Synthesis and Antiviral Evaluation of N-Glycosides Derived From 6-Amino-3-Aryl-2-Methyl-4-(3h)-Quinazolinones

Saleh, Mohamed A.; Abbas, Y. A.; Eabdel-Hai, Fouad; Shaban, Shaban Y.

doi:10.1081/ncn-100107200

Cited by 11 publications

(5 citation statements)

References 10 publications

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“…In the 1 H NMR spectrum, the anomeric proton appeared as a triplet (at δ 4.50) due to the coupling with neighboring NH and CH protons. These NMR data were consistent with those reported (δ C 84.9 and δ H 4.43) for related β- N -glucosides, indicating 5 to be the β- N -glucosylation product. The presence of a signal due to a chelated NH 2 at δ 8.41 in its 1 H NMR spectrum further confirmed that the glucosylation occurred at the C-2 amino group.…”

supporting

confidence: 91%

Microbial Transformation of Amino- and Hydroxyanthraquinones by Beauveria bassiana ATCC 7159

Zhan

Gunatilaka

2006

J. Nat. Prod.

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Microbial biotransformation of four amino- and hydroxyanthraquinones catalyzed by Beauveria bassiana ATCC 7159 has been studied. Incubation of 1,2-diaminoanthraquinone (1) with B. bassiana ATCC 7159 afforded 1-amino-2-(4'-O-methyl-2beta-N-D-glucopyranosylamino)anthraquinone (5) in a hitherto unprecedented biotransformation involving N-glycosylation of an amine. Biotransformation of 1-aminoanthraquinone (2) yielded 1-amino-2-(4'-O-methyl-2beta-O-D-glucopyranosyloxy)anthraquinone (6) as a result of microbial hydroxylation of C-2 followed by 4'-O-methyl-glucosylation of the newly introduced hydroxyl group. 1,8-Dihydroxyanthraquinone (3) and 1,2-dihydroxyanthraquinone (4) afforded 8-hydroxy-1-(4'-O-methyl-1beta-O-D-glucopyranosyloxy)anthraquinone (7) and 1-hydroxy-2-(4'-O-methyl-2beta-O-D-glucopyranosyloxy)anthraquinone (8), respectively, resulting from 4'-O-methyl-glucosylation of the existing hydroxyl groups of the substrates. The efficiency of these conversions suggests that microbial biotransformation reactions offer an attractive alternative to chemical 4'-O-methyl-glucosylation of amino- and hydroxyanthraquinones.

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supporting

confidence: 91%

Microbial Transformation of Amino- and Hydroxyanthraquinones by Beauveria bassiana ATCC 7159

Zhan

Gunatilaka

2006

J. Nat. Prod.

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“…On the other hand, various therapeutic activities have been reported for both pyrazole [ 10 , 11 , 12 ] as well as pyrimidine moieties [ 13 , 14 ]. As a part of our continued program on the chemistry of 3H-quinazolin-4-one ring systems, we recently developed a simple and efficient approach to a wide range of such derivatives [ 15 , 16 , 17 , 18 , 19 , 20 ]. These results prompted us to synthesize a series of novel 3H-quinazolin-4-one derivatives containing a pyrazolinone, pyrazole or pyrimidinone ring, with the aim of obtaining some novel heterocyclic systems with potentially enhanced biological properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel 3H-Quinazolin-4-ones Containing Pyrazolinone, Pyrazole and Pyrimidinone Moieties

et al. 2003

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The diazonium salt of 3-(4-aminophenyl)-2-methyl-3H-quinazolin-4-one (2a) and its 6-bromo derivative 2b reacted with some active methylene compounds, namely ethyl acetoacetate (3), ethyl cyanoacetate (4) and acetylacetone (5), to afford the corresponding hydrazono quinazolinone derivatives 6-8. Treatment of 6a,b with hydrazine hydrate or phenyl hydrazine in refluxing ethanol afforded the corresponding pyrazolin-5-one derivatives of 3H-quinazolin-4-one 9a-d. Cyclization of 7a,b with hydrazine hydrate yielded the corresponding products 10a,b. Reaction of 8a,b with phenyl hydrazine or with urea afforded the corresponding derivatives 11a,b and 12a,b, respectively. Compounds 6-12 were identified by C,H,N analysis, IR, 1H-NMR, 13C-NMR and mass spectroscopy.

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“…14 gives mp 136-139 °C. 1 H NMR (DMSO-d 6 ): δ (ppm) 8.91 (dd, 1H, J = 1.5, 7.2 Hz), 8.85 (dd, 1H, J = 1.5, 9.4 Hz), 7.74 (s, 1H), 7.35 (ddd, 1H, J = 1.2, 6.3, 9.3 Hz), 7.14 (ddd, 1H, J = 1.5, 6.4, 7.2 Hz), 5.41 (s, 2H), 4.31 (q, 2H, J = 7.2 Hz), 1.34 (t, 3H, J = 7.2 Hz).General procedure for synthesis of N-glycosides (ref 15. ) A mixture of appropriate heterocyclic amine 5 (1.5 mmol) and sugar (1.5 mmol) was refluxed in MeOH (6 mL) in the presence of acetic acid (0.3 mL) for 2 h. Mixture was then cooled and precipitated product was collected by suction and dried on air.…”

mentioning

confidence: 99%

Synthesis and Characterisation of Some New N-Glycosides Containing Substituted Pyridopyrimidinone, Pyrimidopyridazinone, Thiazolopyrimidinone and Quinolizin-4-one Moiety

Šimůnek¹,

Svete²,

Stanovnik³

2008

HETEROCYCLES

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A series of new N-glycosides (D-glucosides, D-mannosides, L-and D-arabinosides, D-xylosides and one D-galactoside) containing heterocyclic moiety have been prepared by reaction of the corresponding heterocyclic amines with pyranoses in boiling methanol. The structures of the prepared compounds have been studied by means of proton and carbon NMR spectroscopy. In the most cases the products existed in DMSO solution as the single anomers.

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Synthesis and Antiviral Evaluation of N-Glycosides Derived From 6-Amino-3-Aryl-2-Methyl-4-(3h)-Quinazolinones

Cited by 11 publications

References 10 publications

Microbial Transformation of Amino- and Hydroxyanthraquinones by Beauveria bassiana ATCC 7159

Microbial Transformation of Amino- and Hydroxyanthraquinones by Beauveria bassiana ATCC 7159

Synthesis of Novel 3H-Quinazolin-4-ones Containing Pyrazolinone, Pyrazole and Pyrimidinone Moieties

Synthesis and Characterisation of Some New N-Glycosides Containing Substituted Pyridopyrimidinone, Pyrimidopyridazinone, Thiazolopyrimidinone and Quinolizin-4-one Moiety

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