Developing and excavating new agrochemicals with highly active and safe is an important tactic for protecting crop health and food safety.In this paper,to discover the new bactericide candidates,we designed,prepared a...Developing and excavating new agrochemicals with highly active and safe is an important tactic for protecting crop health and food safety.In this paper,to discover the new bactericide candidates,we designed,prepared a new type of1,2,3,4-tetrahydro-β-carboline(THC)derivatives and evaluated the in vitro and in vivo bioactivities against the Xanthomonas oryzae pv.oryzae(Xoo),Xanthomonas axonopodis pv.citri(Xac),and Pseudomonas syringae pv.actinidiae(Psa).The in vitro bioassay results exhibited that most title molecules possessed good activity toward the three plant pathogenic bacteria,the compound A17 showed the most active against Xoo and Xac with EC50 values of 7.27 and 4.89 mg mL^(-1)respectively,and compound A8 exhibited the best inhibitory activity against Psa with EC50value of 4.87 mg mL^(-1).Pot experiments showed that compound A17 exhibited excellent in vivo antibacterial activities to manage rice bacterial leaf blight and citrus bacterial canker,with protective efficiencies of 52.67 and 79.79%at 200 mgmL^(-1),respectively.Meanwhile,compound A8 showed good control efficiency(84.31%)against kiwifruit bacterial canker at 200 mg mL^(-1).Antibacterial mechanism suggested that these compounds could interfere with the balance of the redox system,damage the cell membrane,and induce the apoptosis of Xoo cells.Taken together,our study revealed that tetrahydro-β-carboline derivatives could be a promising candidate model for novel broadspectrum bactericides.展开更多
Four 1, 2,3,4-tetrahydro - β - c arboline amino acid esters with a heterocycle at the C- 1position were used as chiral ligands in the enantioselective addition reactions. The differentpositions of the heteroatoms gav...Four 1, 2,3,4-tetrahydro - β - c arboline amino acid esters with a heterocycle at the C- 1position were used as chiral ligands in the enantioselective addition reactions. The differentpositions of the heteroatoms gave different effects, and medium but opposite enantioselectivitywas recorded.展开更多
A new β-carboline alkaloid, 4-(9H-β-carbolin-1-yl)-4-oxobutyric acid and a new derivate of isoferulic acid, (E)-3-(3-hydroxy-4-methoxyphenyl)acrylic acid carboxymethyl ester, were isolated from the roots of An...A new β-carboline alkaloid, 4-(9H-β-carbolin-1-yl)-4-oxobutyric acid and a new derivate of isoferulic acid, (E)-3-(3-hydroxy-4-methoxyphenyl)acrylic acid carboxymethyl ester, were isolated from the roots of Anemone altaica. Their structures were determined on the basis of spectral data.展开更多
Sixβ-carboline alkaloids including three new ones,trifilines A-C(1-3)were isolated from Trigonostemon filipes,along with a newβ-carboline alkaloid,trigonoine C(7)isolated from Trigonostemon lii.Their structures were...Sixβ-carboline alkaloids including three new ones,trifilines A-C(1-3)were isolated from Trigonostemon filipes,along with a newβ-carboline alkaloid,trigonoine C(7)isolated from Trigonostemon lii.Their structures were elucidated by extensive spectroscopic techniques.Trifilines A(1)and B(2)showed weak anti-HIV-1 activity with EC50 values of 54.61μg/mL and 9.75μg/mL,along with TI(Therapeutic index)values of 1.52 and 1.42,respectively.This is the first time to report the chemical constituents of Trigonostemon filipes.展开更多
