13210-52-1

Usage

Uses

1-(3-Amino-pyridin-4-yl)-ethanone is used as a chemical intermediate in the chemical industry for the synthesis of various chemical products. Its unique structure allows it to be a versatile building block in the creation of more complex molecules.
Used in Pharmaceutical Industry:
1-(3-Amino-pyridin-4-yl)-ethanone is used as a precursor in the development of new pharmaceuticals, potentially contributing to the synthesis of novel drugs with specific therapeutic properties.
Used in Scientific Research:
1-(3-Amino-pyridin-4-yl)-ethanone is used as a research compound in academic and industrial laboratories, where it may be studied for its chemical reactivity, potential applications in material science, or its interactions with biological systems.

InChI:InChI=1/C7H8N2O/c1-5(10)6-2-3-9-4-7(6)8/h2-4H,8H2,1H3

Upstream product

• 82791-77-3 methyl (3-pivaloylamino-4-pyridyl) ketone 
• 462-08-8 pyridin-3-ylamine 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 161871-65-4 1-(3-nitropyridin-4-yl)ethanone 

Downstream Products

• 161871-69-8 5-amino-2-bromo-4-(1-oxoethyl)pyridine 
• 13210-53-2 N-(4-acetylpyridin-3-yl)benzamide 
• 1616976-45-4 N-methyl-N-phenyl-2-[(2-phenyl-1,7-naphthyridin-4-yl)oxy]propanamide 
• 1616976-53-4 2-phenyl-1,4-dihydro-1,7-naphthyridin-4-one 

Relevant academic research and scientific papers

7-Azacinnolin-4(1H)-one preparation and NMR studies of tautomery

As part of our current investigations of nitropyridines, we hereby report the preparation of a new annulated heterocycle by C-azo coupling. Thus, the azacinnoline, pyrido[3,4-c]pyridazin-4(1H)-one (38%), was prepared from 4-acetyl-3-aminopyridine via diazotization. 1H, 13C, and 15N NMR spectroscopic investigations revealed that the azacinnoline exclusively exists in the NH-keto tautomeric form in DMSO-d6, CD 3OD, and D2O.

Preparation technology for 1-(3-amino-4-pyridyl) aceton

The invention discloses a preparation technology for 1-(3-amino-4-pyridyl) aceton. The preparation technology is characterized by comprising the following steps: (1) by taking 3-aminopyridine as a raw material, participating into amidation reaction, thereby generating 3-teramidyl pyridine; (2) generating N-(4-aceton pyridine-3-group) trimethyl acetamide through the substitution reaction of the 3-teramidyl pyridine; and (3) hydrolyzing the N-(4-aceton pyridine-3-group) trimethyl acetamide, thereby acquiring the target product 1-(3-amino-4-pyridyl) aceton. The raw materials in process route are low in cost and easily acquired, the operation condition is mild and easily controlled and the preparation technology is beneficial to the industrial application.

Synthesis of novel 1,7-naphthyridines by Friedlaender condensation of pyridine substrates

The general ability of appropriate pyridyl compounds (aldehyde or ketone) to undergo Friedlaender condensation to give different 1,7-naphthyridines has been demonstrated. 2,4-Disubstituted 1,7-naphthyridine 8 was prepared from 3-amino-4-acetylpyridine (6) and ketone 4 (82%). The Friedlaender self-condensation of pyridyl substrate 6 is reported, as well. The dimer product, 2-(3-aminopyridin-4-yl)-4-methyl-1,7-naphthyridine (7), was obtained in 97% yield. 2-Aryl-and 2,3-diaryl-1,7-naphthyridines (16-18) were prepared from 3-aminoisonicotinaldehyde (13) and arylketones 4, 14, and 15 (28-71%). The key substrates 6 and 13 are readily available via the improved pyridine nitration method. Copyright

Preparation of 4-substituted 3-amino-2-chloropyridines, synthesis of a nevirapine analogue

A new method for preparing 3-amino-2-chloropyridines with a substituent (methyl, phenyl, carboxamide, methoxycarbonyl, acetyl, benzoyl and cyano) at the 4-position has been developed. An isoquinoline analogue of the reverse transcriptase inhibitor Nevirapine has been synthesized from the 4-amino-3-chloroisoquinoline.

Synthesis, Topoisomerase I Inhibitory Activity, and in Vivo Evaluation of 11-Azacamptothecin Analogs

A series of analogs based on a novel template, 11-aza-(20S)-camptothecin, were obtained from total synthesis and tested as potential anticancer drugs in the topoisomerase I enzyme cleavable complex assay.The parent compound 11-aza-(20S)-camptothecin (8) was derived from a Friedlander condensation between the known aminopyridine derivative 3-(3-amino-4-picolylidene)-p-toluidyne and optically active tricyclic ketone 7.Compound 8 had activity approximately twice that of (20S)-camptothecin in the calf thymus topoisomerase I cleavable complex assay.Compounds were prepared wherein the 11-aza nitrogen atom was quaternized as either the corresponding N-oxide or methyl iodide.Compounds with quaternized N-11 showed improved water solubility and were equipotent to the clinically investigated camptothecin analog topotecan in the cleavable complex assay.These compounds were evaluated in vivo in nude mice bearing HT-29 human colon carcinoma xenografts.The analog 11-aza-(20S)-camptothecin 11-N-oxide was found to significantly retard tumor growth when compared to untreated controls.Finally 7,10-disubstituted 11-azacamptothecin analogs were synthesized using Pd(0) coupling reactions of 10-bromo-7-alkyl-11-aza-(20S)-camptothecins 19 and 20, which in turn were available from a Friedlander condensation of the novel bromopyridine derivatives 17a and 17b with 7.Among the 10-substituted series, a number of analogs displayed extremely high in vitro potency against topoisomerase I and improved aqueous solubility.A significant number of the compounds were found to be active in whole cell cytotoxicity assays and several were evaluated in nude mice bearing the HT-29 tumor xenografts.The most effective of these proved to be (S)-11-aza-7-ethyl-10-(aminohydroximinomethyl)camptothecin trifluoroacetic acid salt (27), a potent topoisomerase I inhibitor which demonstrated excellent efficacy in both short term and in extended in vivo assays.A comparison between in vitro enzyme data and in vivo data from nude mouse studies in other compounds in this series revealed a poor overall correlation between topoisomerase inhibition in vitro and antitumor efficacy in vivo.