16036-79-6

Usage

Uses

Used in Pharmaceutical Industry:
5-(3-CHLORO-PROPYL)-10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPINE is used as a key intermediate compound for the synthesis of various pharmaceutical agents. Its application is primarily due to its ability to be incorporated into the molecular structure of pain relievers, anti-inflammatory drugs, and psychopharmacological medications, enhancing their therapeutic effects and potentially leading to the development of novel treatments for various conditions.
Used in Pain Management:
5-(3-CHLORO-PROPYL)-10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPINE is used as an active pharmaceutical ingredient (API) for the development of pain management medications. Its incorporation into these drugs aids in alleviating pain and discomfort associated with various conditions, such as chronic pain, post-operative pain, and neuropathic pain.
Used in Anti-Inflammatory Applications:
This dibenzazepine derivative is also utilized as an API in the creation of anti-inflammatory drugs. Its role in these medications helps to reduce inflammation, swelling, and other symptoms associated with conditions like arthritis, tendonitis, and other inflammatory disorders.
Used in Psychopharmacological Treatments:
5-(3-CHLORO-PROPYL)-10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPINE is employed as a crucial component in the development of psychopharmacological agents, particularly those aimed at treating mental health disorders such as depression, anxiety, and schizophrenia. Its inclusion in these medications contributes to their effectiveness in managing the symptoms and improving the overall quality of life for patients suffering from these conditions.

InChI:InChI=1/C17H18ClN/c18-12-5-13-19-16-8-3-1-6-14(16)10-11-15-7-2-4-9-17(15)19/h1-4,6-9H,5,10-13H2

Upstream product

• 19054-67-2 3-chloro-1-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propanone 
• 494-19-9 9,10-dihydrodibenzazepine 
• 109-70-6 1.3-chlorobromopropane 
• 107167-08-8 1-bromo-1-chloropropane 

Downstream Products

• 5499-80-9 4-(4-Chlorophenyl)-1-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-4-piperidinol 
• 65100-49-4 5-[3-(N-trideuteromethylamino)propyl]iminodibenzyl 
• 2095-95-6 didesmethylimipramine 
• 183785-98-0 1-(3-(10,11-dihydro-5H-dibenz[b,f]-azepin-5-yl)-1-propyl)-4-piperidineacetic acid ethyl ester 

Relevant academic research and scientific papers

Influence of chain length and N-alkylation on the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene

Comparison of the serotonin 5-HT2A receptor affinities of chain lengthened and N-alkylated analogues of the novel ligand 9-aminomethyl-9.10-dihydroanthracene (AMDA) and a structurally similar prototypical tricyclic amine imipramine suggests that the two agents bind to the receptor in different fashions. The demonstration that AMDA is highly selective for serotonin receptors (5-HT2A, Ki = 20 nM: 5-HT2C, Ki = 43 nM) versus the dopamine D2 receptor (Ki > 10,000 nM). as well as the serotonin and norepinephrine transporters (Ki >10.000nM) further suggests that AMDA and the nonselective ligand imipramine interact with these target macromolecules in different ways.

Reversed isoniazids: Design, synthesis and evaluation against Mycobacterium tuberculosis

Novel reversed isoniazid (RINH) agents were synthesized by covalently linking isoniazid with various efflux pump inhibitor (EPI) cores and their structural motifs. These RINH agents were then evaluated for anti-mycobacterial activity against sensitive, isoniazid mono-resistant and MDR clinical isolates of M. tuberculosis and a selected number of compounds were also tested ex vivo for intracellular activity as well as in the ethidium bromide (EB) assay for efflux pump inhibition efficacy. The potency of some compounds against various strains of M. tuberculosis (4a–c, 7 and 8; H37Rv-MIC99 ≤1.25 μM, R5401-MIC99 ≤2.5 μM, X_61-MIC99 ≤5 μM) demonstrated the potential of the reversed anti-TB agent strategy towards the development of novel anti-mycobacterial agents to address the rapidly growing issue of resistance. Further, macrophage activity with >90% inhibition by 1a–c and 3b (MIC90 ≤13.42 μM) and inhibition of EB efflux demonstrated by these compounds are encouraging.

