2525-16-8

Usage

Chemical Properties

Colorless liquid

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 588, 1963Tetrahedron Letters, 20, p. 4671, 1979 DOI: 10.1016/S0040-4039(01)86679-X

InChI:InChI=1/C7H13NO/c1-9-7-5-3-2-4-6-8-7/h2-6H2,1H3

Upstream product

• 105-60-2 caprolactam 
• 77-78-1 dimethyl sulfate 
• 71-43-2 benzene 
• 100-64-1 cyclohexanone-oxime 
• 98-09-9 benzenesulfonyl chloride 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 67-56-1 methanol 
• 111238-46-1 1-azido-1-methoxycyclohexane 

Downstream Products

• 2309-49-1 theacrine 
• 116598-69-7 6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-ylacetonitrile 
• 100718-16-9 p-toluic acid-(4,5,6,7-tetrahydro-3H-azepin-2-yl ester) 
• 109717-32-0 N-hexahydroazepin-2-ylidene-DL-phenylalanine 
• 31030-25-8 hexahydro-azepin-2-one-hydrazone 
• 1013-01-0 1,3-dimethyl-1H-quinazoline-2,4-dione 
• 46339-16-6 cyclohexyl-hexahydroazepin-2-yliden-amine 
• 100371-96-8 benzoic acid-(4,5,6,7-tetrahydro-3H-azepin-2-yl ester) 
• 16595-44-1 hexahydroazepin-2-ylidene-(4-methoxy-phenyl)-amine 
• 51828-07-0 3-phenyl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine 
• 4425-23-4 7,8,9,10-tetrahydro-6H-azepino[2,1-b]quinazolin-12-one 
• 108877-44-7 3-(2-Hydroxyphenyl)-4,5-pentamethylen-1,2,4-triazol 
• 100610-89-7 4-nitro-benzoic acid hexahydroazepin-2-ylidenehydrazide 
• 28669-82-1 (2-chloro-phenyl)-hexahydroazepin-2-yliden-amine 

Relevant academic research and scientific papers

Synthesis and bronchodilatory activity of some nitrogen bridgehead compounds

A series of tricyclic nitrogen bridgehead compounds 7-22 have been synthesised and evaluated for their in vitro bronchodilatory activity using isolated guinea pig tracheal chain, precontracted with acetylcholine. The relaxant effect of 2,3,4,5-tetrahydroazepino[2,1-b]-8,9-dimethoxyquinazolin-11(1H)-one (7) (DPJ-386) was greater than that of theophylline, aminophylline and quinazoline derivative 3, which lacks methoxy groups at positions 8 and 9. Various nitrogen containing functionalities such as benzylamino, acetamido, benzamido and phthalimido were also introduced at 9 position of 3. This resulted in loss of relaxation activity in precontracted guinea pig tracheal chain. These results show that the better relaxation property possessed by compound 7 hydrochloride is due to methoxy groups at 8 and 9 positions.

Synthesis of [1,2-A]-fused tricyclic dihydroquinolines by palladiumcatalyzed intramolecular C-N cross-coupling of polarized heterocyclic enamines

A simple methodology for [1,2-A]-fused tricyclic dihydroquinolines is established. The key ste of the methodology is an intramolecular Buchwald-Hartwig amination reaction of suitabl halogenated (both bromo and chloro) cyclic enaminoketones, enaminoesters and enaminonitrile with various ring size (from five-to seven-membered). Optimal reaction conditions (palladiu source, base, ligand) depend on the ring size of the starting enamine, giving 65-98% yield of th tricyclic product. A treatment of the products with perchloric acid gives respective quinoliniu perchlorates.

Pyrrolopyrimidine Derivatives as Novel Inhibitors of Multidrug Resistance-Associated Protein 1 (MRP1, ABCC1)

Five series of pyrrolo[3,2-d]pyrimidines were synthesized and evaluated with respect to potency and selectivity toward multidrug resistance-associated protein 1 (MRP1, ABCC1). This transport protein is a major target to overcome multidrug resistance in cancer patients. We investigated differently substituted pyrrolopyrimidines using the doxorubicin selected and MRP1 overexpressing small cell lung cancer cell line H69 AR in a calcein AM and daunorubicin cell accumulation assay. New compounds with high potency and selectivity were identified. Piperazine residues at position 4 bearing large phenylalkyl side chains proved to be beneficial for MRP1 inhibition. Its replacement by an amino group led to decreased activity. Aliphatic and aliphatic-aromatic variations at position 5 and 6 revealed compounds with IC50 values in high nanomolar range. All investigated compounds had low affinity toward P-glycoprotein (P-gp, ABCB1). Pyrrolopyrimidines with small substituents showed moderate inhibition against breast cancer resistance protein (BCRP, ABCG2).

