4698-21-9Relevant academic research and scientific papers
Synthesis and biological evaluation of 4-arylcoumarins as potential anti-Alzheimer's disease agents
Miao, Yuhang,Sun, Jie,Wang, Xiaojing,Yang, Jie,Yun, Yinling
, (2020/01/03)
Alzheimer's disease (AD) is a progressive neurological degenerative disease that has complex pathogenesis. A variety of studies in humans indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted 4-arylcoumarin derivatives were synthesised, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity, MAO inhibitory activity, and antioxidant activity. Most of the compounds were found to exhibit high inhibitory activity, and individual compounds have extremely excellent activities. Therefore 4-arylcoumarins provides an idea for drugs design for the development of therapeutic or preventive agents for AD.
Synthesis and Computational Studies Demonstrate the Utility of an Intramolecular Styryl Diels-Alder Reaction and Di-t-butylhydroxytoluene Assisted [1,3]-Shift to Construct Anticancer dl-Deoxypodophyllotoxin
Saavedra, Diana I.,Rencher, Benjamin D.,Kwon, Doo-Hyun,Smith, Stacey J.,Ess, Daniel H.,Andrus, Merritt B.
, p. 2018 - 2026 (2018/02/23)
Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic de
Synthesis and biological evaluation of novel neoflavonoid derivatives as potential antidiabetic agents
Wang, Bing,Li, Na,Liu, Teng,Sun, Jie,Wang, Xiaojing
, p. 34448 - 34460 (2017/07/22)
Various substituted neoflavonoid derivatives were synthesized using sulfated montmorillonite K-10 as a catalyst. This method is environmental friendly, sustainable and economical, convenient in isolation and purification processes, with little byproducts, using earth-abundant catalysts and has relatively high yield. Those neoflavonoid derivatives were screened for antioxidant, a-glucosidase inhibitory, aldose reductase 2 (ALR2) inhibitory and advanced glycation end-product formation inhibitory effects. Most compounds exhibited significant antioxidant and advanced glycation end-product (AGE) formation inhibitory activities. It was interesting to note that out of thirty compounds, 8k and 8l were found to have greater ALR2 inhibitory activity than the standard drug quercetin. The pharmacological studies suggested neoflavonoid with adjacent 7,8-dihydroxy groups were more effective in inhibiting ALR2. Antidiabetic activity studies had shown that compounds 8l and 8m were equipotent to the standard drug glibenclamide in vivo. In summary, the target compound 8l provided a potential drug design concept for the development of therapeutic or prophylactic agents of diabetes and diabetes complications.
Synthesis of Terminal Allenes via a Copper-Catalyzed Decarboxylative Coupling Reaction of Alkynyl Carboxylic Acids
Lim, Jeongah,Choi, Jinseop,Kim, Han-Sung,Kim, In Seon,Nam, Kye Chun,Kim, Jimin,Lee, Sunwoo
, p. 303 - 308 (2016/01/15)
Synthesis of terminal allenes via a copper-catalyzed decarboxylative coupling reaction was developed. Aryl alkynyl carboxylic acid, paraformaldehyde, and dicyclohexylamine were reacted with CuI (20 mol %) in diglyme at 100°C for 2 h to produce the terminal allene in moderate to good yields. The method showed good functional group tolerance.
Palladium-catalyzed oxidative aminocarbonylation by decarboxylative coupling: Synthesis of alkynyl amides
Hwang, Jinil,Choi, Jinseop,Park, Kyungho,Kim, Wonyoung,Song, Kwang Ho,Lee, Sunwoo
, p. 2235 - 2243 (2015/04/14)
Alkynyl amides were synthesized from a palladium-catalyzed coupling reaction of alkynyl carboxylic acids and amines under carbon monoxide. The reaction was conducted with palladium(II) acetate (5 mol-%) and silver(I) oxide (1.0 equiv.) in acetonitrile at 80 °C for 1 h. This method provides good to moderate product yields and good functional group tolerance towards ketone, ester, and nitrile groups.
