91634-11-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1-METHYL-1H-INDOLE-5-CARBONITRILE is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and reactivity contribute to the development of new and effective compounds for medical and agricultural applications.
Used in Dye and Pigment Production:
1-METHYL-1H-INDOLE-5-CARBONITRILE is also employed as an intermediate in the production of dyes and pigments, where its chemical properties are harnessed to create a wide range of colorants for different industries.
Used in Organic Chemistry Research:
1-METHYL-1H-INDOLE-5-CARBONITRILE is a valuable compound in organic chemistry research, where its structure and reactivity are studied to understand and develop new synthetic pathways and methodologies.

InChI:InChI=1/C10H8N2/c1-12-5-4-9-6-8(7-11)2-3-10(9)12/h2-6H,1H3

Upstream product

• 15861-24-2 1H-indole-5-carbonitrile 
• 74-88-4 methyl iodide 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 192182-55-1 (1-methyl-1H-indol-5-yl)boronic acid 
• 10075-52-2 5-bromo-1-methyl-H-indole 
• 616-38-6 carbonic acid dimethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 77287-34-4 formamide 
• 75-05-8 acetonitrile 
• 7321-55-3 2,2-dimethylmalononitrile 
• 119072-55-8 tert-butylisonitrile 
• 280563-07-7 1-methyl-5-iodoindole 
• 105-56-6 ethyl 2-cyanoacetate 
• 1121707-33-2 1-methyl-6-trimethylsilyl-1H-indol-5-yl trifluoromethanesulfonate 

Downstream Products

• 256934-83-5 1-methyl-5-[5-(3,4,5-trimethoxy-phenyl)-4,5-dihydro-oxazol-2-yl]-1H-indole 
• 256934-83-5 1-methyl-5-[5-(3,4,5-trimethoxy-phenyl)-4,5-dihydro-oxazol-2-yl]-1H-indole 
• 884507-17-9 (1-methyl-1H-indol-5-yl)methanamine 
• 741709-19-3 1-methyl-2-phenyl-1H-indole-5-carbonitrile 
• 128742-76-7 methyl 1-methyl-1H-indole-5-carboxylate 

Relevant academic research and scientific papers

Revisiting the synthesis of aryl nitriles: a pivotal role of CAN

Facilitated by the dual role of Ceric Ammonium Nitrate (CAN), herein we report a cost-effective approach for the cyanation of aryl iodides/bromides with CAN-DMF as an addition to the existing pool of combined cyanation sources. In addition to being an oxidant, CAN acts as a source of nitrogen in our protocol. The reaction is catalyzed by a readily available Cu(ii) salt and the ability of CAN to generate ammonia in the reaction medium is utilized to eliminate the additional requirement of a nitrogen source, ligand, additive or toxic reagents. The mechanistic study suggests an evolution of CN?leading to the synthesis of a variety of aryl nitriles in moderate to good yields. The proposed mechanism is supported by a series of control reactions and labeling experiments.

Tandem iridium-catalyzed decarbonylative c-h activation of indole: Sacrificial electron-rich ketone-assisted bis-arylsulfenylation

Described herein is a decarbonylative tandem C-H bis-arylsulfenylation of indole at the C2 and C4 C-H bonds through the use of pentamethylcyclopentadienyl iridium dichloride dimer ([Cp?IrCl2]2) catalyst and disulfides. A new sacrificial electron-rich adamantoyl-directing group facilitates indole C-H bis-functionalization with a traceless in situ removal. Various differently substituted disulfides can be easily accommodated in this reaction by a coordination to Ir(III) through the formation of six- and five-membered iridacycles at the C2 and C4 positions, respectively. Mechanistic studies show that a C-H activation-induced C-C activation is involved in the catalytic cycle.

HTS-based discovery and optimization of novel positive allosteric modulators of the α7 nicotinic acetylcholine receptor

HTS campaign of the corporate compound collection resulted in a novel, oxalic acid diamide scaffold of α7 nACh receptor positive allosteric modulators. During the hit expansion, several derivatives, such as 4, 11, 17 demonstrated not only high in vitro potency, but also in vivo efficacy in the mouse place recognition test. The advanced hit molecule 11 was further optimized by the elimination of the putatively mutagenic aromatic-amine building block that resulted in a novel, aminomethylindole compound family. The most balanced physico-chemical and pharmacological profile was found in case of compound 55. Docking study revealed an intersubunit binding site to be the most probable for our compounds. 55 demonstrated favorable cognitive enhancing profile not only in scopolamine-induced amnesia (place recognition test in mice) but also in natural forgetting (novel object recognition test in rats). Compound 55 was, furthermore, active in a cognitive paradigm of high translational value, namely in the rat touch screen visual discrimination test. Therefore, 55 was selected as a lead compound for further optimization. Based on the obtained favorable results, the invented aminomethylindole cluster may provide a viable approach for cognitive enhancement through positive allosteric modulation of α7 nAChRs.

