Iodine was found to be an efficient catalyst for the one pot synthesis of α-amino phosphonate from aldehydes, anilines and diethyl phosphite. The influences of the iodine loading, reaction solvent, the structure of a...Iodine was found to be an efficient catalyst for the one pot synthesis of α-amino phosphonate from aldehydes, anilines and diethyl phosphite. The influences of the iodine loading, reaction solvent, the structure of aldehyde and aniline on the reaction were studied.展开更多
Three-component reactions of aldehydes, amines, and diethyl phosphite catalyzed by FeCl3 in EtOH or under solvent-free and mild conditions afforded the corresponding α-amino phosphonates in excellent yields.
目的寻找具有内皮依赖性舒张血管活性的新结构胺基膦酸酯类化合物。方法运用一种新型的类M ann ich反应,以生物电子等排体原理设计合成了一系列α-胺基苄基膦酸酯类化合物,并运用离体大鼠血管环和离体豚鼠回肠收缩实验观察其舒张血管活...目的寻找具有内皮依赖性舒张血管活性的新结构胺基膦酸酯类化合物。方法运用一种新型的类M ann ich反应,以生物电子等排体原理设计合成了一系列α-胺基苄基膦酸酯类化合物,并运用离体大鼠血管环和离体豚鼠回肠收缩实验观察其舒张血管活性及其对M受体的激动作用。结果共合成了7个新的α-胺基苄基膦酸酯类目标化合物,其结构经IR,1H NMR和元素分析确定。初步离体血管环实验和离体豚鼠回肠收缩实验结果显示,化合物2a,2b和2 c有一定的舒张血管活性且不激活平滑肌M受体。结论在浓度为1×10-5mol.L-1时,化合物2b和2 c有较强的舒张血管活性,其舒张率分别为(67±21)%,(82±18)%,而且不激动M受体,其中,化合物2b有内皮依赖性的舒张血管反应。展开更多
Six barium substituted aminothyl phosphonate BaO3PCH2CH2NR1R2（2a～f）supports are synthesized by using barium chloride reacted with substituted aminoethyl phosphonic acids H2O3PCH2CH2NR1R2（1a～f）.6 of solid bases ...Six barium substituted aminothyl phosphonate BaO3PCH2CH2NR1R2（2a～f）supports are synthesized by using barium chloride reacted with substituted aminoethyl phosphonic acids H2O3PCH2CH2NR1R2（1a～f）.6 of solid bases （3a～f）are prepared by treating of the supports with 5% of sodium hydroxied solution.The solid bases are characterized by IR,TG,DTG DSC,basic strength and free base number in water.Basic strengths of the solid bases are about 9.3 to 15.0 by indicator method,and the free base numbers in water of the supports or the solid bases are measured using of benzoic acid titration method.The effect of refluxing time in the preparation of the support on the free base number in water is discussed.Three typical Knoevenagel condensation reactions catalyzed by the solid base are carried out with the merits of high yields,little side readctions and convnient workup.The solid base catalysts can be reused for 8 times and easy to be regenerated.It is a type of environmently friendly catalysts.展开更多
In this paper,CoMFA studies were performed on a set of α-(substituted phenoxy acetoxy)alkyl phosphonates.On the basis of the 60 molecules and with the help of ’optimizing QSAR’,Nut only not only built model,Which a...In this paper,CoMFA studies were performed on a set of α-(substituted phenoxy acetoxy)alkyl phosphonates.On the basis of the 60 molecules and with the help of ’optimizing QSAR’,Nut only not only built model,Which a good CoMFA model,which with the conventional r^2 and crossvalidated coefficient(q^2) up to 0.94 and 0.82,but also 5120 new structures and their predicted activities were obtained.This work provided a potential direction for the further synthesis.展开更多
Using methanol-water mixtures as the mobile phase, the chromatographic retention parameters k' and Rf were determined by reversed-phase high-performance liquid chromatography (RP-HPLC) and reversed-phase high-perf...Using methanol-water mixtures as the mobile phase, the chromatographic retention parameters k' and Rf were determined by reversed-phase high-performance liquid chromatography (RP-HPLC) and reversed-phase high-performance thin-layer chromatography (RP-HPTLC) for N-(benzothiazol-2-yl)-α-amino alkyl phosphoric diesters and the correlation with lipophilicity parameter (Clog P) was established. Log Kw values obtained from RP-HPLC and Rm values obtained from RP-HPTLC can be used to evaluate the lipophilicity of this kind of compounds. Chromatographic method is a good alternative for lipophilicity measurement.展开更多
