Poly[(alanino ethyl ester)0.67 (glycino ethyl ester)0.33 phosphazene] (PAGP) was synthesized, and morphology and diameter of the electrospun PAGP nanofibers were systematically evaluated by using a cool field em...Poly[(alanino ethyl ester)0.67 (glycino ethyl ester)0.33 phosphazene] (PAGP) was synthesized, and morphology and diameter of the electrospun PAGP nanofibers were systematically evaluated by using a cool field emission scanning electron microscope (SEM) with changing the important processing variables such as applied voltage, polymeric concentration, and ambient temperature. The average diameter of PAGP nanofibers was inversely proportional to the applied voltage, but increased with the increase of solution concentration. Lower environmental temperature was unfavorable due to the nanofibers conglutination.展开更多
Four kinds of new macrocycles containing amino acids and nyl-heterocyclic units were synthesized by the condensation of di-esters containing Ts-amino acids units with di-halogenated compounds at room temperature. The ...Four kinds of new macrocycles containing amino acids and nyl-heterocyclic units were synthesized by the condensation of di-esters containing Ts-amino acids units with di-halogenated compounds at room temperature. The macrocycles were characterized by elemental analysis, IR,MS(FAB) and 1H NMR展开更多
Lipophilic complexes of macrocyclic 12-membered dioxotetraamine ligand bearing bis-hydroxy groups as functional pendants are effective catalysts for the hydrolysis of amino acid esters in micellar media, and the rate ...Lipophilic complexes of macrocyclic 12-membered dioxotetraamine ligand bearing bis-hydroxy groups as functional pendants are effective catalysts for the hydrolysis of amino acid esters in micellar media, and the rate enhancement of more than 10-fold were observed.展开更多
The binding mode of the amino acid ethyl esters(guest) by 5 (2 carboxylphenyl) 10,15,20 triphenylporphyrinatozinc(Ⅱ)(host 1) was studied by means of 1H NMR spectra. The binding mode is the hydrogen bonding between th...The binding mode of the amino acid ethyl esters(guest) by 5 (2 carboxylphenyl) 10,15,20 triphenylporphyrinatozinc(Ⅱ)(host 1) was studied by means of 1H NMR spectra. The binding mode is the hydrogen bonding between the amino group of the guest and the carboxyl group of host 1 plus the coordination between the zinc atom of porphyrinatozinc(Ⅱ) and the carbonyl group of the guest. This is a novel binding mode of the metalloporphyrin to amino acid derivatives.展开更多
A novel malonamide-linked zinc bisporphyrinate[Zn_(2)-1]has been designed and synthesized.UV-vis and NMR spectroscopic studies suggest the molecule aggregates in solution.Such zinc bisporphyrinate is very CD-sensitive...A novel malonamide-linked zinc bisporphyrinate[Zn_(2)-1]has been designed and synthesized.UV-vis and NMR spectroscopic studies suggest the molecule aggregates in solution.Such zinc bisporphyrinate is very CD-sensitive when it is mixed with amino acid ethyl esters.The amplitude value of the induced circular dichroism(ICD)is up to ca.1500 L•mol^(−1)•cm^(−1).Further studies by ^(1)H NMR and UV-vis spectroscopies reveal amino acid esters function as monodentate ligands,and[Zn_(2)-1]interacts with amino acid ethyl esters through coordination and hydrogen bonding interactions.展开更多
Nine racemic homocamptothecin derivatives were synthesized and in vitro antitumor activities were evaluated by standard MTT method. The results showed that some of the compound had higher antitumor activity than irite...Nine racemic homocamptothecin derivatives were synthesized and in vitro antitumor activities were evaluated by standard MTT method. The results showed that some of the compound had higher antitumor activity than iritecan.展开更多
With the aid of a Pyrolysis-GC/TOF MS technique, the pyrolysis behaviour of two menthyl esters of N-benzoxycarbonyl amino acid was investigated. A clear pattern emerges involving the cleavage of the bond linking the m...With the aid of a Pyrolysis-GC/TOF MS technique, the pyrolysis behaviour of two menthyl esters of N-benzoxycarbonyl amino acid was investigated. A clear pattern emerges involving the cleavage of the bond linking the menthyl ring to the carboxy group, followed by further degradation of the fragments. The major pyroproducts were p-menth-l-ene pyrolysed at a higher temperature or p-menth-2-ene pyrolysed at a lower temperature, and various derivatives of cyclohexene pyrolyzed from the menthyl ring. In addition, some of the products were also iden- tified as derivatives of benzene from the pyrolysis of benzyloxyl moiety.展开更多
