14469-89-7Relevant academic research and scientific papers
Α - Herba Asari (asarum herb) alcohol and its preparation method and application
-
Paragraph 0009; 0026-0028, (2017/03/08)
The invention relates to (E)-3-(2,4,5-trimethoxy-phenyl)-prop-2-en-1-ol, and a preparation method and application thereof. Related (E)-3-(2,4,5-trimethoxy-phenyl)-prop-2-en-1-ol has the structural formula I shown in the specification. The related preparation method comprises: performing decarboxylation reaction on 2,4,5-trimethoxybenzaldehyde, isopropylidene malonate (meldrum's acid) and a fatty alcohol under catalytic effect of pyridine and piperidine, so as to obtain (E)-2,4,5-trimethoxycinnamate, and processing by using a reducing agent, so as to obtain (E)-3-(2,4,5-trimethoxy-phenyl)-prop-2-en-1-ol. The preparation method is simple and relatively high in yield. The related application comprises that (E)-3-(2,4,5-trimethoxy-phenyl)-prop-2-en-1-ol is applied to prepare medicines for calming, tranquilizing, resisting senile dementia, resisting convulsion, resisting epilepsy or protecting heart and cerebral vessels.
Ethyl cinnamate derivatives as promising high-efficient acaricides against Psoroptes cuniculi: Synthesis, bioactivity and structure-activity relationship
Zhang, Bingyu,Lv, Chao,Li, Weibo,Cui, Zhiming,Chen, Dongdong,Cao, Fangjun,Miao, Fang,Zhou, Le
, p. 255 - 262 (2015/04/22)
This paper reported the synthesis, structure-activity relationship (SAR) and acaricidal activity in vitro against Psoroptes cuniculi, a mange mite, of 25 ethyl cinnamate derivatives. All target compounds were synthesized and elucidated by means of MS, 1H- and 13C-NMR analysis. The results showed that 24 out of 25 tested compounds at 1.0 mg/mL demonstrated acaricidal activity in varying degrees. Among them, 6, 15, 26, 27 and 30 showed significant activity with median lethal concentration values (LC50) of 89.3, 119.0, 39.2, 29.8 and 41.2 μg/mL, respectively, which were 2.1- to 8.3-fold the activity of ivermectin (LC50=247.4 μg/mL), a standard drug in the treatment of Psoroptes cuniculi. Compared with ivermectin, with a median lethal time value (LT50) of 8.9 h, 27 and 30 showed smaller LTM50 values of 7.9 and 1.3 h, respectively, whereas 6, 15 and 26 showed slightly larger LT50 values of 10.6, 11.0 and 10.4 h at 4.5 μmol/mL. SARs showed that the presence of o-NO2 or m-NO2 on the benzene ring significantly improved the activity, whereas the introduction of a hydroxy, methoxy, acetoxy, methylenedioxy, bromo or chloro group reduced the activity. (E)-Cinnamates were more effective than their (Z)-isomer. Nevertheless, the carbon-carbon double bond in the acrylic ester moiety was proven not to be essential to improve the activity of cinnamic acid esters. Thus, the results strongly indicate that cinnamate derivatives, especially their dihydro derivatives, should be promising candidates or lead compounds for the development of novel acaricides for the effective control of animal or human acariasis.
Synthesis of 2,3-syn-diarylpent-4-enamides via acyl-Claisen rearrangements of substituted cinnamyl morpholines: Application to the synthesis of magnosalicin
Dickson, Benjamin D.,Dittrich, Nora,Barker, David
scheme or table, p. 4464 - 4468 (2012/09/25)
The acyl-Claisen rearrangement of substituted phenylacetyl chlorides and cinnamyl morpholines gives 2,3-syn-diarylpent-4-enamides. Electron-rich cinnamyl morpholines containing alkoxy substituents only reacted with phenylacetyl chlorides; replacement of t
Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells
Barcelos, Rosimeire Coura,Pastre, Julio Cezar,Caixeta, Vanessa,Vendramini-Costa, Débora Barbosa,De Carvalho, Jo?o Ernesto,Pilli, Ronaldo Aloise
experimental part, p. 3635 - 3651 (2012/07/27)
The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the γ-pyrones and the aza-goniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin (1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds.
A microwave-accelerated esterification of α,β-unsaturated acids with alkyl or aryl carbonochloridate and triethylamine in acetonitrile as a novel esterifying reagent mixture
Pathania, Vinod,Sharma, Anuj,Sinha, Arun K.
, p. 811 - 816 (2007/10/03)
An efficient synthesis of α,β-unsaturated esters by treatment of the corresponding acids with alkyl or aryl carbonochloridate, triethylamine, and acetonitrile was accomplished for the first time under microwave irradiation for 10 min. The esters 1b-24b were isolated in 71-97% yield.
Substituent Effects in the Reaction of t-Butylmagnesium Chloride with Substituted Ethyl Cinnamates. A Correlation with 13C NMR Chemical Shifts
Jalander, Lars
, p. 419 - 428 (2007/10/02)
The reaction of t-butylmagnesium chloride with some substituted ethyl (E)-cinnamates gave mainly 1,3-, 1,4-, 1,2- and 1,4-addition products and minor amounts of 1,2- and 1,3-addition products.The relative amounts of 1,3-addition products has been shown to correlate with 13C NMR chemical shifts of C-α of the ethyl cinnamates.The correlation indicates that the regio selectivity of the reactions is to a great extent dependent of polar effects and that the t-butyl radical has a nucleophilic character.
