5825-45-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Amino-1,2,3,4-tetrahydroquinoline is used as a building block for the development of bioactive molecules and medicinal drugs due to its unique chemical structure and potential therapeutic properties.
Used in Alzheimer's Treatments:
1-Amino-1,2,3,4-tetrahydroquinoline is used as a potential therapeutic agent for Alzheimer's disease, leveraging its inhibitory effects on certain brain receptors that may contribute to the progression of the condition.
Used in Antidepressant Development:
1-Amino-1,2,3,4-tetrahydroquinoline is used as a component in the formulation of antidepressant medications, with its receptor-inhibiting properties potentially offering relief for individuals suffering from depression.
Safety Measures:
Due to its potential hazardous characteristics, careful safety measures must be taken when handling 1-Amino-1,2,3,4-tetrahydroquinoline to ensure the safety of both individuals and the environment.

InChI:InChI=1/C9H12N2/c10-11-7-3-5-8-4-1-2-6-9(8)11/h1-2,4,6H,3,5,7,10H2

Upstream product

• 5825-44-5 N-nitroso-1,2,3,4-tetrahydroquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 2739-17-5 1,2,3,4-tetrahydroquinoline hydrochloride 

Downstream Products

• 33131-92-9 1-(2-Aminoethyl)-5,6-dihydro-2-methyl-4H-pyrrolo<3.2.1-i,j>chinolin 
• 40619-71-4 2-(2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-6-yl)ethylamine 
• 1421281-40-4 1-methyl-2-phenyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline 
• 97631-21-5 ethyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]-quinoline-2-carboxylate 
• 313670-69-8 4-((7aR,11aS)-5,6,8,9,11,11a-hexahydro-4H,7aH-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-yl)-1-(4-fluorophenyl)-1-butanone 
• 313670-67-6 4-((7aS,11aR)-5,6,8,9,11,11a-hexahydro-4H,7aH-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-yl)-1-(4-fluorophenyl)-1-butanone 
• 41631-40-7 2-methyl-1-phenyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]-quinoline 
• 5825-43-4 1,2-dimethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline 

Relevant academic research and scientific papers

Structure - Antitussive activity relationships of naltrindole derivatives. Identification of novel and potent antitussive agents

We have previously reported antitussive effects of naltrindole (NTI), a typical δ opioid receptor antagonist, in a rat model. The ED50 values of NTI by intraperitoneal and peroral injections were 104 μg/kg and 1840 μg/kg, respectively, comparable to those of codeine. Codeine, one of the most reliable centrally acting antitussive drugs, has μ agonist activity and thus the same side effects as morphine, e.g., constipation, dependency, and respiratory depression. Because NTI is a δ opioid antagonist, its derivatives have potential as highly potent antitussives, free from the μ opioid agonist side effects. We attempted to optimize the NTI derivatives to develop novel antitussive agents. On the basis of the studies of structure - antitussive activity relationships of alkyl substituted NTI derivatives, we designed NTI derivatives with extra ring fused structures. As a clinical candidate, we identified a highly potent new compound, (5R,9R,13S,14S)-17- cyclopropylmethyl-6,7-didehydro-4,5-epoxy-5′,6′-dihydro-3-methoxy- 4′H-pyrrolo[3,2,1-ij]quinolino[2′,1′:6,7]morphinan-14-ol (5b) methanesulfonate (TRK-850) which was effective even by oral administration (ED50 6.40 μg/kg).

ION CHANNEL INHIBITOR COMPOUNDS FOR CANCER TREATMENT

The present invention concerns a compound of following general formula (I): where: either R is an R1 group and R′ is an -A1-Cy1 group, or R is an -A1-Cy1 group and R′ is an R1 group, R1 particularly being H or (C1-C6)alkyl group;A1 being an —NH— radical or —NH—CH2— radical;Cy1 particularly being a phenyl group,A is a fused (hetero)aromatic ring having 5 to 7 atoms, for use for treating cancer.

N-Isocyanodialkylamines generated in situ for the Joullié–Ugi reaction with indolenines

N-Isocyanodialkylamines are rare isocyanide surrogates for the Ugi-type reactions. To avoid problems with instability and the obnoxious smell of these reagents, we optimized and employed a convenient protocol for in situ dehydration of N,N-dialkyl-N′-formyl hydrazines to give the respective N-isocyanodialkylamines which were utilized in the reaction with indolenines and acetic acid. The reaction was demonstrated to give modest to excellent yields of products incorporating the N-isocyanodialkylamine but not the carboxylic acid component.

Selective reduction of N-nitroso aza-aliphatic cyclic compounds to the corresponding N-amino products using zinc dust in CO2–H2O medium

[Figure not available: see fulltext.] A new method for reduction of N-nitroso aza-aliphatic cyclic compounds employing zinc in pressurized CO2–H2O medium has been developed. H2O and NH4Cl were used as hydrogen donors, and reduction was performed under environmentally benign conditions. The presented approach allowed to obtain the respective N-amino products selectively and in excellent yields (up to 97%).

TRICYCLIC INDOLE MCL-1 INHIBITORS AND USES THEREOF

The present invention provides for compounds that inhibit the activity of an anti-apoptotic Bcl-2 family member Myeloid cell leukemia-1 (Mcl-1) protein. The present invention also provides for pharmaceutical compositions as well as methods for using compounds for treatment of diseases and conditions (e.g., cancer) characterized by the over-expression or dysregulation of Mcl-1 protein.

Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino- N -Boc-enamines

Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines was demonstrated. The scope and limitation, experimental mechanistic studies, and a proposed reaction mechanism were also described.

A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles

A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.

Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant

A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.

1-[(imidazolin-2-yl)amino]indoline and 1-[(imidazolin-2-yl)amino]1,2,3,4-tetrahydroquinoline derivatives: New insights into their circulatory activities

N-[(Imidazolin-2-yl)amino]indolines and N-[(imidazolin-2-yl)amino]-1,2,3,4-tetrahydroquinolines, previously described in patent literature as hypertensive agents, were synthesized and tested in vitro for their affinities to α1- and α2-adrenoceptors as well as imidazoline I1 and I2 receptors. The compounds most potent at either α1- or α2-adrenoceptors were administered intravenously to normotensive Wistar rats to determine their effects on mean arterial blood pressure and heart rate. Upon intravenous administration at dose of 0.1 mg/kg to normotensive male Wistar rats, the initial transient pressor effect was followed by long-lasting hypotension and bradycardia. In view of the above results the 1-[(imidazolin-2-yl)amino]indolines and [(imidazolin-2-yl)amino]-1,2,3,4-tetrahydroquinolines are now found to possess circulatory profile characteristic of the centrally acting clonidine-like hypotensive imidazolines.

Discovery of a tetracyclic quinoxaline derivative as a potent and orally active multifunctional drug candidate for the treatment of neuropsychiatric and neurological disorders

We report the synthesis and structure-activity relationships of a class of tetracyclic butyrophenones that exhibit potent binding affinities to serotonin 5-HT2A and dopamine D2 receptors. This work has led to the discovery of 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H- pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8-yl) -1-(4-fluorophenyl)-butan-1-one 4-methylbenzenesulfonate (ITI-007), which is a potent 5-HT2A antagonist, postsynaptic D2 antagonist, and inhibitor of serotonin transporter. This multifunctional drug candidate is orally bioavailable and exhibits good antipsychotic efficacy in vivo. Currently, this investigational new drug is under clinical development for the treatment of neuropsychiatric and neurological disorders.