The review considers in detail methods of synthesis of thiazolo3,2-
a
pyrimidines, synthesis and chemical properties of their 2-substituted derivatives, and crystal structures of ...2-(arylmethylidene)1,3thiazolo3,2-
a
pyrimidines. High antitumor, antibacterial, and anti-inflammatory activities of these compounds have been demonstrated.
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DOBA, EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, IZUM, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PILJ, PNG, SAZU, SBCE, SBJE, SBMB, UILJ, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
An economical, simple and efficient one-pot method has been developed for the synthesis of thiazolo3,2-apyrimidine hydrobromide derivatives. ...2,4-diaryl-6,7,8,9-tetrahydro-4H-benzo4,5thiazolo3,2-apyrimidine hydrobromides were synthesized by the α-bromination of cyclohexanone with N-Bromosuccinamide (NBS) and followed by cyclization with 3,4-dihydropyrimidine-2(1H)-thiones, respectively, in the presence of p-toluenesulfonic acid (PTSA) in acetonitrile. However when cyclohexanone was replaced by acetyl acetone and alpha-tetralone gave the corresponding 1-(3-methyl-5,7-diaryl-5H-thiazolo3,2-apyrimidin-2-yl)ethan-1-one hydrobromide and 9,11-diaryl-6,11-dihydro-5H-naphtho1′,2′:4,5thiazolo3,2-apyrimidine hydrobromide derivatives, respectively. The significant features of this method are novel, simple, inexpensive experimental procedure, short reaction time, and good yield. The some of the synthesized compounds were evaluated for cytotoxic activity against human lung adenocarcinoma cell line (A549), human breast carcinoma cell line (MCF-7), human cervical cancer cell line (HeLa) and human neuronal carcinoma cell lines (SKNSH). Tested compounds 5(b-e) showed the excellent anticancer activity against various cell lines. Particularly compound 5c with IC50 value of 2.2 ± 0.6 μM against A549 and compound 5e with IC50 value of 5.6 ± 0.4 μM against HeLa showed best cytotoxic effects. Furthermore, Molecular docking study was performed for some of the synthesized compounds 5(b-e) against topoisomerase-II by using Auto dock method. Docking results of the compounds 5c, 5d, and 5e exhibited higher cytotoxic activity than the standard doxorubicin.
An efficient one-pot method has been developed for the synthesis of novel series of 2,4-diaryl-6,7,8,9-tetrahydro-4H-benzo4,5thiazolo3,2-apyrimidine hydrobromide, 1-(3-methyl-5,7-diaryl-5H-thiazolo3,2-apyrimidin-2-yl)ethan-1-one hydrobromide and 9,11-diaryl-6,11-dihydro-5H-naphtho1′,2′:4,5thiazolo3,2-apyrimidine hydrobromide derivatives by the α-bromination of ketone (Cyclohexanone/acetyl acetone/alpha-tetralone) with N-Bromosuccinamide (NBS) and followed by cyclization with 3,4-dihydropyrimidine-2(1H)-thiones, respectively, in the presence of p-toluenesulfonic acid (PTSA) in acetonitrile. The significant features of this method are novel, simple, inexpensive experimental procedure, short reaction time, and good yield. The some of the synthesized compounds were evaluated for the cytotoxic activity against human lung adenocarcinoma cell line (A549), human breast carcinoma cell line (MCF-7), human cervical cancer cell line (HeLa) and human neuronal carcinoma cell lines (SKNSH). Tested compounds 5(b-e) showed the excellent anticancer activity against various cell lines. Particularly compounds 5c and 5e with IC50 values of 2.2 ± 0.6 μM, and 5.6 ± 0.4 μM showed best cytotoxic effects against A549 and HeLa cancer cell lines. Furthermore, Molecular docking study was performed for synthesized compounds 5(b-e) against topoisomerase-II by using Auto dock method. Docking results of the compound 5e exhibited highest docking score than the standard doxorubicin. Display omitted
•The synthesized novel thiazolo3,2-apyrimidine derivatives exhibited more potent anticancer activity.•Molecular docking of synthesized compounds against topoisomerase-II reveals, the compounds showed best docking score than the standard doxorubicin.•The significant features of this synthesis methodology are novel, simple, inexpensive experimental procedure, Short reaction time, Good yield, Low temperature and Metal free synthesis.•The present research results may be considered for designing new class of drugs in anticancer treatment•Thiazolo3,2-apyrimidine derivatives were synthesized in one-pot approach and the structure of thiazolopyrimidines were characterized using FT-IR, 1H NMR, 13C NMR and HRMS techniques.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPCLJ, UPUK, ZAGLJ, ZRSKP
A series of new 2-hydroxy-3-methoxybenzylidenethiazolo3,2-
pyrimidines with different aryl substituents at the 5 position are synthesized and characterized by
H/
C NMR and IR-spectroscopy and ...mass-spectrometry, as well as single crystal X-ray diffraction (SCXRD). It was demonstrated that the type of hydrogen bonding can play a key role in the chiral discrimination of these compounds in the crystalline phase. The hydrogen bond of the O-H...N type leads to 1D supramolecular heterochiral chains or conglomerate crystallization in the case of the formation of homochiral chains. The hydrogen bond of O-H...O type gave racemic dimers, which are packed into 2D supramolecular layers with a parallel or angular dimers arrangement. Halogen bonding of the N...Br or O...Br type brings a new motif into supramolecular self-assembly in the crystalline phase: the formation of 1D supramolecular homochiral chains instead 2D supramolecular layers. The study of cytotoxicity against various tumor cells in vitro was carried out. It was found that 2-hydroxy-3-methoxybenzylidenethiazolo3,2-
pyrimidines with 3-nitrophenyl substituent at C5 carbon atom demonstrated a high efficiency against M-HeLa (cervical adenocarcinoma) and low cytotoxicity against normal liver cells.
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IZUM, KILJ, NUK, PILJ, PNG, SAZU, UL, UM, UPUK
A series of new thiazolo3,2-
pyrimidines different by aryl substituents in 2 and 5 positions are synthesized and characterized in solution as well as in the crystalline phase using
H and
C NMR-, ...IR-spectroscopies, mass-spectrometry methods, and single crystal X-ray diffraction (SCXRD). The SCXRD study revealed the role of intermolecular H-bonding in the formation of supramolecular architectures (racemic monomers, centrosymmetric racematic dimers, or homochiral 1D chains) of obtained thiazolo3,2-
pyrimidines derivatives depending on solvents (aprotic DMSO or protic EtOH) used upon the crystallization process. Moreover, the in vitro study of cytotoxicity toward different tumor cells showed their high or moderate efficiency with moderate cytotoxicity against normal liver cells which allows to consider the obtained thiazolo3,2-
pyrimidine derivatives as promising candidates for application as antitumor agents.
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IZUM, KILJ, NUK, PILJ, PNG, SAZU, UL, UM, UPUK
An efficient synthesis of new pyrazolo-, triazolo-, and thiazolopyrimidinyl-substituted derivatives of 1-phenylpyrazol-3-one on the basis of a product of the condensation of 4-acetylpyrazolone ...difluoroboron chelate with dimethylformamide dimethyl acetal has been developed.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
In this paper, thiazolo3,2-apyrimidine-2,3-dicarboxylate and oxazolo3,2-apyrimidine-2,3-dicarboxylate derivatives are produced in excellent yields via the multicomponent reaction of anilines, ethyl ...acetoacetate, aldehydes, urea or thiourea, activated acetylenic esters and triphenylphosphine in the presence of Ag/KF/CP@MWCNT as a high efficient catalyst in aqueous media at ambient temperature. The Ag/KF/CP@MWCNT is generated by water extract of rhizome Petasites hybridus as an environmentally media and moderate base. Also, Ag/KF/CP@MWCNT leads to increasing of yield of products and has notable reusability. Antioxidant ability of the resulted compounds is studied by DPPH (radical trapping of diphenyl-picrylhydrazine) and ferric reduction power tests. Also, the antimicrobial activity of some products is determined with the disk diffusion experiment on Gram-positive and Gram-negative bacteria. The advantages of this protocol include of short reaction time, high efficiency and easy separation of products and use of simple catalyst.
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BFBNIB, GIS, IJS, KISLJ, NUK, PNG, UL, UM, UPUK
A number of 5-alkyl-6-methyl-2-thiouracils were obtained, the further introduction of which into the reaction with dialkyl chloroethynylphosphonates afforded a series of new dialkyl ...(6-alkyl-5-oxo-7-methyl-5
H
-thiazolo3,2-
a
pyrimidin- 3-yl)phosphonates.
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DOBA, EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, IZUM, KILJ, KISLJ, MFDPS, NLZOH, NUK, OBVAL, OILJ, PILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UILJ, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
Triazolo4,3-apyrimidine is one of the promising structural fragments for the development of drugs, including anticancer drugs. This work is devoted to the synthesis of a number of new 2-arylhydrazone ...derivatives of thiazolo3,2-apyrimidine, which are synthetic precursors for triazolo4,3-apyrimidines. The crystal structure of 6-acetyl-7-methyl-5-phenyl-2-(2-phenylhydrazineylidene)-5H-thiazolo3,2-apyrimidin-3(2H)-one was established by SCXRD. In the reduction reaction of the compound, the following system was used: vanadium(V) oxide, and sodium borohydride in ethanol at room temperature, which led to the formation of only one pair of diastereomers (1R*)-1-((5S*,6R*,7R*)-(1-(hydroxymethyl)-7-methyl-1,5-diphenyl-1,5,6,7-tetrahydro1,2,4triazolo4,3-apyrimidin-6-yl)ethan-1-ol.
Thiazolopyrimidines are attractive to medical chemists as new antitumor agents due to their high inhibitory activity against the replication process of tumor cells and the easy modification of their ...structure by changing the number and nature of substituents. The presence of asymmetric C5 carbon atoms requires the development of racemic mixture separation procedures for these heterocycles. One of the most effective methods is the crystallization of a racemic compound in the form of a conglomerate. The prerequisite for such separation is the construction of chiral, supramolecular ensembles in the crystalline state. Halogen-π interactions were chosen as supramolecular synthons. In this context, ethyl 7-methyl-3-oxo-2,3-dihidro-5H-thiazolo3,2-apyrimidine-6-carboxylate containing a 4-bromophenyl fragment at C5 was synthesized. The crystal structure of the resulting compound was established using SCXRD. The role of the halogen-π interaction on the formation of one-dimensional homochiral chains is revealed.
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IZUM, KILJ, NUK, PILJ, PNG, SAZU, UL, UM, UPUK
Thiazolopyrimidines are attractive to medical chemists as new antitumor agents due to their high inhibiting activity towards the tumor cells replication process and easy modification of their ...structure by varying of the number and nature of substituents. The presence of asymmetric C5 carbon atoms requires the development of racemic mixture separation procedures for these heterocycles. One of the more effective ways is the crystallization of a racemic compound as a conglomerate. A prerequisite for such separation is the formation of non-centrosymmetric crystals presenting Sohncke space groups. For the construction of chiral supramolecular ensembles in a crystalline state, hydrogen bonds were chosen as supramolecular synthons. In this context, salicylic derivatives at the C2 atom of thiazolopyrimidines were synthesized. The crystal structures of the obtained compounds were established by SCXRD. The regularities of the solvent’s influence on the crystal packaging were revealed. The conditions for the preparation of crystals with the chiral space group due to intermolecular hydrogen bonds were discovered.