Synthesis of 3-halogenated 2,3′-biindoles by a copper-mediated 2,3-difunctionalization of indoles

A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3′-biindoles is described herein. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allows the regioselective formation of C-C and C-X (X = Cl & Br) bonds in one single operation. Here the copper metal salt serves not only as a catalyst but also as a reactant to provide the source of halogen. This operationally simple procedure avoids the utilization of environmentally unfriendly reagents and displays good functional group compatibility. Noteworthily, the introduction of halogen into molecules would offer great potential for further chemical transformations. This journal is

Design, synthesis and biological evaluation of 1-alkyl-5/6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbonitriles as novel xanthine oxidase inhibitors

Xanthine oxidase (XO) has emerged as an important target for the treatment of hyperuricemia and gout. In this study, to obtain novel nonpurine XO inhibitors, a series of 1-alkyl-5/6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbonitriles (1a-1u, 2c, 2e, 2h and 2n) were designed using a bioisosteric replacement strategy and were synthesized through a five-step procedure with good yields. Thereafter, the in vitro XO inhibitory potencies of these compounds were evaluated by spectrophotometry, showing inhibitory profiles in the micromolar/submicromolar range. Particularly, compound 1h emerged as the strongest XO inhibitor, with an IC50 value of 0.36 μM, which was approximately 21-fold more potent than the positive control allopurinol. Additionally, the structure-activity relationships revealed that the 5-oxo-4,5-dihydro-1,2,4-oxadiazole moiety linked at the 5-position of the indole scaffold was more preferable than the 6-position for the XO inhibitory potency. Enzyme kinetic studies indicated that compound 1h acted as a mixed-type XO inhibitor. Moreover, molecular modeling studies were performed on compound 1h to gain insights into its binding modes with XO. The results showed that the 5-oxo-4,5-dihydro-1,2,4-oxadiazole moiety could interact with Arg880 and Thr1010 in the innermost part of the active pocket through hydrogen bonds, while the cyano group could form hydrogen bonds with Asn768 and Lys771 in the subpocket. Furthermore, the in vivo hypouricemic effect of compound 1h was further investigated in a hyperuricemia rat model induced by potassium oxonate. The results suggested that compound 1h could effectively reduce serum uric acid levels at an oral dose of 10 mg/kg. Therefore, compound 1h could be a promising lead compound for the treatment of hyperuricemia and gout.

3-substituted indole-5-oxo-4, 5-dihydro-1, 2, 4-oxadiazole compound and application thereof

The invention belongs to the technical field of medicines, and particularly relates to a 3-substituted indole-5-oxo-4, 5-dihydro-1, 2, 4-oxadiazole compound and application thereof. The compound has astructure as shown in a general formula I or II, and R1 is described in the claims and the specification. The invention also relates to salts, tautomers and solvates of the compound, pharmaceutical compositions containing the salts, the tautomers and the solvates, and application of the salts, the tautomers and the solvates in preparation of medicines for treating and (or) preventing hyperuricemia and gout diseases.

Electrosynthesis of Dihydropyrano[4,3-b]indoles Based on a Double Oxidative [3+3] Cycloaddition

Oxidative [3+3] cycloadditions offer an efficient route for six-membered-ring formation. This approach has been realized based on an electrochemical oxidative coupling of indoles/enamines with active methylene compounds followed by tandem 6π-electrocyclization leading to the synthesis of dihydropyrano[4,3-b]indoles and 2,3-dihydrofurans. The radical–radical cross-coupling of the radical species generated by anodic oxidation combined with the cathodic generation of the base from O2 allows for mild reaction conditions for the synthesis of structurally complex heterocycles.

SPIROCHROMANE DERIVATIVES

The invention relates to spirochromane derivatives, or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof, as well as to pharmaceutical compositions containin

SUBSTITUTED (AZA)INDOLE DERIVATIVES

The invention relates to substituted (aza)indole derivatives, or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof, as well as to pharmaceutical compositions containing them and to their use as modulators of α7 nicotinic acetylcholine receptor activity in a mammalian subject. (I)

Discovery of Novel Indole-Based Allosteric Highly Potent ATX Inhibitors with Great in Vivo Efficacy in a Mouse Lung Fibrosis Model

Autotaxin (ATX) is the dominant catalytic enzyme accounting for the lipid mediator lysophosphatidic acid (LPA) through hydrolysis of lysophosphatidylcholine (LPC). There is great interest in developing nonacidic ATX inhibitors with a specific binding mode to serve as potential in vivo effective therapeutic tools. Herein, dating from a high-throughput screening (HTS) product Indole-1 (740 nM), a dedicated optimization campaign was implemented through derivatizing the-COOH group to versatile linkers that well-bridged the indole skeleton and the hydrophobic pocket binding groups. Ultimately, it was established that the coexistence of a carbamate linker and-OH-group-containing amines could generally furnish excellent indole-based ATX inhibitors with even below 1 nM in vitro activities. Two optimal entities were advanced to a bleomycin-induced mice pulmonary fibrosis model, which exerted promising efficacy in alleviating the damaged lung texture caused by bleomycin exposure. The novel carbamate-containing indole-based ATX inhibitors with a concrete binding mode may contribute to the identification of potential therapeutic agents to intervene in fibrotic diseases.