4125-45-5Relevant academic research and scientific papers
Antibacterial and antioxidant bio-based networks derived from eugenol using photo-activated thiol-ene reaction
Modjinou, Tina,Versace, Davy-Louis,Abbad-Andallousi, Samir,Bousserrhine, Noureddine,Dubot, Pierre,Langlois, Valérie,Renard, Estelle
, p. 47 - 53 (2016)
Bio-based networks derived from eugenol and linalool were prepared with an eco-friendly process by photoactivated thiol-ene reactions. Allyl derivative Eugenol, AE, prepared by a nucleophilic substitution was combined with linalool, L, a monoterpene prese
Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis
Braga, Felipe C.,Gallou, Fabrice,Lee, Nicholas R.,Lippincott, Daniel J.,Lipshutz, Bruce H.,Moghadam, Farbod A.,Zhu, Bingchun
supporting information, (2020/07/15)
Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.
Epoxy (meth) acrylate compounds and pharmaceutical compositions containing curable composition
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Paragraph 0096-0099, (2019/04/17)
[Problem] To provide an epoxy (meth)acrylate compound that serves as a material for a protective film that is unlikely to cause migration to an electrically conductive pattern, and a curable composition containing the epoxy (meth)acrylate compound. [Solut
DDQ-mediated oxidation of allylarenes: Expedient access to cinnamaldehyde-containing phenylpropanoids
Jiang, Tao-Shan,Zhang, Qingqing,Li, Guohui,Cheng, Xi,Cai, Yongping
, p. 4611 - 4616 (2019/02/01)
Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization-ring-closing-metathesis strategy.
Eugenol derived immunomodulatory molecules against visceral leishmaniasis
Charan Raja, Mamilla R.,Velappan, Anand Babu,Chellappan, Davidraj,Debnath, Joy,Kar Mahapatra, Santanu
, p. 503 - 518 (2017/08/22)
Visceral leishmaniasis (VL) is a life threatening infectious disease caused by Leishmania donovani. It leads to the severe immune suppression in the host defense system. Higher cytotoxicity, rigorous side effects and lower therapeutic indexes (TI) of current antileishmanial drugs have created a necessity to develop new molecules with better antileishmanial activity and high TI value. In this study, we have synthesized 36 derivatives of eugenol and screened them for their activity against promastigote and amastigote forms of L. donovani. Among the synthesized derivatives, comp.35 showed better antileishmanial activity against extra cellular promastigotes (IC50- 20.13 ± 0.91 μM) and intracellular amastigotes (EC50-4.25 ± 0.26 μM). The TI value (82.24 ± 3.77) was found to improve by 10–13 fold compared to Amphotericin B and Miltefosine respectively. Treatment with comp.35 (5 μg/ml) enhanced the nitric oxide (NO) generation, iNOS2 mRNA expression (～8 folds increase) and decreased the arginase-1 activity (～4 folds) in L. donovani infected peritoneal macrophages. Comp.35 had also increased the IL-12 (～6 folds) and decreased the IL-10 (～3 folds) mRNA expression and release in vitro. Results of in vivo studies revealed that comp.35 treatment at 25 mg/kg body weight efficiently cleared the hepatic and splenic parasite burden with enhanced Th1 response in L. donovani infected BALB/c mice. Hence, this study clearly represents comp.35, as an immunomodulatory molecule, can induce host protective immune response against visceral leishmaniasis through enhanced NO generation and Th1 response, which are essentials against this deadly disease.
UV-thermal dual cured anti-bacterial thiol-ene networks with superior performance from renewable resources
Dai, Jinyue,Ma, Songqi,Zhu, Lixia,Wang, Sheng,Yang, Lijing,Song, Zhenlun,Liu, Xiaoqing,Zhu, Jin
, p. 215 - 222 (2016/12/07)
Bio-based anti-bacterial cross-linked films with superior properties were prepared via UV-thermal induced thiol-ene “click” reaction of diallyl itaconate (DAI), eugenol allyl ether (EAE) with trimethylolpropane tris (3-mercaptopropionate). DAI and EAE were made from one-step reaction of itaconic acid and eugenol with allyl bromide, respectively. The curing behaviors studied by Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC) and gel content measurement illustrated that UV-thermal dual cure technology made the thiol-ene reaction more completely and produced films with higher performance compared with UV cure technology. The investigation of the thermal and mechanical properties of the cross-linked films by DSC, thermogravimetric analysis (TGA) and tensile test indicated that the glass transition temperature, tensile strength and modulus of the films were significantly improved after introducing DAI, and all the films exhibited similar and high thermal stability. Meanwhile, these bio-based polymer films showed excellent efficiency in killing common bacterias, e.g. S.?aureus and E.?coli in the dynamic shake test.
NOVEL MONOMERS FROM BIOMASS
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Paragraph 0266-0270, (2017/09/02)
Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.
Highly efficient Tsuji-Trost allylation in water catalyzed by Pd-nanoparticles
Llevot,Monney,Sehlinger,Behrens,Meier
supporting information, p. 5175 - 5178 (2017/07/12)
Palladium nanoparticles stabilized by poly(vinylpyrrolidone) catalyze Tsuji-Trost allylations in water with very high turnover numbers. The di-allylation of methylene active compounds and the allylation of bio-based phenols was performed in high yield. The allylation of lignin showed a high selectivity towards the phenolic OH groups.
Bio-based thermosetting resins composed of aliphatic polyol-derived polymaleimides and allyleugenol
Shibata, Mitsuhiro,Shimasaki, Toshiaki,Satoh, Hiroyuki,Iwai, Misaki,Neda, Makiyo
, p. 69 - 76 (2015/11/09)
Bio-based bismaleimide (2MPD), trismaleimide (3MGC) and tetramaleimide (4MDG) were synthesized by reactions of 4-isocyanatophenylmaleimide with 1,3-propanediol, glycerol and α,α′-diglycerol, respectively. Although 2MPD did not melt until the temperature w
Hydrazone-palladium-catalyzed allylic arylation of cinnamyloxyphenylboronic acid pinacol esters
Watanabe, Kohei,Mino, Takashi,Abe, Taichi,Kogure, Taketo,Sakamoto, Masami
, p. 6695 - 6702 (2014/08/05)
Allylic arylation of cinnamyloxyphenylboronic acid pinacol esters 3, which have arylboronic acid moiety and allylic ether moiety, using a hydrazone 1d-Pd(OAc)2 system proceeded and gave the corresponding 1,3-diarylpropene derivatives 4 with a phenolic hydroxyl group via a selective coupling reaction of the π-allyl intermediate to the boron-substituted position of the leaving group.
