Tag: M.W:100-200

Hamada, Yoshiki; Takeuchi, Isao published the article 《Syntheses of nitrogen containing compounds. XVIII. Syntheses of naphthyridines by improved one-step process》. Keywords: naphthyridine amino pyridine.They researched the compound: 4-Methyl-1,8-naphthyridine( cas:1569-17-1 ).Related Products of 1569-17-1. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1569-17-1) here.

1,5-Naphthyridine and 1,8-naphthyridines were synthesized by the reaction of 3- or 2-aminopyridines with glycerol, in the presence of Na m-nitrobenzenesulfonate, boric acid, and ferrous sulfate, in sulfuric acid. Application of the same method to 3- and 4-aminoquinolines afforded 4,6-phenanthroline and 5-methyl-1,6-phenanthroline. 1,6-Naphthyridine was obtained in a high yield by the reaction of 4-aminopyridine and glycerol, in the presence of sulfonating mixture, boric acid, and ferrous sulfate.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

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 Conference, Applied Biocatalysis called Chemo-enzymatic synthesis of (S)-1,2,3,4-tetrahydroisoquinoline carboxylic acids using D-amino acid oxidase, Author is Ju, Shuyun; Qian, Mingxin; Xu, Gang; Yang, Lirong; Wu, Jianping, which mentions a compound: 91523-50-1, SMILESS is OC(=O)C1NCCC2=C1C=CC(O)=C2, Molecular C10H11NO3, Quality Control of 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid.

In this context, an (R)-selective D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was found through genome mining. This enzyme was applied for the kinetic resolution of a range of racemic 1- and 3-carboxyl substituted THIQs with different substitutions on the aryl rings. Preparative-scale deracemization of racemic 1,2,3,4- tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid was further demonstrated.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, is researched, Molecular C10H11NO3, CAS is 91523-50-1, about Chemo-enzymatic synthesis of (S)-1,2,3,4-tetrahydroisoquinoline carboxylic acids using D-amino acid oxidase, the main research direction is tetrahydroisoquinoline carboxylic acid FsDAAO catalyst enantioselective enzymic resolution; chiral tetrahydroisoquinoline carboxylic acid preparation.Application In Synthesis of 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid.

In this context, an (R)-selective D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was found through genome mining. This enzyme was applied for the kinetic resolution of a range of racemic 1- and 3-carboxyl substituted THIQs with different substitutions on the aryl rings. Preparative-scale deracemization of racemic 1,2,3,4- tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid was further demonstrated.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Kinetics of quaternization of some naphthyridines and methylnaphthyridines, the main research direction is quaternization kinetics heterocycle; kinetics quaternization heterocycle; heterocycle quaternization kinetics; naphthyridines quaternization kinetics; quinoline quaternization kinetics; isoquinoline quaternization kinetics.SDS of cas: 1569-17-1.

The 2nd order rate constants for the reaction of MeI with some naphthyridines and methylnaphthridines in MeCN were determined by a conductimetric method. The following results were obtained at 24.8° (compound, and rate constant × 10-4 l./mole/sec. given): quinoline, 0.517; isoquinoline, 4.23; 1,5-naphthyridine, 0.232; 1,6-naphthyridine, 1.66; 1,8-naphthyridine, 4.25; 2-methyl-1,8-naphthyridine, 3.61; 3-methyl-1,8-naphthyridine, 5.74; 4-methyl-1,8-naphthyridine, 7.26; and 2,7-dimethyl-1,8-naphthyridine, 1.85. The rate constants are used to deduce the quaternization kinetics of the reactions.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol( cas:16710-11-5 ) is researched.Application In Synthesis of 4-Methyl-6-(methylthio)pyrimidin-2-ol.Felczak, Krzysztof; Drabikowska, Alicja; Vilpo, Juhani A.; Kulikowski, Tadeusz; Shugar, David published the article 《6-Substituted and 5,6-Disubstituted Derivatives of Uridine: Stereoselective Synthesis, Interaction with Uridine Phosphorylase, and in Vitro Antitumor Activity》 about this compound( cas:16710-11-5 ) in Journal of Medicinal Chemistry. Keywords: structure activity nucleoside antitumor phosphorylase substrate; uridine preparation antitumor cytotoxicity phosphorylase substrate; nucleoside preparation antitumor cytotoxicity phosphorylase substrate. Let’s learn more about this compound (cas:16710-11-5).