In the present investigation, we carried a phytochemical study of an ethanol-soluble extract from the root barks of Aspidistra typica Baill., a traditional food and herb medicine, leading to the isolation of four diff...In the present investigation, we carried a phytochemical study of an ethanol-soluble extract from the root barks of Aspidistra typica Baill., a traditional food and herb medicine, leading to the isolation of four different kinds of compounds, including one benzene substituted coumarin, two organic phosphonic compounds, and one xanthone. The novel benzene substituted coumarin typicacoumarin A(1) was a new type of coumarin, and the two new organic phosphonic compounds, typicalphosphine A(2) and typicalphosphine B(3) were isolated for the first time, and their structures were elucidated by spectral techniques, viz.1 D, 2 D NMR spectra and HR-ESI-MS. The xanthone compound typicaxanthone A(4) was discovered from nature for the first time. The two new organic phosphonic chlorides(2, 3) showed stronger antibacterial activities, which were comparable to berberine hydrochloride. And typicaxanthone A(4) showed much stronger antibacterial activity against Escherichia coli ATCC-25922 bacterial strain, while typicacoumarin A(1) showed moderate antibacterial activities, weaker than berberine hydrochloride.展开更多
2-Amino substituted benzothiazole 4a--4I and p-acetamidobenzenesulfonyl chloride 2 were used to prepare 2-（p-aminophenylsulfonamido） substituted benzothiazole 6a--6I using mixture of pyridine and acetic anhydride wh...2-Amino substituted benzothiazole 4a--4I and p-acetamidobenzenesulfonyl chloride 2 were used to prepare 2-（p-aminophenylsulfonamido） substituted benzothiazole 6a--6I using mixture of pyridine and acetic anhydride which formed an electrophilic complex （N-acetyl pyridinium） to facilitate condensation to give desired product by removal of HC1. 2-{p-[（3-Carboxypyrid-2-y1）amino]phenylsulfonamido}benzothiazoles 8a--81 were synthesized from 2-chloropyridine-3-carboxylic acid 7 and 6a--6I in 2-ethoxy ethanol using Cu-powder and K2CO3. Acid chlorides 9a--91 were condensed with 2-hydroxyethyl piperazine 10 and 2,3-dichloropiperazine 11 for amide deriva- tives 2-（p-（（3-（4-（2-hydroxyethy1）piperazin-1-ylcarbonyl）pyrid-2-y1）amino）phenylsulfonamido）benzothiazoes 12a -121 and 2-{p-[3-（2,3-dichloropiperazin-l-ylcarbonyl）pyrid-2-ylamino]phenylsulfonamido}benzothiazoles 13a- 131 respectively. The structures of the new compounds have been established on the basis of their chemical analysis and spectral data （IR, 1↑H NMR and mass）. All the compounds have been screened for their antibacterial and antifungal activities.展开更多
基金Financial support for this research was provided by the National Natural Science Foundation of China （No.20472061） and Sun Yat-sen University.
文摘Iodine was found to be an efficient catalyst for the one pot synthesis of α-amino phosphonate from aldehydes, anilines and diethyl phosphite. The influences of the iodine loading, reaction solvent, the structure of aldehyde and aniline on the reaction were studied.
基金Project supported by the National Natural Science Foundation of China （No. 20502004）, Ministry of Education of China, the Science and Technology Commission of Shanghai Municipality （No. 05ZR14013） and Fudan University.
文摘Three-component reactions of aldehydes, amines, and diethyl phosphite catalyzed by FeCl3 in EtOH or under solvent-free and mild conditions afforded the corresponding α-amino phosphonates in excellent yields.
文摘Six barium substituted aminothyl phosphonate BaO3PCH2CH2NR1R2（2a～f）supports are synthesized by using barium chloride reacted with substituted aminoethyl phosphonic acids H2O3PCH2CH2NR1R2（1a～f）.6 of solid bases （3a～f）are prepared by treating of the supports with 5% of sodium hydroxied solution.The solid bases are characterized by IR,TG,DTG DSC,basic strength and free base number in water.Basic strengths of the solid bases are about 9.3 to 15.0 by indicator method,and the free base numbers in water of the supports or the solid bases are measured using of benzoic acid titration method.The effect of refluxing time in the preparation of the support on the free base number in water is discussed.Three typical Knoevenagel condensation reactions catalyzed by the solid base are carried out with the merits of high yields,little side readctions and convnient workup.The solid base catalysts can be reused for 8 times and easy to be regenerated.It is a type of environmently friendly catalysts.
文摘In this paper,CoMFA studies were performed on a set of α-(substituted phenoxy acetoxy)alkyl phosphonates.On the basis of the 60 molecules and with the help of ’optimizing QSAR’,Nut only not only built model,Which a good CoMFA model,which with the conventional r^2 and crossvalidated coefficient(q^2) up to 0.94 and 0.82,but also 5120 new structures and their predicted activities were obtained.This work provided a potential direction for the further synthesis.
基金Project supported by the Fund of State Key Laboratory of Elemento-Organic Chemistry, Nankai University
文摘Using methanol-water mixtures as the mobile phase, the chromatographic retention parameters k' and Rf were determined by reversed-phase high-performance liquid chromatography (RP-HPLC) and reversed-phase high-performance thin-layer chromatography (RP-HPTLC) for N-(benzothiazol-2-yl)-α-amino alkyl phosphoric diesters and the correlation with lipophilicity parameter (Clog P) was established. Log Kw values obtained from RP-HPLC and Rm values obtained from RP-HPTLC can be used to evaluate the lipophilicity of this kind of compounds. Chromatographic method is a good alternative for lipophilicity measurement.
基金supported by the Research Platform for the project of the application basic plan in Sichuan Province(No.2014JY0113)the project of Department of Science in Sichuan Province,China(No.14ZA0003)
文摘In the present investigation, we carried a phytochemical study of an ethanol-soluble extract from the root barks of Aspidistra typica Baill., a traditional food and herb medicine, leading to the isolation of four different kinds of compounds, including one benzene substituted coumarin, two organic phosphonic compounds, and one xanthone. The novel benzene substituted coumarin typicacoumarin A(1) was a new type of coumarin, and the two new organic phosphonic compounds, typicalphosphine A(2) and typicalphosphine B(3) were isolated for the first time, and their structures were elucidated by spectral techniques, viz.1 D, 2 D NMR spectra and HR-ESI-MS. The xanthone compound typicaxanthone A(4) was discovered from nature for the first time. The two new organic phosphonic chlorides(2, 3) showed stronger antibacterial activities, which were comparable to berberine hydrochloride. And typicaxanthone A(4) showed much stronger antibacterial activity against Escherichia coli ATCC-25922 bacterial strain, while typicacoumarin A(1) showed moderate antibacterial activities, weaker than berberine hydrochloride.
文摘2-Amino substituted benzothiazole 4a--4I and p-acetamidobenzenesulfonyl chloride 2 were used to prepare 2-（p-aminophenylsulfonamido） substituted benzothiazole 6a--6I using mixture of pyridine and acetic anhydride which formed an electrophilic complex （N-acetyl pyridinium） to facilitate condensation to give desired product by removal of HC1. 2-{p-[（3-Carboxypyrid-2-y1）amino]phenylsulfonamido}benzothiazoles 8a--81 were synthesized from 2-chloropyridine-3-carboxylic acid 7 and 6a--6I in 2-ethoxy ethanol using Cu-powder and K2CO3. Acid chlorides 9a--91 were condensed with 2-hydroxyethyl piperazine 10 and 2,3-dichloropiperazine 11 for amide deriva- tives 2-（p-（（3-（4-（2-hydroxyethy1）piperazin-1-ylcarbonyl）pyrid-2-y1）amino）phenylsulfonamido）benzothiazoes 12a -121 and 2-{p-[3-（2,3-dichloropiperazin-l-ylcarbonyl）pyrid-2-ylamino]phenylsulfonamido}benzothiazoles 13a- 131 respectively. The structures of the new compounds have been established on the basis of their chemical analysis and spectral data （IR, 1↑H NMR and mass）. All the compounds have been screened for their antibacterial and antifungal activities.
