61861-88-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-5-nitro-1H-indole is utilized as a building block for the synthesis of various organic compounds. Its role in the creation of pharmaceuticals is significant due to its potential biological activities, which include anti-tumor and anti-inflammatory properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Methyl-5-nitro-1H-indole serves as a key component in the synthesis of different organic compounds. Its application is crucial for developing new agrochemical products that can address various agricultural needs.

Upstream product

• 60891-75-0 2-methyl-6-nitroindolizine 
• 6146-52-7 5-nitroindole 
• 6625-96-3 5-nitro-1H-indole-3-carbaldehyde 
• 4769-96-4 6-nitroindole 
• 10553-13-6 6-nitro-1H-indole-3-carboxaldehyde 
• 100-16-3 4-nitrophenylhydrazone 
• 13296-94-1 2-bromo-4-nitroaniline 
• 67-56-1 methanol 
• 106-95-6 allyl bromide 
• 121-87-9 2-Chloro-4-nitroaniline 
• 3078-02-2 1-(4-nitrophenyl)-2-propylidenehydrazine 

Downstream Products

• 1640122-63-9 N-acetyl-3-(4-methoxyphenyl)-3-methyl-5-nitroindoline 
• 1640122-68-4 N-acetyl-3-(4-methoxyphenyl)-3-methyl-6-nitroindoline 

Relevant academic research and scientific papers

A Preclinical Candidate Targeting Mycobacterium tuberculosis KasA

Published Mycobacterium tuberculosis β-ketoacyl-ACP synthase KasA inhibitors lack sufficient potency and/or pharmacokinetic properties. A structure-based approach was used to optimize existing KasA inhibitor DG167. This afforded indazole JSF-3285 with a 30-fold increase in mouse plasma exposure. Biochemical, genetic, and X-ray studies confirmed JSF-3285 targets KasA. JSF-3285 offers substantial activity in an acute mouse model of infection and in the corresponding chronic infection model, with efficacious reductions in colony-forming units at doses as low as 5 mg/kg once daily orally and improvement of the efficacy of front-line drugs isoniazid or rifampicin. JSF-3285 is a promising preclinical candidate for tuberculosis. Inoyama et al. disclose the optimization of an indazole antitubercular targeting the β-ketoacyl-ACP synthase KasA. A structure-based approach has overcome significant issues with mouse metabolic stability and pharmacokinetics. A preclinical drug candidate has been delivered with efficacy in a mouse model of chronic M. tuberculosis infection at 5 mg/kg dosing.

FUSED TETRAZOLES AS LRRK2 INHIBITORS

The present invention is directed to fused tetrazoles of formula (IA) which are inhibitors of LRRK2 and are useful in the treatment of CNS disorders.

THERAPEUTIC INDOLES

The invention provides compounds of formula I and salts thereof wherein R1-R4 have any of the meanings described in the specification. The compounds are useful for treating bacterial infections (e.g. tuberculosis).

Diamine monomer containing N-pyrimidinyl indole structure and preparation method thereof

The invention discloses a diamine monomer containing an N-pyrimidinyl indole structure and a preparation method thereof. The preparation method specifically comprises the following steps of enabling a compound A, a nitrophenylboronic acid compound, silver trifluoroacetate and a catalyst [RhCp*C12]2 to react in methanol, so as to obtain a nitro compound B; under the protection of N2, dissolving the nitro compound B in dimethyl sulfoxide, under conditions of active iron powder and acetic acid, refluxing, and carrying out a reaction, and reducing nitro to amino, so that the diamine monomer C containing the N-pyrimidinyl indole structure is obtained. The diamine monomer containing the N-pyrimidinyl indole structure, which is provided by the invention, is simple in preparation method, easy in the control of a reaction process, further, is higher in yield, can be used as a diamine monomer for synthesizing polyimide, and has potential application values in special fields of high temperature resistance, flexible display substrates and the like.

Iridium-catalyzed methylation of indoles and pyrroles using methanol as feedstock

Iridium-catalyzed methylation of indoles and pyrroles using methanol as the methylating agent was achieved. This transformation takes place via a borrowing hydrogen methodology under an air atmosphere, which constitutes a direct route to 3-methyl-indoles and methyl-pyrroles.

Regioselective hydroarylation reactions of C3 electrophilic N-acetylindoles activated by FeCl3: An entry to 3-(Hetero)arylindolines

A method for the direct and rare umpolung of the 3 position of indoles is reported. The activation of N-acetylindole with iron(III) chloride allows the C-H addition of aromatic and heteroaromatic substrates to the C2-C3 double bond of the indole nucleus to generate a quaternary center at C3 and leads regioselectively to 3-arylindolines. Optimization, scope (50 examples), practicability (gram scale, air atmosphere, room temperature), and mechanistic insights of this process are presented. Synthetic transformations of the indoline products into drug-like compounds are also described.

Enamine rearrangement of pyridinium salts to indole ring: A combined experimental and molecular modeling study

N-Alkyl pyridinium (II) and N-alkyl isoquinolinium salts V undergo cyclization reaction when heated with sodium bicarbonate to give the corresponding indolizine derivatives III and VI, respectively, which undergo ring opening and recyclization reactions when heated with aqueous sodium hydroxide to give the corresponding indole derivatives IV and IX, respectively. Molecular modeling tools including Molecular Mechanics using Augmented MM3 parameters followed by geometry optimization calculations in MO-G using PM3 parameters were performed to gain better understanding and more insights on the thermodynamic properties of the recyclization reactions of compounds IIa-g to the corresponding IIIa-g and IIIa-g to the corresponding IVa-g. The results were in excellent agreement with the experimental data and hence were proven to be a good tool in explaining different yields % because of the steric and electronic effects of electron-withdrawing groups on the reactivity of the pyridine ring for nucleophilic attack.

One-pot N-alkylation/Heck approach to substituted indoles

Here, we report the palladium-catalyzed one-pot N-alkylation/Heck cyclization of anilines to substituted indoles employing Pd(OAc)2/XPhos. The scope and limitations of this methodology will be described.