Category: 20198-19-0

Reference of 2-Aminoquinazolin-4(3H)-one. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Crystal Structures of tRNA-guanine Transglycosylase (TGT) in Complex with Novel and Potent Inhibitors Unravel Pronounced Induced-fit Adaptations and Suggest Dimer Formation Upon Substrate Binding. Author is Stengl, Bernhard; Meyer, Emmanuel A.; Heine, Andreas; Brenk, Ruth; Diederich, Francois; Klebe, Gerhard.

The bacterial tRNA-guanine transglycosylase (TGT) is a tRNA modifying enzyme catalyzing the exchange of guanine 34 by the modified base preQ1. The enzyme is involved in the infection pathway of Shigella, causing bacterial dysentery. As no crystal structure of the Shigella enzyme is available the homologous Zymomonas mobilis TGT was used for structure-based drug design resulting in new, potent, lin-benzoguanine-based inhibitors. Thorough kinetic studies show size-dependent inhibition of these compounds resulting in either a competitive or non-competitive blocking of the base exchange reaction in the low micromolar range. Four crystal structures of TGT-inhibitor complexes were determined with a resolution of 1.58-2.1 Å. These structures give insight into the structural flexibility of TGT necessary to perform catalysis. In three of the structures mol. rearrangements are observed that match with conformational changes also noticed upon tRNA substrate binding. Several water mols. are involved in these rearrangement processes. Two of them demonstrate the structural and catalytic importance of water mols. during TGT base exchange reaction. In the fourth crystal structure the inhibitor unexpectedly interferes with protein contact formation and crystal packing. In all presently known TGT crystal structures the enzyme forms tightly associated homodimers internally related by crystallog. symmetry. Upon binding of the fourth inhibitor the dimer interface, however, becomes partially disordered. This result prompted further analyses to investigate the relevance of dimer formation for the functional protein. Consultation of the available TGT structures and sequences from different species revealed structural and functional conservation across the contacting residues. This suggests that bacterial and eukaryotic TGT could possibly act as homodimers in catalysis. It is hypothesized that one unit of the dimer performs the catalytic reaction whereas the second is required to recognize and properly orient the bound tRNA for the catalytic reaction.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Synthesis of imidazopyrimidines and imidazoquinazolines with a common nitrogen atom, the main research direction is imidazopyrimidine; imidazoquinazoline; cyclocondensation ketone aminopyrimidine aminoquinazoline; pyrimidine amino cyclocondensation ketone; quinazoline amino cyclocondensation ketone.Application of 20198-19-0.

Condensing 2-aminopyrimidine with RCOCHBrR1 (I; R = alkyl aryl, heterocyclyl; R1 = H, alkyl) gave 50-99% imidazopyrimidines II. Thus, 2-amino-4-hydroxy-6-methylpyrimidine and BrCH2COC6H4NO2-p gave 80% III and 18% IV. Similarly, 4-aminopyrimidine V (R2 = H, MeO; R3 = Cl, MeO) with I gave 68-90% VI. The analogous reaction of 2-chloro- or 2-amino-4-quinazolone or 4-aminoquinazoline gave 41-99% VII (R = alkyl, aryl; R1 = H, alkyl; R2 = H, alkyl, aryl) and 47-88% VIII (R = alkyl, aryl, heterocyclyl; R1 = H, alkyl), resp. Hydrolysis of VIII (R = p-BrC6H4, R1 = H) gave 1-(p-bromophenacyl)-1,4-dihydroquinazolin-4-one. 4-Quinazolone and p-BrC6H4COCH2Br gave 3-(p-bromophenacyl)-3,4-dihydroquinazolin-4-one.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Reference of 2-Aminoquinazolin-4(3H)-one. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Synthesis of Size-Expanded Nucleobase Analogues for Artificial Base-Pairing Using a Ligand-Free, Microwave-Assisted Copper(I)-Catalyzed Reaction. Author is Radhakrishnan, K.; Das, Soumi; Kundu, Lal Mohan.

In order to incorporate valuable properties to the size-expanded nucleobases, a new catalog of highly substituted 2-aminoquinazolinone derivatives, e.g., I have been synthesized in a one-pot, microwave-directed reaction. Syntheses were carried out using simple reactants such as ortho-halo aromatic carboxylic acids, e.g., 4-bromo-3-thiophenecarboxylic acid and guanidine hydrochloride, in absence of any addnl. ligand. The usefulness of the methodol. could be justified by the diversity of the compounds synthesized, containing functional groups, natural nucleobases, fluorophores or peptide bonds.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzodiazlnes. VI. Synthesis of 2-substituted-4-hydrazinoquinazolines, 5-substituted [3,4-c]-s-triazolo-, and [1,5-c]tetrazoloquinazolines》. Authors are Postovskii, I. Ya.; Vereschagina, N. N.; Mertsalov, S. L..The article about the compound:2-Aminoquinazolin-4(3H)-onecas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2).Reference of 2-Aminoquinazolin-4(3H)-one. Through the article, more information about this compound (cas:20198-19-0) is conveyed.