2-Benzyl-7-butoxyl-9-isobutyl-1-methyl-β-carboline bromide(H-2-65) was synthesized by the reaction of Harmine with 1-iodobutane via N9-alkylation, demethyl and N2-quaternarization to obtain the new compound. The re...2-Benzyl-7-butoxyl-9-isobutyl-1-methyl-β-carboline bromide(H-2-65) was synthesized by the reaction of Harmine with 1-iodobutane via N9-alkylation, demethyl and N2-quaternarization to obtain the new compound. The results demonstrate that H-2-65 has more remarkable anticancer activities in vitro. The results of 1H NMR, 13 C NMR, DEPT, g COSY, g HSQC, g HMBC, MS, single-crystal X-ray diffraction and elemental analysis showed that the title compound crystallizes in the triclinic system, space group P1 with a = 9.545(5), b = 11.724(5), c = 11.839(6) , α = 77.530(6), β = 87.169(6), γ = 72.823(5)o, Z = 2, V = 1235.8(10)3, Dc = 1.294 g·cm-3, F(000) = 504, the final R = 0.0453, wR = 0.1262 and S = 1.044.展开更多
This study reports the isolation of four newβ-carboline alkaloids(1−4)and six previously identified alkaloids(5−10)from the roots of Peganum harmala L.Among these compounds,1 and 2 were characterized as rareβ-carbol...This study reports the isolation of four newβ-carboline alkaloids(1−4)and six previously identified alkaloids(5−10)from the roots of Peganum harmala L.Among these compounds,1 and 2 were characterized as rareβ-carboline-quinazoline dimers exhibiting axial chirality.Compound 3 possessed a unique 6/5/6/7 tetracyclic ring system with an azepine ring,and compound 4 was a novel annomontineβ-carboline.The structures of these compounds were elucidated by spectroscopic data and quantum mechanical calculations.The biosynthetic pathways of 1−3 were proposed.Additionally,the cytotoxicity of some isolates against four cancer cell lines(HL-60,A549,MDA-MB-231,and DU145)was evaluated.Notably,compound 4 exhibited significant cytotoxicity against HL-60,A549,and DU145 cells with IC_(50) values of 12.39,12.80,and 30.65μmol·L^(−1),respectively.Furthermore,compound 2 demonstrated selective cytotoxicity against HL-60 cells with an IC_(50) value of 17.32μmol·L^(−1).展开更多
The 9-octadecanoic acid-hexadecanoic acid-tetrahydrofuran-3,4-diyl ester from neem oil was investigated for antibacterial activity against three bacterial strains viz., Staphylococcus aureus ATCC No. 25923, Escherichi...The 9-octadecanoic acid-hexadecanoic acid-tetrahydrofuran-3,4-diyl ester from neem oil was investigated for antibacterial activity against three bacterial strains viz., Staphylococcus aureus ATCC No. 25923, Escherichia coli ATCC No. 44102 and Salmonella sp. ATCC No. 50 041 in vitro. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of the 9-octadecanoic acid-hexadecanoic acid-tetrahydrofuran-3,4-diyl ester were determined by using the broth microdilution dilution (BMD) method at different concentrations ranging from 20 to 0.625 mg mL-1. Its time-inhibition curve against E. coli was also tested and showed that the MIC values for the bacterial strains S. aureus, E. coli and Salmonella sp. were 20, 5 and 10 mg mL-1, respectively. Its MBC values were 20, 20 and 10 mg mL-1, respectively. The antibacterial activity of 9-octadecanoic acid-hexadecanoic acid-tetrahydrofuran-3,4-diyl ester against three strain tested showed the relationship with time and concentration.展开更多
