6208-60-2

Usage

Uses

Used in Pharmaceutical Research:
2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole is used as a research compound for studying its psychoactive properties and potential role in various biological and pharmacological processes. Its action as a serotonin receptor agonist makes it a valuable tool for investigating the mechanisms of serotonin signaling and its implications in neurological disorders.
Used in Toxicology and Mutagenesis Studies:
Norharmane is used as a model compound in toxicology and mutagenesis research to understand its potential carcinogenic effects and its ability to form DNA adducts. This research helps in assessing the risks associated with exposure to norharmane and contributes to the development of strategies for mitigating its harmful effects.
Used in Neuroprotection Research:
2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole is used as a neuroprotective agent in preclinical studies, exploring its potential to protect neurons from damage and degeneration. Its neuroprotective effects are of interest in the context of neurodegenerative diseases, such as Alzheimer's and Parkinson's, where novel therapeutic agents are urgently needed.
Used in Food Industry:
Norharmane, being a component of grilled meats, is used in the food industry for its potential flavor-enhancing properties. However, due to its potential mutagenic and carcinogenic effects, its presence in food products is closely monitored and regulated to ensure consumer safety.

InChI:InChI=1/C11H12N2/c1-2-4-10-8(3-1)9-7-12-6-5-11(9)13-10/h1-4,12-13H,5-7H2

Upstream product

• 63277-54-3 ethyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate 
• 244-69-9 γ-carboline 
• 41979-39-9 4-piperidone hydrochloride 
• 59-88-1 phenylhydrazine hydrochloride 
• 100-63-0 phenylhydrazine 
• 627869-56-1 tert‐butyl 1,3,4,5‐tetrahydro‐2H‐pyrido[4,3‐b]indole‐2‐carboxylate 
• 41661-47-6 piperidin-4-one 
• 6208-43-1 2-benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 29976-53-2 N-ethoxycarbonyl-4-piperidone 

Downstream Products

• 1236142-69-0 2-(3-[3-fluoro-5-(4-methoxytetrahydro-4H-4-pyranyl)phenoxy]propyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 1354547-51-5 tert-butyl 5-(4-(methoxycarbonyl)benzyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate 
• 1354547-52-6 methyl 4-((3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-53-7 methyl 4-((2-ethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-54-8 methyl 4-((2-isopropyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-55-9 methyl 4-((2-allyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-57-1 methyl 4-((2-(3-methoxybenzyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-58-2 methyl 4-((2-(4-methoxybenzyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-59-3 methyl 4-((2-(pyridin-4-ylmethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-60-6 methyl 4-((2-(3-amino-3-oxopropyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-61-7 methyl 4-((2-(2-amino-2-oxoethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-62-8 methyl 4-((2-(4-amino-4-oxobutyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 1354547-28-6 tert-butyl 5-(4-(hydroxycarbamoyl)benzyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate 
• 1354547-30-0 4-((3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)-N-hydroxybenzamide TFA 

Relevant academic research and scientific papers

Method for protecting sulfonyl of deamination amine

The invention discloses a method for removing sulfenyl protection of amine. The method comprises the following steps: dissolving N - sulfonyl-protected amine and a base in a reaction solvent, then adding diphenylphosphine to uniformly mix and maintain 90 °C. When TCL detection reaction is complete, a recrystallization method or an extraction separation method is adopted to obtain the target product. The method disclosed by the invention adopts diphenylphosphine as an extraction reagent, is good in reaction activity, high in selectivity and wide in application range, and can replace the use of a hazardous reagent under the basic heating condition. Prodrug research and development and industrial production are of great significance.

METHODS AND MATERIALS FOR INCREASING OR MAINTAINING NICOTINAMIDE MONONUCLEOTIDE ADENYLYL TRANSFERASE-2 (NMNAT2) POLYPEPTIDE LEVELS

This document provides methods and materials for increasing or maintaining NMNAT2 polypeptide levels within cells. For example, compounds (e.g., organic compounds) having the ability to increase or maintain NMNAT2 polypeptide levels within cells, formulations containing compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for making compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for making formulations containing compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for increasing or maintain NMNAT2 polypeptide levels within cells, and methods for treating mammals (e.g., humans) having a condition responsive to an increase in NMNAT2 polypeptide levels are provided (or for preventing said condition).

