5318-27-4

Usage

Uses

Used in Pharmaceutical Industry:
6-Aminoindole is used as a reactant for the preparation of various inhibitors and blockers, playing a significant role in the development of new drugs for treating different medical conditions. Its applications include:
1. Inhibitors of mammalian target of rapamycin (mTOR) protein: These inhibitors are essential in the treatment of various cancers by regulating cell growth and proliferation.
2. Inhibitors of the AcrAB-TolC efflux pump: These inhibitors help combat antibiotic resistance by preventing the efflux of antibiotics from bacterial cells.
3. Inhibitors of Gli1-mediated transcription in the Hedgehog pathway: These inhibitors are crucial in the treatment of certain cancers and congenital disorders by targeting the Hedgehog signaling pathway.
4. Potent DNA-topoisomerase II poisons and anti-MDR agents: These agents are used to inhibit the activity of DNA-topoisomerase II, a crucial enzyme in DNA replication, and to overcome multidrug resistance in cancer cells.
5. Protein kinase C θ (PKCθ) inhibitors: These inhibitors are involved in the regulation of immune cell activation and are being explored for their potential in treating autoimmune diseases and cancer.
Used in Pain Management:
6-Aminoindole is used as a building block for the development of potent and selective blockers of the Nav1.8 sodium channel, which are potential analgesics for the treatment of neuropathic and inflammatory pain.
Used in TRPV1 Antagonists:
6-Aminoindole is used as a reactant for the synthesis of piperidine carboxamide and 5,6-fused heteroaromatic ureas, which are TRPV1 antagonists. These antagonists have potential applications in the treatment of pain, inflammation, and other conditions related to the transient receptor potential cation channel subfamily V member 1 (TRPV1).
Used in Allosteric Enhancers:
6-Aminoindole is used as a reactant for the preparation of allosteric enhancers of the A3 adenosine receptor, which have potential therapeutic applications in various diseases, including cancer, inflammation, and neurodegenerative disorders.
Used in Type 2 Diabetes Treatment:
6-Aminoindole is used as a reactant for the synthesis of human liver glycogen phosphorylase (HLGP) inhibitors, which are being investigated for their potential in the treatment of type 2 diabetes by regulating glucose metabolism.

InChI:InChI=1/C18H20ClN3O2/c1-3-22(4-2)16-9-8-14(17(23)11-16)12-20-21-18(24)13-6-5-7-15(19)10-13/h5-12,20H,3-4H2,1-2H3,(H,21,24)/b14-12+

Upstream product

• 61293-29-6 (E)-2-(2,4-dinitrophenyl)-N,N-dimethyl-1-ethenamine 
• 121-14-2 2,4-dinitrotoluene 
• 496-15-1 1-indoline 
• 19727-83-4 6-nitroindoline 
• 104447-74-7 5-bromo-6-nitro-1H-indole 
• 99365-39-6 3-(4-bromo-2-nitrophenyl)-2-oxopropanoic acid 
• 16732-65-3 6-bromo-indole-2-carboxylic acid(Ref_.7.) 
• 4769-96-4 6-nitroindole 

Downstream Products

• 171896-30-3 N-(1H-indol-6-yl)acetamide 
• 127348-07-6 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(1H-indol-6-ylamino)-tetrahydro-pyran-3-yl ester 
• 127348-41-8 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(1H-indol-6-ylamino)-tetrahydro-pyran-3-yl ester 
• 52415-29-9 6-bromo-1H-indole 
• 616243-13-1 6-amino-1-(2-(4-pyridyl)ethyl)indole 
• 5577-26-4 N-(1H-indol-6-yl)benzamide 
• 135855-72-0 6-N-(β,γ-dihydroxypropyl)aminoindole 
• 1007197-90-1 C₁₉H₁₃ClN₂O₂ 
• 1028353-72-1 1,1,1-trifluoro-4-(6-amino-1H-indol-3-yl)-but-3-en-2-one 
• 888036-84-8 1-(3-Trifluoromethyl-phenyl)-piperidine-4-carboxylic acid (1H-indol-6-yl)-amide 
• 2462-30-8 6-amino-L-tryptophan 
• 1160849-35-3 5-bromo-4-(1H-indol-6-ylamino)-6-methylnicotinonitrile 
• 1175018-51-5 (6-chloro-pyrazin-2-yl)-(1H-indol-6-yl)-amine 
• 1023867-63-1 C₁₆H₁₃N₃OS 

Relevant academic research and scientific papers

Structure-based drug design, synthesis, In vitro, and In vivo biological evaluation of indole-based biomimetic analogs targeting estrogen receptor-α inhibition

Offering novel scaffolds targeting estrogen receptor creates huge necessity to overcome the evolving resistance developed by tumors. Structure-based drug design coupled with ring opening strategy of the steroids skeleton revealed the potential of indole-based analogs to be synthesized targeting the ligand binding domain of estrogen receptor-α. In vitro studies revealed the potential of the total sub-classes of the synthesized analogs to show anti-proliferative activity against estrogen receptor-dependent cancer cell lines at IC50 ranging from 28.23 to 57.13 μM. This was further validated by evaluating the potential of the synthesized analogs to compete along with estradiol via ER-α ELISA assay to show inhibitory profile at IC50 ranging from 1.76 to 204.75 nM. Two analogs (YMA-005 and YMA-006) showed significant reduction in tumor size at two dose levels with extensive degeneration and necrosis. Both YMA-005 and YMA-006 showed in-situ reduction of ER-α Immunohistochemical expression at both dose levels. Ultimately, novel analogs of indole-based biomimetic of estrone scaffolds were offered as estrogen receptor-α inhibitors.