The synthesis of the bis-isoxazolyl-1,2,5,6-tetrahydro pyridine-3-carboxylates is achieved in high yield without the production of toxic waste products by using room temperature ionic liquid (RTILs) triethyl ammonium ...The synthesis of the bis-isoxazolyl-1,2,5,6-tetrahydro pyridine-3-carboxylates is achieved in high yield without the production of toxic waste products by using room temperature ionic liquid (RTILs) triethyl ammonium acetate (TEAA). The RTIL TEAA played the dual role of efficient green solvent as well as recyclable catalyst.展开更多
3,5,6,8-Tetrahydro-4H-thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidin-4-ones(7) were synthesized via the base catalytic reactions of amines or phenols with carbodiimides(5), which were obtained from the aza-Wittig ...3,5,6,8-Tetrahydro-4H-thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidin-4-ones(7) were synthesized via the base catalytic reactions of amines or phenols with carbodiimides(5), which were obtained from the aza-Wittig reac tions of iminophosphoranes(4) with aromatic isocyanates.展开更多
A series of 6-fluoro-3,3a,4,5-tetrahydro-2H-pyrazolo[4,3-c]quinoline-2-carboxamide derivatives was designed based on the bioisosterism and combination principle in drug design. The target compounds were synthesized fr...A series of 6-fluoro-3,3a,4,5-tetrahydro-2H-pyrazolo[4,3-c]quinoline-2-carboxamide derivatives was designed based on the bioisosterism and combination principle in drug design. The target compounds were synthesized from substituted aniline through Michael addition, cyclization, Mannich reaction and condensation with 4-substituted semicarbazides, and the structures were confirmed by mass spectrometry(MS) and 1H NMR. The antifungal assay was carried out in vitro by two-fold dilution. The result shows that all the compounds are of antifungal activities against the tested fungi at different levels.展开更多
The title compound, acetic acid-3,5-diacetoxy-2-acetoxymethyl-6-(4-quinoxalin- 2-yl-phenoxy)-tetrahydro-pyran-4-yl-ester 8 (C28H28N2O10, Mr = 552.54), has been synthesized and its crystal structure was determined ...The title compound, acetic acid-3,5-diacetoxy-2-acetoxymethyl-6-(4-quinoxalin- 2-yl-phenoxy)-tetrahydro-pyran-4-yl-ester 8 (C28H28N2O10, Mr = 552.54), has been synthesized and its crystal structure was determined by X-ray diffraction analysis. It crystallizes in monoclinic, space group P21, a = 10.060(8), b = 5.648(4), c = 24.11(2)A, β = 91.078(10)°, Z = 2, V= 1369.9(19)A^3, Dc = 1.339 g/cm^3,μ(MoKa) = 1.03 cm^-1, F(000) = 580.00, T =. 193.1 Kx-9 θmax = 25.03, (△/σ)max = 0.0000, Flack = -0.0(24), the final R = 0.0680 and wR = 0.140 (w = 1/[0.0016Fo^2 + 1.00000(Fo^2)]/(4Fo^2)) for 3126 observed reflections (1 〉 20(/)). The pyranoid ring adopts chair conformation in the sugar moiety, and all of the acetyl groups are in the e bond of the pyranoid ring, so the sugar moiety is very stable.展开更多
The crystal structure of 1, l-dichloro-la, 3-diphenyl-l, la, 2, 3-te-trahydro-azirino[2, l-d ] [l, 5]benzothizeapine (C22H17Cl2NS, Mr= 398. 35) has beendetermined. The title compound crystallizes in orthorhombic space...The crystal structure of 1, l-dichloro-la, 3-diphenyl-l, la, 2, 3-te-trahydro-azirino[2, l-d ] [l, 5]benzothizeapine (C22H17Cl2NS, Mr= 398. 35) has beendetermined. The title compound crystallizes in orthorhombic space group Pbca with celldimensions a= 11. 579(3), b= 15. 14O(4), c=2l. 534(5) A, V= 3775. 04(5) A 3, Z= 8, D. = 1' 402g. cm-3, MoKa(λ= 0. 7l073 A ), F (000) = lO64, μ= O. 245mm-1. The structure was solved by using direct methods and refined by full-matrixleast-Squares method, and the final crystallographic discrepancy factor is 0. 046 for4l94 observed rcflections. The molecular backbone is a tricyclic system with the centralseven-membered l, 5-thiazepine ring in twisted boat-like conformation and cis-fused toboth azirine ring and benzene ring.展开更多
