34602-86-3Relevant academic research and scientific papers
Polygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic α-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study
Bai, Yajun,He, Xirui,Bai, Yujun,Sun, Ying,Zhao, Zefeng,Chen, Xufei,Li, Bin,Xie, Jing,Li, Yang,Jia, Pu,Meng, Xue,Zhao, Ye,Ding, Yanrui,Xiao, Chaoni,Wang, Shixiang,Yu, Jie,Liao, Sha,Zhang, Yajun,Zhu, Zhiling,Zhang, Qiang,Zhao, Yuhui,Qin, Fanggang,Zhang, Yi,Wei, Xiaoyang,Zeng, Min,Liang, Jing,Cuan, Ye,Shan, Guangzhi,Fan, Tai-Ping,Wu, Biao,Zheng, Xiaohui
, (2019/09/18)
Inspired by the traditional Chinese herbal pair of Polygala tenuifolia-Acori Tatarinowii for treating epilepsy, 33 novel substituted cinnamic α-asaronol esters and analogues were designed by Combination of Traditional Chinese Medicine Molecular Chemistry (CTCMMC) strategy, synthesized and tested systematically not only for anticonvulsant activity in three mouse models but also for LDH inhibitory activity. Thereinto, 68–70 and 75 displayed excellent and broad spectra of anticonvulsant activities with modest ability in preventing neuropathic pain, as well as low neurotoxicity. The protective indices of these four compounds compared favorably with stiripentol, lacosamide, carbamazepine and valproic acid. 68–70 exhibited good LDH1 and LDH5 inhibitory activities with noncompetitive inhibition type, and were more potent than stiripentol. Notably, 70, as a representative agent, was also shown as a moderately positive allosteric modulator at human α1β2γ2 GABAA receptors (EC50 46.3 ± 7.3 μM). Thus, 68–70 were promising candidates for developing into anti-epileptic drugs, especially for treatment of refractory epilepsies such as Dravet syndrome.
Synthesis of polyhydroxylated flavonoids bearing a lipophilic decyl tail as potential therapeutic antioxidants
Caldwell, Stuart T.,McPhail, Donald B.,Duthie, Garry G.,Hartley, Richard C.
, p. 23 - 33 (2012/03/07)
Antioxidants have potential for the treatment of stroke and neurodegeneration, and chimeric compounds that combine a flavon-3-ol head group related to myricetin and a lipophilic decyl tail are known to protect membranes from oxidative damage at least as well as vitamin E. New flavon-3-ols that are highly hydroxylated in the B ring in ways not found in natural flavon-3-ols and bearing a lipophilic decyl tail have been prepared from trimethoxy-and tetramethoxybenzoic acids accessed by lithiation-carboxylation reactions. Direct enolate acylation was preferred over Baker-Venkataraman rearrangement when there were methoxy groups at both the 2-and the 6-position of the benzoic acid derivatives.
A self-immolative spacer that enables tunable controlled release of phenols under neutral conditions
Schmid, Kyle M.,Jensen, Lasse,Phillips, Scott T.
experimental part, p. 4363 - 4374 (2012/06/18)
A current challenge in the area of responsive materials is the design of reagents and polymers that provide controlled release of phenols in environments that are less polar than water. In these contexts, a molecular strategy that enables release of nearl
A synthetic study on bauhinoxepin J: Construction of a dibenzo[bf]oxepin ring system by a DDQ-promoted oxidative dearomatization-cyclization approach
Yoshida, Masahiro,Maeyama, Yohei,Shishido, Kozo
experimental part, p. 623 - 629 (2010/04/27)
Efforts to construct a dibenzo[b,f]oxepin ring system for a synthesis of bauhinoxepin J are described. A DDQ-promoted oxidative dearomatization-cyclization of the 2-phenoxyethyl-substituted tetramethoxybenzene was used to construct a tricyclic quinone mon
Efficient total synthesis of (-)-ilimaquinone
Poigny, Stephane,Guyot, Michele,Samedi, Mohammad
, p. 5890 - 5894 (2007/10/03)
The total synthesis of (-)-ilimaquinone, a metabolite isolated from sea sponges, is described. The key step of the synthesis is the attachment of the quinone moiety to the drimane skeleton. Alkylation of enone 11 obtained in four steps from the readily available diketone 8, with tetramethoxybenzyl bromide 15 as the alkylating agent, led to addition product 16 in excellent yield. The presence of the tetramethoxybenzyl group induced stereoselective hydrogenation of the exo olefin 18, leading to the required isomer in a 9:1 ratio. Treatment of compound 21 with ceric ammonium nitrate (CAN) afforded formation of the quinone and deprotection of only one methyl ether in one step to furnish the desired ilimaquinone 1.
SYNTHESIS OF OXIRANYLQUIONOES AS NEW POTENTIAL BIOREDUCTIVE ALKYLATING AGENTS
Syper L.,Mlochowsky, J.,Kloc, K.
, p. 781 - 792 (2007/10/02)
1,4-Benzoquinones and 1,4-naphtoquinones carrying oxiranyl substituents have been synthesized as potential bioreductive alkylating agents.The method presented here involves the syntheses of 1,4-dimethoxybenzaldehydes or 1,4-dimethoxynaphtaldehydes, and co
