- Synthesis of 1-(β-D-glycopyranosyl)-3-deazapyrimidines from 2-hydroxy and 2-mercaptopyridines
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The synthesis of new 4- and 5-substituted-3-cyanopyridine nucleosides has been performed by reacting the silylated pyridines and penta-O-aeetyl-α -Dglycopyranose in dichloroethane in the presence of SnCl4. The free nucleosides were tested for their potential activity against HIV and different types of tumor.
- Attia, Adel M.,Elgemeie, Galal H.,Alnaimi, Ibrahim S.
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- Polysubstituted thieno[2,3-b]pyridine derivatives, and preparation method and application thereof
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The invention discloses polysubstituted thieno[2,3-b]pyridine derivatives, and a preparation method and an application thereof. The structural formula of the derivatives are represented by formula I shown in the description. A compound for inhibiting a urea transporter is screened by using an erythrocyte model. Experimental results show that the compounds (represented by formula I-1) can inhibit the permeation of a urea transporter UT-B mediated erythrocyte membrane to urea, and the effect of the compounds has a dose-dependent relationship; the compounds represented by the formula I-1 have nocytotoxic effect on MDCK cells within an effective dose range, so the effect of the compounds represented by the formula I-1 on inhibiting cell permeation urea is irrelevant to the cytotoxicity of thecompounds; the inhibition effect of the compounds represented by the formula I-1 on the urea transporter UT-B is gradually enhanced; the inhibiting effect of the compounds represented by the formulaI-1 on the UT-B is reversible; and in-vivo test results show that the compounds represented by the formula I-1 can significantly increase the urination volume of rats, reduce the concentration of ureain rat urine and reduce the osmotic pressure, so that the compounds represented by the formula I-1 generate a urea selective diuresis effect in vivo.
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Paragraph 0117; 0120
(2020/01/12)
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- Synthesis and evaluation of pyrido-thieno-pyrimidines as potent and selective Cdc7 kinase inhibitors
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Cdc7 kinase plays a critical role in the regulation of DNA replication in eukaryotic cells and has been proposed as a target for cancer therapy. We have identified a class of Cdc7/Dbf4 inhibitors with a pyrido-thieno-pyrimidine core structure. Synthesis o
- Zhao, Chunlin,Tovar, Christian,Yin, Xuefeng,Xu, Qui,Todorov, Ivan T.,Vassilev, Lyubomir T.,Chen, Li
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scheme or table
p. 319 - 323
(2011/02/26)
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- Synthesis of 2,3,5,6-tetrasubstituted pyridines from enamines derived from N,N-dimethylformamide dimethyl acetal
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Reactions of 1,3-dicarbonyl compounds with N,N-dimethylformamide dimethyl acetal, followed by cyanothioacetamide or cyanoacetamide and sodium hydride, then acidification, give 5,6-disubstituted 3-cyanopyridine-2(1H)-thiones or 5,6-disubstituted 3-cyanopyridin-2(1H)-ones 4. Analogous reactions with the malononitrile dimer give 5,6-disubstituted 3-cyano-2-(dicyanomethylene)-1,2-dihydropyridines 9.
- Abu-Shanab,Redhouse,Thompson,Wakefield
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p. 557 - 560
(2007/10/02)
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- Chemical synthesis and biological activities of 5-deazaaminopterin analogues bearing substituent(s) at the 5- and/or 7-position(s)
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Condensation of cyanothioacetamide (4) with ethyl α-(ethoxymethylene)acetoacetate (5b), ethyl 4-ethoxy-2-(ethoxymethylene)-3-oxobutanoate (5c), ethyl 2-(ethoxymethylene)-3-oxo-4-phenylpropanoate (5d) afforded exclusively the corresponding 6-substituted pyridines (6b-d). Cyclization of 4 with 3-carbethoxybutane-2,4-dione (5e) gave 3-cyano-5-(ethoxycarbonyl)-4,6-dimethylpyridine-2(1H)-thione (6e), whereas reaction of 4 with 3-carbethoxy-1-phenylpropane-1,3-dione (5f) yielded two products, 3-cyano-5-(ethoxycarbonyl)-4-methyl-6-phenylpyridine-2(1H)-thione (6f) and the 6-methyl-4-phenyl isomer 6g. The structural assignments for 6f and 6g are made on the basis of 1H and 13C NMR spectral analyses of the 2-(methylthio)nicotinates (7f,g) prepared from 6f and 6g by treatment with MeI/K2CO3. Nicotinates 7b,d-g were converted into their corresponding 2,4-diaminopyrido[2,3-d]pyrimidines 12b,d-g in five steps, via reduction, protection, oxidation, condensation with guanidine, and deprotection. The 7-mono- and 5,7-disubstituted-5-deazaaminopterins (1b,d-g) were prepared from the respective pyrido[2,3-d]pyrimidines 12b,d-g. Preliminary biological studies showed that 7-methyl and 5,7-dimethyl analogues (1b and 1e) were less active than methotrexate against human leukemic HL-60 and murine L-1210 cells in tissue culture. Compound 1e produced and ILS of 71% at 100 mg/kg per day x 5 (ip) in BDF mice inoculated ip with 106 L-1210 cells.
- Su,Huang,Chou,Otter,Sirotnak,Watanabe
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p. 1209 - 1215
(2007/10/02)
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