β-咔啉结构广泛存在于生物活性分子之中,为探索非酸性反应条件下合成β-咔啉衍生物的方法,以色胺类化合物和醛类为原料,以改进的Pictet-Spengler反应为关键步骤,再经氧化脱氢合成4个多取代β-咔啉化合物(2a~2d),其结构经1 H NMR和MS(E...β-咔啉结构广泛存在于生物活性分子之中,为探索非酸性反应条件下合成β-咔啉衍生物的方法,以色胺类化合物和醛类为原料,以改进的Pictet-Spengler反应为关键步骤,再经氧化脱氢合成4个多取代β-咔啉化合物(2a~2d),其结构经1 H NMR和MS(ESI)确证。经过对Pictet-Spengler反应步骤中物料比、溶剂、反应温度与时间进行考察后发现:在色胺类化合物为2.0 mmol,醛为3.0 mmol,六氟异丙醇钙为0.4 mmol,二氯甲烷为20.0 mL,室温反应24 h的最优条件下,四氢-β-咔啉化合物中间体(1a~1d)的收率为75%~89%,反应存在取代基效应,含芳香性基团底物收率较高。展开更多
基金the supports from National Natural Science Foundation of China(21877021,32160661,and 32202359)the Guizhou Provincial S&T Project China(2018[4007])+2 种基金the the Guizhou Province China[Qianjiaohe KY number(2020)004]the Program of Introducing Talents of Discipline to Universities of China(D20023,111 Program)the Guizhou University(GZU)Found for Newly Enrolled Talent China(202229)。
文摘Developing and excavating new agrochemicals with highly active and safe is an important tactic for protecting crop health and food safety.In this paper,to discover the new bactericide candidates,we designed,prepared a new type of1,2,3,4-tetrahydro-β-carboline(THC)derivatives and evaluated the in vitro and in vivo bioactivities against the Xanthomonas oryzae pv.oryzae(Xoo),Xanthomonas axonopodis pv.citri(Xac),and Pseudomonas syringae pv.actinidiae(Psa).The in vitro bioassay results exhibited that most title molecules possessed good activity toward the three plant pathogenic bacteria,the compound A17 showed the most active against Xoo and Xac with EC50 values of 7.27 and 4.89 mg mL^(-1)respectively,and compound A8 exhibited the best inhibitory activity against Psa with EC50value of 4.87 mg mL^(-1).Pot experiments showed that compound A17 exhibited excellent in vivo antibacterial activities to manage rice bacterial leaf blight and citrus bacterial canker,with protective efficiencies of 52.67 and 79.79%at 200 mgmL^(-1),respectively.Meanwhile,compound A8 showed good control efficiency(84.31%)against kiwifruit bacterial canker at 200 mg mL^(-1).Antibacterial mechanism suggested that these compounds could interfere with the balance of the redox system,damage the cell membrane,and induce the apoptosis of Xoo cells.Taken together,our study revealed that tetrahydro-β-carboline derivatives could be a promising candidate model for novel broadspectrum bactericides.
文摘Four 1, 2,3,4-tetrahydro - β - c arboline amino acid esters with a heterocycle at the C- 1position were used as chiral ligands in the enantioselective addition reactions. The differentpositions of the heteroatoms gave different effects, and medium but opposite enantioselectivitywas recorded.
文摘A new β-carboline alkaloid, 4-(9H-β-carbolin-1-yl)-4-oxobutyric acid and a new derivate of isoferulic acid, (E)-3-(3-hydroxy-4-methoxyphenyl)acrylic acid carboxymethyl ester, were isolated from the roots of Anemone altaica. Their structures were determined on the basis of spectral data.
基金supported financially by the National Natural Science Foundation of China(30830114 and 21072199)the Ministry of Science and Technology of China(2009CB522300 and 2009CB940900)+1 种基金the Natural Science Fund of Yunnan Province(2009CD112)the Foundation of Chinese Academy of Sciences to H.P.He,the Yong Academic and Technical Leader Raising Foundation of Yunnan Province(2010CI047).
