- Synthesis, biological and molecular dynamics investigations with a series of triazolopyrimidine/triazole-based benzenesulfonamides as novel carbonic anhydrase inhibitors
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In the presented work, we report the design and synthesis of different new sets of triazolopyrimidine-based (9a-d) and triazole-based (11a-h, 13a-c, 15a,b, 17a,b and 21a-g) benzenesulfonamides. The newly synthesized sulfonamides were assessed for their inhibitory activities toward four human (h) metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms; hCA I, II, IX and XII. The four examined isoforms were inhibited by the prepared sulfonamides (9a-d, 11a-h, 13a-c, 15a,b, 17a,b and 21a-g) in variable degrees with KIs ranges: 94.4–4953.5 nM for hCA I, 6.9–837.6 nM for hCA II, 3.3–85.0 nM for hCA XI, and 4.4–105.0 nM for hCA XII. In particular, sulfonamides 11e, 21a and 21e emerged as single-digit nanomolar hCA IX and hCA XII inhibitors. Interestingly, triazolopyrimidine-based sulfonamide 9d and triazole-based sulfonamide 21e were found to be the most selective hCA IX inhibitors over hCA I (SI = 100.85 and 210.58, respectively) and hCA II (SI = 18.54 and 38.36, respectively). Thereafter, sulfonamides 9d and 21e were docked into the active site of CAs II, IX and XII, then poses showing the best scoring values and favorable binding interactions were subjected to a MM-GBSA based refinement and, limited to CA IX and XII, to a cycle of 100 ns molecular dynamics.
- Said, Mohamed A.,Eldehna, Wagdy M.,Nocentini, Alessio,Bonardi, Alessandro,Fahim, Samar H.,Bua, Silvia,Soliman, Dalia H.,Abdel-Aziz, Hatem A.,Gratteri, Paola,Abou-Seri, Sahar M.,Supuran, Claudiu T.
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- Synthesis of novel pyrimidine derivatives with (pyridin-3-ylmethyl)thio and phenylamino moieties and evaluation of their antifungal activity
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A series of novel pyrimidine derivatives with (pyridin-3-ylmethyl)thio and phenylamino moieties were synthesized from ethyl acetoacetate, thiourea, 3-pyridinylmethyl chloride hydrochloride, and substituted anilines by multi-step reactions. The structures of the target compounds were characterized by IR, 1H NMR, 13C NMR and elemental analysis. The in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum were evaluated. The result showed that N-phenyl-6-methyl-2- ((pyridin-3-ylmethyl)thio) pyrimidin-4-amine (4a) displayed high inhibition activity against Botrytis cinerea with 87.5%inhibition at 100?μg/mL; 4a, and N-(4-isopropylphenyl)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin-4-amine (4c), N-(4-methoxyphenyl)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin-4-amine (4d) and N-(2-hydroxy-5-chloro)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin- 4-amine (4h) exhibited sufficient activities against Sclerotinia sclerotiorum with 86.6% –93.7% inhibitions at the same concentration.
- Wang, Shi-Chun,Gao, Ji-Gang,Zhang, Shuai,Liu, Si,Jiang, Lin
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- Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives
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A convenient, accessible, and high yield method for preparing of 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1) by treatment of acetoacetic acid ethyl ester with thiourea in sodium methylate was developed. The alkylation of the latter with 3-chloro-pentane-2,4-dione and further regioselective cyclization of intermediate compound (2) in high yield afforded 2-acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one (3). The halogenation and some transformations of synthesized thiazolo[3,2-a]pyrimidine (3) due to its ketone group were carried out to obtain the corresponding carboxamide, carbothioamide, sulfonohydrazide, and oxime and its alkylated derivatives (5). At preliminary biological studies the synthesized compounds have shown growth stimulant properties. The activity of four of them was higher than 70%, compared with heteroauxin.
- Pivazyan, Vergush A.,Ghazaryan, Emma A.,Shainova, Roza S.,Tamazyan, Rafael A.,Ayvazyan, Armen G.,Yengoyan, Aleksandr P.