Amino acid methyl ester phosphates were synthesized and determined by using positive-ion mode dectrospmy ionization mass spectrometry(ESIMS) in combination with multistage tandem mass spectrometry. The fragmentation...Amino acid methyl ester phosphates were synthesized and determined by using positive-ion mode dectrospmy ionization mass spectrometry(ESIMS) in combination with multistage tandem mass spectrometry. The fragmentation pathways were investigated, and it was observed that most fragment ions contained the phosphoryl group. It was interesting to observe that the fragmentation pathways of the protonated molecule show some differences when compared with those of the sodium ion adduct. The methoxy group of amino acid methyl ester can migrate from the carbonyl group to the phosphoryl group in the sodium ion adduct.展开更多
A series of novel phosphonoacetic acid derivatives, N-(ethoxycarbonylmethy-ethoxyphosphonyl)-α-amino acid esters and α-amino phosphonates, were synthesized via the reaction of the corresponding phosphonyl chloride ...A series of novel phosphonoacetic acid derivatives, N-(ethoxycarbonylmethy-ethoxyphosphonyl)-α-amino acid esters and α-amino phosphonates, were synthesized via the reaction of the corresponding phosphonyl chloride with amino acid ester hydrochlorides or amino phosphonates in the presence of a base. The preliminary bioassay shows that some compounds show significant anti-viral activity against tobacco mosaic virus (TMV)展开更多
A facile and efficient method for the stereoselective synthesis of β-amino acid esters via SmI2-promoted imino-Reformatsky reaction is described.Asymmetric addition of tert-butyl bromoacetate to N-tert-butanesulfinyl...A facile and efficient method for the stereoselective synthesis of β-amino acid esters via SmI2-promoted imino-Reformatsky reaction is described.Asymmetric addition of tert-butyl bromoacetate to N-tert-butanesulfinyl aldimines afforded β-amino acid esters in moderate to high yields with excellent diastereoselectivities.The synthetic utilities of the tert-butyl β-amino acid esters were expanded by the preparation of β-lactams and 3-aminoindan-1-ones derivatives.展开更多
The reductive alkylation of amine with carbonyl compounds using sodium hydrogen telluride has been investigated in recent years. Application of this method to the synthesis of N-alkyl derivatives of biologically impor...The reductive alkylation of amine with carbonyl compounds using sodium hydrogen telluride has been investigated in recent years. Application of this method to the synthesis of N-alkyl derivatives of biologically important amino acids and their esters is described.展开更多
We herein report our studies into the effects of microwave irradiation on the solvent-free esterification of L-leucine with alcohols. In the absence of solvent, microwave irradiation accelerated the reaction compared ...We herein report our studies into the effects of microwave irradiation on the solvent-free esterification of L-leucine with alcohols. In the absence of solvent, microwave irradiation accelerated the reaction compared to conventional oil bath heating. Measurement of the dielectric properties under the reaction conditions revealed that the high dielectric loss factor of the reaction mixture containing L-leucine, n-butanol, and a p-toluene sulfonic acid catalyst could be attributed to the acceleration of the reaction. The depth of microwave penetration into the reaction mixture as derived from the in-situ measurement of the dielectric properties was ~13 mm, which suggested that a thinner reaction vessel was favorable for the esterification of L-leucine. In addition to the batch reaction using a desktop microwave reactor, two types of flow reaction were also performed using a desktop tubular reactor and a semi-bench-scale tubular reactor. These flow reactions also exhibited high performances, thus allowing the scale-up of this reaction system for industrial use.展开更多
Several cyclic amino acids (1-4) were synthesized from glycine. Isocyanate ester was prepared as the key intermediate and reacted with dibromoalkanes to afford the target compounds.
