- Programmed photodegradation of polymeric/oligomeric materials derived from renewable bioresources
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Renewable polymeric materials derived from biomass with built-in phototriggers were synthesized and evaluated for degradation under irradiation of UV light. Complete decomposition of the polymeric materials was observed with recovery of the monomer that was used to resynthesize the polymers.
- Rajendran, Saravanakumar,Raghunathan, Ramya,Hevus, Ivan,Krishnan, Retheesh,Ugrinov, Angel,Sibi, Mukund P.,Webster, Dean C.,Sivaguru, Jayaraman
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Read Online
- Pd-Catalysed Decarbonylation Free Approach to Carbonylative Esterification of 5-HMF to Its Aryl Esters Synthesis Using Aryl Halides and Oxalic Acid as C1 Source
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A decarbonylation free, polystyrene-supported, Pd (Pd@PS)-catalysed carbonylative esterification of the hydroxy group of 5-hydroxymethyl furfural (5-HMF) to its corresponding aryl esters has been developed. The use of Pd@PS, oxalic acid as CO source, and aryl halides was first explored for the aryl ester of 5-HMF synthesis. Here, we investigated the vital role of a polystyrene support to avoid the commonly known decarbonylation of 5-HMF. The reaction exhibits vast substrate scope with comparably good yield and catalyst recyclability.
- Singh Chauhan, Arvind,Kumar, Ajay,Kumar Sharma, Ajay,Das, Pralay
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supporting information
p. 12971 - 12975
(2021/08/06)
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- PRODRUG AND PROTECTED FORMS OF 5-HYDROXYMETHYLFURFURANAL (5-HMF) AND ITS DERIVATIVES
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Prodrugs and derivatives of 5-hydoxymethyl-2-furfural (5-HMF) with protected or modified aldehyde and/or alcohol moieties are provided. The prodrugs or derivatives exhibit increased bioavailability, e.g. due to having extended half-lives in circulation. The drugs are therefore administered i) at lower doses and/or ii) less frequently than 5-HMF, while still maintaining the beneficial therapeutic effects of 5-HMF.
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Page/Page column 34
(2018/02/27)
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- Design, Synthesis, and Biological Evaluation of Ester and Ether Derivatives of Antisickling Agent 5-HMF for the Treatment of Sickle Cell Disease
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Candidate drugs to counter intracellular polymerization of deoxygenated sickle hemoglobin (Hb S) continue to represent a promising approach to mitigating the primary cause of the pathophysiology associated with sickle cell disease (SCD). One such compound is the naturally occurring antisickling agent, 5-hydroxymethyl-2-furfural (5-HMF), which has been studied in the clinic for the treatment of SCD. As part of our efforts to develop novel efficacious drugs with improved pharmacologic properties, we structurally modified 5-HMF into 12 ether and ester derivatives. The choice of 5-HMF as a pharmacophore was influenced by a combination of its demonstrated attractive hemoglobin modifying and antisickling properties, well-known safety profiles, and its reported nontoxic major metabolites. The derivatives were investigated for their time- and/or dose-dependent effects on important antisickling parameters, such as modification of hemoglobin, corresponding changes in oxygen affinity, and inhibition of red blood cell sickling. The novel test compounds bound and modified Hb and concomitantly increased the protein affinity for oxygen. Five of the derivatives exhibited 1.5- to 4.0-fold higher antisickling effects than 5-HMF. The binding mode of the compounds with Hb was confirmed by X-ray crystallography and, in part, helps explain their observed biochemical properties. Our findings, in addition to the potential therapeutic application, provide valuable insights and potential guidance for further modifications of these (and similar) compounds to enhance their pharmacologic properties.
- Xu, Guoyan G.,Pagare, Piyusha P.,Ghatge, Mohini S.,Safo, Ronni P.,Gazi, Aheema,Chen, Qiukan,David, Tanya,Alabbas, Alhumaidi B.,Musayev, Faik N.,Venitz, Jürgen,Zhang, Yan,Safo, Martin K.,Abdulmalik, Osheiza
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p. 3499 - 3511
(2017/10/11)
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- Palladium-catalyzed regioselective allylation of five-membered heteroarenes with allyltributylstannane
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Palladium-catalyzed allylation reactions of 2-(chloromethyl)thiophenes, 2-(chloromethyl)furans, and N-protected 2-(chloromethyl)-1H-pyrroles with allyltributylstannane were described in this study. This type of allylation reaction regioselectively occurred on the heteroarene rings to produce allylated dearomatization products or allylated heteroarenes with satisfactory yields.