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- NOVEL ANTIPARASITIC COMPOUNDS AND METHODS
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Novel compounds for treating or inhibiting leishmaniasis and other parasitic protozoan diseases are disclosed herein. The compounds bind to Leishmania tubulin, induce parasite microtubule polymerization, stall Leishmania cell division, and have broad antiparasitic activity.
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Page/Page column 92
(2021/04/23)
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- Novel triazole-sulfonamide bearing pyrimidine moieties with carbonic anhydrase inhibitory action: Design, synthesis, computational and enzyme inhibition studies
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A series of new triazole-sulfonamide bearing pyrimidine derivatives were designed and synthesized via click chemistry. All new compounds (SH-1 to SH-28) were validated by 1HNMR, 13CNMR, HRMS, and SH-3 was further structurally validated by X-Ray single diffraction study. These compounds (SH-1 to SH-28) were tested as inhibitors of human carbonic anhydrase (hCA) isoforms, such as hCA I, II, IX and XII, using a stopped flow CO2 hydrase assay. Most of the compounds exhibited significant inhibitory activity against hCA II and weak inhibitory activity against hCA I. The target compounds also displayed moderate to excellent inhibitory activity against tumor-related hCAs IX and XII. Some compounds, e.g., SH-20 (Ki = 9.4 nM), SH-26 (Ki = 1.8 nM) and SH-28 (Ki = 0.82 nM) exhibited excellent inhibitory activity and selectivity profile against hCAs XII over IX. SH-23 displayed promising inhibitory activity and selectivity profile against both tumor-related hCAs IX (Ki = 2.9 nM) as well as XII (Ki = 0.82 nM) over hCA I and II. To understand the molecular interactions, molecular docking study of compounds SH-20, SH-23, SH-26 and SH-28 with hCA XII and SH-23 also with hCA IX were performed. The computational study evidenced favorable interaction between the inhibitors and active residues of both proteins. Some of these derivatives are promising leads for the development of selective, anticancer agents based on CA inhibitors.
- Hoda, Nasimul,Manzoor, Shoaib,Petreni, Andrea,Raza, Md Kausar,Supuran, Claudiu T.
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supporting information
(2021/07/16)
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- Design, synthesis, and acaricidal activity of phenyl methoxyacrylates containing 2-alkenylthiopyrimidine
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A series of novel phenyl methoxyacrylate derivatives containing a 2-alkenylthiopyrimidine substructure were designed, synthesized, and evaluated in terms of acaricidal activity. The structures of the title compounds were identified by 1H NMR, 13C NMR and high-resolution mass spectra (HRMS). Compound (E)-methyl 2-(2-((2-(3,3-dichloroallylthio)-6-(trifluoromethyl)pyrimidin-4-yloxy) methyl)phenyl)-3-methoxyacr-ylate (4j) exhibited significant acaricidal activity against Tetranychus cinnabarinus (T. cinnabarinus) in greenhouse tests possessing nearly twice the larvicidal and ovicidal activity compared to fluacrypyrim. Furthermore, the results of the field trials demonstrated that compound 4j could effectively control Panonychuscitri with long-lasting persistence and rapid action. The toxicology data in terms of LD50 value confirmed that compound 4j has a relatively low acute toxicity to mammals, birds, and honeybees.
- Hao, Shulin,Cai, Zengfei,Cao, Yangyang,Du, Xiaohua
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- SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE
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The present invention relates to compounds that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are envisaged to be useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.
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Page/Page column 211
(2020/12/11)
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- Some Features of the Reaction of 6-Methyl-2S-substituted Pyrimidin-4-ols with the Vilsmeier–Haack Reagent
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Abstract: Formylation of 6-methyl-2S-substituted pyrimidin-4-ols under the conditions of the Vilsmeier–Haack reaction leads to the formation of nucleophilic substitution products of the hydroxyl group. The formation of the expected formylation products does not occur.
- Ofitserova, E. S.,Shklyarenko, A. A.,Yakovlev, I. P.
