55211-66-0Relevant academic research and scientific papers
An enantioselective total synthesis of the stilbenolignan (-)-aiphanol and the determination of its absolute stereochemistry
Banwell, Martin G.,Chand, Satish,Savage, G. Paul
, p. 1645 - 1654 (2005)
The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-β to give triol (1R,2R)-1-(3′,5′-dimethoxy-4′-methoxymethoxyphenyl) -2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2′ and C-3′.
Synthesis and in vitro biological evaluation of novel dendrocandin analogue as potential anti-tumor agent
Yan, Jing-Yun,Yang, Hao-Nan,Yang, Ning,Xie, Yin-Rong,Sun, Xiu-Li,Huang, Ye-Wei,Zi, Cheng-Ting,Wang, Xuan-Jun,Sheng, Jun
supporting information, (2021/03/26)
Dendrocandins are characteristic chemical structures of D. officinale and have strong physiological bioactivities. In this study, a dendrocandin analogue (1) has been prepared by total synthesis (9 steps, 12.6% overall yield) in which coupling reaction and Wittig reaction as the key steps. Compound 1 was also evaluated for its anticancer activity in vitro against six human cancer cells (MCF-7, A549, A431, SW480, HepG-2 and HL-60) using MTT assays. Compound 1 showed potent cytotoxicity, with the IC50 value 16.27 ± 0.26 μM. The expression levels of apoptotic proteins indicated that compound 1 can up-regulate the expression of apoptotic proteins, leading to apoptosis. This compound suggested that it’s potential as anticancer agent for further development.
Syringaldehyde derivative and applications in preparation of anti-gynecological tumor drug
-
Paragraph 0033; 0040-0041; 0044, (2020/06/02)
The invention discloses a syringaldehyde derivative, which has a structure represented by a formula (I), wherein in the formula (I), an R substituent group is selected from one or a plurality of groups selected from alkoxy, halogen, CF3, dimethylamino, alkyl, hydroxyl, cyclohexyl, NO2 and NH2. According to the invention, the research results show that the syringaldehyde derivative has good anti-gynecological tumor activity, and the anti-tumor activity and the targeting property of the syringaldehyde derivative are far higher than those of syringaldehyde.
Method for synthesizing compound Paulownione C and Tomentodiplone O
-
Paragraph 0027; 0034; 0035, (2019/06/13)
The invention relates to a method for synthesizing natural products Tomentodiplacone O and Paulownione C. The method adopts 2, 4, 6-Trihydroxyacetophenone monohydrate compound, citral, clove aldehydeand vanillin as initial raw materials, general inorganic alkali as a catalyst, and methanol with low toxicity as a solvent; high-toxicity pyridine is avoided, and two natural products Tomentodiplone Oand Paulownione C are prepared through five steps. The method has the advantages of simple synthetic route, simple operation, green and high efficiency, thereby solving the problem of high toxicity and low yield of the prepared benzopyran compound, and the method has certain industrial economic value.
A rapid, solvent-free deprotection of methoxymethyl (MOM) ethers by pTSA; An eco-friendly approach
Pandurangan, Nanjan
, p. 231 - 235 (2017/07/15)
Background: Ease of preparation and alkaline stability of methoxymethyl (MOM) makes it an important hydroxyl protecting group. A number of methods are available for the deprotection of MOM. Though the methods are good in general, they use solvents, require prolonged reaction time and tedious work up. A solvent free, solid phase, fast deprotection of MOM has been developed and is the major theme of this paper. Methods: A mixture of MOM protected compounds and pTSA is triturated in a mortar (5 min) and left at room temperature for 30 min. On addition of water (4°C), pTSA, methanol and formaldehyde dissolved leaving the products as precipitates. Results: A series of different MOM ethers were deprotected by this method in good to excellent yield (85-98%). The compatibility of MOM in the presence of other protections such as methoxyl, benzyl, ester, amide, allyl and lactone was also established. Acetate protection is not stable under these conditions. Conclusion: An efficient, selective and high yielding deprotection MOM groups by pTSA under solvent free condition is described. The process is environment friendly since no solvent was used in the deprotection process. The reaction conditions are mild and should be useful for the deprotection of MOM derivatives of complex and labile molecules.
(E)-1-(5-METHOXY-2,2-DIMETHYL-2H-CHROMEN-8-YL)-3-(4-METHOXYPHENYL)PROP-2-EN-1-ONE AND ANALOGS THEREOF, AS WELL AS PREPARATION METHOD AND USE THEREOF
-
Paragraph 0168; 0169; 0204, (2015/05/26)
The present invention relates to millepachine ((E)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-methoxyphenyl)prop-2-en-1-one) and its analogues. The present invention provides methods for preparing these compounds, pharmaceutical compositions includin
Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents
Wang, Guangcheng,Wu, Wenshuang,Peng, Fei,Cao, Dong,Yang, Zhuang,Ma, Liang,Qiu, Neng,Ye, Haoyu,Han, Xiaolei,Chen, Jinying,Qiu, Jingxiang,Sang, Yun,Liang, Xiaolin,Ran, Yan,Peng, Aihua,Wei, Yuquan,Chen, Lijuan
experimental part, p. 793 - 803 (2012/09/08)
In this paper, 38 millepachine derivatives have been designed, synthesized and evaluated for their in vitro and in vivo antiproliferative activity. Among these novel derivatives, 15 displayed more potent antiproliferative activity than millepachine agains
Peroxynitrite generation from a NO-releasing nitrobenzene derivative in response to photoirradiation
Ieda, Naoya,Nakagawa, Hidehiko,Horinouchi, Taeko,Peng, Tao,Yang, Dan,Tsumoto, Hiroki,Suzuki, Takayoshi,Fukuhara, Kiyoshi,Miyata, Naoki
supporting information; experimental part, p. 6449 - 6451 (2011/06/27)
Photocontrollable ONOO- generation from a nitrobenzene derivative was demonstrated. The designed compound released NO in response to photoirradiation, and the resulting semiquinone reduced molecular oxygen to generate O2-; reaction of the two generated ONOO -, as confirmed with an ONOO- fluorescent probe, HKGreen-3.
Anti-ulcer agent comprising chalcone derivative as effective ingredient and novel chalcone derivative
-
, (2008/06/13)
The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: STR1 wherein X and Y independently stand for a hydrogen atom or together form a single bond, R1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R3 stands for hydroxyl group or a methoxy group, R4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R7 stands for a hydrogen atom or a methoxy group.