Palladium-catalyzed sonogashira reaction for the synthesis of arylalkynecarboxylic acids from aryl bromides at low temperature
Park, Kyungho,You, Jung-Min,Jeon, Seungwon,Lee, Sunwoo
, p. 1973 - 1978 (2013/05/09)
A variety of aryl bromides were coupled with propiolic acid in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and catalyst Pd(PPh 3)4 to afford the corresponding arylalkynecarboxylic acids in good yields at low temperature. This method showed good tolerance toward functional groups such as alkoxy, ketone, ester, aldehyde, cyano, nitro, and hydroxy. Under these conditions, propiolic acid showed higher reactivity than any other compound containing terminal alkyne groups. According to the mechanistic studies, the key reaction step for the high reactivity of propiolic acid might be ligand exchange between the acetylide and bromide at palladium, and/or reductive elimination, but not the oxidative addition step. A variety of aryl bromides were coupled with propiolic acid in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and catalyst Pd(PPh3) 4 to afford the corresponding arylpropiolic acids in good yields at low temperature.
Synthesis and biological activities of new furo[3,4-b]carbazoles: Potential topoisomerase II inhibitors
Hajbi, Youssef,Neagoie, Cléopatra,Biannic, Bérenger,Chilloux, Aurélie,Vedrenne, Emeline,Baldeyrou, Brigitte,Bailly, Christian,Mérour, Jean-Yves,Rosca, Sorin,Routier, Sylvain,Lansiaux, Amélie
experimental part, p. 5428 - 5437 (2010/12/25)
New 1,5-Dihydro-4-(substituted phenyl)-3H-furo[3,4-b]carbazol-3-ones were synthesised via a key step Diels-Alder reaction under microwave irradiation. 3-Formylindole was successfully used in a 6-step synthesis to obtain those complex heterocycles. The Diels-Alder reaction generating the carbazole ring was optimised under thermal conditions or microwave irradiation. After cleavage of functional groups, DNA binding, topoisomerase inhibition and cytotoxic properties of the new-formed furocarbazoles were investigated. These carbazoles do not present a strong interaction with the DNA, and do not modify the relaxation of the DNA in the presence of topoisomerase I or II except for one promising compound. This compound is a potent topoisomerase II inhibitor, and its cellular activity is not moderated compared to etoposide. The synthesis of these molecules allowed the generalisation of the method using indole and 5-OBn indole and several benzaldehydes. The synthesis of these molecules produced chemical structures endowed with promising cytotoxic and topoisomerase II inhibition activities.
Synthesis of tetrahydrofurocarbozolones via intramolecular Diels-Alder reactions
Madalengoitia,Macdonald
, p. 6237 - 6240 (2007/10/02)
10-Aryl-3a,4,10,10a-tetrahydrofuro[3,4-b]carbazol-1-ones were synthesized by an intramolecular Diels-Alder reaction. Exo/endo product ratios were found to be sensitive to both solvent and temperature. The synthesis of isoelliptitoxin 2, a hybrid molecule
Studies on the Constituents of the Seeds of Hernandia ovigera L. VII. Syntheses of (+/-)-Hernolactone and (+/-)-Hernandin
Tanoguchi, Mariko,Kashima, Tatsuhiko,Saika, Hideyuki,Inoue, Taishi,Arimoto, Masao,Yamaguchi, Hideo
, p. 68 - 72 (2007/10/02)
Two new lignans, hernolactone (1) and hernandin (2), isolated from the seeds of Hernandia ovigera L. were synthesized in racemic forms.Firstly, (+/-)-1 was obtained by utilizing the conjugate addition reaction of 4 with butenolide followed by alkylation with trimethoxybenzyl bromide and subsequent removal of the protecting groups.Synthesis of 2 was pursued using the corresponding 4-phenyl-1,2-dihydronaphthalene lactone (18).The cleavage of the lactone moiety of 18 afforded an unsaturated hydroxy acid (22).Subsequent hydrogenation of 22 followed by acidification with concentrated hydrochloric acid gave isopicrohernandin (21), leaving the 2,3-trans, 3,4-cis hydroxy acid (23), which was lactonized by means of N,N-dicyclohexylcarbodiimide to afford (+/-)-2.Keywords: Hernandia ovigera; hernolactone; hernandin; lignan; dibenzylbutyrolactone lignan; phenyltetralin lignan; isopicrohernandin; Diels-Alder reaction
