19367-38-5Relevant academic research and scientific papers
Synthesis of n-hydroxycinnamides capped with a naturally occurring moiety as inhibitors of histone deacetylase
Huang, Wei-Jan,Chen, Ching-Chow,Chao, Shi-We,Lee, Shoei-Sheng,Hsu, Fen-Lin,Lu, Yeh-Lin,Hung, Ming-Fang,Chang, Chung-I
, p. 598 - 607 (2010)
Histone deacetylase (HDAC) inhibitors are regarded as promising therapeutics for the treatment of cancer. All reported HDAC inhibitors contain three pharmacophoric features: a zinc-chelating group, a hydrophobic linker, and a hydrophobic cap for surface recognition. In this study we investigated the effectiveness of osthole, a hydrophobic Chinese herbal compound, as the surface recognition cap in hydroxamate-based compounds as inhibitors of HDAC. Nine novel osthole-based N-hydroxycinnamides were synthesized and screened for enzyme inhibition activity. Compounds 9d, 9e, 9g exhibited inhibitory activities (IC50=24.5, 20.0, 19.6 nm) against nuclear HDACs in HeLa cells comparable to that of suberoylanilide hydroxamic acid (SAHA; IC 50=24.5 nm), a potent inhibitor clinically used for the treatment of cutaneous T-cell lymphoma (CTCL). While compounds 9d and 9e showed SAHA-like activity towards HDAC1 and HDAC6, compound 9g was more selective for HDAC1. Compound 9d exhibited the best cellular effect, which was comparable to that of SAHA, of enhancing acetylation of either a-tubulin or histone H3. Molecular docking analysis showed that the osthole moiety of compound 9d may interact with the same hydrophobic surface pocket exploited by SAHA and it may be modified to provide class-specific selectivity. These results suggest that osthole is an effective hydrophobic cap when incorporated into N-hydroxycinnamide-derived HDAC inhibitors.
Nitrification inhibitors from the root tissues of Brachiaria humidicola, a tropical grass
Gopalakrishnan, Subramaniam,Subbarao, Guntur V.,Nakahara, Kazuhiko,Yoshihashi, Tadashi,Ito, Osamu,Maeda, Ikuko,Ono, Hiroshi,Yoshida, Mitsuru
, p. 1385 - 1388 (2007)
Nitrification inhibitory activity was found in root tissue extracts of Brachiaria humidicola, a tropical pasture grass. Two active inhibitory compounds were isolated by activity-guided fractionation, using recombinant Nitrosomonas europaea containing luxAB genes derived from the bioluminescent marine gram-negative bacterium Vibrio harveyi. The compounds were identified as methyl-p-coumarate and methyl ferulate, respectively. Their nitrification inhibitory properties were confirmed in chemically synthesized preparations of each. The IC50 values of chemically synthesized preparations were 19.5 and 4.4 μM, respectively. The ethyl, propyl, and butyl esters of p-coumaric and ferulic acids inhibited nitrification, whereas the free acid forms did not show inhibitory activity.
Cyclopalladated complexes of tertiary arylamines as highly efficient catalysts using in the Heck reactions
Yang, Fan,Zhang, Yangming,Zheng, Rui,Tang, Jie,He, Mingyuan
, p. 146 - 148 (2002)
Cyclopalladated complexes of tertiary arylamines are reported in this paper as highly efficient catalysts for the Heck reactions of iodoarenes with methylacrylate. The monomeric complexes (2 and 4), which contain mixed phosphorous-nitrogen (P-N) donors, w
Renewable benzoxazine monomers from Lignin-like naturally occurring phenolic derivatives
Comí, Marc,Lligadas, Gerard,Ronda, Juan C.,Galià, Marina,Cádiz, Virginia
, p. 4894 - 4903 (2013)
The benzoxazines of three naturally occurring phenylpropanoid phenols: ferulic, coumaric, and phloretic acids, and their esters are described. Benzoxazines with conjugated unsaturated chains exhibit unusual poor thermal stability and degrade partially at the polymerization temperature making necessary the use of a catalyst (BF3.Et2O) to low the polymerization temperature and prevent degradation. Polybenzoxazines are prepared thermally and characterized by DSC and TGA techniques. The resulting materials have superior Tgs when compared with those prepared from an unsubstituted monofuctional benzoxazine due to the additional crosslinking through the ester and carboxylic moieties.
Synthesis of alkyl coumarate esters by celite-bound lipase of Bacillus licheniformis SCD11501
Sharma, Shivika,Dogra, Priyanka,Chauhan, Ghanshyam S.,Kanwar, Shamsher S.
, p. 80 - 86 (2014)
Coumaric acid and its derivatives are known to inhibit UV-induced melanogenesis, skin erythema, angiogenesis, platelet accumulation and osteoclastogenesis besides regulation of bone formation, anti-oxidant and anti-microbial activities. The present study is a novel piece of work in which the syntheses of a series of alkyl coumarates (methyl coumarate, ethyl coumarate, propyl coumarate and butyl coumarate) have been achieved using celite-immobilized lipase of Bacillus licheniformis strain SCD11501 in a water-free medium at 55 C under shaking in a chemical reactor. The maximum yield(s) of coumaric acid based esters i.e. methyl coumarate (69.0%), ethyl coumarate (63.1%), n-propyl coumarate (59.8%) and n-butyl coumarate (55.1%) using celite-immobilized lipase could be achieved after optimizing various reaction parameters such as incubation time, incubation temperature, relative molar concentration of reactants, biocatalyst concentration and amount of molecular sieves added to the reaction system. Molecular sieves had an important effect on the ester synthesis resulting in an enhanced yield. Maximum yield was recorded for methyl coumarate (69.0%) possibly because methyl group causes less stearic hindrance to the catalytic site of the lipase due to which it becomes more accessible for immobilized lipase to undergo esterification. The characterization of synthesized esters was done through FTIR spectroscopy and 1H NMR spectra.