文摘Sixβ-carboline alkaloids including three new ones,trifilines A-C(1-3)were isolated from Trigonostemon filipes,along with a newβ-carboline alkaloid,trigonoine C(7)isolated from Trigonostemon lii.Their structures were elucidated by extensive spectroscopic techniques.Trifilines A(1)and B(2)showed weak anti-HIV-1 activity with EC50 values of 54.61μg/mL and 9.75μg/mL,along with TI(Therapeutic index)values of 1.52 and 1.42,respectively.This is the first time to report the chemical constituents of Trigonostemon filipes.
基金Supported by the National Key Technology Research and Development Program of the Ministry of Science and Technology of China(No.2012BAI30B00)
文摘2-Benzyl-7-butoxyl-9-isobutyl-1-methyl-β-carboline bromide(H-2-65) was synthesized by the reaction of Harmine with 1-iodobutane via N9-alkylation, demethyl and N2-quaternarization to obtain the new compound. The results demonstrate that H-2-65 has more remarkable anticancer activities in vitro. The results of 1H NMR, 13 C NMR, DEPT, g COSY, g HSQC, g HMBC, MS, single-crystal X-ray diffraction and elemental analysis showed that the title compound crystallizes in the triclinic system, space group P1 with a = 9.545(5), b = 11.724(5), c = 11.839(6) , α = 77.530(6), β = 87.169(6), γ = 72.823(5)o, Z = 2, V = 1235.8(10)3, Dc = 1.294 g·cm-3, F(000) = 504, the final R = 0.0453, wR = 0.1262 and S = 1.044.
基金supported by the National Natural Science Foundation of China(No.81773604)the National Science and Technology Major Project of the Ministry of Science and Technology of China(No.2018ZX09735005)+1 种基金the Doctoral Scientific Research Fund Project of Nanyang Institute of Technology(No.510197)the Interdisciplinary Sciences Project,Nanyang Institute of Technology(No.520097).
文摘This study reports the isolation of four newβ-carboline alkaloids(1−4)and six previously identified alkaloids(5−10)from the roots of Peganum harmala L.Among these compounds,1 and 2 were characterized as rareβ-carboline-quinazoline dimers exhibiting axial chirality.Compound 3 possessed a unique 6/5/6/7 tetracyclic ring system with an azepine ring,and compound 4 was a novel annomontineβ-carboline.The structures of these compounds were elucidated by spectroscopic data and quantum mechanical calculations.The biosynthetic pathways of 1−3 were proposed.Additionally,the cytotoxicity of some isolates against four cancer cell lines(HL-60,A549,MDA-MB-231,and DU145)was evaluated.Notably,compound 4 exhibited significant cytotoxicity against HL-60,A549,and DU145 cells with IC_(50) values of 12.39,12.80,and 30.65μmol·L^(−1),respectively.Furthermore,compound 2 demonstrated selective cytotoxicity against HL-60 cells with an IC_(50) value of 17.32μmol·L^(−1).
基金supported by the program for Changjiang Scholars and Innovative Research Team in University,China (PCSIRT0848)Sichuan Agricultural University Youth Fundation,China(2006C18)the State Key Laboratory of Veterinary Etiologocal Biology,Lanzhou Veterinary Research Institute,Chinese Acad-emy of Agricultural Sciences(SKLVEB2009KFKT022)
文摘The 9-octadecanoic acid-hexadecanoic acid-tetrahydrofuran-3,4-diyl ester from neem oil was investigated for antibacterial activity against three bacterial strains viz., Staphylococcus aureus ATCC No. 25923, Escherichia coli ATCC No. 44102 and Salmonella sp. ATCC No. 50 041 in vitro. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of the 9-octadecanoic acid-hexadecanoic acid-tetrahydrofuran-3,4-diyl ester were determined by using the broth microdilution dilution (BMD) method at different concentrations ranging from 20 to 0.625 mg mL-1. Its time-inhibition curve against E. coli was also tested and showed that the MIC values for the bacterial strains S. aureus, E. coli and Salmonella sp. were 20, 5 and 10 mg mL-1, respectively. Its MBC values were 20, 20 and 10 mg mL-1, respectively. The antibacterial activity of 9-octadecanoic acid-hexadecanoic acid-tetrahydrofuran-3,4-diyl ester against three strain tested showed the relationship with time and concentration.