A series of novel N-[α-(isoflavone-7-O-)acetyl] amino acid methyl esters were prepared from the efficient and regioselective alkylation of isoflavones with chloroacetyl amino acid derivatives under mild condition.
β-Amino esters were synthesized via ZnCl2-catalyzed Mannich-type reaction of imines and malonate esters under solvent-free conditions in 6 min. The β-amino ester was converted into the corresponding aspartic acid de...β-Amino esters were synthesized via ZnCl2-catalyzed Mannich-type reaction of imines and malonate esters under solvent-free conditions in 6 min. The β-amino ester was converted into the corresponding aspartic acid derivatives.展开更多
Urokinase-type plasminogen activator (uPA) plays a crucial role in the regulation of plasminogen activation, tumor cell adhesion and migration. The inhibition of uPA activity is a promising mechanism for anti-cancer...Urokinase-type plasminogen activator (uPA) plays a crucial role in the regulation of plasminogen activation, tumor cell adhesion and migration. The inhibition of uPA activity is a promising mechanism for anti-cancer therapy. Most current uPA inhibitors employ a highly basic group (either amidine or guanidine group) to target the S1 pocket of uPA active site, which leads to poor oral bioavailability. Here we study the possibility of using less basic 2-aminobenzothiazole (ABT) as S1 pocket binding group. We report the crystal structures of uPA complexes with ABT or 2-amino-benzothiazole-6-carboxylic acid ethyl ester (ABTCE). The inhibitory constants of these two inhibitors were measured by a chromogenic competitive assay, and it was found that ABTCE is a better inhibitor for uPA (Ki = 656 μM) than ABT (Ki = 5.03 mM). This work shows that 2-amniobenzothiazole can be used as P1 group which may have better oral bioavailability than the commonly used amidine or guanidine group. We also found the ethyl ester group occupies the characteristic oxyanion hole and contacts to uPA 37- and 60-loops. Such work provides structural information for further improvements of potency and selectivity of this new class of uPA inhibitor.展开更多
A series of chiral N-Boc-α-aminoaldehydes were synthesized in good yields and high purity via esterification of Boc-L-amino acids followed by reduction with sodium bis (2-methoxy- ethoxy)aluminum hydride.
基金Funded by the National Natural Science Foundation of China (No.50873012)
文摘Poly[(alanino ethyl ester)0.67 (glycino ethyl ester)0.33 phosphazene] (PAGP) was synthesized, and morphology and diameter of the electrospun PAGP nanofibers were systematically evaluated by using a cool field emission scanning electron microscope (SEM) with changing the important processing variables such as applied voltage, polymeric concentration, and ambient temperature. The average diameter of PAGP nanofibers was inversely proportional to the applied voltage, but increased with the increase of solution concentration. Lower environmental temperature was unfavorable due to the nanofibers conglutination.
文摘Four kinds of new macrocycles containing amino acids and nyl-heterocyclic units were synthesized by the condensation of di-esters containing Ts-amino acids units with di-halogenated compounds at room temperature. The macrocycles were characterized by elemental analysis, IR,MS(FAB) and 1H NMR
文摘Lipophilic complexes of macrocyclic 12-membered dioxotetraamine ligand bearing bis-hydroxy groups as functional pendants are effective catalysts for the hydrolysis of amino acid esters in micellar media, and the rate enhancement of more than 10-fold were observed.
