19685-84-8

Usage

Uses

Used in Pharmaceutical Research:
8-CHLORO-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]-INDOLE is used as a chemical compound in pharmaceutical research for its potential biological activities. Its unique structure may contribute to the development of new drugs and therapeutic agents.
Used in Drug Development:
In the field of drug development, 8-CHLORO-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]-INDOLE is utilized as a starting material or intermediate in the synthesis of novel pharmaceuticals. Its heterocyclic nature and chloro substituent may offer advantages in the design of drugs with specific target affinities and therapeutic effects.
Used in Chemical Synthesis:
8-CHLORO-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]-INDOLE is employed as a building block in chemical synthesis, particularly for the preparation of other heterocyclic compounds and organic molecules with potential applications in various industries.
Used in Medicinal Chemistry:
In medicinal chemistry, 8-CHLORO-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]-INDOLE serves as a structural motif for the design and optimization of new bioactive molecules. Its unique backbone and functional groups may be exploited to enhance the potency, selectivity, and pharmacokinetic properties of drug candidates.

InChI:InChI=1/C11H11ClN2/c12-7-1-2-10-8(5-7)9-6-13-4-3-11(9)14-10/h1-2,5,13-14H,3-4,6H2

Upstream product

• 41661-47-6 piperidin-4-one 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 41979-39-9 4-piperidone hydrochloride 
• 63277-56-5 8-Chloro-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester 

Downstream Products

• 1095263-16-3 (1R,2R)-2-[(8-chloro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)carbonyl]-N-(1-cyanocyclopropyl)cyclohexanecarboxamide 
• 19686-26-1 1-(8-chloro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)ethan-1-one 
• 1456735-61-7 [2-amino-4-((8-chloro-2,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl)methyl)-thiophen-3-yl](4-chlorophenyl)methanone 
• 1456735-31-1 2-[3-(4-chlorobenzoyl)-4-(8-chloro-2,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-ylmethyl)-thiophen-2-yl]-isoindole-1,3-dione 
• 1456734-92-1 2-[5-bromo-3-(4-chlorobenzoyl)-4-(8-chloro-2,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-ylmethyl)-thiophen-2-yl]-isoindole-1,3-dione 
• 1443130-05-9 ethyl 2-(2-benzoyl-8-chloro-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetate 

Relevant academic research and scientific papers

Biomimetic Oxidative Coupling Cyclization Enabling Rapid Construction of Isochromanoindolenines

Herein, we report a biomimetic oxidative coupling cyclization strategy for the highly efficient functionalization of tetrahydrocarbolines (THCs). This process enables rapid access to complex isochromanoindolenine scaffolds in moderate to excellent yields.

Discovery of lead compounds targeting the bacterial sliding clamp using a fragment-based approach

The bacterial sliding clamp (SC), also known as the DNA polymerase III β subunit, is an emerging antibacterial target that plays a central role in DNA replication, serving as a protein-protein interaction hub with a common binding pocket to recognize linear motifs in the partner proteins. Here, fragment-based screening using X-ray crystallography produced four hits bound in the linear-motif-binding pocket of the Escherichia coli SC. Compounds structurally related to the hits were identified that inhibited the E. coli SC and SC-mediated DNA replication in vitro. A tetrahydrocarbazole derivative emerged as a promising lead whose methyl and ethyl ester prodrug forms showed minimum inhibitory concentrations in the range of 21-43 μg/mL against representative Gram-negative and Gram-positive bacteria species. The work demonstrates the utility of a fragment-based approach for identifying bacterial sliding clamp inhibitors as lead compounds with broad-spectrum antibacterial activity.

Targeting low-druggability bromodomains: Fragment based screening and inhibitor design against the BAZ2B bromodomain

Bromodomains are epigenetic reader domains that have recently become popular targets. In contrast to BET bromodomains, which have proven druggable, bromodomains from other regions of the phylogenetic tree have shallower pockets. We describe successful tar

(1 R,2 R)-N-(1-cyanocyclopropyl)-2-(6-methoxy-1,3,4,5-tetrahydropyrido[4,3- b]indole-2-carbonyl)cyclohexanecarboxamide (AZD4996): A potent and highly selective cathepsin k inhibitor for the treatment of osteoarthritis

Directed screening of nitrile compounds revealed 3 as a highly potent cathepsin K inhibitor but with cathepsin S activity and very poor stability to microsomes. Synthesis of compounds with reduced molecular complexity, such as 7, revealed key SAR and demonstrated that baseline physical properties and in vitro stability were in fact excellent for this series. The tricycle carboline P3 unit was discovered by hypothesis-based design using existing structural information. Optimization using small substituents, knowledge from matched molecular pairs, and control of lipophilicity yielded compounds very close to the desired profile, of which 34 (AZD4996) was selected on the basis of pharmacokinetic profile.

Antipsychotic Activity of Substituted γ-Carbolines

Several novel substituted γ-carbolines were synthesized and examined in a series of in vitro and in vivo pharmacological tests to determine potential antipsychotic activity.Most compounds were orally active in blocking the conditioned avoidance response (CAR) in rats but did not antagonize apomorphine-induced stereotyped behavior.Compound 17 (Wy-47,384), a γ-carboline with a 3-(3-pyridinyl)propyl side chain, was selected for development as an atypical antipsychotic agent because of its potent and selective profile in preclinical psychopharmacological tests.It blocked CAR in rats with an AB50 of 14 mg/kg po, showed weak affinity for the D2 receptor site (Ki = 104 nM), and showed differential potency in antagonizing apomorphine-induced stereotyped behavior (ED50 = 11 mg/kg ip) and climbing behavior (ED50 = 4 mg/kg ip).Such activities are suggestive of antipsychotic efficacy combined with a low potential for extrapyramidal side effect (EPS) liability.