- 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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- Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium
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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.
- Tomanová, Monika,Jedinák, Luká?,Canka?, Petr
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supporting information
p. 2621 - 2628
(2019/06/03)
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- Production method of dipyridamole bulk drug
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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.
- -
-
Paragraph 0005; 0017
(2018/06/04)
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- Substrate specificity of E. coli uridine phosphorylase. Further evidences of high-syn conformation of the substrate in uridine phosphorolysis
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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.
- Alexeev,Sivets,Safonova,Mikhailov
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p. 107 - 121
(2017/02/05)
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- Synthesis of new 2,4-diaryl-6-methyl-5-nitropyrimidines as antibacterial and antioxidant agents
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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.
- Sura, Mallikarjun Reddy,Peddiahgari, Vasu Govardhana Reddy,Bhoomireddy, Rajendra Prasad Reddy,Vadde, Rama Krishna
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p. 1395 - 1399
(2014/01/06)
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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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- PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
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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.
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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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- A simple approach for the regioselective synthesis of imidazo[1,2-a] pyrimidiones and pyrimido[1,2-a]pyrimidinones
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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.
- Font, David,Linden, Anthony,Heras, Montserrat,Villalgordo, José M.
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p. 1433 - 1443
(2007/10/03)
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- Azines and azoles: CXXII. New regioselective synthesis of 1-substituted 6-alkyluracils
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Readily available 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones with primary alkyl- and arylamines in mild conditions (boiling in propan-2-ol) to give Schiff bases. In more rigid conditions (boiling in DMF), the reaction is accompanied by COS liberation and provides 1-substituted 6-alkyluracils. This previously unknown reaction possesses a considerable synthetic potential and can be considered as a new, general, and regioselective synthetic approach to 1-substituted 6-alkyluracils.
- Yuskovets,Moskvin,Mikhailov,Ivin
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p. 134 - 146
(2007/10/03)
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- Desulfurization of 2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with oxiranes and 2-haloacetonitriles
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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.
- Novakov,Orlinson,Navrotskii
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p. 607 - 609
(2007/10/03)
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- Solid-phase synthesis (SPS) of substituted uracils via Oxone cleavage methodology
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An original and highly efficient Oxone cleavage methodology for the solid-phase synthesis of substituted uracils has been developed. An example of application of this methodology to the solid-phase synthesis of uridine derivatives is also reported.
- Petricci, Elena,Renzulli, Michela,Radi, Marco,Corelli, Federico,Botta, Maurizio
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p. 9667 - 9670
(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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- Fungal and bacterial regioselective hydroxylation of pyrimidine heterocycles
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The bacterium Rhodococcus erythropolis is employed to hydroxylate the anxiolytic lesopitron, and this bacterium, together with Agrobacterium sp. and the fungus Beauveria bassiana, are used to extend the field of hydroxylation of heteroaromatic compounds to a series of unexplored pyrimidines. Of all the substrates investigated, only the carbamate 11a is regioselectively hydroxylated by B. bassiana at the C-5 position of the pyrimidine ring; in contrast, the bacteria are able to regioselectively oxidize, when free, the C-2 and/or C-4 positions of the pyrimidine moiety of all the substrates 1a - 12a up to a maximum of two oxidations.
- Gotor, Vicente,Quiros, Margarita,Ramon, Liz,Frigola, Jordi,Fernandez, Rosa
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p. 6421 - 6432
(2007/10/03)
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- Synthesis of some polycyclic noncondenced pyrimidine structures
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Method for the synthesis of compounds containing two of more pyrimidine rings linked through aliphatic chains with different numbers of carbon atoms are described. - Key words: hydroxy- and mercaptopyrimidines; uracils; dihaloalkanes; α,ω-bis(hydroxypyrimidinyl)alkanes.
- Reznik, V. S.,Salikhov, I. Sh.,Shvetsov, Yu. S.,Efremov, Yu. Ya.,Rizvanov, I. Kh.
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p. 326 - 332
(2007/10/02)
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- Research on antiviral agents. 4. Studies on the chemistry of 6-methyl-2-methoxy-4-O-acyloxy and 6-methyl-2,4-di-O-acyloxypyrimidine derivatives as new acylation reagents and inhibitors of uracil DNA glycosylases.
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The synthesis of 6-methyl-2-methoxy-4-O-acyloxy and 6-methyl-2,4-di-O-acyloxypyrimidine derivatives 2 and 5 along with their properties as acylating agents of amines, alcohols, thiols and α-amino acids have been reported. Interestingly some of the title products revealed an inhibitory activity against the human and herpetic DNA glycosylases.
- Botta,Saladino,Gentile,Summa,Nicoletti,Verri,Focher,Spadari
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p. 3603 - 3618
(2007/10/02)
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- Oxidation of substituted 2-thiouracils and pyrimidine-2-thione with ozone and 3,3-dimethyl-1,2-dioxirane
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Ozone and 3,3-dimethyl-1,2-dioxirane react with substituted 2-thiouracils and pyrimidine-2-thione to afford several interesting desulfurized products. The effect of the solvent, protic as opposed to nonprotic, on the course of oxidation was striking.