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p. 750 - 752
(2020/06/30)
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- NOVEL SCAFFOLD OF ADENYLYL CYCLASE INHIBITORS FOR CHRONIC PAIN AND OPIOID DEPENDENCE
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The present invention relates to a method of treatment for chronic pain, opioid dependence, alcohol use disorder or autism using a class of pyrimidinone compounds, an adenylyl cyclase 1 (AC1) inhibitor. The invention described herein also pertains to pharmaceutical compositions and methods for treating diseases in mammals using those compounds disclosed herein.
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Paragraph 0152
(2019/02/05)
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- Unsaturated hydrocarbon pyrimidine sulfoether compound as well as preparation method and application thereof
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The invention discloses an unsaturated hydrocarbon pyrimidine sulfoether compound as well as a preparation method and application thereof. The structure is as shown in formula (I), and the definitionof various substituent in the formula is shown in the description. The compound of the formula (I) has high insecticidal activity for harmful acarid, and adults, larva and eggs of insects in the technical field of agriculture, civil use and animals. The compound has good antibacterial activity, and can be widely used as an insecticide and/or bactericide in the agriculture and other industries. (Shown in the description).
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Paragraph 0133-0136
(2018/08/03)
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- Laccase-catalyzed green synthesis and cytotoxic activity of novel pyrimidobenzothiazoles and catechol thioethers
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The laccase-catalyzed reaction between unsubstituted catechol and 2-thioxopyrimidin-4(1H)-ones using aerial O2 as the oxidant delivers novel pyrimidobenzothiazoles with high yields in an aqueous solvent system under mild reaction conditions. With 4-substituted catechols, catechol thioethers are formed exclusively. The synthetic protocols developed provide a sustainable approach for these compound classes. In addition, the cytotoxicity of the products against HepG2 cell line is reported. Most compounds exhibit antiproliferative activities with IC50 values at the micromolar level. A structure-activity relationship study will facilitate the further development of these compounds as cytotoxic agents.
- Abdel-Mohsen,Conrad,Harms,Nohr,Beifuss
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p. 17427 - 17441
(2017/03/31)
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- 6-Susbtituted-2-(benzimidazole-2-methylenethio)pyrimidine compounds with 4 position containing chalcone construction unit, and preparation method and use of compounds
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The invention belongs to the field of pharmaceutical chemistry, and discloses 6-susbtituted-2-(benzimidazole-2-methylenethio)pyrimidine compounds with the 4 position containing a chalcone construction unit, and a preparation method and a use of the compounds. The compounds have a structure represented by general formula I; and in the formula I, R1 is a methyl group or a phenyl group, and R2 is a 3,4,5-trimethoxyphenyl group, a 4-bromophenyl group, a 4-fluorophenyl group, a 3-fluorophenyl group, a 3-nitrophenyl group, a 3-bromophenyl group, a 3,5-difluorophenyl group, a 2-fluoro-4-bromophenyl group, a 3-bromo-4-fluorophenyl group, a 3-hydroxyphenyl group, a 2-thienyl group, a 2-furyl group, a 3,5-difluorophenyl group or a 3,5-dichlorophenyl group. Primary in vitro antitumor activity evaluation finds that the above series of the compounds has an obvious inhibiting and killing effect on various tumor cells. The compounds can be processed to develop new medicines, and can be applied to clinic prevention and cancer treatment as an active component.
