40522-46-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Heptylquinoline-4(1H)-one is used as a pharmaceutical compound for its potential therapeutic applications. Its lipophilic properties allow it to interact with cellular membranes and other biological targets, making it a candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 2-Heptylquinoline-4(1H)-one serves as a valuable compound for studying the structure-activity relationships of quinolone derivatives. Its unique structure provides insights into the design and synthesis of novel quinolone-based molecules with potential applications in various industries.
Used in Material Science:
The lipophilic nature of 2-Heptylquinoline-4(1H)-one also makes it a candidate for use in material science, particularly in the development of new materials with specific properties. Its interaction with other molecules and its solubility characteristics can be exploited to create materials with tailored properties for various applications.

Biochem/physiol Actions

HHQ stimulates vesicle formation but not as much as PQS.

Upstream product

• 13195-66-9 ethyl 3-oxodecanoate 
• 62-53-3 aniline 
• 22348-96-5 methyl 3-oxodecanoate 
• 3452-09-3 1-nonyne 
• 6630-33-7 ortho-bromobenzaldehyde 
• 529-23-7 o-aminobenzaldehyde 
• 16714-25-3 2-azidobenzaldehyde 
• 16662-90-1 3-(2-aminophenyl)-3-oxopropanoic acid 
• 1264-52-4 octanoyl coenzyme A 
• 103576-44-9 2,2-dimethyl-5-octanoyl-1,3-dioxane-4,6-dione 
• 13283-92-6 β-ketodecanoic acid 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 42405-64-1 2-heptyl-quinolin-4-ol hydrochloride 
• 66696-81-9 5-(1-hydroxyoctylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 

Downstream Products

• 80554-59-2 2-heptyl-4-methoxyquinoline 
• 80554-58-1 schinifoline 
• 402718-53-0 3-formyl-2-heptyl-4-quinolone 
• 113550-21-3 4-(benzyloxy)-2-heptylquinoline 

Relevant academic research and scientific papers

Synthesis of 2-heptyl-1-hydroxy-4(1H)-quinolone - Unexpected rearrangement of 4-(alkoxycarbonyloxy)quinoline N-oxides to 1-(alkoxycarbonyloxy)-4(1H)- quinolones

2-Heptyl-4(1H)-quinolone was converted in two steps into the 4-ethoxycarbonyloxy-, 4-(tert-butoxycarbonyloxy)-, and 4- (dimethylaminocarbonyloxy)quinoline N-oxides. While the former two rearranged to the corresponding 1-(alkoxycarbonyloxy)-4(1H)-quinolones at room temperature, the latter was stable, even at 140°C in refluxing xylenes. Basic hydrolysis of these compounds furnished 2-heptyl-1-hydroxy-4(1H)-quinolone. Georg Thieme Verlag Stuttgart.

Discovery of antagonists of PqsR, a key player in 2-alkyl-4-quinolone- dependent quorum sensing in Pseudomonas aeruginosa

The pqs quorum sensing communication system of Pseudomonas aeruginosa controls virulence factor production and is involved in biofilm formation, therefore playing an important role for pathogenicity. In order to attenuate P. aeruginosa pathogenicity, we followed a ligand-based drug design approach and synthesized a series of compounds targeting PqsR, the receptor of the pqs system. In vitro evaluation using a reporter gene assay in Escherichia coli led to the discovery of the first competitive PqsR antagonists, which are highly potent (Kd,app of compound 20: 7 nM). These antagonists are able to reduce the production of the virulence factor pyocyanin in P. aeruginosa. Our finding offers insights into the ligand-receptor interaction of PqsR and provides a promising starting point for further drug design.

QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF

The present invention relates to quinolones of formula (I) and process for its preparation by amine insertion into aryl-ynones thereof. [Formula I] The invention further relates to the process to obtain the natural products such as: graveoline, graveolinine, pseudane IV, pseudane VII, pseudane VIII and pseudane XII. The invention also describes the process for the total synthesis of waltherione F in concise approach from the quinolone synthesized. [Formula II]

Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F

An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

Selectively methylated analogues of naturally occurring 2-heptyl-4(1H)-quinolones, which are alkaloids common within the Rutaceae family and moreover are associated with quorum sensing and virulence of the human pathogen Pseudomonas aeruginosa, have been prepared. While the synthesis by direct methylation was successful for 3-unsubstituted 2-heptyl-4(1H)-quinolones, methylated derivatives of the Pseudomonas quinolone signal (PQS) were synthesized from 3-iodinated quinolones by methylation and iodine–metal exchange/oxidation. The two N- and O-methylated derivatives of the PQS showed strong quorum sensing activity comparable to that of PQS itself. Staphylococcus aureus, another pathogenic bacterium often co-occurring with P. aeruginosa especially in the lung of cystic fibrosis patients, was inhibited in planktonic growth and cellular respiration by the 4-O-methylated derivatives of HQNO and HHQ, respectively.

Gold-catalyzed cyclization of 1-(2′-Azidoaryl) propynols: Synthesis of polysubstituted 4-quinolones

An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-Azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-Activated triple bonds in a 6-endo-dig manner and subsequent gold-Assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.