SUBSTITUTED IMIDAZOHETEROCYCLE DERIVATIVES

The present invention provides substituted imidazoheterocycles having the general structure of formula (I), wherein Y is chosen from -O-, -OCRgRh-, -CRgRhO-, -CRgRh-, -(CRgRh)2-, -NRi-, -CRgRhNRi- and -NRiCRgRh-. Also provided are pharmaceutically acceptable salts, acid salts, hydrates, solvates and stereoisomers of the compounds of formula I. The compounds are useful as modulators of cannabinoid receptors and for the prophylaxis and treatment of cannabinoid receptor-associated diseases and conditions, such as pain, inflammation and pruritis.

Targeting the polyamine transport system with benzazepine- and azepine-polyamine conjugates

The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.

α′-Hydroxyenones as mechanistic probes and scope-expanding surrogates for α,β-unsaturated aldehydes in N-heterocyclic carbene-catalyzed reactions

N-heterocyclic carbene-catalyzed reactions of α,β-unsaturatedaldehydes and a variety of electrophiles allow the facile preparation o f a diverse array of annulation products including trisubstituted cyclopentenes, γ-lactams, and bicyclic β-lactams. The substrate scope of these reactions, however, is limited by the difficulties of preparing the starting α,β-unsaturated aldehydes. We now report that α′- hydroxyenones, which can be prepared in a single convenient step from aromatic and heteroaromatic aldehydes, can serve as efficient surrogates for enals in the annulation reactions. This protocol allows the facile preparation and use of substrates bearing nitrogen heterocycles. These reagents have also allowed us to demonstrate that, in contrast to other classes of aldehydes, the formation of the Breslow intermediate from enals and N-heterocyclic carbenes is irreversible under the reaction conditions.

Potent antimalarial activity of 2-aminopyridinium salts, amidines, and guanidines

We describe the design, synthesis, and antimalarial activity of 60 bis-tertiary amine, bis-2(1H)-imino-heterocycle, bis-amidine, and bis-guanidine series. Bis-tertiary amines with a linker from 12 to 16 methylene groups were active against the in vitro growth of Plasmodium falciparum within the 10 -6-10-7 M concentration range. IC50 decreased by 2 orders of magnitude for bis-2-aminopyridinium salts, bis-amidines, and bis-guanidines (27 compounds with IC50 a over 12.5. Maximal activity occurs for bis-2-aminopyridinium, two C-duplicated bis-amidines, and three bis-guanidines, with IC50 values lower than 1 nM. In comparison to similar quaternary ammonium salts, amidinium compounds have distinct structural requirements for antimalarial activity and likely additional binding opportunities on account of their hydrogen-bond-forming properties.

Adamantyl triazoles as selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1

Adamantyl triazoles were identified as selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). They are active both in in vitro and in in vivo pharmacodynamic models. The synthesis and structure-activity relationships of these inhibitors are presented.

THE R-ISOMER OF BETA AMINO ACID COMPOUNDS AS INTEGRIN RECEPTOR ANTAGONISTS DERIVATIVES

The present invention relates to a class of compounds represented by the Formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula (I), and methods of selectively inhibiting or antagonizing the αVβ3 and/or the αV β5 integrin without significantly inhibiting the αV β6 integrin

Process for producing ε-caprolactam

The present invention provides a method for producing ε-caprolactam which comprises the step of treating, with water, a reaction product containing 1-aza-2-alkoxy-1-cycloheptene, which is obtained by gas phase Beckmann rearrangement reaction of cyclohexanone oxime using a solid catalyst in the presence of alcohol, to eliminate the 1-aza-2-alkoxy-1-cycloheptene. The resulting ε-caprolactam usually has a 1-aza-2-alkoxy-1-cycloheptene content of 100 ppm or less, preferably 25 ppm or less, more preferably 10 ppm or less and, therefore, has low free basicity and good qualities.