cf. CA 63, 13256g. 2-R-substituted quinazol-4-ones (I), -4-chloroquinazolines (II), and -4-hydrazinoquinazolines (III) were prepared Treatment of II with CS(NH2)2 gave the corresponding isothiuronium salts, which on treatment with NaOH gave 2-R-substituted-quinazoline-4-thiones (IV). III with HNO2 gave 5-R-substituted[1,5-c]tetrazoloquinazolines (V), with CH(OEt)3 gave 5-R-substituted[3,4-c]-s-triazoloquinazolines (VI). V treated with HCl gave I (a, R = Me) (b, R = Ph) (c, R = α-furyl) (d, R = γ-pyridyl). Thus, 12.5 g. thioisonicotinamide and 12.5 g. anthranilic acid was heated at 150-60° 1 hr. to give 7.5 g. Id, m. 250° (dioxane). IIa-c were prepared according to Scarborough et al. (CA 57, 7263h). IIa m. 86-8° (heptane); IIb m. 124-6° (heptane); IIc m. 122-4° (heptane). A mixture of 7.5 g. Id, 60 cc. POCl3, and 10 g. PCl5 was boiled 4 hrs., POCl3 distilled, the mixture poured onto ice, neutralized with NH3, and filtered, the precipitate washed with H2O and dried, the residue extracted with boiling C6H6, and the extract filtered and evaporated gave 6.5 g., IId, m. 164-6° (heptane). II (0.02 mole) in C6H6 was stirred and cooled, 5-fold excess NH2NH2.H2O in C6H6 added, and the mixture stirred 2 hrs. gave III. II (0.01 mole), 0.01 mole CS(NH2)2, and 50 cc. EtOH boiled 1 hr. and evaporated, the residue dissolved in NaOH, the mixture filtered, and the filtrate acidified with AcOH gave IV. The following III and IV were prepared (R, III m.p., III % yield, IV m.p., and IV % yield given): Me, 180-2° (CHCl3), 80, 217-18° (EtOH), -; Ph, 214-15° (CHCl3), 81, 216-18° (EtOH), 63; α-furyl, 249-50° (dioxane), 76, 219-20° (dioxane), 85; γ-pyridyl, 200-2° (CHCl3,), 97, -, -. Treatment of IIa with NH2NH2.H2O in EtOH gave 50% N,N’-bis(2-methylquinazolyl)-4-hydrazine (VII), m. 280° (isoPrOH). III (0.002 mole) boiled I hr. with 5-fold excess CH(OEt)3 gave VI. NaNO2 (0.002 mole) was added to 0.002 mole III in 2N HCl at 3-5° and the mixture stirred 1 hr. to give V. V were also prepared by treating II with NaN3 in EtOH. The following VI and V were prepared (R, VI m.p., VI % yield, V m.p., and V % yield given): Me, >280°, 50, 163-5°, 60; Ph, 204-6°, 97, 162-3°, 70; α-furyl, 260-2°, 98, 194-6°, 73; γ-pyridyl, 206-7°, 80, 200-2°, 80. Boiling IV with 15-fold excess NH2NH2.H2O in EtOH until no more H2S evolved (8-10 hrs.) gave III. Treatment of V with HCl (1:1) 3 hrs. gave I. The compounds with R = Me differ considerably from the others, both in color and in stability of the intermediate reaction products.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Effect of substrate analogs on the circular dichroic spectra of thymidylate synthetase from Lactobacillus casei, published in 1975, which mentions a compound: 20198-19-0, Name is 2-Aminoquinazolin-4(3H)-one, Molecular C8H7N3O, Formula: C8H7N3O.

CD studies at 290-400 nm with thymidylate synthetase from L. casei revealed characteristic Cotton effects in the presence of various folate analogs plus 5-fluoro-2′-deoxyuridylate (I). Omission of either substrate analog prevented the appearance of the Cotton effects. When I and racemic 5,10-methylenetetrahydrofolate (II) were mixed with the enzyme, a ternary complex resulted which gave distinctive minor neg. ellipticity bands at 285 and 332 nm and a major pos. band at 305 nm. Similar results were obtained with the ternary complex containing (+)-II but the enzymically inactive (-)-II induced only the pos. band at 305 nm. More intense Cotton effects were elicited by (±)-5,11-methylenetetrahydrohomofolate with a major pos. ellipticity band at 308 nm and a minor neg. band at 335 nm. A ternary complex was also formed with dihydrofolate, which provided a major CD band at 305 nm and a broad minor neg. band in the region of 335 nm. Deoxyuridylate and thymidylate also formed ternary complexes with dihydrofolate, but their ellipticity bands were much less intense. Other folate analogs that formed ternary complexes with I to provide characteristic CD spectra were tetrahydrofolate, tetrahydrohomofolate, 10-methyltetrahydrofolate, and 2-amino-4-hydroxyquinazoline. By measuring the increment in ellipticity at 305 nm on addition of specific ligands to enzyme solutions, it was determined that the L. casei thymidylate synthetase contains 2 binding sites for I and for each of the diastereoisomers of II. An improved procedure is presented for the large-scale purification and crystallization of L. casei thymidylate synthetase.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《New route to diazine mono-N-oxides》. Authors are Taylor, E. C.; Jefford, C. W..The article about the compound:2-Aminoquinazolin-4(3H)-onecas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2).Recommanded Product: 2-Aminoquinazolin-4(3H)-one. Through the article, more information about this compound (cas:20198-19-0) is conveyed.