Stereoselective procedures are described for the synthesis of 6-alkyluridines, e.g. I (R = F, OH, R1 = H, F), by Lewis acid-catalyzed condensation of trimethylsilylated 6-alkyl-4-alkylthiouracils with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (ABR) and trimethylsilylated 6-alkyl-3-benzyluracils with ABR. For all the foregoing nucleosides in the fixed syn conformation about the glycosyl bond, 1H NMR spectroscopy further demonstrated that the pentose rings exist predominantly in the conformation N (3′-endo). Most of the nucleosides were weak substrates of Escherichia coli pyrimidine nucleoside phosphorylase. The 5-fluoro-6-substituted uridines were the poorest substrates. Cytotoxicities of the nucleosides were examined vs the human tumor cell lines MOLT-3, U-937, K-562, and IM-9, as well as PHA-stimulated human lymphocytes. Two of the analogs, 5-fluoro-6-(fluoromethyl)uridine and 5-fluoro-6-(hydroxymethyl)uridine, exhibited cytotoxicities comparable to that of 5-fluorouracil.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol(SMILESS: CSC1=NC(O)=NC(C)=C1,cas:16710-11-5) is researched.Computed Properties of C5H3IO2. The article 《6-Substituted and 5,6-Disubstituted Derivatives of Uridine: Stereoselective Synthesis, Interaction with Uridine Phosphorylase, and in Vitro Antitumor Activity》 in relation to this compound, is published in Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:16710-11-5).

Stereoselective procedures are described for the synthesis of 6-alkyluridines, e.g. I (R = F, OH, R1 = H, F), by Lewis acid-catalyzed condensation of trimethylsilylated 6-alkyl-4-alkylthiouracils with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (ABR) and trimethylsilylated 6-alkyl-3-benzyluracils with ABR. For all the foregoing nucleosides in the fixed syn conformation about the glycosyl bond, 1H NMR spectroscopy further demonstrated that the pentose rings exist predominantly in the conformation N (3′-endo). Most of the nucleosides were weak substrates of Escherichia coli pyrimidine nucleoside phosphorylase. The 5-fluoro-6-substituted uridines were the poorest substrates. Cytotoxicities of the nucleosides were examined vs the human tumor cell lines MOLT-3, U-937, K-562, and IM-9, as well as PHA-stimulated human lymphocytes. Two of the analogs, 5-fluoro-6-(fluoromethyl)uridine and 5-fluoro-6-(hydroxymethyl)uridine, exhibited cytotoxicities comparable to that of 5-fluorouracil.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

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, Journal of the American Chemical Society called Thiouracils. 2. Tautomerism and infrared spectra of thiouracils. Matrix-isolation and ab initio studies, Author is Rostkowska, H.; Szczepaniak, K.; Nowak, M. J.; Leszczynski, J.; KuBulat, K.; Person, Willis B., which mentions a compound: 16710-11-5, SMILESS is CSC1=NC(O)=NC(C)=C1, Molecular C6H8N2OS, Formula: C6H8N2OS.

A study of the IR spectra of thiouracils isolated in low-temperature inert matrixes demonstrated that 2- and 4-thiouracils together with their N1- and N3-methylated derivatives as well as 2,4-dithiouracil exist under these conditions only in the oxothione or dithione tautomeric forms. In contrast, S2- and S4-methylated derivatives exist as a mixture of hydroxy and oxo tautomeric forms under the same conditions. The ratio of concentrations of the oxo and hydroxy tautomers and the free energy differences, were exptl. estimated, from the ratio of the absorbances of the NH and OH stretches. An assignment of the observed IR bands, particularly those related to the C:S stretching vibrations, is proposed on the basis of the comparison of the matrix spectra with those calculated by using ab initio methods (3-21G* basis set).

