专利号:US-2008194678-A1 优先权日:2005-07-15 标 题:Process To Obtain Synthetic And Semi-Synthetic Lignan Derivatives, Their Antiparasitic Activities And Corresponding Pharmaceutical Formulations, Including The Therapeutic Method Using Said Lignan For The Treatment Of Parasitosis 发明人:SILVA MARCIO LUIS ANDRADE E; SILVA ROSANGELA DA; RODRIGUES VANDERLEI; PEREIRA OLAVO DOS SANTOS; SILVA FILHO ADEMAR ALVES DA; DONATE PAULO MARCOS; ALBUQUERQUE SERGIO; BASTOS JAIRO KENUPP 权利人:FUNDACAO DE AMPARO A PESQUISSA 摘要:A process to obtain synthetic and semi-synthetic derivatives of lignans, especially dibenzylbutyrolactonic, tetrahydrofuranic, aryltetralynic, furofuranic and dibenzocyclooctanic lignans obtained by means of partial synthesis and/or full synthesis or also by isolation from plant extracts. It refers to a process to obtain synthetic and semi-synthetic derivatives of (−)-cubebin, such as: (−)-O-acetylcubebin; (−)-O-methylcubebin; (−)-O—N,N-(dimethylamino-ethyl)-cubebin; (−)-hinokinin; (−)-6,6′-dinitroinokinine; (−)-O-benzylcubebin; (−)-6,6′-diaminoinokinin, (−)-6,6′-dinitroinokinin, as well as to obtain dibenzocyclooctanic lignans from dibenzylbutyrolactoinic lignans by means of structural modifications in the positions 7, 7′, 8, 8′, 9′ and in the aromatic rings (introduction and/or substitution of functional groups such as: —OH, —CO 2 H, —CO 2 CH 3 , —NO 2 , —NH 2 , —OCH 3 , —OAc, —SO 2 CH 3 , —SO 2 NH 2 , prenyl and halogens) is provided. A therapeutic method using the derivatives is also provided.
1: Somani GS, Nahire MS, Parikh AD, Mulik MB, Ghumatkar PJ, Laddha KS, Sathaye S. Neuroprotective effect of Cubebin: A dibenzylbutyrolactone lignan on scopolamine-induced amnesia in mice. Indian J Med Res. 2017 Aug;146(2):255-259. doi: 10.4103/ijmr.IJMR_156_14. 2: Lima TC, Lucarini R, Volpe AC, de Andrade CQJ, Souza AMP, Pauletti PM, Januário AH, Símaro GV, Bastos JK, Cunha WR, Borges A, da Silva Laurentiz R, Conforti VA, Parreira RLT, Borges CHG, Caramori GF, Andriani KF, E Silva MLA. In vivo and in silico anti-inflammatory mechanism of action of the semisynthetic (-)-cubebin derivatives (-)-hinokinin and (-)-O-benzylcubebin. Bioorg Med Chem Lett. 2017 Jan 15;27(2):176-179. doi: 10.1016/j.bmcl.2016.11.081. Epub 2016 Nov 29.
合成参考文献
参考文献:10.1515/znc-2009-11-1204 摘要:Silva ML, Martins CH, Lucarini R, Sato DN, Pavanb FR, Freitas NH, Andrade LN, Pereira AC, Bianco TN, Vinholis AH, Cunha WR, Bastos JK, Silva R, Da Silva Filho AA. Antimycobacterial activity of natural and semi-synthetic lignans. Z Naturforsch C J Biosci. 2009 Nov;64(11-12):779–84. doi: 10.1515/znc-2009-11-1204.