A new pleuromutilin derivative, 14-O-[(4,6-diaminopyrimidine-2-yl) thioacetate] mutilin, was synthesized and structurally characterized by IR, NMR spectra and single-crystal X-ray diffraction. This compound contains a...A new pleuromutilin derivative, 14-O-[(4,6-diaminopyrimidine-2-yl) thioacetate] mutilin, was synthesized and structurally characterized by IR, NMR spectra and single-crystal X-ray diffraction. This compound contains a 5-6-8 tricyclic carbon skeleton and a pyrimidine ring. Its crystal is of orthorhombic system, space group P21 with a = 10.0237(6), b = 12.6087(7), c = 10.3749(8) ?, β = 101.48(1)°, V = 1284.99(14) ?3, Z = 2, F(000) = 540, Dc(Mg/m3) = 1.299, μ = 0.165 mm-1, R = 0.0649 and w R = 0.0797. The in vitro antibacterial activity study using Oxford cup assay showed this compound displayed more potent activity than pleuromutilin and similar antibacterial activity to that of tiamulin.展开更多
The title structure of 14-O-[(4-amino-6-hydroxy-pyrimidine-2-yl)thioacetyl] mutilin, C_(26)H_(47)N_3O_5S, has been synthesized using 22-O-tosyl pleuromutilin and 4-amine-6-hydroxy-2-mercatopyrimidine monohydrate, and ...The title structure of 14-O-[(4-amino-6-hydroxy-pyrimidine-2-yl)thioacetyl] mutilin, C_(26)H_(47)N_3O_5S, has been synthesized using 22-O-tosyl pleuromutilin and 4-amine-6-hydroxy-2-mercatopyrimidine monohydrate, and its structure was characterized by IR, NMR, H RMS and single-crystal X-ray diffraction. This compound has a 5-6-8 tricyclic carbon skeleton and a pyrimidine ring. It crystallizes in orthorhombic, space group P2_12_12_1 with a = 10.494(3), b = 16.997(5), c = 16.997 ?, Z = 4, D_c = 1.275 Mg×m^(–3), μ = 0.220 mm^(–1), F(000) = 1248, wR(F^2) = 0.1159 and R = 0.0381. The preliminary biological test showed that the title compound has more potent inhibitions to Staphylococcus aureus, MRSA and MRSE than that of tiamulin fumarate in vitro.展开更多
Two new pleuromutilin derivatives, 14-O-[(4-amino-6-methoxyl-pyrimidine-2-yl)-thioacetyl] mutilin(4) and 14-O-[4-amino-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)thioacetyl] mutilin(5), were synthesized and structurally...Two new pleuromutilin derivatives, 14-O-[(4-amino-6-methoxyl-pyrimidine-2-yl)-thioacetyl] mutilin(4) and 14-O-[4-amino-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)thioacetyl] mutilin(5), were synthesized and structurally characterized by IR, NMR spectra, HRMS and single-crystal X-ray diffraction. These compounds contain a 5-6-8 tricyclic carbon skeleton and a pyrimidine ring. Compound 4 is in the monoclinic system, space group P1211 with a = 10.2517(4), b = 12.5655(4), c = 10.3435(4) ?, V = 1315.69(8) ?~3, Z = 2, Dc = 1.309 g/cm3, F(000) = 558, μ = 0.166 mm^(-1), S = 1.047, R = 0.0457 and w R = 0.0934 for 4721 unique reflections(R_(int) = 0.0322) with I > 2σ(I). Compound 5 belongs to the orthorhombic system, space group P2_12_12_1 with a = 7.3667(4), b = 13.9990(7), c = 29.0434(13) ?, V = 2995.1(2) ?~3, Z = 4, D_c = 1.250 g/cm^3, F(000) = 1216, μ = 0.153 mm^(-1), S = 1.031, R = 0.0545 and wR = 0.0982 for 5242 unique reflections(R_(int) = 0.0476) with I > 2σ(I)). The in vitro antibacterial activity study showed the title compounds 4 and 5 displayed slightly less activity against methicillin-resistant Staphylococcus aureus(MRSA) and methicillin-resistant Staphylococcus epidermidis(MRSE), and lower potent against Escherichia coli(E.coli) and Bacillus subtilis(B.subtilis) when compared to those of tiamulin fumarate.展开更多
The title compound 14-O-[(2-chloroacetamide-6-aminopyrimidine-2-yl) thioacetyl] mutilin(4), C_(28)H_(39)ClN_4O_5S, was prepared and characterized by IR, NMR, HRMS and singlecrystal X-ray diffraction. The title compoun...The title compound 14-O-[(2-chloroacetamide-6-aminopyrimidine-2-yl) thioacetyl] mutilin(4), C_(28)H_(39)ClN_4O_5S, was prepared and characterized by IR, NMR, HRMS and singlecrystal X-ray diffraction. The title compound crystallizes in orthorhombic system, space group P2_12_12_1 with a = 11.5388(8), b = 14.5282(10), c = 19.8301(14) ?, V = 3324.3(4) ?~3, Z = 4, D_c = 1.396 g/cm^3, μ(Mo Kα) = 0.462 mm^(-1), F(000) = 1464, S = 1.003, R = 0.0386 and wR = 0.1014 for 5170 independent reflections(Rint = 0.0224) with I > 2σ(I)). The preliminary in vitro antibacterial bioassay against methicillin-resistant Staphylococcus aureus(MRSA-ATCC25923), Staphylococcus aureus(S. aureus), Escherichia coli(E. coli), and Staphylococcus warneri(S.warneri) were screened and the MIC values of the title compound were 0.125, 0.0625, 8 and 0.5 μg/m L, respectively.展开更多
基金Supported by Basic Scientific Research Funds in Central Agricultural Scientific Research Institutions(No.1610322014003)the Agricultural Science and Technology Innovation Program(ASTIP)
文摘A new pleuromutilin derivative, 14-O-[(4,6-diaminopyrimidine-2-yl) thioacetate] mutilin, was synthesized and structurally characterized by IR, NMR spectra and single-crystal X-ray diffraction. This compound contains a 5-6-8 tricyclic carbon skeleton and a pyrimidine ring. Its crystal is of orthorhombic system, space group P21 with a = 10.0237(6), b = 12.6087(7), c = 10.3749(8) ?, β = 101.48(1)°, V = 1284.99(14) ?3, Z = 2, F(000) = 540, Dc(Mg/m3) = 1.299, μ = 0.165 mm-1, R = 0.0649 and w R = 0.0797. The in vitro antibacterial activity study using Oxford cup assay showed this compound displayed more potent activity than pleuromutilin and similar antibacterial activity to that of tiamulin.
