52962-06-8Relevant articles and documents
Synthesis and QSAR study of novel α-methylene-γ-butyrolactone derivatives as antifungal agents
Wu, Yong-Ling,Wang, De-Long,Guo, En-Hui,Song, Shuang,Feng, Jun-Tao,Zhang, Xing
, p. 1284 - 1290 (2017)
Thirty-six new α-benzylidene-γ-lactone compounds based α-methylene-γ-butyrolactone substructure were prepared and characterized by spectroscopic analysis. All compounds were evaluated for antifungal activities in vitro against six plant pathogenic fungi and the half maximal inhibitory concentration (IC50) against Botrytis cinerea and Colletotrichum lagenarium were investigated. Compounds 5c-3 and 5c-5 with the halogen atom exhibited excellent fungicidal activity against B. cinerea (IC50?=?22.91, 18.89?μM). The structure-activity relationships (SARs) analysis indicated that the derivatives with electron-withdrawing substituents at the meta- or para-positions improves the activity. Via the heuristic method, the generated quantitative structure-activity relationship (QSAR) model (R2?=?0.961) revealed a strong correlation of antifungal activity against B. cinerea with molecular structures of these compounds. Meanwhile, the cytotoxicity of 20 representative derivatives was tested in the human tumor cells line (HepG2) and the hepatic L02 cells line, the result indicated that the synthesized compounds showed significant inhibitory activity and limited selectivity. Compound 5c-5 has the highest fungicidal activity with IC50?=?18.89?μM (against B. cinerea.) but low cytotoxicity with IC50?=?35.4?μM (against HepG2 cell line) and IC50?=?68.8?μM (against Hepatic L02 cell line). These encouraging results can be providing an alternative, promising use of α-benzylidene-γ-lactone through the design and exploration of eco-friendly fungicides with low toxicity and high efficiency.
Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids
Xu, Xiao-Long,Li, Zhi
supporting information, p. 5078 - 5081 (2019/09/03)
Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.
New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
Jun-Tao, Feng,De-Long, Wang,Yong-Ling, Wu,He, Yan,Xing, Zhang
supporting information, p. 4393 - 4397 (2013/07/26)
Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the α-methylene-γ-butyrolactone ring, a natural pharmacophore. All structures were confirmed by 1H and 13C NMR, MS, and single-c
Titanocene(III) chloride mediated radical-induced one-pot synthesis of α-methylene-γ-butyrolactones
Paira, Moumita,Banerjee, Biplab,Jana, Samaresh,Mandal, Samir Kumar,Roy, Subhas Chandra
, p. 3205 - 3207 (2007/10/03)
A simple and efficient methodology has been developed for the one-pot preparation of α-methylene-γ-butyrolactones by free-radical induced Barbier-type reaction of methyl 2-(bromomethyl)acrylate and aldehydes followed by in situ lactonization. The radical
Lead-promoted 2-carboethoxyallylation or 2-carboxylallylation of aldehydes: A new and facile method for the synthesis of α-methylene-γ-butyroactones
Zhou,Jia,Yao,Wu
, p. 2397 - 2406 (2007/10/03)
In the presence of powdered lead, the reaction of aldehydes and α-bromomethylacrylate (or α-bromomethylacrylic acid) can be carried out under mild condition, the products 4-hydroxy-2-methylenebutanoates (or 4-hydroxy-2-methylenebutanoic acids) can be easi
An SnCl2-Promoted α-Methylene-γ-butirolactone Synthesis in an Aqueous Medium
Uneyema, Kenji,Ueda, Kunimasa,Torii, Sigeru
, p. 1201 - 1202 (2007/10/02)
Reaction of α-bromomethylacrylic acid with aldehydes in an SnCl2-MeOCH2CH2OH-H2O system provides γ-substituted-α-methylene-γ-butirolactones.
