75597-96-5Relevant academic research and scientific papers
A concise total synthesis of deoxyschizandrin and exploration of its antiproliferative effects and those of structurally related derivatives
Zheng, Shaojun,Aves, Sarah J.,Laraia, Luca,Galloway, Warren R. J. D.,Pike, Kurt G.,Wu, Wenjun,Spring, David R.
, p. 3193 - 3198 (2012/05/19)
The natural product deoxyschizandrin has been shown to have a wide range of biological activities. In recent years the therapeutic potential of this compound against cancers has attracted significant interest. Herein we describe a concise de novo total synthesis of deoxyschizandrin based around a double organocuprate oxidation strategy. In addition, we present the results of biological studies exploring the ability of deoxyschizandrin and synthetic precursors lacking the medium ring biaryl unit to inhibit the proliferation of a human cancer cell line. These studies led to the identification of a structurally novel agent with in vitro anticancer activity. Copyright
Simple synthesis of enantiomerically pure sauriols A and B
Mori, Naoki,Watanabe, Hidenori,Kitahara, Takeshi
, p. 1750 - 1753 (2008/02/05)
Sauriols A and B belong to a class of diarylbutane-lignans and exhibit antifeedant activity. We succeeded in the first synthesis of sauriols A and B by using a simple and efficient asymmetric dimerization of a cinnamic acid derivative as the key step.
Structure-activity relationships of lignans from Schisandra chinensis as platelet activating factor antagonists
Lee, Im Seon,Jung, Keun Young,Oh, Sei Ryang,Park, Si Hyung,Ahn, Kyung Seop,Lee, Hyeong-Kyu
, p. 265 - 267 (2007/10/03)
We studied the structure-activity relationships of lignans from Schisandra chinensis and their derivatives as platelet activating factor (PAF) antagonists. Strong activity was shown in lignans without an ester group at C-6, a hydroxyl group at C-7 or a methylene dioxy moiety and with an R-biphenyl configuration. 6(7)-Dehydroschisandrol A, a derivative of schisandrol A, showed the highest activity (IC50, 2.1 x 10-6 M) in this study.
Ruthenium dioxide in fluoro acid medium V. Application to the non phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins
Dhal,Landais,Lebrun,Lenain,Robin
, p. 1153 - 1164 (2007/10/02)
Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the non phenolic oxidative coupling of diarylbutanes. We observed along with the expected aryl-aryl coupling, an unusual aryl-benzyl coupling, leading to a known class of lignans, the aryltetralins. Conformational studies of resultant cis and trans deoxyschizandrins were performed using high resolution NMR and molecular models.
Intramolecular Oxidative Coupling of Aromatic Compounds. VI. An Efficient Synthesis of Some Dibenzocyclooctene Lignans
Carroll, Anthony R.,Taylor, Walter C.
, p. 937 - 942 (2007/10/02)
The 1,4-diaryl-2,3-dimethylbutanes (4) and (5) were readily prepared by reductive coupling of an arylacetone precursor followed by hydrogenation.Intramolecular oxidative coupling (dichlorodicyanobenzoquinone/trifluoroacetic acid) gave dibenzocyclooctene derivatives in good yield. (+/-)-Deoxyschizandrin and the corresponding trans isomer, existing in two distinct conformations, were prepared.
Intramolecular Oxidative Coupling of Aromatic Compounds. V. para-para Diphenolic Oxidative Coupling as a Possible Route to the Eupodienone Skeleton
Carroll, Anthony R.,Krauss, Adrian S.,Taylor, Walter C.
, p. 277 - 292 (2007/10/02)
The synthesis of (2RS,3RS)-1,4-bis(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-one (9) is described.Diphenolic oxidative coupling of (9) gave the unstable dienone (24), which decomposed in methanol to give what is believed to be the acetal (26).Syn
Intramolecular Oxidative Coupling of Aromatic Compounds. IV. Oxidation of Non-Phenolic Substrates
Krauss, Adrian S.,Taylor, Walter C.
, p. 935 - 939 (2007/10/02)
Intramolecular non-phenolic coupling of (2RS,3SR)-1,4-bis(4-benzyloxy-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-one (6) failed.Oxidation of the derived butane (9) gave the aryltetralin (14) in low yield.
NEOLIGNANS FROM LICARIA AUREA
Barbosa-Filho, Jose M.,Silva, Marcelo S. da,Yoshida, Massayoshi,Gottlieb, Otto R.
, p. 2209 - 2211 (2007/10/02)
Key Word Index - Licaria aurea; Lauraceae; diaryltetrahydrofuran neolignans; β-aryloxy-arylpropane neolignans.Abstract - The fruit calyces of Licaria aurea were found to contain the diaryltetrahydrofuran type neolignans grandisin, de-O-methylgrandisin and dide-O-methylgranidisin, as well the β-aryloxy-arylpropane type neolignans virolongin A and virolongin B.
Syntheses of (+/-)-Deoxyschizandrin and the Lignan, 1,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane
Gunasekaran, A.,Balasubramanian, K.
, p. 308 - 310 (2007/10/02)
(+/-)-Deoxyschizandrin (1) has been synthesised through a dimerisation reaction as a key step.The Grignard reagent from 1-(3,4,5-trimethoxyphenyl)-2-bromopropane (10) on reaction with 2-t-butyl-3-phenyloxaziridine gives 1,4-bis(3,4,5-trimethoxyphenyl)-2,3-dimethylbutane (11), which is cyclised using vanadium oxytrifluoride to get deoxyschizandrin (1).Following the above methodology, 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane (2), a lignan has also been prepared.
SYNTHESIS OF DIARYLBUTANES FROM CORDIGERINES AND REINVESTIGATION OF THEIR OXIDATIVE COUPLINGS IN DEOXYSCHIZANDRINS. - AN UNUSUAL FORMATION OF PHENYLTETRALIN LIGNANS -
Landais, Y.,Lebrun, A.,Lenain, V.,Robin, J.-P.
, p. 5161 - 5164 (2007/10/02)
Dibenzylbutanolide lignans including cordigerines were synthetized and transformed in the corresponding diarylbutane lignans which were submitted to non-phenolic oxidative coupling conditions by using RuO2 or Tl2O3 in trifluoroacetic medium to give deoxyschizandrins.A concurently aryl-benzyl coupling leads to the formation of the corresponding phenyltetralin of which the structure was confirmed by total synthesis.