文摘The binding mode of the amino acid ethyl esters(guest) by 5 (2 carboxylphenyl) 10,15,20 triphenylporphyrinatozinc(Ⅱ)(host 1) was studied by means of 1H NMR spectra. The binding mode is the hydrogen bonding between the amino group of the guest and the carboxyl group of host 1 plus the coordination between the zinc atom of porphyrinatozinc(Ⅱ) and the carbonyl group of the guest. This is a novel binding mode of the metalloporphyrin to amino acid derivatives.
基金This work was supported by the Natural Science Foundation of China(No.21271133)the Priority Academic Program Development of Jiangsu Higher Education Institutions.
文摘A novel malonamide-linked zinc bisporphyrinate[Zn_(2)-1]has been designed and synthesized.UV-vis and NMR spectroscopic studies suggest the molecule aggregates in solution.Such zinc bisporphyrinate is very CD-sensitive when it is mixed with amino acid ethyl esters.The amplitude value of the induced circular dichroism(ICD)is up to ca.1500 L•mol^(−1)•cm^(−1).Further studies by ^(1)H NMR and UV-vis spectroscopies reveal amino acid esters function as monodentate ligands,and[Zn_(2)-1]interacts with amino acid ethyl esters through coordination and hydrogen bonding interactions.
基金the National Natural Science Foundation of China (No.30371689)Shanghai Major Program Science and Technology Foundation (No.064319009)Shanghai Leading Academic Discipline Project (No.B906).
文摘Nine racemic homocamptothecin derivatives were synthesized and in vitro antitumor activities were evaluated by standard MTT method. The results showed that some of the compound had higher antitumor activity than iritecan.
基金Supported by the Key Project on Anhui Province Natural Science Study by Colleges and Universities(No.KJ2008A094)
文摘With the aid of a Pyrolysis-GC/TOF MS technique, the pyrolysis behaviour of two menthyl esters of N-benzoxycarbonyl amino acid was investigated. A clear pattern emerges involving the cleavage of the bond linking the menthyl ring to the carboxy group, followed by further degradation of the fragments. The major pyroproducts were p-menth-l-ene pyrolysed at a higher temperature or p-menth-2-ene pyrolysed at a lower temperature, and various derivatives of cyclohexene pyrolyzed from the menthyl ring. In addition, some of the products were also iden- tified as derivatives of benzene from the pyrolysis of benzyloxyl moiety.
基金Supported by the National Natural Science Foundation of China(No.20572061).
文摘Amino acid methyl ester phosphates were synthesized and determined by using positive-ion mode dectrospmy ionization mass spectrometry(ESIMS) in combination with multistage tandem mass spectrometry. The fragmentation pathways were investigated, and it was observed that most fragment ions contained the phosphoryl group. It was interesting to observe that the fragmentation pathways of the protonated molecule show some differences when compared with those of the sodium ion adduct. The methoxy group of amino acid methyl ester can migrate from the carbonyl group to the phosphoryl group in the sodium ion adduct.
文摘A series of novel phosphonoacetic acid derivatives, N-(ethoxycarbonylmethy-ethoxyphosphonyl)-α-amino acid esters and α-amino phosphonates, were synthesized via the reaction of the corresponding phosphonyl chloride with amino acid ester hydrochlorides or amino phosphonates in the presence of a base. The preliminary bioassay shows that some compounds show significant anti-viral activity against tobacco mosaic virus (TMV)
基金Financial support from the National Natural Science Foundation of China (20721003)the Chinese Academy of Sciences, the State Key Laboratory of Drug Research, SIMM and National Science & Technology Major Project (2009ZX09301-001 & 2008ZX09401-004) is acknowledged
文摘A facile and efficient method for the stereoselective synthesis of β-amino acid esters via SmI2-promoted imino-Reformatsky reaction is described.Asymmetric addition of tert-butyl bromoacetate to N-tert-butanesulfinyl aldimines afforded β-amino acid esters in moderate to high yields with excellent diastereoselectivities.The synthetic utilities of the tert-butyl β-amino acid esters were expanded by the preparation of β-lactams and 3-aminoindan-1-ones derivatives.
