75887-43-3Relevant academic research and scientific papers
Resolution of chiral (trimethylenemethane) iron (tricarbonyl) complexes
Franck-Neumann, Michel,Stoeber, Paul,Passmore, Guy
, p. 3193 - 3202 (1996)
Reaction of (S)-(-)-ethyl lactate and (R)-(+)-α-methylbenzylamine with the racemic crystalline activated TMM ester 3, obtained in 3 steps from β,β'-dimethylacrylic acid, provides the easily separable diastereomeric esters 2a/2b and amides 10a/10b. From the esters and the N-BOC amides 11a/11b, simple reactions allow the synthesis of other optically active TMM Fe(CO)3 complexes of high enantiomeric purity and known absolute configuration. Copyright (C) Elsevier Science Ltd.
Synthesis and Spectral Study of Some New 4-substituted but-2-enolide Derivatives
Altaee, Enas A.,Al-Sabawi, Ammar H.
, p. 7017 - 7022 (2021/11/16)
A variety of some new substituted 4-amino-4-(bromomethyl)butolides (4a-g) have been synthesized by reactions 4-(Bromomethyl)but-2-enolide (2) with some (substituted benzylidene) benzene-1,4-diamine (3a-g) in the presence of absolute ethanol as a solvent to give the Michael addition products, while in the case of its reaction in the presence of pyridine as a solvent and base be added to the β- and ?- positions to be yield substituted 4-amino-4- (aminomethyl)butolides (5a-g). 4-(Bromomethyl)but-2-enolide (2) is prepared by the reaction 3,3-dimethylacrylic acid and N-bromo succinimide with benzoyl peroxide to give 3,3-Bis(bromomethyl)acrylic acid (1) and then the ring-closure reaction is carried out in basic media. All newly synthesized compounds were confirmed by spectral analysis and the corresponding reactions were monitored by TLC.
Application of the palladium-catalysed norbornene-assisted catellani reaction towards the total synthesis of (+)-linoxepin and isolinoxepin
Qureshi, Zafar,Weinstabl, Harald,Suhartono, Marcel,Liu, Hongqiang,Thesmar, Pierre,Lautens, Mark
supporting information, p. 4053 - 4069 (2014/07/08)
Our ongoing effort towards the development of highly selective transition-metal-catalysed C-H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/Pd IV-catalysed domino reaction, an aryl iodide, alkyl iodide and tert-butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The enantioselective total synthesis of the natural product (+)-linoxepin has been accomplished in eight steps starting from commercial materials. The key Pd-catalysed Catellani step served to combine aryl iodide, alkyl iodide and tert-butyl acrylate in a domino sequence. By tuning the final Heck reaction, both the natural product and its structural isomer were synthesized. Copyright
Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions
Fort, Diego A.,Woltering, Thomas J.,Nettekoven, Matthias,Knust, Henner,Bach, Thorsten
supporting information, p. 2989 - 2991 (2013/05/09)
Intramolecular [2+2] photocycloaddition reactions of diversely substituted N-Boc protected 4-(allylaminomethyl)-2(5H)-furanones resulted in rigid products (53-75%) with three spatially defined positions for further functionalisation. The Royal Society of Chemistry.
Triazole-dithiocarbamate based selective lysine specific demethylase 1 (LSD1) inactivators inhibit gastric cancer cell growth, invasion, and migration
Zheng, Yi-Chao,Duan, Ying-Chao,Ma, Jin-Lian,Xu, Rui-Min,Zi, Xiaolin,Lv, Wen-Lei,Wang, Meng-Meng,Ye, Xian-Wei,Zhu, Shun,Mobley, David,Zhu, Yan-Yan,Wang, Jun-Wei,Li, Jin-Feng,Wang, Zhi-Ru,Zhao, Wen,Liu, Hong-Min
, p. 8543 - 8560 (2013/12/04)
Lysine specific demethylase 1 (LSD1), the first identified histone demethylase, plays an important role in epigenetic regulation of gene activation and repression. The up-regulated LSD1's expression has been reported in several malignant tumors. In the cu
Substituted pyrazolones require N2 hydrogen bond donating ability to protect against cytotoxicity from protein aggregation of mutant superoxide dismutase 1
Trippier, Paul C.,Benmohammed, Radhia,Kirsch, Donald R.,Silverman, Richard B.
