56024-44-3Relevant academic research and scientific papers
Semi-aromatic biobased polyesters derived from lignin and cyclic carbonates
Horn, Jessica,Locklin, Jason,Ring, John,White, Evan M.,Winfield, Demichael
supporting information, p. 9658 - 9668 (2021/12/09)
The synthesis of biobased aromatic polyesters from lignin-derived monomers has become well described in the literature, but robust extrusion, thermomechanical, tensile and degradation studies of these materials is lacking. In this work, we have systematically investigated the mechanical and biodegradation properties of semi-aromatic polyesters that can potentially be derived from lignin. AB monomers were synthesized from reduced analogues of coumaric, ferulic, and sinapic acids along with cyclic carbonates, where the synthetic methodology was assessed using E-Factor and EcoScale. Polymerization yielded both semi-crystalline and amorphous polyesters with mechanical properties varying over three orders of magnitude. Detailed characterization revealed a wide array of properties including a highly ductile thermoplastic, a strong and rigid thermoplastic, and an elastomer. Composting biodegradation tests showed both degradable and nondegradable polymers can be achieved in this class. This work demonstrates the versatility of this class of polymers and illustrates their potential to replace non-sustainably derived plastics. This journal is
First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry
Adamo, Mauro F. A.,Bencivenni, Grazia,Gillick-Healy, Malachi W.,Kelly, Brian G.,Moccia, Maria,Ravelli, Andrea
supporting information, p. 1091 - 1094 (2020/02/22)
Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls - a technology previously reported by us. A series of optically active naturally occurring sulfonic acids are prepared in their natural and unnatural configurations, and their absolute configurations are unequivocally confirmed by single crystal X-ray diffractometry.
Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates
Li, Xiaoxun,Liu, Jitian,Tang, Weiping,Wang, Shuojin,Ye, Wenjing,Zheng, Junrong
, (2020/03/19)
x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.
Comparison of Phenylacetates with Benzoates and Phenylpropanoates as Antifeedants for the Pine Weevil, Hylobius abietis
Unelius, C. Rikard,Bohman, Bj?rn,Nordlander, G?ran
, p. 11797 - 11805 (2018/11/21)
This study concludes an extensive investigation of antifeedants for the pine weevil, Hylobius abietis (Coleoptera: Curculionidae), an economically important pest of planted conifer seedlings. Building on the previously reported antifeedant effects of benzoates and phenylpropanoids (aromatic compounds with one- or three-carbon-atom substituents on the benzene ring), we here report the antifeedant effects of compounds with two-carbon-atom side chains (i.e., phenylacetates). We also present new results; the best antifeedants from the benzoate class were tested at 10-fold lower concentrations in order to find the optimal antifeedants. Generally, for all three compound classes, efficient antifeedants were found to have one or two methyl, chloro, or methoxy substituents on the aromatic ring. For monosubstituted phenylpropanoids, the substituent preferably should be in the para-position. In the search for synergistic antifeedant effects among the three compound classes, combinations of compounds from the three classes were tested in binary and ternary mixtures.
Transition Metal Free C-N Bond Forming Dearomatizations and Aryl C-H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent
Farndon, Joshua J.,Ma, Xiaofeng,Bower, John F.
supporting information, p. 14005 - 14008 (2017/10/17)
We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C-N bond forming dearomatization or aryl C-H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines.
(-)-Tarchonanthuslactone: Design of New Analogues, Evaluation of their Antiproliferative Activity on Cancer Cell Lines, and Preliminary Mechanistic Studies
Toneto Novaes, Luiz Fernando,Martins Avila, Carolina,Pelizzaro-Rocha, Karin Juliane,Vendramini-Costa, Débora Barbosa,Pereira Dias, Marina,Barbosa Trivella, Daniela Barreto,Ernesto De Carvalho, Jo?o,Ferreira-Halder, Carmen Veríssima,Pilli, Ronaldo Aloise
supporting information, p. 1687 - 1699 (2015/10/06)
Natural products containing the α,β-unsaturated δ-lactone skeleton have been shown to possess a variety of biological activities. The natural product (-)-tarchonanthuslactone (1) possessing this privileged scaffold is a popular synthetic target, but its biological activity remains underexplored. Herein, the total syntheses of dihydropyran-2-ones modeled on the structure of 1 were undertaken. These compounds were obtained in overall yields of 17-21 % based on the Keck asymmetric allylation reaction and were evaluated in vitro against eight different cultured human tumor cell lines. We further conducted initial investigation into the mechanism of action of selected analogues. Dihydropyran-2-one 8 [(S,E)-(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl 3-(3,4-dihydroxyphenyl)acrylate], a simplified analogue of (-)-tarchonanthuslactone (1) bearing an additional electrophilic site and a catechol system, was the most cytotoxic and selective compound against six of the eight cancer cell lines analyzed, including the pancreatic cancer cell line. Preliminary studies on the mechanism of action of compound 8 on pancreatic cancer demonstrated that apoptotic cell death takes place mediated by an increase in the level of reactive oxygen species. It appears as though compound 8, possessing two Michael acceptors and a catechol system, may be a promising scaffold for the selective killing of cancer cells, and thus, it deserves further investigation to determine its potential for cancer therapy. Fighting the big C: We describe the synthesis of a new family of analogues based on the scaffold of the natural product (-)-tarchonanthuslactone; these compounds were evaluated in vitro against tumor cell lines. We further conducted an initial investigation into the mechanism of action, including the inhibition of phosphatases and glutathione-S-transferase and the production of reactive oxygen species.