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Paragraph 0033-0035
(2017/04/25)
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- Synthesis and biological evaluation of DAPY-DPEs hybrids as non-nucleoside inhibitors of HIV-1 reverse transcriptase
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A series of new DAPY-DPEs hybrids, combined the important pharmacophores of DAPYs and DPEs, has been synthesized and biologically evaluated for their anti-HIV activities against wild-type HIV-1 strain IIIB, double RT mutant (K103N + Y181C) strain RES056 and HIV-2 strain ROD in MT-4 cell cultures. Many promising candidates with potent inhibitory activity (wild-type) within the EC50 range from 0.16 to 0.013 μM were obtained. In particular, 3c, 3p, 3r and 3s displayed low nM level EC50 values (35, 13, 50 and 17 nM, respectively) and high selectivity (9342, 25131, 2890 and 11338, respectively), which were much more potent than NVP (EC50 = 0.31 μM, SI = 48), 3TC (EC50 = 2.24 μM, SI > 39), DDI (EC50 = 23.20 μM, SI > 9) and DLV (EC50 = 0.65 μM, SI > 67), and comparable to AZT (EC50 = 0.0071 μM, SI > 13144) and EFV (EC50 = 0.0062 μM, SI > 1014). The HIV-1 reverse transcriptase inhibitory assay confirmed that these DAPY-DPEs hybrids targeted HIV-1 RT. Molecular simulation was performed to investigate the potential binding mode of the newly synthesized compounds. And reasonable explanation for the activity results was discussed with docking method.
- Wu, Hai-Qiu,Yao, Jin,He, Qiu-Qin,Chen, Wen-Xue,Chen, Fen-Er,Pannecouque, Christophe,De Clercq, Erik,Daelemans, Dirk
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p. 624 - 631
(2015/01/30)
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- Synthesis, in vitro antimicrobial and cytotoxic activities of novel pyrimidine-benzimidazol combinations
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A series of novel 4-substituted-2-{[(1H-benzo[d]imidazol-2-yl)methyl] thio}-6-methylpyrimidine derivatives were designed, synthesized and evaluated for their cytotoxic activities against four human cancer cell lines and inhibitory activities against five type culture strains in vitro. Some of synthetic pyrimidine-benzimidazol combinations showed good inhibitory activities against Stenotrophomonas maltophilia, especially compounds 7b and 7c. Compounds 7a and 7d exhibited enhanced activities against MGC-803 in vitro, when compared to 5-Fu.
- Chen, Peng-Ju,Yang, Ang,Gu, Yi-Fei,Zhang, Xiao-Song,Shao, Kun-Peng,Xue, Deng-Qi,He, Peng,Jiang, Teng-Fei,Zhang, Qiu-Rong,Liu, Hong-Min
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supporting information
p. 2741 - 2743
(2014/06/09)
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- Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors
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36 new compounds with the typical skeleton of 4-anilino-5-vinyl/ethynyl pyrimidine, 4-anilino-3-cyano-5-vinyl/ethynyl/phenyl pyridine, and m-amino-N-phenylbenzamide, are designed, synthesized and selectively tested on EGFR, ErbB-2 kinases, and A-549, HL60 cells growth inhibition. Results from the bioactivity and chemical structures yield preliminary structure-activity relationships (SARs). The most potent 5-ethynylpyrimidine derivative 20a has an IC50 value of 45 nM to EGFR kinase. Several compounds of other series also show IC50 values 1 μM for EGFR and 5 μM for A-549 and HL60 cells growth inhibition.
- Mao, Yongjun,Zhu, Wenxiu,Kong, Xiaoguang,Wang, Zhen,Xie, Hua,Ding, Jian,Terrett, Nicholas Kenneth,Shen, Jingkang
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p. 3090 - 3104
(2013/07/11)
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- Synthesis of pyridinylketones, and their cyclic derivatives produced from 6-methyl-2-thiouracil
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A possibility to obtain pyrimidines, containing oxoalkyl moiety in 2 position of the ring from the available 6-methyl-2-thiouracil was shown.
- Yavolovskii,Grishchuk,Rakipov,Ivanov,Stepanov,Kamalov
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experimental part
p. 725 - 728
(2012/10/07)
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- Identification of novel, exosite-binding matrix metalloproteinase-13 inhibitor scaffolds
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Matrix metalloproteinase-13 (MMP-13) has been implicated as the protease responsible for collagen degradation in cartilage during osteoarthritis (OA). Compounds that inhibit the metalloproteinase at the Zn binding site typically lack specificity among MMP family members. Analogs of the low-micromolar lead MMP-13 inhibitor 4, discovered through high-throughput screening, were synthesized to investigate structure-activity relationships in this inhibitor series. Systematic modifications of 4 led to the discovery of MMP-13 inhibitors 20 and 24 which are more selective than 4 against other MMPs. Compound 20 is also approximately fivefold more potent as an MMP-13 inhibitor than the original HTS-derived lead compound 4.
