3977-29-5Relevant academic research and scientific papers
Synthesis and Plant Growth Stimulating Action of 2-Amino-6-methylpyrimidine-4(3H)-thione Derivatives
Hambardzumyan, E. N.,Shahbazyan, L. V.,Vorskanyan, A. S.,Yengoyan, A. P.
, p. 208 - 216 (2020)
Abstract: A series of new pyrimidine derivatives, including those containing an azole or azine heterocycle linked through a sulfur atom or a thiomethylene group, was synthesized based on 2-amino-6-methylpyrimidine-4(3H)-thione. The synthesized compounds exhibited a pronounced stimulating effect on plants growth in the range of 43–96% compared to heteroauxin.
Synthesis, crystal structure, and ADME prediction studies of novel imidazopyrimidines as antibacterial and cytotoxic agents
Abdel-Mohsen, Heba T.,Abood, Amira,El Diwani, Hoda I.,Flanagan, Keith J.,Meindl, Alina,Senge, Mathias O.
, (2020)
In the present study, a novel series of polyfunctionalized imidazopyrimidines 6a–u and 9a–d were efficiently constructed by a domino reaction between 2-imino-6-substituted-2,3-dihydropyrimidin-4(1H)-ones 4a–d or 8a–c and 2-bromoacetophenones 5a–i under mild basic conditions. The synthesized series were screened for their antibacterial activity against Staphylococcus aureus and Bacillus subtilis as Gram-positive (+) bacteria, as well as against Gram-negative (?) bacteria Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Salmonella typhi. Most of the synthesized derivatives of imidazopyrimidines 6 and 9 showed remarkable selectivity against Gram(?) bacteria over the Gram(+) ones. Compounds 6c, 6f, and 6g displayed potent and broad-spectrum antibacterial activity against all tested strains. Compounds 6f and 6g displayed promising inhibitory activity on GryB ATPase from E. coli with IC50 = 1.14 and 0.73 μM, respectively. Simultaneously, some of the synthesized imidazopyrimidines were screened for their antiproliferative activity against 60 cancer cell lines at a concentration of 10 μM. Compound 9d showed potent activity against most of the tested cell lines, with a mean growth inhibition of 37%. The ADME (absorption, distribution, metabolism, and excretion) prediction study demonstrated that the synthesized hits have, in addition to their promising chemotherapeutic activity, acceptable pharmacokinetic properties, and a drug-likeness nature to be further developed.
Regioselective synthesis of 6-substituted-2-amino-5-bromo-4(3H)- pyrimidinones and evaluation of their antiviral activity
Singh, Kamaljit,Singh, Kawaljit,Balzarini, Jan
, p. 428 - 433 (2013)
A series of 2-amino-5-bromo-4(3 H)-pyrimidinone derivatives bearing different substituents at the C-6 position were synthesized using a highly regioselective lithiation-substitution protocol, and the effect of structural variation at the C-6 position on their antiviral activity in cell culture was evaluated. Although some of the derivatives were found to be active against various virus strains, they were effective only close to their toxicity threshold.
2-Pivalamido-3H-pyrimidin-4-one derivatives: Convenient pivalamide hydrolysis using Fe(NO3)3 in MeOH
Bavetsias,Henderson,McDonald
, p. 5643 - 5644 (2004)
A simple methodology for pivalamide (trimethylacetamide, pivaloylamino) hydrolysis has been discovered using Fe(NO3)3 in MeOH at room temperature. The pivalamido group of 2-pivalamido-3H-pyrimidin-4-ones or fused 2-pivalamido-3H-pyrimidin-4-ones such as 2-pivalamido-3H-quinazolin-4-ones and 2-pivalamido-3H-pteridines have been hydrolysed under these conditions to afford the corresponding amine.
Theoretical investigation on the reactivity and photophysical properties of cobalt(II) and manganese(II) complexes constructed using Schiff base ligands based on ALIE and TDDFT calculations
Prasad, Kollur Shiva,Pillai, Renjith Raveendran,Armakovi?, Stevan,Armakovi?, Sanja J.
, p. 141 - 148 (2017)
Herein, we describe the synthesis of two novel Schiff base ligands, 2-[(3-bromo-5-hydroxybenzylidene)-amino]-6-methylpyrimidin-4-ol (1) and 3-bromo-5-[(5-methylthiazol-2-ylimino)methyl]phenol (2), and their Co(II) and Mn(II) complexes (4–6). The molecular
Ultrasound-assisted rapid synthesis of 2-aminopyrimidine and barbituric acid derivatives
Bayramo?lu, Duygu,Kurtay, Gülbin,Güllü, Mustafa
, p. 649 - 658 (2020/02/11)
Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned substrates with diethyl malonate, diethyl-2-alkyl malonate, pentane-2,4-dione, or ethyl-3-oxobutanoate yielded corresponding products. Significant advantages of this sonochemical synthetic protocol with regard to the conventional thermal methods include easy reaction setup and work-up steps, reasonably mild conditions, shorter reaction times (～30 min) and comparably high product yields. The characterization of the synthesized compounds was based on melting points, FT-IR, GC-MS, 1H-NMR techniques, and the obtained data were also checked from the previously published studies.
