93554-96-2Relevant articles and documents
Manganese-organic framework assembled by 5-((4′-(tetrazol-5″-yl)benzyl)oxy)isophthalic acid: A solvent-free catalyst for the formation of carbon–carbon bond
Jiang, Yansong,Xu, Jianing,Zhu, Ziqian,Jiang, Changwei,Ma, Lin,Wang, Hui,Wang, Li,Fan, Yong
supporting information, (2020/05/25)
A new three-dimensional manganese-based metal–organic framework Mn4L2(HL)(H2O)5, (1), based on semi-rigid 5-((4′-(tetrazol-5′’-yl)benzyl)oxy)isophthalic acid ligand (H3L) have been prepared and charac
Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications
Zheng, Yu-Cong,Xu, Jian-He,Wang, Hui,Lin, Guo-Qiang,Hong, Ran,Yu, Hui-Lei
, p. 1185 - 1193 (2017/04/13)
Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products. (Figure presented.).
The discovery of a potent series of carboxamide TRPA1 antagonists
Pryde,Marron,West,Reister,Amato,Yoger,Padilla,Turner,Swain,Cox,Skerratt,Ryckmans,Blakemore,Warmus,Gerlach
, p. 2145 - 2158 (2016/11/18)
A series of potent and selective carboxamide TRPA1 antagonists were identified by a high throughput screen. Structure-activity relationship studies around this series are described, resulting in a highly potent example of the series. Pharmacokinetic and skin flux data are presented for this compound. Efficacy was observed in a topical cinnamaldehyde flare study, providing a topical proof of pharmacology for this mechanism. These data suggest TRPA1 antagonism could be a viable mechanism to treat topical conditions such as atopic dermatitis.
Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles
Kadunce, Nathaniel T.,Reisman, Sarah E.
supporting information, p. 10480 - 10483 (2015/09/28)
A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild conditions at room temperature and precludes the need to pregenerate organometallic nucleophiles.
Synthesis of maculalactone A and derivatives for environmental fate tracking studies
Bader, Samuel L.,Luescher, Michael U.,Gademann, Karl
supporting information, p. 199 - 206 (2015/02/19)
Maculalactone A (1) constitutes a promising antifouling agent, inhibiting the formation of biofilms in marine and freshwater systems. In this study, we developed a new route, based on a late-stage formation of the butenolide core, leading to the total synthesis of maculalactone A (three steps, overall yield of 45%) and delivering material on a gram scale. In addition, analogues of the title compound were assayed concerning their biological activity, utilizing Artemia franciscana and Thamnocephalus platyurus. The most active analogue was functionalized with a rhodamine B fluorophore and was utilized in an in vivo staining experiment in Artemia salina. Two different tissues were found to accumulate this maculalactone A derivative. This journal is
Facile preparation of 1,2-diketones
Nowak, Pawel,Malwitz, David,Cole, Derek C.
experimental part, p. 2164 - 2171 (2010/08/13)
Easily accessible lead-like libraries of heterocyclic molecules useful for high-throughput screening are of continuous interest to the pharmaceutical industry. A number of drug-like libraries are derived from aromatic 1,2-diketones; however, nonsymmetrical 1,2-diketones are challenging to prepare. This communication describes a simple and practical synthesis of 1,2-diketones based on a controlled cross benzoin-like condensation reaction. Copyright Taylor & Francis Group, LLC.
Neutral π-nucleophile-catalyzed cyanation of aldehydes and ketones
Wang, Xiu,Tian, Shi-Kai
, p. 1416 - 1420 (2008/03/11)
1-Methoxy-2-methyl-1-(trimethylsiloxy)propene, a neutral π-nucleophile, was found to be able to efficiently catalyze the cyanation (cyanosilylation and cyanocarbonation) of various aldehydes and ketones, and this study provided the first illustration of u
An improved synthesis of cyanohydrins in the presence of solid LiClO4 under solvent-free conditions
Azizi, Najmedin,Saidi, Mohammad R.
, p. 283 - 285 (2007/10/03)
Several cyanohydrins were synthesized by the reaction of trimethylsilyl cyanide with carbonyl compounds in the presence of solid lithium perchlorate in high yields under solvent-free conditions.
Synthesis of Grevillins, Novel Pyrandione Pigments of Fungi. Biogenetic Interrelationships between Grevillins, Pulvinic Acids, Terphenylquinones and Xylerythrins
Pattenden, Gerald,Pegg, Neil A.,Kenyon, Ronald W.
, p. 2363 - 2372 (2007/10/02)
A synthesis of the grevillin group of pyrandione pigments, e.g. 3, 23 and 24 present in fungi is described.The synthesis, which is based on a biogenetic model, uses bis-benzylacyloins 9 and their corresponding oxalate derivatives as key intermediates (Scheme 3).Treatment of the grevillins 25a-c with sodium ethoxide in ethanol effects their quantitative isomerisation into the corresponding terphenylquinone pigments 4a-c.Perkin-type condensations between the terphenylquinones 4 and arylacetic acids in the presence of sodium acetate-acetic anhydride then produces the xylerythrin pigments 29a-e, whereas rearrangements of 4 in the presence of dimethyl sulphoxide leads to pulvinic acid derivative, e.g. 31, 32 and 5.These synthetic studies interrelate the biosynthetic origins of the pigment types 3, 4, 5 and 8 together with the related pulvinones 6 and furanone 7 fungal pigments.
Pigments of Fungi. XV An Efficient, Unambiguous Route to Unsymmetrically Substituted Dibenzyl Acyloins and their Use in the Synthesis of Fungus Pigments of the Pulvinone and Grevillin Types
Gill, Melvyn,Kiefel, Milton J.,Lally, Deborah A.,Ten, Abilio
, p. 1497 - 1518 (2007/10/02)
Dibenzyl acyloins including those bearing unsymetrically disposed aryl residues are assembled in high yield by reaction between the O-trimethylsilyl ethers of arylacetaldehyde cyanohydrins and benzyl Grignard reagents.These acyloins are deprotonated with
