A simple and efficient procedure for the synthesis of substituted benzothiazoles through condensation of 2-aminothiophenol with aromatic aldehydes in the presence of H2O2/HCl system in ethanol at room temperature is d...A simple and efficient procedure for the synthesis of substituted benzothiazoles through condensation of 2-aminothiophenol with aromatic aldehydes in the presence of H2O2/HCl system in ethanol at room temperature is described. The target compounds have been characterized by ^1H NMR, ^13C NMR, IR and MS. Short reaction time, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure.展开更多
A benzothiazole-based compound 1, C28H24N4O2S, has been synthesized and characterized by single-crystal X-ray diffraction. It crystallizes in monoclinic, space group P21/c with a = 9.6309（14）, b = 15.230（2）, c = 1...A benzothiazole-based compound 1, C28H24N4O2S, has been synthesized and characterized by single-crystal X-ray diffraction. It crystallizes in monoclinic, space group P21/c with a = 9.6309（14）, b = 15.230（2）, c = 17.197（3）A, β = 105.222（2）°, V = 2433.9（6） A^3, Z = 4, F（000） = 1008, Dc = 1.311 Mg/m^3, Mr = 480.57, μ = 0.166 mm^-1, the final R = 0.0509 and wR = 0.1481 for 6643 observed reflections with I 〉 2σ（I）. The crystal structure of compound 1 is stabilized by C–H…O, N–H…N, N–H…O, O–H…N and C–H…N hydrogen bonds. The spectroscopic studies of the title compound toward various metal ions were also investigated in 25%（V/V） ethanol aqueous solution, and the result showed that it can selectively recognize Cu^2＋ with fluorescence quenching.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
C<sub>14</sub>H<sub>9</sub>NO<sub>2</sub>S<sub>2</sub>Mo,Mr=383.29,triclinic,space group P1,a=11.658（4）,b=16.218（8）,c=7.895（3）,a=97.58（4）,β=106.04（3）,γ=85.62...C<sub>14</sub>H<sub>9</sub>NO<sub>2</sub>S<sub>2</sub>Mo,Mr=383.29,triclinic,space group P1,a=11.658（4）,b=16.218（8）,c=7.895（3）,a=97.58（4）,β=106.04（3）,γ=85.62（3）°,V=1421（2）,Z=4,D<sub>c</sub>=1.79 g/cm￣3,μ=11.81 cm￣（-1）.F（000）=760.Refinement converged to R=0.049 and Rω=0.058 for 3153 independent observed reflections.The compound is a mononuclear molybdenum complex containing benzothiazole-2-thiolato ligand.The molybdenum atom is coordinated by the two carbonyl carbon atoms,tlie cyclopentadienyl carbon atoms,and the nitrogen atom and sulfur atom of benzothiazole-2-thiolate.The coordination polyhedron may be described as a trapezoidal pyramid with the Cp ring centroid as a top.展开更多
The one-pot three-component reaction of 2-aminobenzothiazole, benzaldehyde derivatives and β-ketoester, β-diketone or malonate derivatives in solvent-free conditions provides the corresponding pyrimido [2,1-b] benzo...The one-pot three-component reaction of 2-aminobenzothiazole, benzaldehyde derivatives and β-ketoester, β-diketone or malonate derivatives in solvent-free conditions provides the corresponding pyrimido [2,1-b] benzothiazole derivatives at 60?C in 60% - 72% yields without using any catalyst in an optimistic time.展开更多
The crystal structure of 3-(4-methoxyphenyl)- l-methyl-pyrrolo[2,1-b] benzothiazole (C18H15NOS, Mr = 293. 38) has been determined. The title com-pound crystallizes in monoclinic space group P21/n with cell dimensions ...The crystal structure of 3-(4-methoxyphenyl)- l-methyl-pyrrolo[2,1-b] benzothiazole (C18H15NOS, Mr = 293. 38) has been determined. The title com-pound crystallizes in monoclinic space group P21/n with cell dimensions a= l. 3308(4)'b=0. 8403(2), c= l. 4l47 (4)nm, β= 68. 08(2)°, V= 1. 4676(5)nm3, Z= 4, Dc=1. 328g. cm-3, F(000) = 6l6,μ= l8. 18cm-l, CuKa(η= O. 154l8nm). The struc-ture was solved by direct methods and refined by full matrix least-Squares. The finaldiscrepancy factor is 0. 053 for 1522 observed reflections. The molecular backbone is anearly planar tricyclic system.展开更多
Treatment of 2-(benzo[d]thiazol-2’-ylthio)acetohydrazide (3) with acetylacetone afforded N-(4-oxopentan-2-ylidine) acetohydrazide derivative 5. The acetohyrazide derivatives 3 and 5 were utilized as a key intermediat...Treatment of 2-(benzo[d]thiazol-2’-ylthio)acetohydrazide (3) with acetylacetone afforded N-(4-oxopentan-2-ylidine) acetohydrazide derivative 5. The acetohyrazide derivatives 3 and 5 were utilized as a key intermediate for the synthesis of a novel heterocyclic compounds. The synthesis of a novel series of condensation and substituted derivatives of 2-(benzo[d]thiazol-2’-ylthio) acetohydrazide in good yield has been reported. The newly synthesized compounds were characterized by elemental analysis 1H-NMR, <sup>13</sup>C-NMR spectra and X-ray crystallographic investigations. The reported crystal structures of these novel 2-(benzo[d] thiazol-2’-ylthio)acetohydrazide derivatives are expected to be a remarkable contribution to the crystallographic database of heterocyclic compounds.展开更多
基金Education Department of Zhejiang Province(No.20060811) for the financial support of this work.
