present invention controls the overproduction of nitrogen oxide (NO) derived by the treatment of LPS in histiocytes. The chlorogenic acid derivative compound of the present invention inhibits the activation of NF-κB which is an important signal transmittal intermediated transcription factor in oxidant stress and inflammation promoting routes. The chlorogenic acid derivative compound of the present invention has a high possibility of being developed into an agent for treating various inflammatory diseases by inhibiting the overproduction of NO and the activation of NF-κB.

Design, synthesis, and evaluation of caffeic acid amides as synergists to sensitize fluconazole-resistant Candida albicans to fluconazole

A series of caffeic acid amides were designed, synthesized, and their synergistic activity with fluconazole against fluconazole-resistant Candida albicans was evaluated in vitro. The title caffeic acid amides 3-30 except 26 exhibited potent activity, and the subsequent SAR study was conducted. Compound 3, 5, 21, and 34c, at a concentration of 1.0 μg/ml, decreased the MIC80 of fluconazole from 128.0 μg/ml to 1.0-0.5 μg/ml against the fluconazole-resistant C. albicans. This result suggests that the caffeic acid amides, as synergists, can sensitize drug-resistant fungi to fluconazole. The SAR study indicated that the dihydroxyl groups and the amido groups linking to phenyl or heterocyclic rings are the important pharmacophores of the caffeic acid amides.

Design, synthesis and biological evaluation of caffeic acid amides as selective MMP-2 and MMP-9 inhibitors

Strategy, Management and Health Policy Preclinical Research A series of caffeic acid amides with extended P1' groups were synthesized and tested for their inhibitory activities on matrix metalloproteinase (MMP)-1, MMP-2, and MMP-9. Compound 3f showed considerable inhibitory activities against MMP-2, MMP-9, and best selectivity over MMP-1. Preliminary structure-activity relationship analysis and docking studies indicated that caffeic acid amides with electron-donating groups at p-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups. The findings of this study would provide information for the exploitation and utilization of caffeic acid as MMP inhibitor for metastatic tumor treatment.

Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials

A series of caffeic acid amides 1-23 were synthesized and nine of which (13-17, 19-21 and 23) were reported for the first time. The chemical structures of these compounds were confirmed by means of 1H NMR, ESI MS and elemental analyses. Compound 15 was determined by single-crystal X-ray diffraction analysis. All of the compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT method. Compounds 10-12, 15, 18 and 21 showed considerable antibacterial activities against B. subtilis with MICs of 7.95, 6.25, 3.89, 1.18, 3.12 and 15.5?μg/mL, respectively. Structure-activity relationship analysis disclosed that caffeic acid anilides with electron-donating groups at p-position of benzene ring have better inhibitory activities.

Design, synthesis, and discovery of stilbene derivatives based on lithospermic acid B as potent protein tyrosine phosphatase 1B inhibitors

Dihydroxy stilbene derivatives were designed based on lithospermic acid B and were prepared from 4-(chloromethyl)benzoic acid. The inhibitory activities of the novel compounds against protein tyrosine phosphatase 1B (PTP1B) were evaluated. 3,4-Dihydroxy stilbene carbonyl compounds (7, 11b, 27b) inhibited PTP1B with IC50 values comparable to molybdate, while the conjugation-extended compound (15b) showed inhibition 3-fold better than preclinical RK682. The introduction of electron withdrawing groups or amides into the second phenyl ring, or extension of the conjugation into the stilbene molecule may increase stability of the generated radicals.