文摘The synthesis of the bis-isoxazolyl-1,2,5,6-tetrahydro pyridine-3-carboxylates is achieved in high yield without the production of toxic waste products by using room temperature ionic liquid (RTILs) triethyl ammonium acetate (TEAA). The RTIL TEAA played the dual role of efficient green solvent as well as recyclable catalyst.
基金Supported by the National Natural Science Foundation of China(No.20772041)the Key Project of Chinese Ministry of Education(No.107082)
文摘3,5,6,8-Tetrahydro-4H-thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidin-4-ones(7) were synthesized via the base catalytic reactions of amines or phenols with carbodiimides(5), which were obtained from the aza-Wittig reac tions of iminophosphoranes(4) with aromatic isocyanates.
基金Supported by the National Science and Technology Major Projects of China(No.2009ZX09301-012)
文摘A series of 6-fluoro-3,3a,4,5-tetrahydro-2H-pyrazolo[4,3-c]quinoline-2-carboxamide derivatives was designed based on the bioisosterism and combination principle in drug design. The target compounds were synthesized from substituted aniline through Michael addition, cyclization, Mannich reaction and condensation with 4-substituted semicarbazides, and the structures were confirmed by mass spectrometry(MS) and 1H NMR. The antifungal assay was carried out in vitro by two-fold dilution. The result shows that all the compounds are of antifungal activities against the tested fungi at different levels.
基金This project was supported by the Key Laboratory of Organic Synthesis of Jiangsu Province
文摘The title compound, acetic acid-3,5-diacetoxy-2-acetoxymethyl-6-(4-quinoxalin- 2-yl-phenoxy)-tetrahydro-pyran-4-yl-ester 8 (C28H28N2O10, Mr = 552.54), has been synthesized and its crystal structure was determined by X-ray diffraction analysis. It crystallizes in monoclinic, space group P21, a = 10.060(8), b = 5.648(4), c = 24.11(2)A, β = 91.078(10)°, Z = 2, V= 1369.9(19)A^3, Dc = 1.339 g/cm^3,μ(MoKa) = 1.03 cm^-1, F(000) = 580.00, T =. 193.1 Kx-9 θmax = 25.03, (△/σ)max = 0.0000, Flack = -0.0(24), the final R = 0.0680 and wR = 0.140 (w = 1/[0.0016Fo^2 + 1.00000(Fo^2)]/(4Fo^2)) for 3126 observed reflections (1 〉 20(/)). The pyranoid ring adopts chair conformation in the sugar moiety, and all of the acetyl groups are in the e bond of the pyranoid ring, so the sugar moiety is very stable.
文摘The crystal structure of 1, l-dichloro-la, 3-diphenyl-l, la, 2, 3-te-trahydro-azirino[2, l-d ] [l, 5]benzothizeapine (C22H17Cl2NS, Mr= 398. 35) has beendetermined. The title compound crystallizes in orthorhombic space group Pbca with celldimensions a= 11. 579(3), b= 15. 14O(4), c=2l. 534(5) A, V= 3775. 04(5) A 3, Z= 8, D. = 1' 402g. cm-3, MoKa(λ= 0. 7l073 A ), F (000) = lO64, μ= O. 245mm-1. The structure was solved by using direct methods and refined by full-matrixleast-Squares method, and the final crystallographic discrepancy factor is 0. 046 for4l94 observed rcflections. The molecular backbone is a tricyclic system with the centralseven-membered l, 5-thiazepine ring in twisted boat-like conformation and cis-fused toboth azirine ring and benzene ring.