1701-71-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Butyrylpyridine is used as an intermediate in the synthesis of SB 202474 (S154615), a compound structurally similar to p38 MAP kinase inhibitors such as SB 202190 (S154495) and SB 203580 (S154600). These inhibitors play a crucial role in the regulation of cellular processes, including inflammation, cell growth, and apoptosis, making them valuable targets for drug development.
4-Butyrylpyridine is used as a research tool for p38 inhibition studies, aiding in the understanding of the role of p38 MAP kinases in various diseases and the development of potential therapeutic agents targeting this pathway.

Safety Profile

A poison by intraperitoneal route. A flammable liquid. When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C9H11NO/c1-2-3-9(11)8-4-6-10-7-5-8/h4-7H,2-3H2,1H3

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 108-03-2 1-Nitropropane 
• 18085-89-7 1-(pyridin-4-yl)butan-1-ol 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 100-48-1 pyridine-4-carbonitrile 
• 106-94-5 propyl bromide 
• 74-96-4 ethyl bromide 
• 927-77-5 n-propylmagnesium bromide 

Downstream Products

• 317861-31-7 4-aminomethyl-N-[1-(4-butyl-pyridin-2-yl)-2-cyclohexyl-ethyl]-benzamide 
• 317861-29-3 5-Amino-pentanoic acid [(S)-1-(4-butyl-pyridin-2-yl)-2-cyclohexyl-ethyl]-amide 

Relevant academic research and scientific papers

4-Pyridyl carbonyl compounds as thrips lures: Effectiveness for western flower thrips in Y-tube bioassays

In a search for chemical lures to manage the cosmopolitan crop pest western flower thrips (WFT), Frankliniella occidentalis, a Y-tube olfactometer was used to screen 20 compounds, including 18 4-pyridyl compounds. Comparison of Y-tube results for New Zealand flower thrips (NZFT), Thrips obscuratus, with field trapping data for ethyl nicotinate and ethyl isonicotinate, suggested that the minimum attractive dose (MAD) of an odor compound, where significantly (p -3 μL) and ethyl nicotinate (10-2 μL): methyl isonicotinate (10-6 μL), ethyl-2-chloropyridine-4-carboxylate (10-6 μL), ethyl isonicotinate (10-4 μL) and methyl 4-pyridyl ketone (10 -5 μL). The suitability of MAD for selecting compounds for further evaluation of practical lure efficacy is discussed. Comparisons of activities within homologous series of esters and ketones showed that attractant activity decreased with chain length. 4-Formyl pyridine was an attractant at a dose of 10-5 μL, but was repellent at higher doses (10-2- 10° μL).

Rh-Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones

We present herein a novel strategy for the preparation of ketones from aldehydes and allylic boronic esters. This reaction involves the allylation of aldehydes with allylic boronic esters and the Rh-catalyzed chain-walking of homoallylic alcohols. The key to this successful development is the protodeboronation of alkenyl borylether intermediate via a tetravalent borate anion species in the presence of KHF2 and MeOH. This approach features mild reaction conditions, broad substrate scope, and excellent functional group tolerance. Mechanistic studies also supported that the tandem allylation and chain-walking process were involved.

Comparative inhibition of tetrameric carbonyl reductase activity in pig heart cytosol by alkyl 4-pyridyl ketones

Context and objective: The present study is to elucidate the comparative inhibition of tetrameric carbonyl reductase (TCBR) activity by alkyl 4-pyridyl ketones, and to characterize its substrate-binding domain. Materials and methods: The inhibitory effect

A new and highly efficient water-soluble copper complex for the oxidation of secondary 1-heteroaryl alcohols by tert-butyl hydroperoxide

The water-soluble copper complex generated in situ from CuCl2 and 2,2′-biquinoline-4,4′-dicarboxylic acid dipotassium salt (BQC), has been revealed as a highly efficient and selective catalyst for the oxidation of secondary 1-heteroaryl alcohols to the corresponding heteroaromatic ketones with aqueous tert-butyl hydroperoxide, under mild conditions. The catalytic system is compatible with different heterocycles such as pyridines, pyrroles, indoles, thiophens, furans, thiazoles, and imidazoles.

INSECT BEHAVIOUR MODIFYING COMPOUNDS

The invention provides methods for controlling thrips populations using thrips-repelling and/or thrips-attracting agents. The agents are derivatives of pyridine. The invention also provides methods of preventing or minimising damage to plants by use of the same.

The anion of 3-methyl-2-pyridin-4-yl-1,3-oxazine

n-Butyllithium at -78°C readily abstracts the methine proton from the title compound. The anion reacts efficiently with a range of electrophiles to provide 4-pyridyl ketones upon acid hydrolysis.

Structure-based design of six novel classes of nonpeptide antagonists of the bradykinin B2 receptor

Six classes of nonpeptide bradykinin antagonists were designed using a template derived from structural studies of peptide antagonists. Several compounds from each class were synthesized and assayed for binding to the human bradykinin B2 receptor. Each family showed compounds active at the level of the smallest template peptide; three classes contained compounds with K(d) 8 μM. These results provide diverse leads for a medicinal chemistry-based optimization program. (C) 2000 Elsevier Science Ltd.

HENRY CONDENSATION UNDER HIGH PRESSURE. 2. EFFECT OF AROMATIC ALDEHYDE TYPE AND PRESSURE ON THE YIELD OF ω-NITROSTYRENES AND SECONDARY PROCESSES

Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarily ω-nitrostyrenes (Ia, b) - (XXa, b) and small quantities of nitriles (Ic) - (XXc), oximes (Id) - (XXd), and ketones (Ie, f) - (XXe, f).The yields of (Ia, b) - (XXa, b) at P = 1 atm are higher for acceptor substitutents on the aromatic ring whereas at P = 10 kbar, they are higher for donor substituents.High pressures suppress the formation of (Ic-f) - (XXc-f) and the Z-isomers of (Ia, b) - (XXa, b).The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b) - (XXa, b) which are intermediates in the synthesis of the psychotropic β-phenylethylamines.

Ligand interaction of sustituted pyridines with cytochrome P-450.

A series of pyridyl ketones and alkyl pyridines was evaluated as type II ligands for cytochrome P-450. Activity as type II ligands was evaluated in terms of the lipid solubility and the pKa values of the compounds.