- Claudia, Crestini,Mincione, Enrico,Saladino, Raffaele,Nicoletti, Rosario
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p. 3259 - 3272
(2007/10/02)
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- Ozonation of substituted 2-thiouracils and pyrimidine-2-thione
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The ozonation of substituted 2-thiouracils and pyrimidine-2-thione is reported; this provides a new method for the synthesis of several pyrimidine derivatives.
- Crestini, Claudia,Saladino, Raffaele,Nicoletti, Rosario
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p. 1631 - 1634
(2007/10/02)
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- One-electron-reduction potentials of pyrimidine bases, nucleosides, and nucleotides in aqueous solution. Consequences for DNA redox chemistry
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The reduction potentials in aqueous solution of the pyrimidine bases, nucleosides, and nucleotides of uracil (U) and thymine (T) were determined using the technique of pulse radiolysis with time-resolved spectrophotometric detection. The electron adducts of U and T were found to undergo reversible electron exchange with a series of ring-substituted N-methylpyridinium cations with known reduction potential. From the concentrations of the pyrimidine electron adducts and the reduced N-methylpyridinium compounds at electron-transfer equilibrium, the thermodynamical equilibrium constants were obtained and from these the reduction potentials. The results show U and T and their nucleosides and nucleotides to have very similar reduction potentials, ～ -1.1 V/NHE at pH 8, i.e., the effect of methylation at C5, C6, or of substitution at N1 is small, ≤0.1 V. In the case of cytosine (C) the electron adduct is protonated (probably at N3), even up to pH 13. The protonated adduct (C(H)?) undergoes a reversible electron transfer with the N-methylpyridinium cations. This is accompanied in one direction by transfer of a proton but by that of a water molecule in the other direction. As a result of the protonation of the electron adduct, the effective ease of reduction of C in aqueous solution is similar to that of U and T. It is suggested that in DNA the tendency for C?- to be protonated (by its complementary base G) is larger by ≥10 orders of magnitude than that for protonation of T?- by its complementary base A. This results in C and not T being the most easily reduced base in DNA. A further consequence is that lack of neutralization by intrapair proton transfer of T?- enables the irreversible extra-pair protonation on C6 of the radical anion to take place.
- Steenken,Telo,Novais,Candeias
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p. 4701 - 4709
(2007/10/02)
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- A useful methodology for the regioselective deprotection of 1,3-dibenzyluracils
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A practical, regioselective N-1 deprotection of 1,3-dibenzyl uracils 2 a-e is described. The same experimental procedure and longer reaction time afforded the complete deprotection of the uracils.
- Botta,Summa,Saladino,Nicoletti
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p. 2181 - 2187
(2007/10/02)
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- Substituent effects on degradation rates and pathways of cytosine nucleosides.
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A previous report on the influence of a 6-methyl substituent on cytosine nucleoside degradation proposed that N-glycosyl hydrolysis predominated over the deamination pathway which was characteristic of the unsubstituted parent compounds. The UV absorption data which led to this hypothesis were not conclusive. Evidence for N-glycosyl hydrolysis was indirect and the product concentration was not quantitated. In the present study, specific HPLC methods were employed to assay four cytosine nucleosides and their corresponding bases, thus allowing comparison of the N-glycosyl hydrolysis rate to the overall rate of loss for each nucleoside. These data indicated that the 6-methyl nucleosides underwent partial or complete hydrolysis to yield their corresponding sugars and 6-methylcytosine, which then deaminated to 6-methyluracil. An increase in the reactivity and a change in the reaction products of the 6-methyl nucleosides were attributed to an alteration in conformation. In addition, the 6-methyl arabinosyl nucleoside reacted much faster than the 6-methyl ribosyl nucleoside, presumably due to 2'-OH participation. Degradation of 5-methyl deoxycytidine was also re-examined since its degradation was previously attributed solely to N-glycosyl hydrolysis. In the present study, simultaneous deamination and hydrolysis were measured, although N-glycosyl hydrolysis was found to predominate.
- Nguyen,Notari
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p. 802 - 806
(2007/10/02)
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- Kinetic Studies on Dehydrogenation Reaction of 5,6-Dihydro-2,4(1H,3H)-pyrimidinediones in Aqueous Solution Induced by Argon Arc Plasma or Hydrogen-Oxygen Flame
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5,6-Dihydro-2,4(1H,3H)-pyrimidinediones underwent dehydrogenation at the 5- and 6-position producing 2,4(1H,3H)-pyrimidinediones in aqueous solution induced by argon arc plasma or flames.From consideration based on the kinetic study of this reaction, it was found that abstraction of a hydrogen atom took place preferentially at the 6-position of the dihydropyrimidinediones.
- Naraoka, Hiroshi,Takasaki, Michiaki,Nomoto, Shinya,Harada, Kaoru
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p. 414 - 416
(2007/10/02)
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- Conversion of Thiocarbonyl into Carbonyl in Uracil, Uridine, and Escherichia coli Transfer RNA using Hypervalent Iodine Oxidation
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2-Thiouracil, 5-, and 6-methyl-2-thiouracil were converted into uracil, 5-, and 6-methyluracil by PhIO in acetone; the 4-thiouridine site in tRNA was transformed to uridine by PhI(OH)OSO2C6H4Me-p at pH 4.0.
- Moriarty, Robert M.,Prakash, Indra,Clarisse, Diana E.,Penmasta, Raju,Awasthi, Alok K.
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p. 1209 - 1210
(2007/10/02)
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- Reactions of pyrimidine nucleosides with aqueous alkalies: kinetics and mechanisms.
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Kinetics for the reactions of various cytosine and uracil nucleosides and their alkyl derivatives with aqueous sodium hydroxide have been studied by liquid chromatography. Blocking of the glycosyl hydroxyl groups with alkyl groups and changes in the glycon moiety configuration have been observed to exert only moderate effects on the rate of deamination of cytosine nucleosides. Methylation of the 4-amino group retards deamination considerably, while a methyl substituent at C5 is rate accelerating and at C6 only moderately rate retarding. These findings have been accounted for by a mechanism involving a rate limiting bimolecular displacement of the 4-amino group by a hydroxide ion. Analogous comparisons with uracil nucleosides suggest that the decomposition of uridine is initiated by an intermolecular attack of hydroxide ion on the C5 atom of the base moiety. In contrast, beta-D-arabino- and beta-D-lyxo-furanosyl derivatives appear to be cleaved via an intramolecular nucleophilic attack of the ionized 2'-hydroxyl group.
- L?nnberg,Suokas,K?ppi,Darzynkiewicz
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p. 798 - 805
(2007/10/02)
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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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- 6-ALKYL- AND 5,6-DIALKYL-2-METHOXY-4(3H)-PYRIMIDINONES IN THE TRANSFORMATIONS OF PYRIMIDINES. REGIOSPECIFIC 1-N-ACYLATION OF PYRIMIDINES.
-
Transformation of 6- and 5,6-dialkyl-2-methoxy-4(3H)-pyrimidinones (1a and 1b) into 1-N-acylated-pyrimidine derivatives 3(a-f) under Friedel-Craft like conditions is presented.In different acylation conditions 4-O-acylated-pyrimidines (5a and 5b) are also obtained.Compounds (3c) and (3f) can be direcly converted into 1-N-acyl-protected-isouridine analogues (8a and 8b).
- Botta, Maurizio,Angelis, Francesco De,Finizia, Gabriella,Nicoletti, Rosario
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p. 3345 - 3348
(2007/10/02)
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- 6-ALKYL AND 5,6-DIALKYL-2-METHOXY-4(3H)-PYRIMIDINONES IN THE TRANSFORMATIONS OF PYRIMIDINES-2 SYNTHESIS AND CONVERSION INTO ALKYLURACILS AND 2-ALKOXY-4(3H)-PYRIMIDINONES
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The synthesis of 6-alkyl and 5,6-dialkyl-2-methoxy-4(3H)-pyrimidinones 3 is described.Their versatility to be transformed into 6-alkyl and 5,6-dialkyluracils 4(a-h), 6-alkyl and 5,6-dialkyl-3-methyluracils 7(a,e,f) and 6-alkyl and 5,6-dialkyl-2-alkoxy-4(3H)-pyrimidinones 5(a-i) is also shown.
- Botta, M.,Cavalieri, M.,Ceci, D.,Angelis, F. De,Finizia, G.,Nicoletti, R.
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p. 3313 - 3320
(2007/10/02)
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- Synthesis of N-Acylacetoacetamide using 2,2,6-Trimethyl-1,3-dioxin-4-one
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Diketene-acetone adduct (2,2,6-trimethyl-1,3-dioxin-4-one) 1 reacts with amide NH to give the corresponding N-acetoacetates 2.Formamide and basic amides such as picolinamide, on treatment with the adduct, are transformed to the N-acyl-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide (4a and 4p) together with the corresponding N-acetoacetates.Keywords--diketene-acetone adduct; 1,3-dioxin-4-one; acetylketene; diketene; acetoacetylation; 4-pyrone derivatives; N-acylacetoacetamide
- Sato, Masayuki,Kanuma, Norio,Kato, Tetsuzo
-
p. 1315 - 1321
(2007/10/02)
-
- Sulphur Extrusion. Part 4. A Halogen-catalysed Conversion of Thiocarbonyl Compounds into their Corresponding Oxygen Analogues using Alkoxides and Hydroxide
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The conversion of thiocarbonyl compounds (thioureas, thioamides, and thiones) into their oxygen analogues has been performed using either (i) potassium t-butoxide with iodine, bromine, or chlorine, (ii) sodium ethoxide with bromine or chlorine, or (iii) sodium hydroxide with bromine or chlorine under phase transfer catalysis.
- Singh, Harjit,Singh, Paramjit,Malhotra, Nageshwar
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p. 2647 - 2649
(2007/10/02)
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