supporting information, p. 6647 - 6650 (2013/01/14)
Amyotrophic lateral sclerosis (ALS) is a debilitating and fatal neurodegenerative disease. Although the cause remains unknown, misfolded protein aggregates are seen in neurons of sporadic ALS patients, and familial ALS mutations, including mutations in su
Synthesis and in vitro antitumor activity of new butenolide-containing dithiocarbamates
Wang, Xiao-Juan,Xu, Hai-Wei,Guo, Lin-Lin,Zheng, Jia-Xin,Xu, Bo,Guo, Xiao,Zheng, Chen-Xin,Liu, Hong-Min
scheme or table, p. 3074 - 3077 (2011/06/26)
Three series of butenolide-containing dithiocarbamates were designed and synthesized. Their anti-tumor activity in vitro was evaluated. Among them compound I-14 exhibited broad spectrum anti-cancer activity against five human cancer cell lines with IC50 30 μM. Structure-activity relationship analysis showed that the introduction of dithiocarbamate side chains on the C-3 position of butenolide was crucial for anti-tumor activity.
Stereoselective synthesis of desloratadine derivatives as antagonist of histamine
Liu, Gai-Zhi,Xu, Hai-Wei,Chen, Guang-Wei,Wang, Peng,Wang, Ya-Na,Liu, Hong-Min,Yu, De-Quan
experimental part, p. 1626 - 1632 (2010/04/26)
A series of desloratadine derivatives were stereoselectively synthesized and evaluated for H1 antihistamine activity. For the evaluation of H1 antihistamine activity, the in vitro histamine-induced contraction of the guinea-pig ileum assay (HC) was used. The synthesized desloratadine derivatives 7, 8 and 9 are structurally related to rupatadine and were generated by replacement of the 5-methyl-3-pyridine group of rupatadine with γ-alkylidene butenolide. Their H1 antihistamine activities have shown a high dependence on the exact nature of the substituent in the lactone ring. Optimum structures 7, 8a and 8g display potent activity inhibiting histamine-induced effects.
Gas-phase fragmentation of γ-lactone derivatives by electrospray ionization tandem mass spectrometry
Crotti, Antonio E. M.,Bronze-Uhle, Erika S.,Nascimento, Paulo G. B. D.,Donate, Paulo M.,Galembeck, Sergio E.,Vessecchi, Ricardo,Lopes, Norberto P.
experimental part, p. 1733 - 1741 (2010/08/04)
Fragmentation reactions of β-hydroxymethyl-, β-acetoxymethyl- and β-benzyloxymethyl-butenolides and the corresponding γ-butyrolactones were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) using collision-induced dissociation (CID). This study revealed that loss of H2O [M+H-18]+ is the main fragmentation process for β-hydroxymethylbutenolide (1) and β-hydroxymethyl-γ- butyrolactone (2). Loss of ketene ([M+H-42]+) is the major fragmentation process for protonated β-acetoxymethyl-γ-butyrolactone (4), but not for β-acetoxymethylbutenolide (3). The benzyl cation (m/z 91) is the major ion in the ESI-MS/MS spectra of β-benzyloxymethylbutenolide (5) and β-benzyloxymethyl-γ-butyrolactone (6). The different side chain at the β-position and the double bond presence afforded some product ions that can be important for the structural identification of each compound. The energetic aspects involved in the protonation and gas-phase fragmentation processes were interpreted on the basis of thermochemical data obtained by computational quantum chemistry. Copyright
Stereoselective and convergent syntheses of retinoic acid and its ester derivatives by the sulfone olefination reaction
Jeon, Hye-Sun,Yeo, Jung Eun,Jeong, Young Cheol,Koo, Sangho
, p. 2813 - 2820 (2007/10/03)
An extensive study on the stereoselective and convergent syntheses of retinoic acid and its ester derivatives utilizing the Julia sulfone olefination reaction has been reported. Various C5 units of the acid 4a, the esters 4b-e from the chemically and biologically important alcohols, and the furanone 6 have been prepared and coupled with the C15 allylic sulfone 3 to give the C20 compounds 10 and 11, which provided all-(E)-retinoic acid (1a), its ester derivatives 1b-e, and the furanone analogue 12b in a highly stereoselective manner after dehydrosulfonation reaction. The Julia olefination reaction of the C5 diester 13 and the C15 allylic sulfone 3 produced the known C20 diacid 15 which underwent stereoselective mono-decarboxylation to provide either 13-(Z)-retinoic acid (2) or all-(E)-retinoic acid (1) depending on the reagent used.