- Zhang, Sheng,Yu, Xiaoqiang,Feng, Xiujuan,Yamamoto, Yoshinori,Bao, Ming
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supporting information
p. 3842 - 3845
(2015/03/30)
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- Trienamines derived from 5-substituted furfurals: Remote ε-functionalization of 2,4-dienals
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The selective ε-functionalization of 5-substituted furfurals via trienamine intermediates is reported herein. This methodology was successfully applied to several 5-substituted furfurals with different amines via formation of a trienamine through the furan ring. The rationalized reaction mechanism involves the addition of the trienamine intermediate to its corresponding iminium-ion producing new furan-containing scaffolds.
- Coelho, Jaime A. S.,Trindade, Alexandre F.,Andr, Vnia,Teresa Duarte,Veiros, Luis F.,Afonso, Carlos A.M.
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supporting information
p. 9324 - 9328
(2014/12/11)
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- Synthesis and biological evaluation of novel indolin-2-one derivatives as protein tyrosine phosphatase 1b inhibitors
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3-Substituted indolin-2-one derivatives had been designed and synthesized as a novel class ofprotein tyrosine phosphatase 1B (PTP1B) inhibitors. These compounds had been evaluated for their inhibitory activities against PTP1B in vitro with IC50 values in a low micromolar range.Compound 36, the lowest, bore an IC50 value of 3.48 μM. Preliminary structure-activity relationship was summarized.
- Dai, Hou-Ling,Shen, Qiang,Zheng, Jian-Bin,Lib, Jing-Ya,Wen, Ren,Li, Jia
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experimental part
p. 526 - 530
(2012/04/23)
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- FURAN DERIVATIVES FOR PREVENTING AND CURING OSTEOPOROSIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
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The present invention relates to furan derivatives and pharmaceutical compositions containing them to prevent and cure osteoporosis. The furan derivatives of the present invention have effect on bone proliferation with the side effect reduced, so that they can be used for bone disease.
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Page/Page column 6
(2008/12/08)
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- FURAN DERIVATIVES FOR PREVENTING AND CURING OSTEOPOROSIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
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The present invention relates to furan derivatives and pharmaceutical compositions containing them to prevent and cure osteoporosis. The furan derivatives of the present invention have effect on bone proliferation with the side effect reduced, so that they can be used for bone disease.
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- Convenient Synthesis of Chiral Pyranones from Carbohydrates
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2-Acyloxyglycals (2-O-acyl-1,5-anhydrohex-1-enitols) having a D-arabino configuration (1a, b) react highly stereoselectively with alcohols in the presence of a stoichiometric amount of tin(IV) chloride at O-5 deg C to (2S,6S)-6-acyloxymethyl-2-alkoxy-2H-pyran-3(6H)-ones 2 together with furaldehyde by-products 3.In the case of 2-acyloxyglycals having a D-lyxo (1c, d) or an L-lyxo (4) configuration, reaction occurs readily at -20 deg C to form the desired pyranones 2 or 5 without the formation of furaldehydes.All reactions showed high stereoselectivity for α-anomersin the formation of the acetal linkage, except the reaction of the tri-O-benzoyl derivative 1d with methanol.The method reported allows the synthesis of chiral pyranones in higher yield and by a shorter route than the previously reported methods.
- De Fina, Griselda M.,Varela, Oscar,Lederkremer, Rosa M. de
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p. 891 - 893
(2007/10/02)
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- Synthesis of Some Furfural and Syringic Acid Derivatives
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The formation of several derivatives of furfural and syringic acid, including some incorporating both components, is described.Assignments of the 1H and 13C n.m.r. spectra are also included.
- Jogia, Madhu K.,Vakamoce, Veikila,Weavers, Rex T.
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p. 1009 - 1016
(2007/10/02)
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