OLIGOMER-TRICYCLIC CONJUGATES

The invention provides small molecule drugs that are chemically modified by covalent attachment of a water soluble oligomer. A conjugate of the invention, when administered by any of a number of administration routes, exhibits characteristics that are different from the characteristics of the small molecule drug not attached to the water soluble oligomer.

In vitro antiplasmodial activity of triazole-linked chloroquinoline derivatives synthesized from 7-chloro-N-(prop-2-yn-1-yl)quinolin-4-amine

The synthesis and in vitro evaluation of novel triazole-linked chloroquinoline derivatives as potential antiplasmodial agents against Plasmodium falciparum is reported. The 15 synthesized target compounds were obtained by means of a copper(I)-mediated click reaction between a variety of 1,2- and 1,3-azidoamines and 7-chloro-N-(prop-2-yn-1-yl)quinolin-4-amine in moderate to good yields (53-85%). The compounds were screened for antiplasmodial activity against NF54 chloroquine-sensitive and Dd2 chloroquine-resistant strains, alongside chloroquine and artesunate as reference compounds. Six of the test compounds revealed a 3-5 fold increase in antiplasmodial activity against chloroquine-resistant strain Dd2 compared to chloroquine. Among the six compounds with good antiplasmodial activity, a reduced cross-resistance relative to artesunate (>3 fold in comparison to chloroquine) was observed, mainly in derivatives that incorporated chloroquine-resistance reversing pharmacophores. A general trend for reduced chloroquine cross-resistance was also detected among 12 out of the 15 compounds tested.

Synthesis and pharmacological characterization of novel inverse agonists acting on the viral-encoded chemokine receptor US28

G-protein coupled receptors encoded by viruses represent an unexplored class of potential drug targets. In this study, we describe the synthesis and pharmacological characterization of the first class of inverse agonists acting on the HCMV-encoded receptor US28. It is shown that replacement of the 4-hydroxy group of lead compound 1 with a methylamine group results in a significant 6-fold increase in affinity. Interestingly, increasing the rigidity of the spacer by the introduction of a double bond also leads to a significant increase in binding affinity compared to 1. These novel inverse agonists serve as valuable tools to elucidate the role of constitutive signaling in the pathogenesis of viral infection and may have therapeutic potential as leads for new antiviral drugs.

A chimeric ligand approach leading to potent antiprion active acridine derivatives: Design, synthesis, and biological investigations

Human transmissible neurodegenerations including Creutzfeldt-Jakob disease are unique, since they are caused by prions, an infectious agent that replicates without nucleic acids but instead by inducing conversion of a host-resident normal prion protein to a misfolded conformational isoform. For pharmacotherapy of these unusual diseases, tricyclic heterocyclic compounds such as quinacrine have been considered, but with ambiguous success in vivo, so far. On the basis of the synergistic antiprion effects of quinacrine and iminodibenzyl derivatives, we introduce a novel class of potential pharmaceuticals representing structural chimeras of quinacrine and imipramine analogues. We describe the chemical synthesis and bioassays of a focused library of these compounds. The most potent target compound 2a revealed an EC50 value of 20 nM determined with a cell model of prion disease, thus substantially improving the antiprion efficacy of quinacrine.

N-substituted azaheterocyclic carboxylic acids and esters thereof

The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.

HETEROCYCLIC COMPOUNDS FOR TREATING DIABETES

The present invention relates to novel N-substituted amino acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use fo

Substituted dibenz[b,f]azepines and uses thereof

The present invention relates to novel N-substituted azaheterocyclic carboxylic acids andy esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.

N-substituted azaheterocyclic carboxylic acids and esters thereof

The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.