文摘A simple and efficient procedure for the synthesis of substituted benzothiazoles through condensation of 2-aminothiophenol with aromatic aldehydes in the presence of H2O2/HCl system in ethanol at room temperature is described. The target compounds have been characterized by ^1H NMR, ^13C NMR, IR and MS. Short reaction time, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure.
基金financially supported by the National Natural Science Foundation of China(21603069)College Students’ Science and Technology Innovation Project of Hubei Polytechnic University(No.14cx16)Young College Teachers’ Entering into Enterprises Program of Hubei Provincial Department of Education(No.XD2014677)
文摘A benzothiazole-based compound 1, C28H24N4O2S, has been synthesized and characterized by single-crystal X-ray diffraction. It crystallizes in monoclinic, space group P21/c with a = 9.6309（14）, b = 15.230（2）, c = 17.197（3）A, β = 105.222（2）°, V = 2433.9（6） A^3, Z = 4, F（000） = 1008, Dc = 1.311 Mg/m^3, Mr = 480.57, μ = 0.166 mm^-1, the final R = 0.0509 and wR = 0.1481 for 6643 observed reflections with I 〉 2σ（I）. The crystal structure of compound 1 is stabilized by C–H…O, N–H…N, N–H…O, O–H…N and C–H…N hydrogen bonds. The spectroscopic studies of the title compound toward various metal ions were also investigated in 25%（V/V） ethanol aqueous solution, and the result showed that it can selectively recognize Cu^2＋ with fluorescence quenching.
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.
文摘C<sub>14</sub>H<sub>9</sub>NO<sub>2</sub>S<sub>2</sub>Mo,Mr=383.29,triclinic,space group P1,a=11.658（4）,b=16.218（8）,c=7.895（3）,a=97.58（4）,β=106.04（3）,γ=85.62（3）°,V=1421（2）,Z=4,D<sub>c</sub>=1.79 g/cm￣3,μ=11.81 cm￣（-1）.F（000）=760.Refinement converged to R=0.049 and Rω=0.058 for 3153 independent observed reflections.The compound is a mononuclear molybdenum complex containing benzothiazole-2-thiolato ligand.The molybdenum atom is coordinated by the two carbonyl carbon atoms,tlie cyclopentadienyl carbon atoms,and the nitrogen atom and sulfur atom of benzothiazole-2-thiolate.The coordination polyhedron may be described as a trapezoidal pyramid with the Cp ring centroid as a top.
文摘The one-pot three-component reaction of 2-aminobenzothiazole, benzaldehyde derivatives and β-ketoester, β-diketone or malonate derivatives in solvent-free conditions provides the corresponding pyrimido [2,1-b] benzothiazole derivatives at 60?C in 60% - 72% yields without using any catalyst in an optimistic time.
文摘The crystal structure of 3-(4-methoxyphenyl)- l-methyl-pyrrolo[2,1-b] benzothiazole (C18H15NOS, Mr = 293. 38) has been determined. The title com-pound crystallizes in monoclinic space group P21/n with cell dimensions a= l. 3308(4)'b=0. 8403(2), c= l. 4l47 (4)nm, β= 68. 08(2)°, V= 1. 4676(5)nm3, Z= 4, Dc=1. 328g. cm-3, F(000) = 6l6,μ= l8. 18cm-l, CuKa(η= O. 154l8nm). The struc-ture was solved by direct methods and refined by full matrix least-Squares. The finaldiscrepancy factor is 0. 053 for 1522 observed reflections. The molecular backbone is anearly planar tricyclic system.
文摘Treatment of 2-(benzo[d]thiazol-2’-ylthio)acetohydrazide (3) with acetylacetone afforded N-(4-oxopentan-2-ylidine) acetohydrazide derivative 5. The acetohyrazide derivatives 3 and 5 were utilized as a key intermediate for the synthesis of a novel heterocyclic compounds. The synthesis of a novel series of condensation and substituted derivatives of 2-(benzo[d]thiazol-2’-ylthio) acetohydrazide in good yield has been reported. The newly synthesized compounds were characterized by elemental analysis 1H-NMR, <sup>13</sup>C-NMR spectra and X-ray crystallographic investigations. The reported crystal structures of these novel 2-(benzo[d] thiazol-2’-ylthio)acetohydrazide derivatives are expected to be a remarkable contribution to the crystallographic database of heterocyclic compounds.
