626-48-2Relevant articles and documents
Novel triazole-sulfonamide bearing pyrimidine moieties with carbonic anhydrase inhibitory action: Design, synthesis, computational and enzyme inhibition studies
Hoda, Nasimul,Manzoor, Shoaib,Petreni, Andrea,Raza, Md Kausar,Supuran, Claudiu T.
supporting information, (2021/07/16)
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.
Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium
Tomanová, Monika,Jedinák, Luká?,Canka?, Petr
supporting information, p. 2621 - 2628 (2019/06/03)
Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.
Production method of dipyridamole bulk drug
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Paragraph 0005; 0017, (2018/06/04)
The invention provides a production method of a bulk drug of dipyridamole, which relates to the field of the synthesis of chemical bulk drugs. The production method comprises the following steps: protecting carbonyl of urea, performing condensation reaction with 2,3-diaminosuccinic acid, performing chlorination for hydroxyl of a condensation reactant, replacing chlorine with piperidine, hydrolyzing an obtained product, obtaining a compound containing two carbonyls, separating the product, enabling the separated product to have condensation reaction with diethanol amine, obtaining dipyridamole,and refining to obtain a finished product. By adopting the production method, the synthetic procedure of the dipyridamole is simplified, the conversion rate of raw materials can be greatly increased,and the production cost is decreased.
Substrate specificity of E. coli uridine phosphorylase. Further evidences of high-syn conformation of the substrate in uridine phosphorolysis
Alexeev,Sivets,Safonova,Mikhailov
, p. 107 - 121 (2017/02/05)
Twenty five uridine analogues have been tested and compared with uridine with respect to their potency to bind to E. coli uridine phosphorylase. The kinetic constants of the phosphorolysis reaction of uridine derivatives modified at 2′-, 3′- and 5′-positions of the sugar moiety and 2-, 4-, 5- and 6-positions of the heterocyclic base were determined. The absence of the 2′- or 5′-hydroxyl group is not crucial for the successful binding and phosphorolysis. On the other hand, the absence of both the 2′- and 5′-hydroxyl groups leads to the loss of substrate binding to the enzyme. The same effect was observed when the 3′-hydroxyl group is absent, thus underlining the key role of this group. Our data shed some light on the mechanism of ribo- and 2′-deoxyribonucleoside discrimination by E. coli uridine phosphorylase and E. coli thymidine phosphorylase. A comparison of the kinetic results obtained in the present study with the available X-ray structures and analysis of hydrogen bonding in the enzyme-substrate complex demonstrates that uridine adopts an unusual high-syn conformation in the active site of uridine phosphorylase.
Synthesis of new 2,4-diaryl-6-methyl-5-nitropyrimidines as antibacterial and antioxidant agents
Sura, Mallikarjun Reddy,Peddiahgari, Vasu Govardhana Reddy,Bhoomireddy, Rajendra Prasad Reddy,Vadde, Rama Krishna
, p. 1395 - 1399 (2014/01/06)
A new series of 2,4-diaryl-6-methyl-5-nitropyrimidines (5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i) were synthesized in good yields by Suzuki-Miyaura coupling of 2,4-dichloro-6-methyl-5-nitropyrimidine (3) with various aryl boronic esters (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i) in the presence of 1,1′- bis(diphenylphosphino)ferrocene dichloropalladium(II) (Pd(dppf) 2Cl2). Further, antibacterial and antioxidant properties were screened for the title compounds 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i. Most of the compounds possessed significant activity against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis and Gram-negative bacteria Escherichia coli and Klebsiella pneumoniae. The antioxidant activity of the title compounds showed significant antioxidant activity when compared with vitamin C.
Microwave assisted one-pot synthesis of nitrogen and oxygen containing heterocycles from acyl Meldrum's acid
More,Mahulikar
experimental part, p. 745 - 747 (2011/06/27)
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.
Fe(III) and cobalt(II) coordination compounds of 5-bromo-6-methyl-2- morpholinepyrimidinium-4-amine pyridine-2,6-dicarboxylate
Eshtiagh-Hosseini, Hossein,Yousefi, Zakieh,Shafiee, Maryam,Mirzaei, Masoud
scheme or table, p. 3187 - 3197 (2010/11/24)
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.
PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
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, (2010/03/02)
The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
A simple approach for the regioselective synthesis of imidazo[1,2-a] pyrimidiones and pyrimido[1,2-a]pyrimidinones
Font, David,Linden, Anthony,Heras, Montserrat,Villalgordo, José M.
, p. 1433 - 1443 (2007/10/03)
Several imidazo and pyrimido[1,2-a]pyrimidinones of type 1 and 2 were synthesized through intramolecular cyclization of pyrimidines 9 or pyrimidinones 10 bearing a variety of β and γ-aminoalcohols at the 2-position. Ring closure of the pyrimidinones of type 10 under Mitsunobu conditions lead to mixtures of both bicyclic regioisomers 1 and 2. Treatment of pyrimidines of type 9 with H2SO4 provided an efficient and operationally simple one-pot hydrolysis-cyclization procedure for obtaining imidazo and pyrimido[1,2-a]pyrimidinones 1 in good yields as the sole regioisomeric bicyclic product.
Desulfurization of 2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with oxiranes and 2-haloacetonitriles
Novakov,Orlinson,Navrotskii
, p. 607 - 609 (2007/10/03)
A procedure was developed for the synthesis of tetrahydropyrimidine-2,4- diones by desulfurization of 2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with oxiranes or 2-haloacetonitriles in polar solvents in the presence of a base.
