5460-84-4

Usage

Uses

Used in Cancer Therapy:
HIMAOH is utilized as an inhibitor in cancer therapy, specifically targeting the enzyme IDO. This enzyme's activity is linked to immune tolerance and cancer progression, making HIMAOH a potential agent in managing cancer. By inhibiting IDO, HIMAOH can potentially disrupt the immunosuppressive environment that tumors often create, aiding in the body's fight against cancer.
Used in Immunotherapy:
In the field of immunotherapy, HIMAOH is used as an immunomodulatory agent. Its ability to inhibit IDO can help regulate immune responses, which is crucial in the treatment of various immune-related disorders. This application is still under investigation, but the potential for HIMAOH to contribute to immunotherapy is promising.
Used in Treatment of Immune-Related Disorders:
HIMAOH is being studied for its potential use in treating other immune-related disorders beyond cancer. Its influence on IDO, an enzyme involved in immune system regulation, positions it as a possible therapeutic agent for a range of conditions where immune system modulation is beneficial.
Used in Anti-Inflammatory and Neuroprotective Applications:
HIMAOH has also been investigated for its anti-inflammatory and neuroprotective properties. These potential applications are significant, as they could lead to the development of treatments for inflammatory diseases and neurodegenerative conditions, where inflammation and neuronal damage are key factors.

Upstream product

• 25365-71-3 2-phenyl-1H-indol-3-carboxaldehyde 
• 948-65-2 2-phenyl-indole 
• 1262057-02-2 (E)-1-((2-(phenylethynyl)phenyl)diazenyl)piperidine 
• 1262057-09-9 1-(2-iodophenyl)-2-(piperidin-1-yl)diazene 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 126193-77-9 2-phenyl-3-(3'-hydroxy-4'-oxothiazolidin-2'-yl)indole 
• 95094-68-1 C₁₅H₁₁ClN₂O 
• 51072-85-6 2-phenyl-1H-indole-3-carbonitrile 
• 1258597-25-9 2-phenyl-1H-indole-3-carbaldehyde O-acetyl oxime 
• 95094-71-6 5-Amino-3-(2-phenyl-1H-indol-3-yl)-isoxazole-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes

A new method for synthesizing 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed intramolecular electrophilic amination of 2-arylindole-3-carbaldehyde O-acetyl oximes was developed.

Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1

In our ongoing effort of discovering anticancer and chemopreventive agents, a series of 2-arylindole derivatives were synthesized and evaluated toward aromatase and quinone reductase 1 (QR1). Biological evaluation revealed that several compounds (e.g., 2d, IC50 = 1.61 μM; 21, IC50 = 3.05 μM; and 27, IC50 = 3.34 μM) showed aromatase inhibitory activity with half maximal inhibitory concentration (IC50) values in the low micromolar concentrations. With regard to the QR1 induction activity, 11 exhibited the highest QR1 induction ratio (IR) with a low concentration to double activity (CD) value (IR = 8.34, CD = 2.75 μM), while 7 showed the most potent CD value of 1.12 μM. A dual acting compound 24 showed aromatase inhibition (IC50 = 9.00 μM) as well as QR1 induction (CD = 5.76 μM) activities. Computational docking studies using CDOCKER (Discovery Studio 3.5) provided insight in regard to the potential binding modes of 2-arylindoles within the aromatase active site. Predominantly, the 2-arylindoles preferred binding with the 2-aryl group toward a small hydrophobic pocket within the active site. The C-5 electron withdrawing group on indole was predicted to have an important role and formed a hydrogen bond with Ser478 (OH). Alternatively, meta-pyridyl analogs may orient with the pyridyl 3′-nitrogen coordinating with the heme group.

Selective synthesis of indazoles and indoles via triazene-alkyne cyclization switched by different metals

We described two orthogonal heterocycle syntheses, where an arene bearing both an alkyne and a triazene functionality underwent two distinct cyclization pathways mediated by different transition metals. Starting from the same substrates, a synthesis of 2H

Synthesis of 2-arylindole derivatives and evaluation as nitric oxide synthase and NFκB inhibitors

Development of small molecule drug-like inhibitors blocking both nitric oxide synthase and NFκB could offer a synergistic therapeutic approach in the prevention and treatment of inflammation and cancer. During the course of evaluating the biological potential of a commercial compound library, 2-phenylindole (1) displayed inhibitory activity against nitrite production and NFκB with IC50 values of 38.1 ± 1.8 and 25.4 ± 2.1 μM, respectively. Based on this lead, synthesis and systematic optimization have been undertaken in an effort to find novel and more potent nitric oxide synthase and NFκB inhibitors with antiinflammatory and cancer preventive potential. First, chemical derivatizations of 1 and 2-phenylindole-3-carboxaldehyde (4) were performed to generate a panel of N-alkylated indoles and 3-oxime derivatives 2-7. Second, a series of diversified 2-arylindole derivatives (10) were synthesized from an array of substituted 2-iodoanilines (8) and terminal alkynes (9) by applying a one-pot palladium catalyzed Sonogashira-type alkynylation and base-assisted cycloaddition. Subsequent biological evaluations revealed 3-carboxaldehyde oxime and cyano substituted 2-phenylindoles 5 and 7 exhibited the strongest nitrite inhibitory activities (IC50 = 4.4 ± 0.5 and 4.8 ± 0.4 μM, respectively); as well as NFκB inhibition (IC50 = 6.9 ± 0.8 and 8.5 ± 2.0 μM, respectively). In addition, the 6′-MeO-naphthalen-2′-yl indole derivative 10at displayed excellent inhibitory activity against NFκB with an IC50 value of 0.6 ± 0.2 μM.

Photochemistry of acyloximes: Synthesis of heterocycles and natural products

New applications of the photochemically generated iminyl radicals ring closure onto phenyl, thiophenyl, and pyridinyl rings are presented. The influence on the reactivity of different substituent throughout the acyloxime structure is discussed. Some obser

A versatile synthetic route to 11H-indolo[3,2-c]isoquinolines

A wide variety of indoloisoquinoline derivatives are prepared from the acid-catalyzed cyclization of 3-amido-2-phenylindoles, which in turn were obtained from the Beckmann rearrangement of 2-phenylindole-3-oximes.

Stereochemistry of Indole-2-oximes and Synthesis of Isoxazolylindoles

5-Methylindole-2-carboxaldehydes (1a and 1b) on bromination with NBS yield the corresponding 3-bromo derivatives (2a and 2b) which have been converted into the oximes (3a and 3b).The attempted dehydrobromination of 3a and 3b with ethanolic KOH, K2CO3 in e

A New Route to Indoloisoquinolines

2-Phenylindole-3-carbaldoximes (2a-d) on cyclization with alcoholic sulphuric acid give δ-carbolines, indolo-isoquinolines (5a-d) and not the γ-carbolines.This constitutes a new route to δ-carbolines.