Mild synthesis of mesoporous silica supported ruthenium nanoparticles as heterogeneous catalysts in oxidative Wittig coupling reactions
Carrillo, Adela I.,Schmidt, Luciana C.,Marin, M. Luisa,Scaiano, Juan C.
supporting information, p. 435 - 440 (2014/02/14)
A new efficient approach for the in situ synthesis of anchored ruthenium nanoparticles (RuNP) in three different kinds of mesoporous silica materials, MCM-41, SBA-15 and HMS, has been developed. Solids have been synthesized under very mild conditions from RuCl3·H2O salt reduced in one hour at room temperature in the mesoporous silicas previously grafted with aminopropyltriethoxysilane (APTES). Well-dispersed ruthenium nanoparticles, with an average size of 3 nm, anchored into the silica network by the APTES were obtained. These materials, with a molar ratio of Si/Ru = 40, were found to be catalytically active and selective in the alcohol oxidation-Wittig olefination. Interestingly, while the reaction occurs from the alcohol, control experiments suggest that the aldehyde (the common Wittig substrate) is not involved. The Royal Society of Chemistry.
Development of N-hydroxycinnamamide-based histone deacetylase inhibitors with an indole-containing Cap group
Zhang, Yingjie,Yang, Penghui,Chou, C. James,Liu, Chunxi,Wang, Xuejian,Xu, Wenfang
supporting information, p. 235 - 238 (2013/03/28)
A novel series of histone deacetylase inhibitors combining N-hydroxycinnamamide bioactive fragment and indole bioactive fragment was designed and synthesized. Several compounds (17c, 17g, 17h, 17j, and 17k) exhibited comparable, even superior, total HDACs inhibitory activity and in vitro antiproliferative activities relative to the approved drug SAHA. A representative compound 17a with moderate HDACs inhibition was progressed to isoform selectivity profile, Western blot analysis, and in vivo antitumor assay. Although HDACs isoform selectivity of 17a was similar to that of SAHA, our Western blot results indicated that intracellular effects of 17a at 1 μM were class I selective. It was noteworthy that the effect on histone H4 acetylation of SAHA decreased with time, while the effect on histone H4 acetylation of 17a was maintained and even increased. Most importantly, compound 17a exhibited promising in vivo antitumor activity in a U937 xenograft model.
A singlet oxygen approach to oxaspirocycles
Jones, Kevin M.,Hillringhaus, Tim,Klussmann, Martin
supporting information, p. 3294 - 3297 (2013/06/27)
A method for the preparation of oxygen containing spirocycles using singlet oxygen is reported. A series of phenols were converted into the corresponding peroxy-cyclohexadienone derivatives by irradiation with visible light in the presence of a sensitizer and oxygen. The resulting peroxides could be converted into ether and lactone spirocycles in one or two steps. The synthesis of the oxaspirocycles from the phenols can also be performed in a one-pot fashion, avoiding the isolation of the peroxide intermediates.
Introducing catalytic lossen rearrangements: Sustainable access to carbamates and amines
Kreye, Oliver,Wald, Sarah,Meier, Michael A. R.
supporting information, p. 81 - 86 (2013/03/13)
A new, highly efficient and environmentally benign catalytic variant of the Lossen rearrangement is described. Dimethyl carbonate (DMC) as green activation reagent of hydroxamic acids in presence of catalytic amounts of tertiary amine bases {1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 1,8-biazabicyclo 5.4.0 undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2]octane (DABCO), and triethylamine} and small quantities of methanol initiate the rearrangement. Methyl carbamates were obtained in good to moderate yields when aliphatic hydroxamic acids were employed in this catalytic Lossen rearrangement; under the same conditions aromatic hydroxamic acids yielded anilines. Notably, the mixture of DMC/methanol was recycled several times without observing decreased yields, thus minimizing the produced waste. Moreover, several other organic carbonates were successfully employed in the introduced catalytic Lossen rearrangement procedure. Copyright