Induction of phenolic compounds in two cultivars of cucumber by treatment of healthy and powdery mildew-infected plants with extracts of Reynoutria sachalinensis
Daayf, Fouad,Ongena, Marc,Boulanger, Renald,El Hadrami, Ismail,Belanger, Richard R.
, p. 1579 - 1593 (2000)
Accumulation of phenolic compounds (p-coumaric, caffeic, and ferulic acids and p-coumaric acid methyl ester) was followed in susceptible (Mustang) and tolerant (Flamingo) cucumber (Cucumis sativus) cultivars. The objective was to determine whether these compounds played a role in resistance against powdery mildew following a prophylactic treatment with Milsana (leaf extracts from the giant knot weed Reynoutria sachalinensis, polygonaceae). This treatment significantly reduced the incidence of powdery mildew in both cultivars. Phenolic compounds were extracted from leaves. In the hydrolyzed fraction containing phenolic aglycones, levels of p-coumaric, caffeic, and ferulic acids and of p-coumaric acid methyl ester increased in all treatments (with leaf extracts of R. Sachalinensis, powdery mildew, or both) except the control, one or two days after treatment. In the fraction containing free phenolics, from the tested compounds, only ferulic acid showed an increase in cv. Flamingo (tolerant), and was particularly evident following treatments. On the other hand, the amounts of hydroxycinnamic acids increased rapidly in the two cultivars following Milsana treatment, suggesting their role in disease reduction. All compounds showed antifungal activity when tested against common pathogens of cucumber (Botrytis cinerea, Pythium ultimum, and P. aphanidermatum), but in general methyl esters were more fungitoxic than their corresponding free acids. This study suggests that cucumber is able to release antifungal compounds that are instrumental in repressing powdery mildew infection. This response is seemingly independent from the level of genetic resistance associated with each cultivar.
A novel glycopolymeric ultraviolet absorber covering UV-A and UV-B ranges
Tang, Yanfeng,Gao, Pengfei,Wang, Miao,Zhu, Jinli,Wan, Xiangjian
, p. 22617 - 22620 (2014)
In this communication, a novel biocompatible polymeric ultraviolet absorber (UVA), poly(HAB-co-OAG-co-AMC) (PHOA), covering UV-A and UV-B ranges was designed and prepared. The photo-antioxidant tests indicate that there is a synergism between UV-A and UV-B monomers. The cytotoxic experiments demonstrate that PHOA has good biocompatibility. This journal is the Partner Organisations 2014.
Synthesis and Evaluation of PPARδAgonists That Promote Osteogenesis in a Human Mesenchymal Stem Cell Culture and in a Mouse Model of Human Osteoporosis
Kress, Brian J.,Kim, Dong Hyun,Mayo, Jared R.,Farris, Jeffery T.,Heck, Benjamin,Sarver, Jeffrey G.,Andy, Divya,Trendel, Jill A.,Heck, Bruce E.,Erhardt, Paul W.
, p. 6996 - 7032 (2021/05/29)
We synthesized a directed library of compounds to explore the structure-activity relationships of peroxisome proliferator-activated receptor δ(PPARδ) activation relative to mesenchymal stem cell (MSC) osteogenesis. Our scaffold used para-substituted cinnamic acids as a polar headgroup, a heteroatom and heterocycle core connecting units, and substituted phenyl groups for the lipophilic tail. Compounds were screened for their ability to increase osteogenesis in MSCs, and the most promising were examined for subunit specificity using a quantitative PPAR transactivation assay. Six compounds were selected for in vivo studies in an ovariectomized mouse model of human postmenopausal osteoporosis. Four compounds improved bone density in vivo, with two (12d and 31a) having activity comparable to that of GW0742, a well-studied PPARδ-selective agonist. 31a (2-methyl-4-[N-methyl-N-[5-methylene-4-methyl-2-[4-(trifluoromethyl)phenyl]thiazole]]aminocinnamic acid) had the highest selectivity for PPARδcompared to other subtypes, its selectivity far exceeding that of GW0742. Our results confirm that PPARδis a new drug target for possible treatment of osteoporosis via in situ manipulation of MSCs.
Pd salen complex@CPGO as a convenient, effective heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions
Ghabdian, Mahdieh,Nasseri, Mohammad Ali,Allahresani, Ali,Motavallizadehkakhky, Alireza
, p. 1713 - 1728 (2018/05/25)
A Pd(II) Schiff base complex supported on graphene oxide nanosheets (Pd(II) salen@CPGO) has been synthesized and characterized by FT-IR, ICP-AES, XRD, SEM/EDX and TEM. The synthesized nanocatalyst has been found to be an efficient heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki coupling reactions. Pd(II) salen@CPGO could be separated and recovered easily from the reaction mixture and recycled several times without a discernible decrease in its catalytic activity. The construction of a solid sheet-supported Pd catalyst would be expected to be a promising system to perform heterogeneous catalytic reactions.
BIVALENT LECA INHIBITORS TARGETING BIOFILM FORMATION OF PSEUDOMONAS AERUGINOSA
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Page/Page column 48; 50-51, (2021/05/15)
The present invention relates to divalent compounds binding to LecA. The compounds are useful to block biofilm formation of Pseudomonas aeruginosa. The invention further relates to pharmaceutical compositions comprising these compounds and to therapeutic methods and uses of these compounds, in particular to therapeutic methods and uses for the treatment of Pseudomonas aeruginosa infections in a subject. The invention also relates to imaging of infections, such as biofilms produced by Pseudomonas aeruginosa, by using these divalent compounds.