- Roth, Joshua,Minond, Dmitriy,Darout, Etzer,Liu, Qin,Lauer, Janelle,Hodder, Peter,Fields, Gregg B.,Roush, William R.
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scheme or table
p. 7180 - 7184
(2012/01/15)
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- Synthesis of substituted pyrimidin-4(1H)-one (uracil) derivatives and some of their reactions
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In this paper I described two practical routes for the synthesis of substituted Uracilderivatives and achieved some of their reactions. In the first synthesis which is based on the condensation reaction of ethyl 2- cyanoacetate and thiourea, the cyclized compound 6-amino-2- mercaptopyrimidin-4(3H)-one (I) achieved in the presence of sodium ethanoate. Thecompund (I) react with 2-(chloromethyl)oxirane in the given medium (II) was produced, then treated in medium of ethanol in peresence of KOH which new recyclized product 8-amino-3,4-dihydro-3- hydroxypyrimido[2,1-b][1,3]thiazin-6(2H)-one (III) was obtained.The other ring closing cyclization proceeded 6-methyl-2,3-dihydro-2- thioxopyrimidin-4(1H)-one (IV) by ethyl acetoacetate and thiourea in ethyl alcohol and potassium hydroxide medium. In the next reaction, firstly Sodium Salt of (V) was gained, then it was reacted with 2-(chloromethyl)oxirane. At the end, substitued derivative (VI) was resulted.All synthesized products were confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. All the experimental data is described extensively in this report.
- Barmaki, Mohammad
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experimental part
p. 893 - 899
(2012/03/08)
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- Design, synthesis and biological evaluation of cycloalkyl arylpyrimidines (CAPYs) as HIV-1 NNRTIs
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A series of 18 cycloalkyl arylpyrimidines (CAPYs) were designed from lead compounds diarylpyrimidines (DAPYs), synthesized and evaluated for in vitro anti-HIV activity. Among them, the compound 1p displayed potent anti-HIV-1 activity against WT HIV-1 with an EC50 value of 0.055 μM and a selectivity index (SI) >7290. The preliminary structure-activity relationship (SAR) of this new series of compounds was also investigated, which enriched the SAR of diarylpyrimidines (DAPYs).
- Gu, Shuang-Xi,Yang, Shi-Qiong,He, Qiu-Qin,Ma, Xiao-Dong,Chen, Fen-Er,Dai, Hui-Fang,Clercq, Erik De,Balzarini, Jan,Pannecouque, Christophe
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supporting information; experimental part
p. 7093 - 7099
(2012/01/03)
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- Microwave assisted one-pot synthesis of nitrogen and oxygen containing heterocycles from acyl Meldrum's acid
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One-pot syntheses of biologically active nitrogen and oxygen containing heterocyclic compounds such as uracils and thiouracils and 1,4-benzothiazines, 4-methylcoumarins and 4H-1,4- dihydropyridines, using acyl Meldrum's acids are reported.
- More,Mahulikar
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experimental part
p. 745 - 747
(2011/06/27)
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- Exploring the scope for scale-up of organic chemistry using a large batch microwave reactor
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A new batch microwave reactor has been evaluated in the context of palladium-mediated transformations, condensation reactions, nucleophilic aromatic substitution reactions, and alkylations. Importantly, a linear scaling approach was taken, no changes being made to the protocol when moving from the small, developmental scale to larger scales. In some cases reactions were scaled over 18,000-fold when moving from small (0.1-1 mmol) to large (1-18 mol) runs.
- Schmink, Jason R.,Kormos, Chad M.,Devine, William G.,Leadbeater, Nicholas E.
