784-45-2

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
3-Nitroso-2-phenyl-1H-indole is used as a precursor in organic synthesis for the development of new drugs and therapeutic agents. Its unique structure and properties make it a valuable component in the creation of novel pharmaceutical compounds.
Used in Anticancer Research:
3-Nitroso-2-phenyl-1H-indole is used as a potential anticancer agent in research studies. It has been investigated for its potential to target and combat cancer cells, offering a new avenue for cancer treatment development.
Used in Toxicology and Mutagenesis Studies:
3-Nitroso-2-phenyl-1H-indole is utilized in research to understand its role in the formation of mutagenic and carcinogenic nitrosamines in the human body. This knowledge is crucial for assessing the risks associated with exposure to such compounds and for developing strategies to mitigate their harmful effects.
Overall, 3-Nitroso-2-phenyl-1H-indole is a significant chemical with a wide range of applications, particularly in the fields of medicine and pharmacology, where its potential as a therapeutic agent and its role in understanding toxicological processes are of great interest.

Upstream product

• 948-65-2 2-phenyl-indole 

Downstream Products

• 40288-69-5 N-(2-cyanophenyl)benzamide 
• 4771-06-6 2-phenyl-3-nitro-1H-indole 
• 23041-45-4 3-amino-2-phenylindole 
• 519166-83-7 N-(2-phenyl-1H-indol-3-yl)benzamide 
• 6339-33-9 3-imino-2-phenyl-3H-indole 
• 2989-63-1 2-phenyl-3H-indol-3-one 
• 83506-45-0 ethyl 2-phenylindole-3-carbamate 
• 83506-47-2 2-phenylindole-3-semicarbazide 

Relevant academic research and scientific papers

The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB1 Receptor Positive Allosteric Modulators

The first generation of CB1 positive allosteric modulators (e.g., ZCZ011) featured a 3-nitroalkyl-2-phenyl-indole structure. Although a small number of drugs include the nitro group, it is generally not regarded as being "drug-like", and this is particularly true for aliphatic nitro groups. There are very few case studies where an appropriate bioisostere replaced a nitro group that had a direct role in binding. This may be indicative of the difficulty of replicating its binding interactions. Herein, we report the design and synthesis of ligands targeting the allosteric binding site on the CB1 cannabinoid receptor, in which a CF3 group successfully replaced the aliphatic NO2. In general, the CF3-bearing compounds were more potent than their NO2 equivalents and also showed improved in vitro metabolic stability. The CF3 analogue (1) with the best balance of properties was selected for further pharmacological evaluation. Pilot in vivo studies showed that (±)-1 has similar activity to (±)-ZCZ011, with both showing promising efficacy in a mouse model of neuropathic pain.

Indole-based novel small molecules for the modulation of bacterial signalling pathways

Gram-negative bacteria such as Pseudomonas aeruginosa use N-acylated l-homoserine lactones (AHLs) as autoinducers (AIs) for quorum sensing (QS), a major regulatory and cell-to-cell communication system for social adaptation, virulence factor production, biofilm formation and antibiotic resistance. Some bacteria use indole moieties for intercellular signaling and as regulators of various bacterial phenotypes important for evading the innate host immune response and antimicrobial resistance. A range of natural and synthetic indole derivatives have been found to act as inhibitors of QS-dependent bacterial phenotypes, complementing the bactericidal ability of traditional antibiotics. In this work, various indole-based AHL mimics were designed and synthesized via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N,N′-dicyclohexylcarbodiimide (DCC) mediated coupling reactions of a variety of substituted or unsubstituted aminoindoles with different alkanoic acids. All synthesized compounds were tested for QS inhibition using a P. aeruginosa QS reporter strain by measuring the amount of green fluorescent protein (GFP) production. Docking studies were performed to examine their potential to bind and therefore inhibit the target QS receptor protein. The most potent compounds 11a, 11d and 16a showed 44 to 65% inhibition of QS activity at 250 μM concentration, and represent promising drug leads for the further development of anti-QS antimicrobial compounds.

Methods for treating or preventing erectile dysfunction or urinary incontinence

The present invention relates to methods for treating or preventing erectile dysfunction or urinary incontinence, comprising administering to a subject in need thereof an effective amount of a compound of the invention.

ISOQUINOLINE DERIVATIVES AND METHODS OF USE THEREOF

The present invention relates to Isoquinoline Derivatives, compositions comprising an effective amount of a Isoquinoline Derivative and methods for treating or preventing an inflammatory disease, a reperfusion injury, an ischemic condition, renal failure, diabetes, a diabetic complication, a vascular disease other than a cardiovascular disease, cardiovascular disease, reoxygenation injury resulting from organ transplantation, Parkinson's disease, or cancer, comprising administering to an animal in need thereof an effective amount of a Isoquinoline Derivative.

Isoquinoline derivatives and methods of use thereof

The invention provides novel classes of Isoquinoline Derivatives. Pharmaceutical compositions and methods of making and using the compounds, are also described.

Isoquinoline derivatives and methods of use thereof

The invention provides novel classes of Isoquinoline Derivatives. Pharmaceutical compositions and methods of making and using the compounds, are also described.

Synthesis of Substituted 1,2,3,8-Tetrahydroindolobenzodiazepin-2-ones and 5,6,7,8-Tetrahydroindolobenzodiazepin-6-ones

Nitrosation (NaNO2/AcOH) of 2-phenylindoles (1a-d) and subsequent reduction of the resultant 3-nitroso-2-phenylindoles (2a-d) with sodium dithionite in alkali furnish the corresponding 3-aminoindoles (3a-d), which on condensation with ethyl chloroformate