32780-06-6Relevant articles and documents
Preparation of Some 2,3-Dideoxylactones by an Unusual Catalytic Hydrogenolysis
Lundt, Inge,Pedersen, Christian
, p. 1052 - 1054 (1986)
Hydrogenolysis of 2-bromo-2-deoxyaldono-1,4-lactones in ethanol solution with palladium as catalyst gives good yields of the corresponding 2,3-dideoxylactones with removal of not only the bromine atom but also the C-3 hydroxy group.
Organic solvent- and catalyst-free Baeyer-Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene): A sustainable route to (: S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone
Bonneau, Guillaume,Peru, Aurélien A. M.,Flourat, Amandine L.,Allais, Florent
, p. 2455 - 2458 (2018)
A straightforward and sustainable route to (S)-γ-hydroxymethyl-α,β-butenolide (HBO) and (S)-γ-hydroxymethyl-α,β-butyrolactone (2H-HBO), two valuable chemical platforms for the synthesis of fine chemicals such as drugs, pheromones, flavors and fragrances, has been optimized using renewable cellulose-based levoglucosenone (LGO) and Cyrene as starting materials and aqueous H2O2 as both a solvent and an oxidizing agent. Combined with short-path distillation, this procedure provides enantiopure HBO and 2H-HBO in yield as high as 72% at the kilo scale.
Asymmetric synthesis of enantiopure (+)-(1S,2S) methyl 2-formylcyclopropanecarboxylate and corresponding (Z) and (E) didehydroamino acid derivatives
Le Corre,Hercouet,Bessieres
, p. 683 - 684 (1995)
The title cyclopropane aldehyde and didehydroamino acids have been synthesised from (S)-(+)-γ-butyrolactone-γ-carboxylic acid as a chiral precursor.
Elucidating the interaction of γ-hydroxymethyl-γ-butyrolactone substituents with model membranes and protein kinase C-C1 domains
Borah, Rituparna,Mamidi, Narsimha,Panda, Subhankar,Gorai, Sukhamoy,Pathak, Suraj Kumar,Manna, Debasis
, p. 1389 - 1399 (2015)
The protein kinase C (PKC) family of proteins is an attractive drug target. Dysregulation of PKC-dependent signalling pathways is related to several human diseases like cancer, immunological and other diseases. We approached the problem of altering PKC activities by developing C1 domain-based PKC ligands. In this report γ-hydroxymethyl-γ-butyrolactone (HGL) substituents were investigated in an effort to develop small molecule-based PKC regulators with higher specificity for C1 domain than the endogenous diacylglycerols (DAGs). Extensive analysis of membrane-ligands interaction measurements revealed that the membrane-active compounds strongly interact with the lipid bilayers and the hydrophilic parts of compounds localize at the bilayer/water interface. The pharmacophores like hydroxymethyl, carbonyl groups and acyl-chain length of the compounds are crucial for their interaction with the C1 domain proteins. The potent compounds showed more than 17-fold stronger binding affinity for the C1 domains than DAG under similar experimental conditions. Nonradioactive kinase assay confirmed that these potent compounds have similar or better PKC dependent phosphorylation capabilities than DAG under similar experimental conditions. Hence, our findings reveal that these HGL analogues represent an attractive group of structurally simple C1 domain ligands that can be further structurally altered to improve their potencies.
New phenolic glycosides from Anemone chinensis Bunge and their antioxidant activity
Zhang, Zeng-Guang,Li, Yuan-Yuan,Lin, Bin,Guan, Pei-Pei,Mu, Yu,Qiao, Wen-Jun,Zhang, Jing-Sheng,Huang, Xue-Shi,Han, Li
supporting information, (2021/05/10)
ABATRACT: Nine compounds, five phenolic glycosides (1, 2, 4–6), three phenylpropanoids (7–9), and a furanone glycoside (3), were isolated from aqueous soluble extract of the dried roots of Anemone chinensis Bunge. The structures of new compounds (1–4) were elucidated by comprehensive spectroscopic data analysis as well as chemical evidence. Pulsatillanin A (1) demonstrated significant antioxidant effects through scavenging free radical in DPPH assay, and relieved the oxidative stress in LPS-induced RAW 264.7 cells by reducing ROS production, enhancing antioxidant enzyme SOD activity, replenishing depleted GSH in a dose-dependent manner. Western blot analysis revealed that 1 showed antioxidant activity via activating Nrf2 signaling pathway.
Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone
Sharipov, Bulat T.,Davidova, Anna N.,Ryabova, Alena S.,Galimzyanova, Nailya F.,Valeev, Farid A.
, p. 31 - 37 (2019/02/25)
[Figure not available: see fulltext.] A series of derivatives were synthesized on the basis of levoglucosenone that contained hydroxy groups at the С-4 atom or С-2 and С-4 atoms or a hydroxy and methyl group at the С-4 atom. In addition, 4-hydroxymethylbutanolides were synthesized. Derivatives containing hydroxy groups were obtained as methylsulfanylmethyl ethers. It was established that compounds containing a 6,8-dioxabicyclo[3.2.1]-octane ring exhibited fungicidal activity against Rhizoctonia solani. It was shown that the presence of a methylsulfanylmethyl moiety in the ring could increase the fungicidal activity of compounds.