55792-43-3

Usage

InChI:InChI=1/C12H19NO/c1-2-3-4-5-9-14-12-8-6-7-11(13)10-12/h6-8,10H,2-5,9,13H2,1H3

Upstream product

• 111-25-1 1-bromo-hexane 
• 591-27-5 m-Hydroxyaniline 
• 621-42-1 meta-hydroxyacetanilide 
• 554-84-7 meta-nitrophenol 
• 55792-57-9 acetic acid-(3-hexyloxy-anilide) 

Downstream Products

• 65972-33-0 1-(3-Hexyloxy-phenyl)-6,6-dimethyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine; hydrochloride 
• 744221-61-2 3-(3-hexyloxy-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1442656-61-2 C₁₄H₁₉N₃O₂ 
• 32223-69-1 3-n-Hexyloxyphenylisocyanat 

Relevant academic research and scientific papers

Dibasic derivatives of phenylcarbamic acid against mycobacterial strains: Old drugs and new tricks?

In order to provide a more detailed view on the structure–antimycobacterial activity relationship (SAR) of phenylcarbamic acid derivatives containing two centers of protonation,1-[2-[({[2-/3-(alkoxy)phenyl]amino}carbonyl)oxy]-3-(dipropylammonio)propyl]pyrrolidinium oxalates (1a–d)/dichlorides (1e–h) as wellas1-[2-[({[2-/3-(alkoxy)phenyl]amino}carbonyl)oxy]-3-(di-propylammonio)propyl]azepanium oxalates (1i–l)/dichlorides (1m–p; alkoxy = butoxy to heptyloxy) were physicochemically characterized by estimation of their surface tension (γ; Traube’s stalagmometric method), electronic features (log ε; UV/Vis spectrophotometry) and lipophilic properties (log kw; isocratic RP-HPLC) as well. The experimental log kw dataset was studied together with computational logarithms of partition coefficients (log P) generated by various methods based mainly on atomic or combined atomic and fragmental principles. Similarities and differences between the experimental and in silico lipophilicity descriptors were analyzed by unscaled principal component analysis (PCA). The in vitro activity of compounds 1a–p was inspected against Mycobacterium tuberculosis CNCTC My 331/88 (identical with H37Rv and ATCC 2794, respectively), M. tuberculosis H37Ra ATCC 25177, M. kansasii CNCTC My 235/80 (identical with ATCC 12478), the M. kansasii 6509/96 clinical isolate, M. kansasii DSM 44162, M. avium CNCTC My 330/80 (identical with ATCC 25291), M. smegmatis ATCC 700084 and M. marinum CAMP 5644, respectively. In vitro susceptibility of the mycobacteria to reference drugs isoniazid, ethambutol, ofloxacin or ciprofloxacin was tested as well. A very unique aspect of the research was that many compounds from the set 1a–p were highly efficient almost against all tested mycobacteria. The most promising derivatives showed MIC values varied from 1.9 μM to 8 μM, which were lower compared to those of used standards, especially if concerning ability to fight M. tuberculosis H37Ra ATCC 25177, M. kansasii DSM 44162 or M. avium CNCTC My 330/80. Current in vitro biological assays and systematic SAR studies based on PCA approach as well as fitting procedures, which were supported by relevant statistical descriptors, proved that the compounds 1a–p represented a very promising molecular framework for development of ‘non-traditional’ but effective antimycobacterial agents.

[Cp?RhCl2]2-catalyzed alkyne hydroamination to 1,2-dihydroquinolines

[Cp?RhCl2]2 catalyzes the formation of 1,2-dihydroquinolines from the reaction of two terminal alkynes and an aniline. This reaction is believed to proceed via an alkyne hydroamination followed by an alkyne insertion.

AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY

Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

Design, synthesis, and anticonvulsant activity evaluation of 4-(3-Alkoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-ones

A series of 4-(3-alkoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-ones were synthesized using the appropriate synthetic route and evaluated experimentally in the maximal electroshock test; their neurotoxicities were evaluated by the rotarod neurotoxicity test. The structures of these compounds were confirmed by IR, MS, 1H-NMR, and elementary analysis. All target compounds exhibited anticonvulsant activity to varying degrees in the maximal electroshock test. 4-(3-Benzyloxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one (4i) was the most promising compound with an ED50 value of 30.5 mg/kg and a protective index (PI) of 18.63, showing a higher safety than the standard carbamazepine (PI = 6.45). In addition, the potency of compound 4i against seizures induced by pentylenetetrazole and 3-mercaptopropionic acid suggested its broad-spectrum activity, and the mechanisms of action including inhibition of voltage-gated ion channels and modulation of GABAergic activity might be involved in its anticonvulsant activity. Copyright

Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides

Using N-[4-(hexyloxy)phenyl]piperidine-3-carboxamide (17c) as a structural lead, a number of isomers, derivatives, and ring-opened analogs were synthesized and tested for their ability to block the in vitro aggregation of human platelets induced by adenosine 5′-diphosphate (ADP). For the most active compounds, inhibition of the platelet aggregation triggered by arachidonic acid (AA) and ADP-induced intraplatelet calcium mobilization was also demonstrated. Based on quantitative structure-activity relationships (QSARs), we proved the impact of hydrophobicity on antiplatelet activity by a nonlinear (parabolic or bilinear) relationship between pIC50 and lipophilicity, as assessed by RP-HPLC capacity factors and Clog P (i.e. calculated 1-octanol-water partition coefficients). This study highlighted the following additional SARs: quasi-isolipophilic isomers of 17c (isonipecotanilides and pipecolinanilides) and ring-opened analogs (e.g. anilide of β-alanine) exhibited lower antiplatelet activity; methylation of the piperidine nitrogen of 17c has no effect, whereas alkylation with an n-propyl group decreases the activity by a factor of approximately 2, most likely due to a conformation-dependent decrease in lipophilicity.

CHEMICAL COMPOUNDS

Triazine derivatives of formula (I) or salts thereof, wherein R1 represents a halogen atom or a group selected from hydroxy; C1-8 alkyl C1-6 alkoxy; C1-3 alkoxy C1-3 alkoxy; phenoxy or phenyl C1-3 alkoxy, wherein the phenyl group is optionally substituted by a halogen atom or a group selected from C1-3 alkyl, C1.3 alkoxy, or hydroxy; fluoro C1-3 alkyl; cyano; -CO2R3, wherein R3 represents a hydrogen atom or a C1-4 alkyl group; - CONR4R5, wherein R4 and R5 each independently represents a hydrogen atom or a C1-4 alkyl group, or, together with the nitrogen atom to which they are attached, form a saturated 5- to 7- membered ring, which ring optionally contains one or more atoms selected from an oxygen or a sulphur atom, or a group selected from -NH- or -N(CH3)-; and R2 represents a hydrogen or halogen atom, or a group selected from hydroxy, C1-6 alkyl or C1-6 alkoxy; are inhibitors of the enzyme 5-lipoxygenase. Processes for preparing the triazine derivatives of formula (I) and compositions containing them are also described