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experimental part
p. 205 - 214
(2010/04/29)
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- Microwave-assisted synthesis of substituted: 2-(benzylthio)imidazo[1,2a] pyrimidin-5-ones
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A microwave-assisted solid-phase synthesis of 2-(benzylthio)imidazo[1,2a] pyrimidin-5-ones has been developed. Using microwave irradiation, the reaction time was significantly reduced from a few days to 80 min. A representative set of 10 2-(benzylthio)-6,7-substituted-imidazo[1,2a]pyrimidin-5-ones was prepared. These compounds were subsequently N-alkylated and formylated in good yields.
- Soh, Chai Hoon,Lam, Yulin
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experimental part
p. 286 - 291
(2010/08/20)
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- Fe(III) and cobalt(II) coordination compounds of 5-bromo-6-methyl-2- morpholinepyrimidinium-4-amine pyridine-2,6-dicarboxylate
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New coordination compounds, (bmmpaH)[Fe(pydc)2] (EtOH) 0.8(H2O)0.2 (1), (8QH)[Fe(pydc)2] H2O (2), (2ampyH)2[Mn(pydc)2] H2O (3), (2ampyH)[Cr(pydc)2](2ampy)0.5 H2O (4), [Co(H2O)5-μ (pydc)Co(pydc)] 2H2O (5), [Ni(pydcH)2] H2O (6), and [Cu(pydcH)2] (7), where bmmpa, 8Q, 2ampy, pydcH2 are 5-bromo-6-methyl-2-morpholinepyrimidine-4- amine, 8-hydroxyquinoline, 2-amino-6-methylpyridine, and pyridine-2,6- dicarboxylic acid, respectively, have been synthesized and structurally characterized by elemental analyses, infrared, UV spectroscopic methods, and X-ray crystallography. Metal ions of 1 and 5 are six-coordinate with distorted octahedral geometries. Compound 1 is an anionic mononuclear complex and 5 is a binuclear compound constructed from cationic and anionic parts. The crystal data of 5 reveal that the cationic part is formed by five terminal waters and one μ-carboxylate oxygen O2 from the anionic portion and the anionic complex is built from two deprotonated (pydc)2- moieties. In the compounds, pydcH2 is tridentate by one nitrogen of pyridine ring and two oxygens of carboxylate.
- Eshtiagh-Hosseini, Hossein,Yousefi, Zakieh,Shafiee, Maryam,Mirzaei, Masoud
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scheme or table
p. 3187 - 3197
(2010/11/24)
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- Synthesis of 2-(pyrazol-1-yl)pyrimidine derivatives by cyclocondensation of ethyl acetoacetate (6-methyl-4-oxo-3,4-dihydropyrimidin-2-yl)hydrazone with aromatic aldehydes
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2-(4-Arylidene-3-methyl-5-oxo-4,5-dihydropyrazol-1-yl)-6-methylpyrimidin- 4(3H)-ones were obtained by reaction of ethyl acetoacetate (6-methyl-4-oxo-3,4- dihydropyrimidin-2-yl)hydrazone with aromatic aldehydes. Successful cyclization occurs with aldehydes containing an auxochromic substituent in the para position.
- Erkin,Krutikov,Chubraev
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p. 423 - 427
(2007/10/03)
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- Unified Synthetic Approach to 2-Substituted 6-Methylisocytosines and Their 5-Bromo Derivatives
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6-Methyl-4(3H)-pyrimidinones containing 2-alkyl-, 2-cycloalkyl-, and 2-arylalkylamino groups were synthesized and brominated to obtain 5-bromo derivatives.
- Erkin,Krutikov,Pavlovich
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p. 463 - 466
(2007/10/03)
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- The identification of clinical candidate SB-480848: A potent inhibitor of lipoprotein-associated phospholipase A2
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Modification of the pyrimidone 5-substituent in clinical candidate SB-435495 has given a series of inhibitors of recombinant lipoprotein-associated phospholipase A2 with sub-nanomolar potency. Cyclopentyl fused derivative 21, SB-480848, showed an enhanced in vitro and in vivo profile versus SB-435495 and has been selected for progression to man.
