A mild and efficient n Bu4 NBr-mediated oxidative cycloaromatization to prepareβ-carbolines from readily available tryptophans and aldehydes is described.The reaction is practical and allows the synthesis ofβ-carbol...A mild and efficient n Bu4 NBr-mediated oxidative cycloaromatization to prepareβ-carbolines from readily available tryptophans and aldehydes is described.The reaction is practical and allows the synthesis ofβ-carbolines on gram-scale.Some of products crystallized from the reaction mixture and were easily removed by filtration,obviating the need for chromatographic separation.展开更多
By the condensation of tryptamine with appropriate substituted benzalde- hyde followed by Pictet-Spengler reaction,a series of 1-aryl-tetrahydro-β-carbo- lines(THβCs)were obtained.After dehydrogenation using sulfur,...By the condensation of tryptamine with appropriate substituted benzalde- hyde followed by Pictet-Spengler reaction,a series of 1-aryl-tetrahydro-β-carbo- lines(THβCs)were obtained.After dehydrogenation using sulfur,Pd-C or lead te- traacetate(LTA),these THβCs can give the corresponding β-carbolines(βCs)which exhibit specific binding with rat brain benzodiazepine receptor in vitro.展开更多
A new method to tetrahydro-β-carbolines(βCs) from tryptamine is described and the aromatization of THβCs to βCs by manganese dioxide is reported for the first time in this type of compounds.
Nine indole alkaloids and one aromatic amine were isolated from Evodia rutaecarpa Benth. Their structures were identified as evodiamine(1),rutaecarpine(2),formyldihydrorutaecarpine(3),goshuyuamide I(4),evodiamide(5)...Nine indole alkaloids and one aromatic amine were isolated from Evodia rutaecarpa Benth. Their structures were identified as evodiamine(1),rutaecarpine(2),formyldihydrorutaecarpine(3),goshuyuamide I(4),evodiamide(5),hydroxyevodiamine(6),β carboline(7),1,2,3,4 tetrahydro 1 oxo β carboline(8),dehydroevodiamine(9)and N methylanthranylamide(10).Compound 8 was a new natural product. Compound 7 was for the first time isolated from Evodia.展开更多
The enantiomers of carboline-based cryptates were successfully resolved by chiral HPLC.These complexes show high configurational stability under harsh conditions and their absolute configuration was determined by comp...The enantiomers of carboline-based cryptates were successfully resolved by chiral HPLC.These complexes show high configurational stability under harsh conditions and their absolute configuration was determined by comparing theoretical and expe rimental electronic circular dichroism spectra.The e nantiopure cryptates exhibit strong circularly polarized luminescence with a maximum dissymmetry factor glum=0.25 for the f-f transition 5 D0→7 F1(λ=594 nm)under visible light excitation atλgx=400 nm.展开更多
Prediction of antagonistic activity of <em>β</em>-carboline and its thirteen derivatives has been made using topological descriptors viz, connectivity index, and kappa shape index of different orders. For...Prediction of antagonistic activity of <em>β</em>-carboline and its thirteen derivatives has been made using topological descriptors viz, connectivity index, and kappa shape index of different orders. For evaluation of values of descriptor, molecular modeling and geometry optimization of all the compounds were carried out with CAChe Pro software by opting semiempirical PM3 method using MOPAC 2002. For prediction of activity multiple linear regression analysis (MLR) was performed. MLR analysis has been made by Project Leader Software associated with CAChe by using the above descriptors as independent variables and biological activity as dependent variables. We were performed leave-one-out methods and the result reflected a direct relationship between biological activity and connectivity index of zero order, while indirect relationship with connectivity index of second order and thus connectivity index is a reliable descriptor to predict the biological activity of <em>β</em>-carboline and its various derivatives.展开更多
基金National Natural Science Foundation of China (Nos. 21172120 and 21472093)Tianjin Municipal Science and Technology Commission (No. 14JCYBJC20600) for financial support
文摘A mild and efficient n Bu4 NBr-mediated oxidative cycloaromatization to prepareβ-carbolines from readily available tryptophans and aldehydes is described.The reaction is practical and allows the synthesis ofβ-carbolines on gram-scale.Some of products crystallized from the reaction mixture and were easily removed by filtration,obviating the need for chromatographic separation.
基金Project supported by National Natural Science Foundation of China(No.2870083)
文摘By the condensation of tryptamine with appropriate substituted benzalde- hyde followed by Pictet-Spengler reaction,a series of 1-aryl-tetrahydro-β-carbo- lines(THβCs)were obtained.After dehydrogenation using sulfur,Pd-C or lead te- traacetate(LTA),these THβCs can give the corresponding β-carbolines(βCs)which exhibit specific binding with rat brain benzodiazepine receptor in vitro.
基金Project supported by National Natural Science Foundation of China(No.2870083)
文摘A new method to tetrahydro-β-carbolines(βCs) from tryptamine is described and the aromatization of THβCs to βCs by manganese dioxide is reported for the first time in this type of compounds.
文摘Nine indole alkaloids and one aromatic amine were isolated from Evodia rutaecarpa Benth. Their structures were identified as evodiamine(1),rutaecarpine(2),formyldihydrorutaecarpine(3),goshuyuamide I(4),evodiamide(5),hydroxyevodiamine(6),β carboline(7),1,2,3,4 tetrahydro 1 oxo β carboline(8),dehydroevodiamine(9)and N methylanthranylamide(10).Compound 8 was a new natural product. Compound 7 was for the first time isolated from Evodia.
基金Project supported by the German Research Foundation(DFG,research grant SE1448/7-1 for M.S.)German Academic Scholarship Foundation(Studienstiftung des deutsches Volkes,predoctoral fellowship for E.K.)。
文摘The enantiomers of carboline-based cryptates were successfully resolved by chiral HPLC.These complexes show high configurational stability under harsh conditions and their absolute configuration was determined by comparing theoretical and expe rimental electronic circular dichroism spectra.The e nantiopure cryptates exhibit strong circularly polarized luminescence with a maximum dissymmetry factor glum=0.25 for the f-f transition 5 D0→7 F1(λ=594 nm)under visible light excitation atλgx=400 nm.
文摘Prediction of antagonistic activity of <em>β</em>-carboline and its thirteen derivatives has been made using topological descriptors viz, connectivity index, and kappa shape index of different orders. For evaluation of values of descriptor, molecular modeling and geometry optimization of all the compounds were carried out with CAChe Pro software by opting semiempirical PM3 method using MOPAC 2002. For prediction of activity multiple linear regression analysis (MLR) was performed. MLR analysis has been made by Project Leader Software associated with CAChe by using the above descriptors as independent variables and biological activity as dependent variables. We were performed leave-one-out methods and the result reflected a direct relationship between biological activity and connectivity index of zero order, while indirect relationship with connectivity index of second order and thus connectivity index is a reliable descriptor to predict the biological activity of <em>β</em>-carboline and its various derivatives.