COMPOUND FOR USE AGAINST PATHOGENIC NEISSERIA AND HAEMOPHILUS SPECIES AND MORAXELLA CATARRHALIS

The present invention relates to a compound, which can be used in the prevention and treatment of infections with pathogenic Neisseria species, in particular N. gonorrhoeae and N. meningitidis (the gonococcus and the meningococcus, respectively), and other pathogenic bacteria (e.g. Haemophilus species or Moraxella catarrhalis ), and which can be used for disinfecting a substrate from said bacteria. Moreover, the present invention relates to a corresponding pharmaceutical composition comprising said compound.

PqsL uses reduced flavin to produce 2-hydroxylaminobenzoylacetate, a preferred PqsBC substrate in alkyl quinolone biosynthesis in Pseudomonas aeruginosa

Alkyl hydroxyquinoline N-oxides (AQNOs) are antibiotic compounds produced by the opportunistic bacterial pathogen Pseudomonas aeruginosa. They are products of the alkyl quinolone (AQ) biosynthetic pathway, which also generates the quorum-sensing molecules 2-heptyl-4(1H)-quinolone (HHQ) and 2-heptyl-3-hydroxy-4(1H)-quinolone (PQS). Although the enzymatic synthesis of HHQ and PQS had been elucidated, the route by which AQNOs are synthesized remained elusive. Here, we report on PqsL, the key enzyme for AQNO production, which structurally resembles class A flavoprotein monooxygenases such as p-hydroxybenzoate 3-hydroxylase (pHBH) and 3-hydroxybenzoate 6-hydroxylase. However, we found that unlike related enzymes, PqsL hydroxylates a primary aromatic amine group, and it does not use NAD(P)H as cosubstrate, but unexpectedly required reduced flavin as electron donor. We also observed that PqsL is active toward 2-aminobenzoylacetate (2-ABA), the central intermediate of the AQ pathway, and forms the unstable compound 2-hydroxylaminobenzoylacetate, which was preferred over 2-ABA as substrate of the downstream enzyme PqsBC. In vitro reconstitution of the PqsL/PqsBC reaction was feasible by using the FAD reductase HpaC, and we noted that the AQ:AQNO ratio is increased in an hpaC-deletion mutant of P. aeruginosa PAO1 compared with the ratio in the WT strain. A structural comparison with pHBH, the model enzyme of class A flavoprotein monooxygenases, revealed that structural features associated with NAD(P)H binding are missing in PqsL. Our study completes the AQNO biosynthetic pathway in P. aeruginosa, indicating that PqsL produces the unstable product 2-hydroxylaminobenzoylacetate from 2-ABA and depends on free reduced flavin as electron donor instead of NAD(P)H.

Quinolones modulate ghrelin receptor signaling: Potential for a novel small molecule scaffold in the treatment of cachexia

Cachexia is a metabolic wasting disorder characterized by progressive weight loss, muscle atrophy, fatigue, weakness, and appetite loss. Cachexia is associated with almost all major chronic illnesses including cancer, heart failure, obstructive pulmonary disease, and kidney disease and significantly impedes treatment outcome and therapy tolerance, reducing physical function and increasing mortality. Current cachexia treatments are limited and new pharmacological strategies are needed. Agonists for the growth hormone secretagogue (GHS-R1a), or ghrelin receptor, prospectively regulate the central regulation of appetite and growth hormone secretion, and therefore have tremendous potential as cachexia therapeutics. Non-peptide GHS-R1a agonists are of particular interest, especially given the high gastrointestinal degradation of peptide-based structures, including that of the endogenous ligand, ghrelin, which has a half-life of only 30 min. However, few compounds have been reported in the literature as non-peptide GHS-R1a agonists. In this paper, we investigate the in vitro potential of quinolone compounds to modulate the GHS-R1a in both transfected human cells and mouse hypothalamic cells. These chemically synthesized compounds demonstrate a promising potential as GHS-R1a agonists, shown by an increased intracellular calcium influx. Further studies are now warranted to substantiate and exploit the potential of these novel quinolone-based compounds as orexigenic therapeutics in conditions of cachexia and other metabolic and eating disorders.

An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus

The pathogen Pseudomonas aeruginosa produces over 50 different quinolones, 16 of which belong to the class of 2-alkyl-4-quinolone N-oxides (AQNOs) with various chain lengths and degrees of saturation. We present the first synthesis of a previously proposed unsaturated compound that is confirmed to be present in culture extracts of P. aeruginosa, and its structure is shown to be trans-Δ1-2-(non-1-enyl)-4-quinolone N-oxide. This compound is the most active agent against S. aureus, including MRSA strains, by more than one order of magnitude whereas its cis isomer is inactive. At lower concentrations, the compound induces small-colony variants of S. aureus, reduces the virulence by inhibiting hemolysis, and inhibits nitrate reductase activity under anaerobic conditions. These studies suggest that this unsaturated AQNO is one of the major agents that are used by P. aeruginosa to modulate competing bacterial species.