- Blackie, Josie A.,Bloomer, Jackie C.,Brown, Murray J. B.,Cheng, Hung-Yuan,Hammond, Beverley,Hickey, Deirdre M. B.,Ife, Robert J.,Leach, Colin A.,Lewis, V. Ann,Macphee, Colin H.,Milliner, Kevin J.,Moores, Kitty E.,Pinto, Ivan L.,Smith, Stephen A.,Stansfield, Ian G.,Stanway, Steven J.,Taylor, Maxine A.,Theobald, Colin J.
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p. 1067 - 1070
(2007/10/03)
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- Microwave promoted efficient synthesis of substituted uracils and thiouracils under solvent-free conditions
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Several substituted uracils and thiouracils were synthesized in good yields by one-pot condensation reaction of methyl or ethyl β-ketoesters and urea (or thiourea) in solvent-free conditions under microwave irradiation and in short time.
- Mojtahedi, Mohammad M.,Saidi, Mohammad R.,Shirzi, Jafar S.,Bolourtchian, Mohammad
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p. 851 - 855
(2007/10/03)
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- A C-13 nuclear magnetic resonance study of the pyrimidine synthesis by the reactions of 1,3-dicarbonyl compounds with amidines and ureas
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The detailed mechanistic pathways are elucidated for the reactions of acetylacetone, methyl acetoacetate, and dimethyl malonate with a variety of amidines and ureas.In many cases the identification of a single intermediate allows the definition of the reaction path and identification of two steps.Intermediates characterized include ring-closed dihydroxytetrahydropyrimidines, dihydrohydroxypyrimidinones, open-chain enamides, and carbonyl addition compounds.
- Katritzky, Alan R.,Yousaf, Taher I.
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p. 2087 - 2093
(2007/10/02)
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- REACTIONS OF ETHYL 2-ALKYL-3-OXOBUTANOATE WITH THIOUREA AND METHYLTHIOUREA
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The reaction of ethyl-3-oxobutanoate with N-methylthiourea in alkoxide medium gives a mixture (1:20) of 1,6-dimethyl-2-thiouracil and 3,6-dimethyl-2-thiouracil: the latter isomer has been isolated from the mixture and the former isomer has been prepared by independent synthesis.Dissociation constants of ethyl 2-alkyl-3-oxobutanoates (alkyl = methyl, butyl or isopropyl) have been measured in methanol.Reaction of these esters with thiourea and N-methylthiourea gives the corresponding alkyl derivatives of 6-methyl-2-thiouracil.Kinetics of these reactions have been measured in methoxide medium.Effects of the alkyl groups on the reaction rates have been investigated, and a reaction mechanism is suggested.
- Kavalek, Jaromir,Machacek, Vladimir,Sterba, Vojeslav
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p. 1872 - 1877
(2007/10/02)
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- HYDROLYTIC RING CLEAVAGE OF THIADIAZOLOPYRIMIDINONES
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The alkali and acid hydrolysis of 2-substituted 7-methyl-5H-thiadiazolopyrimidin-5-ones gave 3-amino-6-methyluracil, 3-amino-6-methyl-2-thiouracil and 2-amino-1,3,4-thiadiazole derivatives according to the kind of substituents.While, the treatment of 7-methyl-5H-thiadiazolopyrimidin-5-one with methanolic hydrochloric acid gave 6-methyl-2-thiouracil.
- Tsuji, Tadakazu,Otsuka, Yoshimi
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p. 197 - 200
(2007/10/02)
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- STUDY OF REACTION OF THIOUREA WITH ETHYL 3-OXOBUTANOATE
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Base-catalyzed formation of 6-methyl-2-thiouracil (III) by reaction of thiourea (I) with ethyl 3-oxobutanoate (II) involves N-(3-oxobutanoyl)thiourea (XI) as the reaction intermediate.In acid medium the compounds I and II do not react.In contrast to literature data, base-catalyzed cyclization of ethyl 3-thioureido-2-butenoate (IV) does not produce the compound III, but produces 2-amino-4-methyl-6-oxo-1,3-thiazine.
- Kavalek, Jaromir,El-Bahaie, Said,Machacek, Vladimir,Sterba, Vojeslav
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p. 732 - 739
(2007/10/02)
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