Category: 13958-99-1

Kumpan, Katerina published the artcileStructure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases, HPLC of Formula: 13958-99-1, the main research area is tankyrase inhibitor anticancer antitumor agent pyrimidine naphthyridine preparation; 7-Aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one; Crystal structure; Naphthyridinone; TNKS; Tankyrase.

The tankyrase enzymes [i.e., poly(ADP-ribose) polymerase enzymes] are members of the PARP superfamily. They poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrase enzymes (TRF1, NuMA and axins) are involved in replication of cancer cells. Thus, inhibitors of the tankyrase enzymes may have anticancer activity (antitumor activity). Using a structure-based drug design and by analogy with known 3-aryl-1-isoquinolinone and 2-aryl-4-quinazolinone inhibitors, series of (aryl)naphthyridinone derivatives, (aryl)pyridopyrimidinone derivatives and their tetrahydro-derivatives were synthesized and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-one derivatives, 3-aryl-2,6-naphthyridin-1-one derivatives and 3-aryl-2,7-naphthyridin-1-ones were prepared by an acid-catalyzed cyclization of the corresponding [(aryl)ethynyl]pyridinecarbonitrile derivatives or reaction of (bromo)pyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. A copper-catalyzed reaction of benzamidines with (bromo)pyridinecarboxylic acids furnished 2-(aryl)pyrido[2,3-d]pyrimidin-4-ones. A condensation of benzamidines with Me 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogs of the known inhibitor XAV939. Introduction of a ring-nitrogen in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogs (structure-activity relationship). However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrase enzymes, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 vs. tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.

Bioorganic & Medicinal Chemistry published new progress about Alkylation. 13958-99-1 belongs to class amides-buliding-blocks, name is 3-Bromoisonicotinamide, and the molecular formula is C6H5BrN2O, HPLC of Formula: 13958-99-1.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Slowinski, Franck published the artcileExpeditive Access to 2-Substituted 4H-Pyrido[1,3]oxazin-4-ones via an Intramolecular O-Arylation, COA of Formula: C6H5BrN2O, the main research area is aroyl nicotinamide intramol arylation heterocyclization microwave irradiation; pyrido oxazinone preparation mol crystal structure; microwave irradiation intramol arylation heterocyclization mediator.

Unreported 2-substituted 4H-pyrido[e][1,3]oxazin-4-ones, e.g., I (X-rays single crystal structure shown), are synthesized via an unprecedented intramol. O-arylation of N-aroyl- and N-heteroaroyl-(iso)nicotinamides under microwave irradiations, in good to excellent yields. The broad applicability was demonstrated by 24 examples with a variety of substituents at the 2-position of the final compounds and 3 possible positions for the nitrogen atom of the pyridine ring. In addition, transformation of one of these compounds into 2-hydroxypyridyl-substituted 1,2,4-triazole and 1,2,4-oxazinone was realized. This approach opens a rapid access to a new bicyclic heteroaromatic chem. series with high potential in medicinal chem.

Organic Letters published new progress about Arylation (intramol., O-). 13958-99-1 belongs to class amides-buliding-blocks, name is 3-Bromoisonicotinamide, and the molecular formula is C6H5BrN2O, COA of Formula: C6H5BrN2O.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reitz, David B. published the artcile1H-1,2,4-triazole angiotensin II receptor antagonists: N-phenylpyridinylmethyl and N-pyridinylphenylmethyl analogs of SC-50560, Application of 3-Bromoisonicotinamide, the main research area is triazole angiotensin receptor antagonist preparation structure; phenylpyridinylmethyl triazole angiotensin receptor antagonist preparation; pyridinylphenylmethyl triazole angiotensin receptor antagonist preparation; antihypertensive triazole angiotensin receptor antagonist structure.

Substituting nitrogen for carbon in the four pyridinylphenylmethyl analogs of SC-50560 proved to be detrimental to the angiotensin II receptor-antagonist activity; however, the two phenylpyridinylmethyl analogs of SC-50560 retained their potencies. Of these two analogs, SC-52458 was found to have superior in vivo properties in the rat angiotensin II pressor assay.

Bioorganic & Medicinal Chemistry Letters published new progress about Angiotensin receptors Role: BIOL (Biological Study). 13958-99-1 belongs to class amides-buliding-blocks, name is 3-Bromoisonicotinamide, and the molecular formula is C6H5BrN2O, Application of 3-Bromoisonicotinamide.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Le Falher, Laetitia published the artcilePreparation of Halogen-Containing 4H-Pyrido[e][1,3]oxazin-4-ones and Their Transformation into 2-Hydroxypyridinyl-Substituted 1,2,4-Oxadiazoles and 1,2,4-Triazoles, SDS of cas: 13958-99-1, the main research area is pyridylimide sodium salt intramol arylation; pyridooxazinone halo preparation microwave irradiation hydroxylamine cyclocondensation hydrazine; oxadiazole hydroxypyridyl triazole preparation regioselective.

A complete study on the preparation of original halogen-containing 4H-pyrido[e][1,3]oxazin-4-ones I (R = C6H5, 2-H3CC6H4, 4-ClC6H4, 4-H3COC6H4, etc.; R1 = H, Br) and their transformation into 2-hydroxypyridinyl-substituted 1,2,4-oxadiazoles II (W = O) and 1,2,4-triazoles II (W = NH, NC6H5) is presented. The efficiency of the intramol. O-arylation of pyridyl-imide sodium salts e.g., III was studied on three series of compounds, with different fluoro-, chloro-, and bromophenyl substituents at the C-2 position. The final halogenated compounds I are of interest as new synthons for future functionalization. A rapid, and complementary access to 2-substituted 4H-benzo[e][1,3]oxazinones IV (R2 = 2-bromo-4-pyridyl, phenyl) were discovered. Finally, the one-step transformation of some of these pyrido-oxazinones I into the corresponding II was explored, and the regioselectivity of the reaction was proved by X-ray crystallog.

European Journal of Organic Chemistry published new progress about Acid halides Role: RCT (Reactant), RACT (Reactant or Reagent). 13958-99-1 belongs to class amides-buliding-blocks, name is 3-Bromoisonicotinamide, and the molecular formula is C6H5BrN2O, SDS of cas: 13958-99-1.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Yu, Xiaoqiang published the artcileSynthesis of Quinazolin-4(3H)-ones via the Reaction of 2-Halobenzamides with Nitriles, COA of Formula: C6H5BrN2O, the main research area is quinazolinone preparation; halobenzamide nitrile nucleophilic addition aromatic substitution copper acetate catalyst.

This paper described a convenient method to synthesize quinazolin-4(3H)-ones, e.g. I, from simple and readily available 2-halobenzamides and nitriles. The Lewis acid Cu-catalyzed nucleophilic addition of 2-halobenzamide to nitriles followed by SNAr reaction proceeded smoothly in the presence of t-BuOK as a base to produce the quinazolinone derivatives

Journal of Organic Chemistry published new progress about Benzamides Role: RCT (Reactant), RACT (Reactant or Reagent) (halo). 13958-99-1 belongs to class amides-buliding-blocks, name is 3-Bromoisonicotinamide, and the molecular formula is C6H5BrN2O, COA of Formula: C6H5BrN2O.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics