6960-42-5

Usage

Uses

Used in Pharmaceutical Industry:
7-Nitroindole is used as a reagent for the synthesis of protein kinase inhibitors, which are important in the development of drugs targeting various diseases, including cancer and inflammatory conditions.
Used in Enzyme Inhibition:
7-Nitroindole is used as a reactant for the preparation of inosine monophosphate dehydrogenase (IMPDH) inhibitors, which play a role in the regulation of purine biosynthesis and have potential applications in the treatment of autoimmune diseases and cancer.
Used in Metabolic Regulation:
7-Nitroindole is used as a reactant for the preparation of potential fructose 1,6-bisphosphatase inhibitors, which can help regulate glucose metabolism and may have implications in the treatment of diabetes and other metabolic disorders.
Used in Blood Coagulation:
7-Nitroindole is used as a reactant for the preparation of factor Xa inhibitors, which are involved in the blood coagulation process and can be used in the development of anticoagulant drugs.
Used in Hormone Regulation:
7-Nitroindole is used as a reactant for the preparation of antagonists of the mineralocorticoid receptor, which can help regulate hormone levels and may be useful in the treatment of hypertension and other hormone-related disorders.
Used in Antitumor Therapy:
7-Nitroindole is used as a reactant for the preparation of antitumor sulfonamides, which have potential applications in cancer treatment by inhibiting the growth of tumor cells.
Used in Inflammation Management:
7-Nitroindole is used as a reactant for the preparation of subtype-selective cyclooxygenase (COX) inhibitors, which can help manage inflammation and pain by targeting specific COX enzymes.
Used in Thrombin Receptor Modulation:
7-Nitroindole is used as a reactant for the preparation of thrombin protease-activated receptor (PAR-1) ligands, which can modulate the activity of thrombin receptors and have potential applications in the treatment of thrombotic and inflammatory disorders.
Used in Photochemistry:
7-Nitroindole has also been used as a photochemical precursor of the 2'-deoxyribonucleotide analog, which can be utilized in the synthesis of nucleic acid analogs and has potential applications in the development of antiviral and anticancer drugs.

Synthesis Reference(s)

Canadian Journal of Chemistry, 42, p. 1235, 1964 DOI: 10.1139/v64-189

InChI:InChI=1/C8H6N2O2/c11-10(12)7-3-1-2-6-4-5-9-8(6)7/h1-5,9H

Upstream product

• 6960-45-8 7-nitro-1H-indole-2-carboxylic acid 
• 1826-67-1 vinyl magnesium bromide 
• 528-29-0 1,2-Dinitrobenzene 
• 292853-66-8 2-(2-(2-nitrophenyl)hydrazono)propionic acid ethyl ester 
• 127-17-3 2-oxo-propionic acid 
• 3034-19-3 (2-nitrophenyl)hydrazine 
• 1360891-19-5 7-nitro-1H-indole-3-carboxylic acid 
• 75-07-0 acetaldehyde 
• 88-74-4 2-nitro-aniline 
• 112656-95-8 7-nitroindoline-2,3-dione 
• 6293-87-4 o-nitrophenylhydrazine hydrochloride 
• 53924-05-3 7-chloro-1H-indole 
• 6960-46-9 ethyl 7-nitroindole-2-carboxylate 

Downstream Products

• 5192-04-1 7-aminoindole 
• 165669-14-7 7-nitro-3-chloro-1H-indole 
• 852042-25-2 1-(3,5-dimethyl-phenyl)-7-nitro-1H-indole 
• 397864-11-8 3-bromo-7-nitro-1H-indole 
• 887615-92-1 1-benzenesulfonyl-3-bromo-1H-indol-7-ylamine 
• 887615-89-6 1-benzenesulfonyl-3-bromo-7-nitro-1H-indole 
• 887615-98-7 1-benzenesulfonyl-3-pyridin-4-yl-1H-indol-7-ylamine 
• 1654-34-8 N,N-dimethyl-1-(7-nitro-1H-indol-3-yl)-methanamine 
• 10553-14-7 7-nitro-1H-indole-3-carboxaldehyde 
• 165669-21-6 3-acetyl-7-nitro-1H-indole 
• 1000605-12-8 3-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-7-nitro-1H-indole 
• 1088706-25-5 C₁₇H₁₆N₂O₃ 
• 1088706-35-7 C₁₈H₁₈N₂O₃ 
• 1088706-39-1 C₁₄H₁₆N₂O₂ 

Relevant academic research and scientific papers

Method for catalytically synthesizing indole derivative by using ferrous complex

The invention relates to a method for catalytically synthesizing an indole derivative by using a ferrous complex, which comprises the following step: by taking arylamine and acetaldehyde as raw materials and a ferrous complex containing a meta-carboboryl methylpyridine structure as a catalyst, conducting reacting at room temperature to prepare the indole derivative. Compared with the prior art, the method utilizes the ferrous complex to efficiently catalyze the reaction of arylamine and acetaldehyde at room temperature to prepare the indole derivative, the reaction condition is mild, the substrate range is wide, and the method has high catalytic activity and yield.

Decarboxylation of indole-3-carboxylic acids under metal-free conditions

Two reaction systems have been developed for the decarboxylation of indole-3-carboxylic acids. The decarboxylation can be achieved smoothly under K2CO3-catalyzed or acetonitrile-promoted basic conditions. It provided an efficient and simple method for the transformation of indole-3-carboxylic acids and the corresponding indoles were isolated with good to excellent yields. From the experimental facts, we put forward the possible reaction mechanism.

Method for synthesizing 7-nitroindole

The invention relates to a method for synthesizing 7-nitroindole. The method comprises the following steps: subjecting oxime generated by condensation of o-nitroaniline, hydroxylamine and chloral to anucleophilic substitution reaction in a solvent under the action of an acidic substance and a drying agent, and performing hydrolyzing under alkaline conditions to generate an oximido intermediate; preparing 7-nitroisatin from the oximido intermediate in the presence of an acidic substance; and subjecting the 7-nitroisatin to reduction in a solvent by a system consisting of sodium borohydride andzirconium chloride so as to obtain the product 7-nitroindole. According to the method for synthesizing the 7-nitroindole, the product is obtained through three steps, so a production cycle is remarkably shortened and productivity is improved; used materials are simple and easily-available, so cost is low; reaction conditions are mild; the method is suitable for industrial mass production; meanwhile, the system of sodium borohydride and zirconium tetrachloride is used for replacing borane in the reduction step, so virulent, flammable and combustible raw materials are avoided, and the method issafer and environmentally friendlier.

Discovery of Potent Succinate-Ubiquinone Oxidoreductase Inhibitors via Pharmacophore-linked Fragment Virtual Screening Approach

Succinate-ubiquinone oxidoreductase (SQR) is an attractive target for fungicide discovery. Herein, we report the discovery of novel SQR inhibitors using a pharmacophore-linked fragment virtual screening approach, a new drug design method developed in our laboratory. Among newly designed compounds, compound 9s was identified as the most potent inhibitor with a Ki value of 34 nM against porcine SQR, displaying approximately 10-fold higher potency than that of the commercial control penthiopyrad. Further inhibitory kinetics studies revealed that compound 9s is a noncompetitive inhibitor with respect to the substrate cytochrome c and DCIP. Interestingly, compounds 8a, 9h, 9j, and 9k exhibited good in vivo preventive effects against Rhizoctonia solani. The results obtained from molecular modeling showed that the orientation of the R2 group had a significant effect on binding with the protein.

Sweet anion receptors: Recognition of chiral carboxylate anions by d-glucuronic-acid-decorated diindolylmethane

Anion receptors containing glucuronic acid were synthesized, and their anion binding ability studied. Chirality of anionic guests derived from mandelic acid and amino acids can be distinguished not only in terms of stability constants but also by signific

Benzenesulfonamide derivatives and pharmaceutical composition thereof

The present invention is related to derivatives of benzenesulfonamide represented by formula (I), and the pharmaceutical composition thereof. In addition, the benzenesulfonamide derivatives disclosed in the present invention can serve as potential cell cycle inhibitors, and thereby these benzenesulfonamide derivatives and the pharmaceutical composition thereof can be antitumor drug candidates, which might aim at cell cycle. Particularly, the benzenesulfonamide derivatives disclosed in the present invention may function as antitumor drugs to treat solid cancers.

Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics

(Chemical Equation Presented) An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent

A new and efficient one-pot synthesis of indoles

The synthesis of indoles is accomplished in high yields from phenylhydrazines and pyruvic acid using microwave irradiation.

Synthesis, structure and the binding properties of the amide-based anion receptors derived from 1H-indole-7-amine

Indole-7-amine was investigated as an alternative to aniline in construction of amide-based anion receptors. Replacement of aniline with indolamine introduces additional binding site-indolyl NH, which can enhance anion binding for more than five times. The molecular modelling of indole-containing receptors revealed the correlation between their conformational preferences and their affinity towards anions.

7-Nitroindoles

7-Aminoindole is prepared from a 7-nitroindole, which in turn is prepared from a halo-substituted β-dialkylamino-2-nitrostyrene.