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Application In Synthesis of 2-Aminoquinazolin-4(3H)-one. 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 Identification of the main nitrogen-containing compounds in Ctenopharyngodon idellus by HPLC-Q-TOF-MS. Author is Zhang, You-sheng; Huang, Jia-si; Liu, Xue-ming; Cheng, Jing-rong; Chen, Zhi-yi; Zhang, Ye-hui.

The main nitrogenous compounds in methanol extracts of Ctenopharyngodon idellus were analyzed and identified using high-performance liquid chromatog. coupled with quadrupole time-of-flight mass spectrometry (HPLC-Q-TOF-MS). Both pos. and neg. ionization modes were used to confirm the related chem. compounds and their characteristic fragment ions according to the accurate mol. mass information of the excimer ion peaks and the fragment ions. Using the ChemSpider database, 33 nitrogenous compounds in Ctenopharyngodon idellus were ultimately determined, and the data for the main fragments of each component were analyzed. These 33 nitrogenous compounds included 11 amino acids (eight types of α-amino acids), 12 amines, eight amide compounds, and two heterocyclic nitrogenous compounds The results showed that the structures of monomer compounds in fresh aquatic products and raw materials could be elucidated directly using the HPLC-Q-TOF-MS technique and fragmentation anal. by mass spectrometry, which can improve the efficiency of anal. and identification of chem. components in fresh raw material. This study shows that these techniques are conducive for the identification and anal. of active components and newly generated compounds during the storage of fresh raw materials.

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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

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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Quantitative structure-activity study of some enzyme-inhibitory quinazolines.Name: 2-Aminoquinazolin-4(3H)-one.

Relations are formulated to explain the variation in dihydrofolate reductase [9002-03-3] inhibitory potency for a series of 25 substituted quinazolines I(R = H, OH, NH2, AcNH; R1 = H, NH2, OH, SH; R2 = H, Cl, Me; R3 = H, Me, NH2, Cl, CN, CHO, Br, CH2NH2) with an antineoplastic potential. Highly significant correlations are obtained using CNDO/2-3R calculated indexes and(or) the empirically estimated mol. polarizability as independent variables. The MO calculated indexes employed are the at. polarizability, as defined herein, and bond energy. The mol. polarizability is represented by a simple sum of environment-independent partial at. polarizabilities. The partial polarizabilities, reported here for H, C, N, O, F, S, Cl, and Br, are obtained from a multiple regression forced through the origin.

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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

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Reference of 2-Aminoquinazolin-4(3H)-one. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Quinazolines as inhibitors of dihydrofolate reductase. 1.

2,4-Diaminoquinazolines were potent in vitro inhibitors of rat liver dihydrofolate reductase [9002-03-3]. The most potent compound, 6-bromo-5-chloro-2,4-diaminoquinazoline (I) [41934-85-4], produced 50% inhibition at 0.10 μM, and was thus nearly as effective an inhibitor as pyrimethamine. I was prepared from 5-chloro-2,4,6-triaminoquinazoline [17511-20-5] by diazotization of the 6-amino group in 2N MeSO3H and reaction with CuBr in 50% HBr.

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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

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Category: chiral-nitrogen-ligands. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Synthesis and in vitro evaluation of 2-aminoquinazolin-4(3H)-one-based inhibitors for tRNA-guanine transglycosylase (TGT). Author is Meyer, Emmanuel A.; Furler, Maya; Diederich, Francois; Brenk, Ruth; Klebe, Gerhard.

TRNA-Guanine transglycosylase (TGT) plays a key role in the post-transcriptional modification of tRNA. It has been linked with the pathogenicity of shigellae, the causative agents of bacillary dysentery (shigellosis). Here, we report structure-activity relationships (SARs) for a new series of 2-aminoquinazolin-4(3H)-one-based inhibitors of TGT, resulting from structure-based design (Fig. 2). Versatile synthetic protocols allow selective functionalization of the 2-aminoquinazolin-4(3H)-one core (Schemes 1-6) with H-bond-donor groups in position 6 (for H-bonding to the C = O group of Leu231) and lipophilic residues in position 8 for reaching into a shallow, newly discovered lipophilic pocket lined by Val282, Val45, and Leu68. The binding mode of several of these ligands in the active site of TGT was established by crystal structure analyses (Figs. 4 and 6). A dramatic S effect was observed, with the replacement of the S-atom in the (phenylsulfanyl)methyl residue in position 8 of inhibitor 1c (Ki = 100 nM) by the O-atom (in 1h, Ki = 5.6 μM) or CH2 (in 1i, Ki = 3.6 μM), resulting in a massive loss of activity (Fig. 3). Crystal structure anal. showed that the lipophilic Me group points into a highly polar region of the active site encompassed by the side chains of Asp280 and Asp102 and collides directly (d(C…O) = 3.1 Å) with one of the O-atoms of the carboxylate of Asp102. Similarly, lipophilic linkers departing from position 8 and orienting residues in the shallow hydrophobic pocket presumably encounter analogous unfavorable contacts, accounting for the modest contribution to the binding free enthalpy upon introduction of these residues. These findings provide a valuable starting point for future structure-based lead optimization cycles leading to TGT inhibitors with increased in vitro potency.

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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

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Related Products of 20198-19-0. 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 Reactions of some quinazoline compounds with ethoxymethylenemalonic acid derivatives. Author is Deady, Leslie W.; Mackay, Maureen F.; Werden, Dianne M..

The reactions of Et (1,4-dihydro-4-oxoquinazolin-2-yl)acetate (I, R = CH2CO2Et) and 2-aminoquinazolin-4(1H)-one (I, R = NH2) with ethoxymethylenemalonate derivatives EtOHC:CR1R2 [R1 = R2 = CO2Et (II); R1 = CN, R2 = CN, CO2Et (III)] are reported, and different results are obtained to those previously found with quinoline analogs. Reaction of I (R = CH2CO2Et) with II gives a pyrido[1,2-a]quinazoline, while with III, 2-(pyridin-2-yl)aminobenzoates IV (R2 = CN, R3 = Et, CH2CH2CH; R2 = CO2Et, R3 = Et) are formed, presumably by ring-opening of intermediate pyrido[2,1-b]quinazolines. Reaction of I (R = NH2) with II likewise results in ultimate cyclization onto N-1 of the quinazoline, while reactions with III give isolable pyrimido[2,1-b]quinazolines. These are readily cleaved under mild conditions. The structure of IV (R2 = CN, R3 = Et) was proved by x-ray crystallog.

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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

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensations of isatinic acid with ureas, ethyl carbamate, and guanidine》. Authors are Stefanovic, Gj.; Lorenc, L. J.; Mihailovic, M. Lj..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.

The title condensations gave high yields of 2-derivatives of quinazoline-4-carboxylic acid o-C6H4.N:CR’.N:CCO2R. KOH solution (20% aqueous) containing 0.1 mole KOH added to 14.7 g. isatin (II), the mixture warmed at 40° until yellow, the solution evaporated to dryness in vacuo below 40°, and the residue crystallized from EtOH gave K isatinate (III). Heating 4.06 g. III with 6.0 g. urea at 130-40° 10 hrs., treating the mixture with hot EtOH, and cooling gave 3.84 g. I(R = K, R’ = OH) (IV), which with aqueous AgNO3 was converted to I (R = Ag, R’ = OH) (V). V (2.97 g.) refluxed 6 hrs. with 2.13 g. MeI in 20 ml. anhydrous Et2O, the mixture filtered, the AgI washed with hot EtOH, the filtrate and washings combined, and evaporated to dryness in vacuo gave 2.18 g. crude I (R = Me, R’ = OH) (VI), m. 200-1° (EtOH). When anhydrous MeOH was used for washing and crystallization, VI crystallized with 1 mol. MeOH, m. 216°. IV (9.1 g.) in 90 ml. H2O treated at 5° with an equivalent amount of 8% aqueous HCl, the precipitate filtered off, and washed with cold H2O gave 7.5 g. I (R = H, R’ = OH) (VII).H2O, m. 264-5°, pK 3.10 (H2O-EtOH), which gave the anhydrous acid (VIII) on prolonged drying over P2O5 in vacuo. This (2.08 g.) treated dropwise with excess CH2N2 in anhydrous Et2O at ice-bath temperature gave, after evaporation of solvent, crude I (R = Me, R’ = OMe) (IX), m. 99-100° (EtOH). IX (240 mg.) refluxed 30 min. with 12 ml. 0.1N aqueous NaOH, the solution cooled to 5°, acidified with 5% aqueous HCl to Congo red, and filtered gave 190 mg. I (R = H, R’ = OMe) (X), m. 156° (purification through the Na salt). X (102 mg.) heated at 160° to cessation of CO2 evolution and the product sublimed at 10-15 mm. gave 48.2 mg. 2-methoxyquinazoline, m. 56°. Boiling 7.50 g. VIII in 75 ml. H2O 6 hrs., cooling, and filtering gave 5.0 g. crude 2-quinazolone (XI), converted to the hydrochloride, m. above 300°, by boiling concentrated HCl and addition of EtOH. This gave pure XI, m. 282-4°, with boiling EtOH. III (10.15 g.) heated with (H2N)2C:NH 4 hrs. at 125°, followed by dissolution with H2O, filtration, and acidification of the filtrate with 5% aqueous HCl to Congo red gave 8.9 g. I (R = H, R’ = NH2) (XII), which, after solution in NaHCO3 and precipitation with 5% sq. HCl, gave pure XII, m. 210°. Treating XII at 5° in Et2O with a slight excess of ethereal CH2N2, evaporating the solvent, and crystallizing the crude product from EtOH gave I (R = Me, R’ = NH2) (XIII), m. 144-5°. XII (100 mg.) decarboxylated at 220-5°/10-15 mm. yielded 63 mg. 2-aminoquinazolone, m. 205°, which sublimed during the decarboxylation. IV was also obtained in high yield by reaction of PhNHCONH2, Me2NCONH2, or NH2CO2Et with III. A discussion of lactim-lactam tautomerization was given, based on the methylation reactions and infrared spectra.

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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

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George, Bobby J.; Dib, Hicham H.; Abdallah, Mariam R.; Ibrahim, Maher R.; Khalil, Nasser S.; Ibrahim, Yehia A.; Al-Awadi, Nouria A. published an article about the compound: 2-Aminoquinazolin-4(3H)-one( cas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2 ).Recommanded Product: 2-Aminoquinazolin-4(3H)-one. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:20198-19-0) through the article.

The kinetics, product anal. and theor. studies for selective deprotection of N-arylideneamino pyridone, pyrimidinone and triazinone systems were carried out. Their reactivities were compared with each other and with related compounds previously studied. This reaction represents an efficient, clean and general synthetic procedure for the protection and selective synthesis of potential biol. active pyridines, pyrimidines and triazines and their derivatives

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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

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reactions in sunlight with alcoholic ammonia. VI. The reaction with some indolic compounds》. Authors are Capuano, Salvatore; Giammanco, Lorenzo.The article about the compound:2-Aminoquinazolin-4(3H)-onecas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2).Computed Properties of C8H7N3O. Through the article, more information about this compound (cas:20198-19-0) is conveyed.

In view of the results obtained with pyrrolic compounds (C.A. 50, 7807f), and the fact that O is necessary in the reaction of pyrroles with NH3, the behavior of indole (I), α-phenylindole (II), and isatin (III) was studied. The results show that, here too, O is necessary in the sunlight reaction. I (10 g.) in 500 cc. 95.% EtOH saturated with NH3, exposed (while closed) to sunlight for 1 hr., gives a dark red solution and a brown precipitate, which, purified by EtOH, yields 2,4(1H,3H)-quinazolinedione (IV). II (32 g.) in 1000 cc. alc. NH3, exposed (while closed) to sunlight for 6 months, concentrated in vacuo, allowed to stand until the brown oil has solidified, and the solid purified by dioxane, gives 2-phenyl-4(1H)-quinazolinone (V), m. 232-5°. Addition of H2O to the mother liquor precipitates a greenish resin. V can be prepared by the method of Finger-Schupp [J. prakt. Chem. 74, 154(1906)], or as follows: a mixture of equimolar weights o-H2NC6H4CO2H and HN:CPhNH2.HCl, heated until no more NH3 and NH4Cl are evolved, the yellow oil poured into H2O, and the precipitate purified by EtOH or dioxane, gives V, m. 238-40°. III in alc. NH3 gives a dark red solution, which, exposed to sunlight 3 months, precipitates a mixture of a brown substance and white substance. This mixture extracted with hot EtOH, the extract allowed to stand, and the precipitate purified by EtOH, gives 2-imino-2,3-dihydro-4(1H)-quinazolinone (VI). VI and dilute H2SO4, refluxed a long time, give IV. The alc. mother liquor from the separation of VI, concentrated and allowed to stand, and the precipitate purified by AcOH, gives IV. The results show that with I, II, and III, an oxidation reaction takes place at the β-position and that an NH group is introduced between the α- and β-positions. Significant differences in the behavior of pyrroles and indoles in the sunlight process are discussed.

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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

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Aminoquinazolin-4(3H)-one(SMILESS: O=C1NC(N)=NC2=C1C=CC=C2,cas:20198-19-0) is researched.Quality Control of 2-Aminoquinazolin-4(3H)-one. The article 《Comparative activity of 2-thioxo-, 2-(methylthio)-, 2-(methylseleno)-, and 2-amino-4-quinazolinones toward aromatic amines》 in relation to this compound, is published in O’zbekiston Kimyo Jurnali. Let’s take a look at the latest research on this compound (cas:20198-19-0).

Reactions of title compounds I and II (R = SMe, SeMe, NH2) with arylamines gave II [R = (un)substituted phenyl] were examined The reactivity of the 2-substituents decreased in the following order: SeMe > SMe > NH2 > C:S.

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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

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Computed Properties of C8H7N3O. 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 Regioselective synthesis of pyrimido[5,4-c][2,1]benzothiazines by reactions of β-chloroaldehydes with N-C-N binucleophiles. Author is Popov, Kirill; Volovnenko, Tatyana; Turov, Alexander; Volovenko, Yulian.

Pyrimidine ring fusion at the [c] side of benzothiazines by the reaction of 4-chloro-3,4-dihydro-1H-2,1-benzothiazine-3-carboxaldehyde S,S-dioxides with amidines was described. The formation of structural isomers of reaction products was investigated, and the regioselectivity of the heterocyclization was shown. A number of novel pyrimidobenzothiazines were synthesized.

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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