Thiapyran[4,3-b] indole compound and preparing method and application thereof

The invention discloses a thiapyran[4,3-b] indole compound and a preparing method and application thereof. The structure of the compound is shown in the formula 1, wherein the formula 1 is shown in the description, and R1-R5 are not all hydrogen. The compound has excellent activities of inhibiting mycelial growth, protecting detached leaves, protecting living bodies and treating the living bodiesfor rhizoctonia solani, the effects of the compound are even superior to those of positive control drugs, and the compound has an important application value in preventing and/or treating rice sheathblight.

TRICYCLIC COMPOUNDS FOR USE IN TREATMENT OF PROLIFERATIVE DISORDERS

The present invention relates to compounds of Formula (I) as defined herein, and salts, hydrates and solvates thereof. The present invention also relates to pharmaceutical compositions comprising compounds of Formula (I), and to the use of compounds of Formula (I) in the treatment or prevention of PRMT5-mediated disorders, such as cancer.

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.

Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands

Sigma 1 receptors are associated with neurodegenerative and psychiatric disorders. These receptors, via their chaperoning functions that counteract endoplasmic reticulum stress and block neurodegeneration, may serve as a target for a new generation of antidepressants or neuroprotective agents. The involvement of these receptors has also been observed in neuropathic pain and cancer. Only a few ligands, such as Igmesine and Anavex 2-73, have been involved in clinical trials. Thus the development of sigma 1 ligands is of interest to a new generation of drugs. Previous work in our lab underlined the potency of benzannulated bicyclic compounds as interesting ligands. Herein the work was extended to a series of novel tricyclic compounds. Carboline- and phenothiazine-derivated compounds were designed and synthesized. In vitro competition binding assays for sigma 1 and 2 receptors showed that most of them have high affinity for sigma 1 receptor (Ki = 2.5-18 nM), and selectivity toward sigma 2 receptor, without cytotoxic effects on SY5Y cells.

CARBOLINE COMPOUNDS USABLE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES

The present invention relates to a compound according to Formula (A) or a pharmaceutically acceptable salt, solvate, clathrate, hydrate or polymorph thereof, and its use.

Beta and gamma carboline derivatives as potential anti-Alzheimer agents: A comparison

Nine novel β2- and 3-carboline derivatives bearing either methyl-, propargyl- or phenethyl-residues at the indole nitrogen were synthesized and tested as potential anti-Alzheimer drugs. Antagonism of recombinantly expressed NMDA receptors, inhibition of cholinesterases, and radical scavenging properties were determined for all compounds. Some were additionally tested in vivo for their ability to reverse scopolamine-induced cognitive impairment in an 8-arm radial maze experiment with rats. For the most promising candidates, the interaction with muscarinic M1receptors was also investigated. With this set of compounds assays the influence of the scaffold itself and the substituents can be investigated separately. 5-Methyl-β3-carboline (6) was the most potent (0.25 1/4mol/100 g b.w.) compound in the in vivo test and might be a good starting point for the development of novel anti-Alzheimer drugs.

(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.

Second-generation histone deacetylase 6 inhibitors enhance the immunosuppressive effects of Foxp3+ T-regulatory cells

Second-generation Tubastatin A analogues were synthesized and evaluated for their ability to inhibit selectively histone deacetylase 6 (HDAC6). Substitutions to the carboline cap group were well-tolerated with substitution at the 2-position of both β- and γ-carbolines being optimal for HDAC6 activity and selectivity. Some compounds in this series were determined to have subnanomolar activity at HDAC6 with more than 7000 fold selectivity for HDAC6 versus HDAC1. Selected compounds were then evaluated for their ability to augment the immunosuppressive effect of Foxp3+ regulatory T cells. All compounds tested were found to enhance the ability of regulatory T cells to inhibit the mitotic division of effector T cells both in vitro and in vivo, suggesting that further investigation into the use of these compounds for the treatment of autoimmune disorders is warranted.