Synthesis of N-tetra-O-acetyl-β-d-glucopyranosyl-N′-(4′,6′-diarylpyrimidin-2′-yl)thioureas (original) (raw)
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Design, synthesis and antimicrobial screening of some new thienopyrimidines
Organic Communications, 2021
Heterocyclic compounds play an important role in our life due to their biological importance in the struggle of microorganisms. Herein, a series of novel hybrid compounds of thienopyrimidine with triazine and pyrimidine scaffolds were synthesized starting from difunctionalized compound 5-amino-4-phenyl-2-(p-tolylamino)thieno[2,3d]pyrimidine-6-carbonitrile (1). Moreover, the diazotization of compound 1 with sodium nitrite in an acidic medium gave the chloro-triazine compound 2 which was subjected to the nucleophilic substitution of chlorine atom with different nucleophiles delivered compounds 3a-5c. Furthermore, the reaction of compound 1 with carbon disulfide led to the formation of dithione derivative 6 which was alkylated with ethyl chloroacetate to give compound 7, on the other hand, the reaction of compound 1 with phenyl isothiocyanate produced 4-imino-3,9-diphenyl-7-(p-tolylamino)-3,4dihydropyrimido[4',5':4,5]thieno [2,3-d]pyrimidine-2(1H)-thione (8), while acylation of the amino group in compound 1 with acetic anhydride gave compound 9. All synthesized compounds were characterized by elemental and spectral analysis techniques (IR, 1 H NMR, 13 C NMR, Mass spectroscopy). Furthermore, the synthesized compounds were tested for their antimicrobial activity against different strains of bacteria and fungi, and the results obtained showed good to moderate activity with almost all the strains.
Synthesis and antimicrobial evaluation of some new thienopyrimidine derivatives
ACTA …, 2006
Fused pyrimidines are found in a variety of natural products (e.g., purines, pyrrolopyrimidines, pyridopyrimidines, pteridines), agrochemicals and veterinary products (1-3). Pyrimidine derivatives and heterocyclic annelated pyrimidines continue to attract great interest due to the wide variety of interesting biological activities observed for these compounds, such as anticancer (4), antiviral (5), antitumor (6), anti-inflammatory (7), antimicrobial (8), antifungal (9), antihistaminic (10) and analgesic (11) activities. Aromatic and heteroaromatic compounds bearing an o-aminonitrile or o-aminoester group are useful substrates for the preparation of various condensed pyrimidine heterocyclic systems (12). In view of these reports and as continuation of our earlier studies (13-16), the synthesis of a new series of thieno-pyrimidine derivatives is now reported. Several compounds were screened for their antimicrobial activity. Reaction of heteroaromatic o-aminonitrile with ethyl N--[bis(methylthio)methylene]amino acetate resulted in annelation of a thieno[3,2-e]imidazo[1,2-c]pyrimidine moiety in a one step process. [1,2,4]Triazolo[4,3-c]thieno-[3,2-e]pyrimidine derivatives were prepared by initial treatment of o-aminonitrile with carbon disulfide, followed by methylation with methyl iodide and subsequent reaction with benzhydrazide and thiosemicarbazide, respectively. Hydrazinothieno [2,3-d]pyrimidine was prepared by cyclization of heteroaromatic o-aminoester with formamide, followed by chlorination and subsequent displacement with hydrazine. Treatment of the hydrazino derivative with acetylacetone, benzaldehyde and acetic anhydride afforded pyrazolylpyrimidine, benzylidenehydrazonopyrimidine and triazolopyrimidine derivatives, respectively. Some of these derivatives exhibited pronounced antimicrobial activity.
WORLD JOURNAL OF PHARMACY AND PHARMACEUTICAL SCIENCES, 2014
In continuation to our earlier reported work on the synthesis of novel fused thieno[2,3-d]pyrimidine derivatives, we synthesized two new series of 4{[(aryl)methylene]amino}-2-methyl-5,6-substituted thieno[2,3-d]pyrimidines by the condensation of 4-amino-2,5,6– substituted theino[2,3-d]pyrimidines (ANP and ANH) with nine aromatic aldehydes. The synthesized compounds were characterized by physical and spectral data. The compounds were further evaluated for the antibacterial and antifungal activity employing disc diffusion method.
