90729-87-6

Upstream product

• 7400-08-0 para-coumaric acid 
• 3943-97-3 methyl p-hydroxycinnamate 
• 3011-34-5 4-hydroxy-3-nitrobenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 5927-18-4 trimethyl phosphonoacetate 

Downstream Products

• 1593841-33-8 3-(4-hydroxy-3-((2E,4E)-7-methylocta-2,4-dienamido)phenyl)propanoic acid 

Relevant academic research and scientific papers

Aaph or peroxynitrite‐induced biorelevant oxidation of methyl caffeate yields a potent antitumor metabolite

Hydroxycinnamic acids represent a versatile group of dietary plant antioxidants. Oxidation of methyl‐p‐coumarate (pcm) and methyl caffeate (cm) was previously found to yield potent antitumor metabolites. Here, we report the formation of potentially bioactive products of pcm and cm oxidized with peroxynitrite (ONOOˉ), a biologically relevant reactive nitrogen species (RNS), or with α,α′‐azodiisobutyramidine dihydrochloride (AAPH) as a chemical model for reactive oxygen species (ROS). A continuous flow system was developed to achieve reproducible in situ ONOOˉ formation. Reaction mixtures were tested for their cytotoxic effect on HeLa, SiHa, MCF‐7 and MDA‐MB‐231 cells. The reaction of pcm with ONOOˉ produced two fragments, an o‐ nitrophenol derivative, and a new chlorinated compound. Bioactivity‐guided isolation from the reaction mixture of cm with AAPH produced two dimerization products, including a dihydrobenzofuran lignan that exerted strong antitumor activity in vitro, and has potent in vivo antimetastatic activity which was previously reported. This compound was also detected from the reaction between cm and ONOOˉ. Our results demonstrate the ROS/RNS dependent formation of chemically stable metabolites, including a potent antitumor agent (5), from hydroxycinnamic acids. This suggests that diversity‐oriented synthesis using ROS/RNS to obtain oxidized antioxidant metabolite mixtures may serve as a valid natural product‐based drug discovery strategy.

Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents

Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.

Total synthesis of Carpatamides A–D

A synthetic strategy was developed for the synthesis of the common core structure of Carpatamides A–D. The total synthesis of Carpatamides A and C was completed in 6 steps and of Carpatamides B and D in 7 steps, by employing the Wittig olefination, olefin

Topical anti-inflammatory activity of boropinic acid and its natural and semi-synthetic derivatives

Boropinic acid is a natural isopentenyloxycinnamic acid extracted from the aerial parts of Boronia pinnata Sm. (Rutaceae) with soybean 5-lipoxygenase inhibitory activity. In this paper the topical anti-inflammatory activity of boropinic acid and some of its natural and semi-synthetic derivatives was evaluated using the Croton oil ear test in mice as a model of acute inflammation. Some of the tested compounds (15, 17, 19, 20) revealed an effect comparable (ID50 = 0.18 ÷ 0.72 μmol/cm2) to that of the reference drug indomethacin (ID50 = 0.23 μmol/cm 2), a non-steroidal anti-inflammatory drug.