文摘The reductive alkylation of amine with carbonyl compounds using sodium hydrogen telluride has been investigated in recent years. Application of this method to the synthesis of N-alkyl derivatives of biologically important amino acids and their esters is described.
文摘We herein report our studies into the effects of microwave irradiation on the solvent-free esterification of L-leucine with alcohols. In the absence of solvent, microwave irradiation accelerated the reaction compared to conventional oil bath heating. Measurement of the dielectric properties under the reaction conditions revealed that the high dielectric loss factor of the reaction mixture containing L-leucine, n-butanol, and a p-toluene sulfonic acid catalyst could be attributed to the acceleration of the reaction. The depth of microwave penetration into the reaction mixture as derived from the in-situ measurement of the dielectric properties was ~13 mm, which suggested that a thinner reaction vessel was favorable for the esterification of L-leucine. In addition to the batch reaction using a desktop microwave reactor, two types of flow reaction were also performed using a desktop tubular reactor and a semi-bench-scale tubular reactor. These flow reactions also exhibited high performances, thus allowing the scale-up of this reaction system for industrial use.
基金the National Natural Science Foundation of China(No.20272001)
文摘Several cyclic amino acids (1-4) were synthesized from glycine. Isocyanate ester was prepared as the key intermediate and reacted with dibromoalkanes to afford the target compounds.
文摘A series of novel N-[α-(isoflavone-7-O-)acetyl] amino acid methyl esters were prepared from the efficient and regioselective alkylation of isoflavones with chloroacetyl amino acid derivatives under mild condition.
基金the financial support form National Natural Science Foundation of China(No.20472116).
文摘β-Amino esters were synthesized via ZnCl2-catalyzed Mannich-type reaction of imines and malonate esters under solvent-free conditions in 6 min. The β-amino ester was converted into the corresponding aspartic acid derivatives.
基金Supported by FJIRSM (SZD08003)National Natural Science Foundation of China (30811130467, 30625011)+1 种基金Ministry of Science of Technology (2006AA02A313, 2007CB914304)Chinese Academy of Sciences (KSCX2-YW-R-082)
文摘Urokinase-type plasminogen activator (uPA) plays a crucial role in the regulation of plasminogen activation, tumor cell adhesion and migration. The inhibition of uPA activity is a promising mechanism for anti-cancer therapy. Most current uPA inhibitors employ a highly basic group (either amidine or guanidine group) to target the S1 pocket of uPA active site, which leads to poor oral bioavailability. Here we study the possibility of using less basic 2-aminobenzothiazole (ABT) as S1 pocket binding group. We report the crystal structures of uPA complexes with ABT or 2-amino-benzothiazole-6-carboxylic acid ethyl ester (ABTCE). The inhibitory constants of these two inhibitors were measured by a chromogenic competitive assay, and it was found that ABTCE is a better inhibitor for uPA (Ki = 656 μM) than ABT (Ki = 5.03 mM). This work shows that 2-amniobenzothiazole can be used as P1 group which may have better oral bioavailability than the commonly used amidine or guanidine group. We also found the ethyl ester group occupies the characteristic oxyanion hole and contacts to uPA 37- and 60-loops. Such work provides structural information for further improvements of potency and selectivity of this new class of uPA inhibitor.
基金supported by the National Natural Science Foundation of China(No.30230400)"863"Hi-Tech Program of China(No.2004 AA2 Z3781)the State Key Program of Basic Research of China(No.2004GB518907).
文摘A series of chiral N-Boc-α-aminoaldehydes were synthesized in good yields and high purity via esterification of Boc-L-amino acids followed by reduction with sodium bis (2-methoxy- ethoxy)aluminum hydride.