Treatment of o-O2NC6H4NCO with KCN in aqueous alkali gave o-O2NC6H4NHCOCN, m. 98°, hydrogenation of which in EtOH over PtO2 yielded I, m. 323°. Reduction of I in EtOH-MeNH2 with H and Raney Ni gave 2-amino-3(4H)-quinoxalone, m. >360°. Treatment of H2NCN with o-O2NC6H4COCl in the presence of alkali yielded o-O2NC6H4CONHCN, m. 125°, which was reduced over PtO2 to II, m. 381° (decomposition). Reduction of II with H over Raney Ni gave 2-amino-4(3H)-quinazolone, m. 313° (decomposition).

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Deamination studies on pyrimidine and condensed pyrimidine systems》. Authors are Trattner, Richard B.; Elion, Gertrude B.; Hitchings, George H.; Sharefkin, David M..The article about the compound:2-Aminoquinazolin-4(3H)-onecas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2).Name: 2-Aminoquinazolin-4(3H)-one. Through the article, more information about this compound (cas:20198-19-0) is conveyed.

Five representative 2,4-diaminopyrimidines and condensed pyrimidine systems, such as I, were subjected to several deamination procedures. The amino group in the 2-position of the pyrimidine ring can be removed by treatment with nitrous acid, but is resistant to acid or alk. hydrolysis. The 4-amino group is unreactive toward nitrous acid, but is removed by acid or alk. hydrolysis. The fused ring attached to the pyrimidine ring has a pronounced influence on the reactivity of each amino group. The results are consistent with the hypothesis that the reactive intermediates of the 2,4-diaminopyrimidine ring have a p-quinoid structure rather than an o-quinoid form.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Related Products of 20198-19-0. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about One-carbon compounds as synthetic intermediates. The synthesis of hydropyrimidines and hydroquinazolines by sequential nucleophilic addition to diphenyl cyanocarbonimidate with concomitant cyclization. Author is Garratt, Peter J.; Hobbs, Christopher J.; Wrigglesworth, Roger.

Di-Ph cyanocarbonimidate (PhO)2C:NCN, undergoes nucleophilic addition with ω-amino esters and amines in a sequential manner to give guanidine derivatives that, for the most part, spontaneously cyclize to give hydropyrimidines, e.g. I, or hydroquinazolines. The hydropyrimidines could be dehydrogenated to pyrimidines, and the NCN group could be hydrolyzed to a carbonyl or amine group in the pyrimidine and to an amine group in the quinazoline series. The regiospecificity of the cyclization was determined by a combination of spectroscopic methods and comparison of compounds synthesized by standard routes. The scope of the synthetic route is indicated. Some of the acyclic N-cyano-O-phenylisoureas formed by the first nucleophilic addition exist as mixtures of isomers, and the barriers to interconversion have been determined by NMR spectroscopy.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Aminoquinazolin-4(3H)-one( cas:20198-19-0 ) is researched.Application of 20198-19-0.Masharipov, S. M.; Nazhimov, K. O.; Kasymova, S. S.; Askarov, M. A. published the article 《New acrylic monomers》 about this compound( cas:20198-19-0 ) in Doklady Akademii Nauk UzSSR. Keywords: crotonylquinazolinone preparation polymerization vinyl chloride; quinazolinone crotonyl preparation polymerization; vinyl chloride crotonylquinazolinone copolymer; thermal stability chloroethene crotonylquinazolinone copolymer. Let’s learn more about this compound (cas:20198-19-0).

2-(Crotonoylamino)quinazolin-4-one (I) and 2-(crotonoylamino)-3-methylquinazolin-4-one (II) monomers were prepared by reaction of 2-aminoquinazolin-4-one and 2-amino-3-methylquinazolin-4-one with crotonoyl chloride. During polymerization of the monomers with vinyl chloride (III), the polymerization rate decreased with increasing content of I or II at concentrations ≤5%. The incorporation of I or II in III polymers led to improved oxidative thermal stability, with maximum stability observed at 0.5-0.6% I or II.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Quality Control of 2-Aminoquinazolin-4(3H)-one. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about New methods for the synthesis of 1,2,3,5-tetrahydroimidazo[2,1-b]-quinazoline-2,5-diones. Author is Vlasenko, A. F.; Mazur, I. A.; Kochergin, P. M..

2-Chloro-4-quinazolone reacted with BrCH2CO2Me and then RNH2 (R = H, CH2CH2OH, Bu, Ph, p-MeC6H4, p-ClC6H4) to give the title compounds I (R1 = H). These compounds and I (R = p-ClC6H4, R1 = Et) were also prepared from the corresponding 2-amino-4-quinazolones and BrCHR1CO2H or their esters.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis