2826-91-7

Usage

Uses

Since the provided materials do not specify the exact applications of (E)-2-methyl-3-(2-nitrovinyl)-1H-indole, the following uses are inferred based on its potential biological activities and pharmacological properties:
Used in Pharmaceutical Research:
(E)-2-methyl-3-(2-nitrovinyl)-1H-indole is used as a research chemical for exploring its potential biological activities and pharmacological properties. Its unique structure with a nitrovinyl and methyl group may contribute to its interactions with biological targets, making it a candidate for drug development.
Used in Chemical Synthesis:
In the chemical industry, (E)-2-methyl-3-(2-nitrovinyl)-1H-indole may be used as an intermediate in the synthesis of more complex organic compounds, particularly those with potential applications in medicine or other specialized fields.

InChI:InChI=1/C11H10N2O2/c1-8-9(6-7-13(14)15)10-4-2-3-5-11(10)12-8/h2-7,12H,1H3

Upstream product

• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 75-52-5 nitromethane 
• 95-20-5 2-methyl-1H-indole 
• 73430-27-0 1-dimethylamino-2-nitroethene 
• 82781-92-8 N,N-Dimethyl-2-nitroethylenamin 
• 91-55-4 2,3-dimethylindole 

Downstream Products

• 442633-00-3 2-fluoro-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide 
• 2731-06-8 2-methyltryptamine 
• 1392268-26-6 2-fluoro-4-hydroxy-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide 
• 1392268-27-7 N-(2-(5-chloro-2-methyl-1H-indol-3-yl)ethyl)-2-fluorobenzamide 
• 1392268-28-8 2-fluoro-4-methoxy-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide 
• 1392268-30-2 4-chloro-2-fluoro-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide 
• 442633-41-2 4-chloro-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide 
• 1392268-31-3 3-chloro-2-fluoro-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide 
• 1341160-88-0 3-methoxycarbonyl-3-[1-(2-methylindol-3-yl)-2-nitroethyl]-4-phenyl-2-pyrrolidone 
• 129376-66-5 (1S,2R,5S)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2'R,3S)-2-Methyl-1'-(4-toluenesulfonyl)spiro<3H-indole-3,3'-pyrrolidine>-2'-carboxylate 
• 129376-69-8 (R)-1-Phenyl-2-(<(tert-butyl)diphenylsilyl>oxy)ethyl (2'S,3R)-2-Methyl-1'-(4-toluenesulfonyl)spiro<3H-indole-3,3'-pyrrolidine>-2'-carboxylate 

Relevant academic research and scientific papers

Novel Myocyte Enhancer Factor 2 (MEF2) modulators

The present disclosure provides novel compounds capable of functioning as Myoctye Enhancer Factor 2 (MEF2) modulators, as well as compositions, pharmaceutical formulations, methods of synthesis and kits. Also provided are methods of treating a condition regulatable by MEF2 and/or MEF2 cofactors using the compounds, compositions, pharmaceutical formulations, and kits provided herein.

Visible-Light-Induced Trifluoromethylation of Isonitrile-Substituted Indole Derivatives: Access to 1-(Trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indole and β-Carboline Derivatives

A visible-light-induced trifluoromethylation of isonitrile-substituted indole derivatives has been developed from the reaction of isonitrile-substituted indoles with Togni II reagent, affording 1-(trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indoles in mo

An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives

An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.

Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-Type cascade to construct polycyclic spiroindolines

A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N-dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction.

Rhodium-catalyzed asymmetric addition of arylboronic acids to indolylnitroalkenes

Indolylnitroethanes and their derivatives are key intermediates to many bioactive structures. Most approaches to access chiral indolylnitroethanes involve organocatalyzed or metal-catalyzed asymmetric Friedel-Crafts reaction of indoles with nitroalkenes.

Structural Characterization and Computer-Aided Optimization of a Small-Molecule Inhibitor of the Arp2/3 Complex, a Key Regulator of the Actin Cytoskeleton

CK-666 (1) is a recently discovered small-molecule inhibitor of the actin-related protein 2/3 (Arp2/3) complex, a key actin cytoskeleton regulator with roles in bacterial pathogenesis and cancer cell motility. Although 1 is commercially available, the crystal structure of Arp2/3 complex with 1 bound has not been reported, making its mechanism of action uncertain. Furthermore, its relatively low potency increases its potential for off-target effects invivo, complicating interpretation of its influence in cell biological studies and precluding its clinical use. Herein we report the crystal structure of 1 bound to Arp2/3 complex, which reveals that 1 binds between the Arp2 and Arp3 subunits to stabilize the inactive conformation of the complex. Based on the crystal structure, we used computational docking and free-energy perturbation calculations of monosubstituted derivatives of 1 to guide optimization efforts. Biochemical assays of ten newly synthesized compounds led to the identification of compound 2, which exhibits a threefold increase in inhibitory activity invitro relative to 1. In addition, our computational analyses unveiled a surface groove at the interface of the Arp2 and Arp3 subunits that can be exploited for additional structure-based optimization.

Synthesis of 3-indolylpyrroles via base-mediated cycloaddition of TOSMIC with activated indole-2/3-vinylenes

A synthesis of various types of 3-indolylpyrroles is reported involving a base-mediated 1,3-dipolar cycloaddition of TOSMIC with activated indole-2/3-vinylenes. Copyright Taylor & Francis Group, LLC.

Novel and potent human and rat β3-adrenergic receptor agonists containing substituted 3-indolylalkylamines

A novel series of 2-(3-indolyl)alkylamino-1-(3-chlorophenyl)ethanols was prepared and evaluated for in vitro ability to stimulate cAMP production in Chinese hamster ovary cells expressing cloned human β3-AR. The optically active 30a was found to be the most potent and selective human β3-AR agonist in this series with an EC50 value of 0.062 nM. In addition, 30a selectivity for human β3-AR was 210-fold and 103-fold that for human β2-AR and β1-AR, respectively. Furthermore, 30a showed potent agonistic activity at rat β3-AR.

Indole derivatives with antimycobacterial activity

1,3-Dinitro-2-(indol-3'-yl)-propanes 3 are synthesized by Michael reaction of nitromethane with the indolylnitroethenes 2. - Reaction of the aldehydes 4 and 10 with the benzylamines 12 as well as the reaction of the indolylalkylamines 6a and 9a with the benzaldehydes 11 lead to Schiff bases which are reduced to N-benzyl-(indol-3-ylmethyl)-amines 13 and N-benzyl-(indol-3-ylethyl)-amines 14, respectively; tert amines 16 are synthesized via the formamides 15, amines 18 are prepared according to Mannich. - Inhibitory effects on Mycobacterium tuberculosis H 37 Ra are investigated, a structure-activity relationship is discussed.

48. Diastereoselective Spirocyclization of C-(Alkyloxycarbonyl)formimines of 2-Substituted 1H-Indole-3-ethanamines (= Tryptamines): Basic Studies

C-(Alkoxycarbonyl)formimines of type 15-18 were derived from the 2-substituted tryptamines 2, 9, 10, and 11 and transformed with tosyl chloride into tricyclic 3-spiroindoles of types 19-22 (Scheme 3).The influence of the homochiral alkoxy moieties A-D on the stereochemical outcome of this reaction was studied.Good-to-excellent diastereoselectivities were observed with the (-)-8-(phenylmenth-3-yl)oxy group (B) as homochiral auxiliary.The structures of the tricycles 4, (2'R,3S)-19B, and (2'S,3R)-20C were established by X-ray analysis, the structures of the others by NOE and CD studies, and by chemical correlation.Possibilities to explain the steric course of the spirocyclizations are discussed.