Synthesis and Investigation of Phthalazinones as Antitubercular Agents
Santoso, Kristiana T.,Cheung, Chen-Yi,Hards, Kiel,Cook, Gregory M.,Stocker, Bridget L.,Timmer, Mattie S. M.
supporting information, p. 1278 - 1285 (2019/02/24)
A series of 2- and 7-substituted phthalazinones was synthesised and their potential as anti-tubercular drugs assessed via Mycobacterium tuberculosis (mc26230) growth inhibition assays. All phthalazinones tested showed growth inhibitory activity (MIC 100 μm), and those compounds containing lipophilic and electron-withdrawing groups generally exhibited better anti-tubercular activity. Several lead compounds were identified, including 7-((2-amino-6-(4-fluorophenyl)pyrimidin-4-yl)amino)-2-heptylphthalazin-1(2H)-one (MIC=1.6 μm), 4-tertbutylphthalazin-2(1H)-one (MIC=3 μm), and 7-nitro-phthalazin-1(2H)-one (MIC=3 μm). Mode of action studies indicated that selected pyrimidinyl-phthalazinones may interfere with NADH oxidation, however, the mode of action of the lead compound is independent of this enzyme. MIC=minimum inhibitory concentration.
Structure-based design, synthesis and evaluation of 2,4-diaminopyrimidine derivatives as novel caspase-1 inhibitors
Patel, Shivani,Modi, Palmi,Ranjan, Vishal,Chhabria, Mahesh
, p. 258 - 268 (2018/04/05)
Interleukin-1β converting enzyme contributes in various inflammatory and autoimmune diseases by maturing pro-inflammatory cytokines IL-1β, IL-18 and IL-33. Therefore, inhibition caspase-1 may provide a potential therapeutic strategy for the treatment of chronic inflammatory diseases. Here we have reported structure-based design, synthesis and biological evaluation of 2,4-diaminopyrimidine derivatives (6a-6w) as potential caspase-1 inhibitors. Six compounds 6m, 6n, 6o, 6p, 6q and 6r showed significant enzymatic inhibition with IC5 0 ranging from 0.022 to 0.078 μM. These compounds also displayed excellent cellular potency at sub-micromolar concentration. Moreover, molecular docking studies provided the useful binding insights specific for caspase-1 inhibition. All these results indicated that compounds 6m, 6n and 6o could be potential leads for the development of newer caspase-1 inhibitors as anti-inflammatory agents.
Synthesizing method of 2-amino-4-hydroxyl-6-methylpyrimidine
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Paragraph 0025; 0026; 0027; 0028; 0029; 0034-0039, (2017/10/10)
The invention relates to a synthesizing method of 2-amino-4-hydroxyl-6-methylpyrimidine. The synthesizing method comprises the following steps of (a) synthesizing of 2-methoxyl-2-ethyl butyrate: mixing ethyl acetate and a catalyst, after heating and refluxing, performing self-condensation reaction of the ethyl acetate, so as to obtain the 2-methoxyl-2-ethyl butyrate; (b) synthesizing of 2-amino-4-hydroxyl-6-methylpyrimidine; dissolving the 2-methoxyl-2-ethyl butyrate into methyl alcohol, dissolving, mixing with guanidine hydrochloride, after heating and refluxing, evaporating the residual solvent, adding deionized water until completely dissolving, using diluted hydrochloric acid to adjust the pH (potential of hydrogen) value, separating solid and filtering, spraying the solid by deionized water, obtaining the 2-amino-4-hydroxyl-6-methylpyrimidine, and drying. The synthesizing method has the advantages that the toxicity of the raw material is low, the cost is low, and the green and environment-friendly effects are realized; the traditional synthesizing method using volatile acetone with stronger toxicity or phenylboronic acid with hypertoxicity is improved, the injury to production personnels and environments is decreased, and the difficulty in production is reduced.
9-Benzoyl 9-deazaguanines as potent xanthine oxidase inhibitors
Rodrigues, Marili V.N.,Barbosa, Alexandre F.,Da Silva, Júlia F.,Dos Santos, Deborah A.,Vanzolini, Kenia L.,De Moraes, Marcela C.,Corrêa, Arlene G.,Cass, Quezia B.
, p. 226 - 231 (2015/12/31)
A novel potent xanthine oxidase inhibitor, 3-nitrobenzoyl 9-deazaguanine (LSPN451), was selected from a series of 10 synthetic derivatives. The enzymatic assays were carried out using an on-flow bidimensional liquid chromatography (2D LC) system, which allowed the screening the measurement of the kinetic inhibition constant and the characterization of the inhibition mode. This compound showed a non-competitive inhibition mechanism with more affinity for the enzyme-substrate complex than for the free enzyme, and inhibition constant of 55.1 ± 9.80 nM, about thirty times more potent than allopurinol. Further details of synthesis and enzymatic studies are presented herein.