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

COPPER NANOPARTICLE BASED CHEMOSELECTIVE REDUCTION

The instant invention provides processes for a chemo selective reduction of a nitro group within a compound in the presence of other groups which can also be reduced. This aspect of the present invention provides an ammonia borane (AB) initiated chemoselective reduction process of a nitro group contained within a compound in the presence of a copper (Cu) nanoparticle based catalyst. The invention is also directed to Copper (Cu) nanoparticle (NP) based catalysts, selected from Cu/WOx, Cu/SiO2, and Cu/C; wherein x represents an integer having a value of from about 2 to about 3.5, used in the chemo selective reduction of a nitro group contained within a compound in the presence of other groups which can also be reduced.

Ultrasound-assisted rapid reduction of nitroaromatics to anilines using gallium metal

The reduction of nitroaromatic compounds to anilines is widely used throughout organic synthesis. Typical methods of performing this transformation utilize hydrogenation over a pyrophoric catalyst or a finely divided reducing metal, which often affords heterogeneous mixtures that are difficult to purify. Herein, we report for the first time the use of gallium metal as a reducing agent in organic synthesis. The reaction proceeds under aerobic conditions and affords homogeneous mixtures for a convenient workup. Using this method, twelve anilines were obtained in 33% to quantitative yields with short reaction times of 10-60 minutes.

Flexible Versus Rigid G-Quadruplex DNA Ligands: Synthesis of Two Series of Bis-indole Derivatives and Comparison of Their Interactions with G-Quadruplex DNA

Small molecules that target G-quadruplex (G4) DNA structures are not only valuable to study G4 biology but also for their potential as therapeutics. This work centers around how different design features of small molecules can affect the interactions with G4 DNA structures, exemplified by the development of synthetic methods to bis-indole scaffolds. Our synthesized series of bis-indole scaffolds are structurally very similar but differ greatly in the flexibility of their core structures. The flexibility of the molecules proved to be an advantage compared to locking the compounds in the presumed bioactive G4 conformation. The flexible derivatives demonstrated similar or even improved G4 binding and stabilization in several orthogonal assays even though their entropic penalty of binding is higher. In addition, molecular dynamics simulations with the c-MYC G4 structure showed that the flexible compounds adapt better to the surrounding. This was reflected by an increased number of both stacking and polar interactions with both the residues in the G4 DNA structure and the DNA residues just upstream of the G4 structure.

Room-Temperature Chemoselective Reduction of 3-Nitrostyrene to 3-Vinylaniline by Ammonia Borane over Cu Nanoparticles

We report a new strategy of controlling catalytic activity and selectivity of Cu nanoparticles (NPs) for the ammonia borane initiated hydrogenation reaction. Cu NPs are active and selective for chemoselective reduction of nitrostyrene to vinylaniline under ambient conditions. Their activity, selectivity, and more importantly, stability are greatly enhanced by their anchoring on WO2.72 nanorods, providing a room-temperature full conversion of nitrostyrene selectively to vinylaniline (>99% yield). Compared with all other catalysts developed thus far, our new Cu/WO2.72 catalyst shows much enhanced hydrogenation selectivity and stability without the use of pressured hydrogen. The synthetic approach demonstrated here can be extended to prepare various M/WO2.72 catalysts (M = Fe, Co, Ni), with M being stabilized for many chemical reactions.

A 4, 4 - dimethoxy - 2, 2 - bipyridyl silver catalytic hydrogenation of aromatic nitro compound synthesis of aromatic amines (by machine translation)

The invention discloses a 4, 4 - dimethoxy - 2, 2 - bipyridyl silver catalytic hydrogenation of aromatic nitro compound synthesis of aromatic amines, the method uses a cheap, easy synthesis of 4, 4 - dimethoxy - 2, 2 - bipyridyl silver as catalyst, in order to green, environmental protection, non-toxic as the hydrogen source, the aromatic nitro compound in the relatively mild reaction conditions, one-step reaction can synthesize aromatic amine. The invention has simple operation, catalyst is cheap and easy and small consumption, mild reaction conditions, to substrate demonstrates better functional group tolerant, high product yield, industrial manufacturing cost, it has very good application prospect. (by machine translation)

Chemoselective transfer hydrogenation of nitroarenes by highly dispersed Ni-Co BMNPs

Highly dispread Ni-Co bimetallic nanoparticles (Ni-Co BMNPs) are synthesized and applied as an efficient catalyst in the chemoselective transfer hydrogenation of nitroarenes (CTH) using hydrazine hydrate as the hydrogen donor. The BMNPs can efficiently catalyze the reduction reaction without any additives under mild conditions with high TOF. Significantly higher activity is achieved when compared with corresponding single-component catalysts, optimal composition of the Ni-Co BMNPs was screened which was proved to be crucial in both the selectivity and yields. Excellent performance of Ni-Co BMNPs can be ascribed to the improved dispersion of active sites on the BMNPs surface (compared with Ni NPs) and the electron transfer from cobalt to nickel.

HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.

NOVEL AMINE DERIVATIVE OR SALT THEREOF

A novel amine derivative expressed by general formula (1) (in the formula: G1, G2, and G3 are the same or different and represent CH or a nitrogen atom; R1 represents a chlorine atom, an optionally-substituted C3-8 cycloalkyl group, or the like; R2 represents -COOR5 (in the formula, R5 represents a hydrogen atom or a carboxyl protective group), or the like; R3 represents a hydrogen atom, or the like; and R4 represents an optionally-substituted condensed bicyclic hydrocarbon group, an optionally-substituted bicyclic heterocyclic group, or the like), or a salt thereof is useful in procedures such as the treatment or prevention of conditions related to excessive keratinocyte proliferation.