Tag: M.W=100-200

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.Mackman, Richard L.; Mish, Michael; Chin, Gregory; Perry, Jason K.; Appleby, Todd; Aktoudianakis, Vangelis; Metobo, Sammy; Pyun, Peter; Niu, Congrong; Daffis, Stephane; Yu, Helen; Zheng, Jim; Villasenor, Armando G.; Zablocki, Jeff; Chamberlain, Jason; Jin, Haolun; Lee, Gary; Suekawa-Pirrone, Kimberley; Santos, Rex; Delaney, William E.; Fletcher, Simon P. researched the compound: 2-Aminoquinazolin-4(3H)-one( cas:20198-19-0 ).Name: 2-Aminoquinazolin-4(3H)-one.They published the article 《Discovery of GS-9688 (Selgantolimod) as a Potent and Selective Oral Toll-Like Receptor 8 Agonist for the Treatment of Chronic Hepatitis B》 about this compound( cas:20198-19-0 ) in Journal of Medicinal Chemistry. Keywords: CHB TLR8 agonist optimization binding HBV DNA RNA. We’ll tell you more about this compound (cas:20198-19-0).

Toll-like receptor 8 (TLR8) recognizes pathogen-derived single-stranded RNA fragments to trigger innate and adaptive immune responses. Chronic hepatitis B (CHB) is associated with a dysfunctional immune response, and therefore a selective TLR8 agonist may be an effective treatment option. Structure-based optimization of a dual TLR7/8 agonist led to the identification of the selective TLR8 clin. candidate (R)-2-((2-amino-7-fluoropyrido[3,2-d]pyrimidin-4-yl)amino)-2-methylhexan-1-ol (GS-9688, (R)-7)(I). Potent TLR8 agonism (IL-12p40 EC50 = 220 nM) and >100-fold TLR7 selectivity (IFN-α EC50 > 50μM) was observed in human peripheral blood mononuclear cells (PBMCs). The TLR8-ectodomain:(R)-7 complex confirmed TLR8 binding and a direct ligand interaction with TLR8 residue Asp545. Oral (R)-7 had good absorption and high first pass clearance in preclin. species. A reduction in viral markers was observed in HBV-infected primary human hepatocytes treated with media from PBMCs stimulated with (R)-7, supporting the clin. development of (R)-7 for the treatment of CHB.

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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

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Magyar Kemiai Folyoirat called Alkylation, transalkylation, and dealkylation of 2-amino-4-quinazolinols with amines and ammonia, Author is Lempert, Karoly; Breuer, Judit, which mentions a compound: 20198-19-0, SMILESS is O=C1NC(N)=NC2=C1C=CC=C2, Molecular C8H7N3O, Application In Synthesis of 2-Aminoquinazolin-4(3H)-one.

2-Mercapto-4-quinazolinol (1 g.) dissolved in a mixture of 10 mL. EtOH, 5 mL. H2O, and 0.33 g. KOH was treated with 0.38 mL. MeI at room temperature to yield 56.2% 2-methylthio-4-quinazolinol (I), m. 210-13°. Refluxing 1.35 g. I with 3 mL. morpholine, 1.05 mL. AcOH, and 15 mL. BuOH 45 h. gave 75% 2-morpholino-4-quinazolinol (II), m. 236-8° (BuOH). The 2-benzylamino-(III), 2-butylamino (IV), 2-amino (V) (40 h. at 120° in a sealed tube), 2-diethylaminoethylamino, and 2-anilino (VI) analogs were prepared similarly. Heating a mixture of 0.1 g. V, 1.5 mL. BuNH2, 0.42 mL. AcOH, and 10 mL. BuOH in a sealed tube at 140° 100 h. and steam distilling the product gave 40% IV, m. 184-6°. Heating a mixture of 0.7 g. III, 0.39 g. AcONH4, and 10 mL. absolute EtOH containing 0.2 g. NH3 at 140° in a sealed tube 120 h. gave 62.5% V, m. 306-8° (4:1 EtOH-HCONMe2). A mixture of 0.5 g. II, 0.33 mL. AcOH, 1.03 mL. BuNH2, and 10 mL. BuOH heated at 140° in a sealed tube 100 h. and the residue steam distilled gave 84% IV. A mixture of 0.62 g. VI, 1.43 mL. PhCH2NH2, 0.35 mL. AcOH, and 10 mL. BuOH was refluxed 90 h. and steam distilled to yield 61% III.

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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

Formula: C6H5N5. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about Ferromagnetic interaction and slow magnetic relaxation in a Co3 cluster-based three-dimensional framework. Author is Wu, Bing-Yan; Yang, Chen-I.; Nakano, Motohiro; Lee, Gene-Hsiang.

A Co3 cluster-based 3D framework, [Co3(4-ptz)4(N3)2(H2O)2].4DMF (I; 4-Hptz = 4-(1H-tetrazol-5-yl)pyridine), was prepared and its crystal and mol. structure was determined Crystal data: orthorhombic, Pnnm, a = 12.2143(13), b = 13.8051(15), c = 16.5293(17) Å, Z = 2, 2257 independent reflections, 176 refined parameters, R1 = 10390.0, wR2 = 0.2530 [I > 2σ(I)]. Compound I exhibits ferromagnetic interactions and slow-magnetic relaxation behavior.

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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

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 14389-12-9, is researched, SMILESS is C1(C2=NN=NN2)=CC=NC=C1, Molecular C6H5N5Journal, Polyhedron called Zeolite and sulfated zirconia as catalysts for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide, Author is Teimouri, Abbas; Chermahini, Alireza Najafi, the main research direction is nitrile sodium azide cycloaddition zeolite sulfated zirconia catalyst; tetrazole green preparation.Category: chiral-nitrogen-ligands.

The [2+3] cycloaddition between various nitriles and sodium azide proceeded smoothly in the presence of zeolite and sulfated zirconia as effective catalysts, in water and DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeded through the in situ formation of catalyst azide species, followed by a successive [2+3] cycloaddition with the nitriles. This method has the advantages of high yields, simple methodol. and easy work-up. The catalyst can be recovered by simple filtration and reused with good yields.

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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

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 14389-12-9, is researched, Molecular C6H5N5, about Solvent-dependent luminescent Cu(I) framework based on 5-(4-pyridyl)tetrazole, the main research direction is crystal structure copper pyridyltetrazole coordination polymer; copper pyridyltetrazole coordination polymer ethanol solvate preparation; luminescence copper pyridyltetrazole coordination polymer solvent dependent; solvent copper pyridyltetrazole coordination polymer fluorescence; framework polymer copper pyridyltetrazole nitrogen surface adsorption pore size.Computed Properties of C6H5N5.

A new Cu(I) coordination compound, Cu4(L)4·2EtOH (1), has been obtained from the solvothermal reaction of CuBr, 5-(4-pyridyl) tetrazole (HL), EtOH and NH3·H2O. The structure determination revealed that 1 has a 2D network, where each Cu(I) atom adopts a trigonal coordination mode. The 2D networks stacked in an ABAB sequence through the π-π interaction to form a 3D supramol. framework, giving a 1D channel along the b-axis. The TGA and powder XRD measurements revealed that the framework is stable after removal of the guest mols. Gas (N2) adsorption measurement was carried out for the framework and showed that N2 mols. cannot diffuse into the micropore and that only surface adsorption occurred. The photoluminescent study showed that compound 1 displays an interesting solvent-dependent luminescence.

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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

Product Details of 14389-12-9. 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: 5-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about Click chemistry for the synthesis of 5-substituted 1H-tetrazoles from boron-azides and nitriles. Author is Yao, Yue-Wei; Zhou, Yi; Lin, Bao-Ping; Yao, Cheng.

A novel and metal free catalysis of synthesizing 5-substituted 1H-tetrazoles through 1,3-dipolar cycloaddition of boron-azides and nitriles is reported with broad substrate scope and excellent yields.

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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 Three AgI, CuI and CdII coordination polymers based on the new asymmetrical ligand 2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole: syntheses, characterization and emission properties, published in 2019-12-01, which mentions a compound: 14389-12-9, Name is 5-(4-Pyridyl)-1H-tetrazole, Molecular C6H5N5, Application of 14389-12-9.

The new asym. organic ligand 2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole (L, C17H13N5O), containing pyridine and imidazole terminal groups, as well as potential oxdiazole coordination sites, was designed and synthesized. The coordination chem. of L with soft AgI, CuI and CdII metal ions was investigated and three new coordination polymers (CPs), namely, catena-poly[[silver(I)-μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole] hexafluoridophosphate], {[Ag(L)]PF6}n, catena-poly[[copper(I)-di-μ-iodido-copper(I)-bis(μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole)] 1,4-dioxane monosolvate], {[Cu2I2(L)2]·C4H8O2}n, and catena-poly[[[dinitratocopper(II)]-bis(μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole)]-methanol-water (1/1/0.65)], {[Cd(L)2(NO3)2]·2CH4O·0.65H2O}n, were obtained. The exptl. results show that ligand L coordinates easily with linear AgI, tetrahedral CuI and octahedral CdII metal atoms to form one-dimensional polymeric structures. The intermediate oxadiazole ring does not participate in the coordination interactions with the metal ions. In all three CPs, weak π-π interactions between the nearly coplanar pyridine, oxadiazole and benzene rings play an important role in the packing of the polymeric chains.

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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

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

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 Quinazolines. VIII. Reaction of 2-aminoquinazol-4-one with unsaturated acids.Category: chiral-nitrogen-ligands.

Pyrimidoquinazolinediones I (R = H, Me, Ph, R1 = R2 = H; R = R1 = H, R2 = Me; R = R1 = Me, R2 = H) were obtained in 61-90% yields by cyclocondensation of RR1C:CR2CO2H with 2-amino-4(3H)-quinazolinone 2 h at 160-5°.

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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