ChemInform, 2010
A series of hybrid 5-(2-aminothiazol-4-yl)-3,4-dihydro-4-phenyl pyrimidin-2(1H)-ones (ATDPP) are reported. Efficient cyclocondensation of appropriately substituted 5-(2-bromoacetyl)-3,4-dihydro-4-phenylpyrimidine-2(1H)-ones (BADPP) with thiourea in ethanol proceeds in high yield to furnish the corresponding ATDPPs. Dihydropyrimidine carboxylates (DHPMS) and their bromo derivatives are the key substrates for cyclocondensation. The ATDPPS revealed biological activity as antimicrobial and antifungal agents against S. aureus, P. aurogenosa, K. pneumonae and C. albicans.
Antimicrobial Activity of Novel Synthesized Fused 6-AMINO-2-THIOURACILS
Journal of Agricultural Chemistry and Biotechnology, 2008
Two groups of previously synthesized thiopurine derivatives were subjected to study its antimicrobial activity against both Gram-positive, Gram-negative bacteria, yeast and fungi. The first group of the synthesized compounds, 1-methyl-6substituted-2, 5, 7, 8 tetrahydro-2-thio-4-oxo-pyrimido [4, 5-d] pyrimidines (2-7) and the second group, 8-substituted-3-methyl-7-hydroxy-2-thioxanthines (15-20) were used. The synthesized compounds showed various inhibitory effects against Grampositive and Gram negative bacteria as well as fungi while Yeast showed resistance towards all of the synthesized compounds. It was clear that the inhibition activity depends up on the type of substitution.
Cyclization are 2-amino-5, 6-dihydro-4Hcyclopenta[b]thiophene-3-carboxamide (1) with formamide yeilds 3,5,6,7tertrahydro-4H-cyclopenta thieno [2,3-d] pyrimidine-4(3H)-one (2). The compound (2) on reaction with phosphorous oxychloride gives 4-chloro-3, 5, 6, 7-tetrahydro-4H-Cyclopenta thieno[2,3-d] Pyrimidine (3). Reaction of 4-chloro-3, 5, 6, 7-tetrahydro-4H-Cyclopenta thieno[2,3-d] Pyrimidine (3) with substituted secondary amines yeilded a series of new heterocyclic compound 4a-j. The structures of the compound were confirmed by spectral techniques like IR, NMR. Representative classes of compound were screened for Antibacterial activities against gram positive and gram negative bacteria by disc diffusion method. Some synthesized compound show moderate activities as well as few shows promising Antibacterial activity.
Synthesis and Structural Studies of 4-Thioxopyrimidines with Antimicrobial Activities
Monatshefte Fur Chemie, 2007
This work describes a two-step, one-pot synthetic method for the formal aza-[3 + 3] cycloaddition between N-alkyl substituted enaminones and benzoyl isothiocyanate, which afforded 4-thioxopyrimidines in reasonable yields. Reaction of acyclic enaminone with a sterically hindered group attached to the nitrogen atom afforded pyridine-2-thione, yet in low yield. The antibacterial, antifungal, and trypanocidal activities of the thioxopyrimidines were evaluated and five compounds exhibited moderate activity against Candida albicans, Micrococcus luteus, and Trypanosoma cruzi. The solid state structures of a thioxopyrimidine, an organic disulfide, and a 1,2,4-triazole were determined by X-ray diffraction analysis.
Synthesis of Some Novel Thieno[2, 3-d] pyrimidines and their Antibacterial Activity
E-Journal of Chemistry, 2009
Bromination of intermediate 1-[4-(6, 7-dihydro-5H-cyclopenta [4, 5] thieno[2, 3-d]pyrimidin-4-yl amino) phenyl] ethanone(4)yielded(5). Which upon reaction with different substituted benzothiazoles give a novel series of pyrimidine[6(a-g)]. However reaction of(5)with 4-chloro-2-triflouro acetyl aniline provided(6h). Similarly reaction of(5)with 5-amino tetrazole & 2-amino benzimidazole produced(6i)&(6j)respectively. All the synthesized compounds were tested against bacteria (Gram positive and Gram negative).