基金Supported by Basic Scientific Research Funds in Central Agricultural Scientific Research Institutions(No.1610322016007)National Key Technology Support Program(No.2015BAD11B02)Agricultural Science and Technology Innovation Program(ASTIP,No.CAASASTIP-2014-LIHPS-04)
文摘The title structure of 14-O-[(4-amino-6-hydroxy-pyrimidine-2-yl)thioacetyl] mutilin, C_(26)H_(47)N_3O_5S, has been synthesized using 22-O-tosyl pleuromutilin and 4-amine-6-hydroxy-2-mercatopyrimidine monohydrate, and its structure was characterized by IR, NMR, H RMS and single-crystal X-ray diffraction. This compound has a 5-6-8 tricyclic carbon skeleton and a pyrimidine ring. It crystallizes in orthorhombic, space group P2_12_12_1 with a = 10.494(3), b = 16.997(5), c = 16.997 ?, Z = 4, D_c = 1.275 Mg×m^(–3), μ = 0.220 mm^(–1), F(000) = 1248, wR(F^2) = 0.1159 and R = 0.0381. The preliminary biological test showed that the title compound has more potent inhibitions to Staphylococcus aureus, MRSA and MRSE than that of tiamulin fumarate in vitro.
基金Basic Scientific Research Funds in Central Agricultural Scientific Research Institutions(No.1610322014003)the Agricultural Science and Technology Innovation Program(ASTIP,No.CAAS-ASTIP-2014-LIHPS-04)
文摘Two new pleuromutilin derivatives, 14-O-[(4-amino-6-methoxyl-pyrimidine-2-yl)-thioacetyl] mutilin(4) and 14-O-[4-amino-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)thioacetyl] mutilin(5), were synthesized and structurally characterized by IR, NMR spectra, HRMS and single-crystal X-ray diffraction. These compounds contain a 5-6-8 tricyclic carbon skeleton and a pyrimidine ring. Compound 4 is in the monoclinic system, space group P1211 with a = 10.2517(4), b = 12.5655(4), c = 10.3435(4) ?, V = 1315.69(8) ?~3, Z = 2, Dc = 1.309 g/cm3, F(000) = 558, μ = 0.166 mm^(-1), S = 1.047, R = 0.0457 and w R = 0.0934 for 4721 unique reflections(R_(int) = 0.0322) with I > 2σ(I). Compound 5 belongs to the orthorhombic system, space group P2_12_12_1 with a = 7.3667(4), b = 13.9990(7), c = 29.0434(13) ?, V = 2995.1(2) ?~3, Z = 4, D_c = 1.250 g/cm^3, F(000) = 1216, μ = 0.153 mm^(-1), S = 1.031, R = 0.0545 and wR = 0.0982 for 5242 unique reflections(R_(int) = 0.0476) with I > 2σ(I)). The in vitro antibacterial activity study showed the title compounds 4 and 5 displayed slightly less activity against methicillin-resistant Staphylococcus aureus(MRSA) and methicillin-resistant Staphylococcus epidermidis(MRSE), and lower potent against Escherichia coli(E.coli) and Bacillus subtilis(B.subtilis) when compared to those of tiamulin fumarate.
基金Supported by Lanzhou Science and Technology Development Project(No.2016-3-101)
文摘The title compound 14-O-[(2-chloroacetamide-6-aminopyrimidine-2-yl) thioacetyl] mutilin(4), C_(28)H_(39)ClN_4O_5S, was prepared and characterized by IR, NMR, HRMS and singlecrystal X-ray diffraction. The title compound crystallizes in orthorhombic system, space group P2_12_12_1 with a = 11.5388(8), b = 14.5282(10), c = 19.8301(14) ?, V = 3324.3(4) ?~3, Z = 4, D_c = 1.396 g/cm^3, μ(Mo Kα) = 0.462 mm^(-1), F(000) = 1464, S = 1.003, R = 0.0386 and wR = 0.1014 for 5170 independent reflections(Rint = 0.0224) with I > 2σ(I)). The preliminary in vitro antibacterial bioassay against methicillin-resistant Staphylococcus aureus(MRSA-ATCC25923), Staphylococcus aureus(S. aureus), Escherichia coli(E. coli), and Staphylococcus warneri(S.warneri) were screened and the MIC values of the title compound were 0.125, 0.0625, 8 and 0.5 μg/m L, respectively.