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Synthetic Route of C6H8N2OS. 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: 4-Methyl-6-(methylthio)pyrimidin-2-ol, is researched, Molecular C6H8N2OS, CAS is 16710-11-5, about Pyrimidine nucleosides. I. Synthesis of 6-methylcytidine, 6-methyluridine, and related 6-methylpyrimidine nucleosides. Author is Winkley, Michael W.; Robins, Roland K..

Synthesis of 6-methylprimidine nucleosides was realized. 6-Methylcytidine (I) and 6-methyl-2′-deoxycytidine were prepared by direct utilization of 6-methylcytosine (II) via silylation and subsequent treatment with the appropriate per-O-acetylglycosyl halide in MeCN. Conversion of I into 6-methyluridine was achieved in 65% yield. This direct glycosylation procedure applied to 6-methyluracil gave 6-methyl-3-(β-D-ribofuranosyl)uracil as the major product. Utilization of this general method resulted in preparation of 5,6-dimethyluridine. A new route to the synthesis of II is reported. 31 references.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

HPLC of Formula: 16710-11-5. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol, is researched, Molecular C6H8N2OS, CAS is 16710-11-5, about Bis-s-triazolo[1,5-a:1′,5′-c]pyrimidine and some simple derivatives. Author is Brown, Desmond J.; Shinozuka, Kazuo.

A general synthetic route to the new tricyclic system bis-s-triazolo[1,5-a:1′,5′-c]pyrimidine is reported. Thus the parent heterocycle (I; R = R1 = H) is prepared from the key bicyclic intermediate, s-triazolo[18k-c]pyrimidin-5-ylamine, through the 5-dimethylaminomethyleneamino, 5-hydroxyaminomethyleneamino and 5-acetoxyaminomethyleneamino derivatives, followed by final cyclization. I (R = H, Me, R1 = H, Me, Ph) are prepared similarly. Structures are confirmed by NMR spectra.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Action of Methyl Iodide and of Benzyl Chloride upon 2-Oxy-4-methyl-6-methylmercaptopyrimidine》. Authors are Wheeler, Henry L.; Mcfarland, David F..The article about the compound:4-Methyl-6-(methylthio)pyrimidin-2-olcas:16710-11-5,SMILESS:CSC1=NC(O)=NC(C)=C1).Computed Properties of C6H8N2OS. Through the article, more information about this compound (cas:16710-11-5) is conveyed.

2-Methylmercapto-4-methyl-6-chloropyrimidine, C6H7N2ClS, was made from the oxypyrimidine and PCl5, b32-5 147°, m. 39-40°. This with KSH gave 2-methylmercapto-4-methyl-6-thiopyrimidine, C6H8N2S2, m. 214°, heating at 215-23° gave 2,6-dithio-4-methyluracil. Boiling the mercapto compound with HCl formed 6-thio-4-methyluracil, C6H6ON2S, prisms decompose above 250°, which with NaOH and MeI gives 2-oxy-4-methyl-6-methylmercaptopyrimidine, C6H8ON2S, needles, m. 174-5°. The mercaptopyrimidine with NaOH and PhCH2Cl yielded after treatment with HCl a mixture of 1-benzyl and 3-benzyluracil. The methylation of 2-oxy-4-methyl-6-methylmercaptopyrimidine gave 2-oxy-3,4-dimethyl-6-methylmercaptopyrimidine, C7H10ON2S, m. 170-1° and probably the 1,4-dimethyl product not isolated. 2-Oxy-4-methyl-6-o-nitrobenzylmercaptopyrimidine, m. 205°. 2-Oxy-4-methyl-6-m-dinitrophenylmercaptopyrimidine, m. 208°.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem