10242-03-2

Basic information

• Product Name: 6-NITROINDOLE-3-CARBOXYLIC ACID
• Synonyms: 6-NITROINDOLE-3-CARBOXYLIC ACID;6-NITRO-1H-INDOLE-3-CARBOXYLIC ACID;NSC 82382
• CAS NO: 10242-03-2
• Molecular Formula: C₉H₆N₂O₄
• Molecular Weight: 206.15
• Mol File: 10242-03-2.mol

Chemical Properties

• Melting Point: 265-267℃
• Boiling Point: 520.8 °C at 760 mmHg
• Flash Point: 268.8 °C
• Appearance: /
• Density: 1.632 g/cm³
• Vapor Pressure: 1.13E-11mmHg at 25°C
• Refractive Index: 1.761
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 6-NITROINDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-NITROINDOLE-3-CARBOXYLIC ACID(10242-03-2)
• EPA Substance Registry System: 6-NITROINDOLE-3-CARBOXYLIC ACID(10242-03-2)

Safety Data

• Hazardous Substances Data: 10242-03-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-NITROINDOLE-3-CARBOXYLIC ACID is used as a versatile intermediate for the synthesis of diverse organic compounds. Its unique chemical properties and structural features make it a useful building block in the creation of various complex organic molecules.
Used in Pharmaceutical Industry:
6-NITROINDOLE-3-CARBOXYLIC ACID is used as a key component in the development of new drugs. Its reactivity and structural characteristics allow for the design and synthesis of pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
6-NITROINDOLE-3-CARBOXYLIC ACID is used as an essential intermediate in the production of agrochemicals. Its properties enable the creation of compounds with pesticidal, herbicidal, or other agricultural applications, contributing to the development of effective solutions for crop protection and management.

InChI:InChI=1/C9H6N2O4/c12-9(13)7-4-10-8-3-5(11(14)15)1-2-6(7)8/h1-4,10H,(H,12,13)

Upstream product

• 91090-95-8 6-nitro-indole-3-carboxylic acid ethyl ester 
• 776-41-0 indole-3-carboxylic acid ethyl ester 
• 676476-90-7 2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)ethan-1-one 
• 771-50-6 1H-indole-3-carboxylic acid 
• 4769-96-4 6-nitroindole 
• 109175-09-9 methyl 6-nitro-1H-indole-3-carboxylate 

Downstream Products

• 4769-96-4 6-nitroindole 
• 90417-29-1 6-Amino-indol-carbonsaeure-(3) 
• 109175-09-9 methyl 6-nitro-1H-indole-3-carboxylate 

Relevant articles and documents

Synthesis of a Series of Diaminoindoles

A selection of 3,4-diaminoindoles were required for a recent drug discovery project. To this end, a 10-step synthesis was developed from 4-nitroindole. This synthesis was subsequently adapted and used to synthesize 3,5-; 3,6-; and 3,7-diaminoindoles from

Design and synthesis of indoleamine 2,3-dioxygenase 1 inhibitors and evaluation of their use as anti-tumor agents

Indoleamine 2,3-dioxygenase (IDO) 1 is the key enzyme for regulating tryptophan metabolism and is an important target for interrupting tumor immune escape. In this study, we designed four series of compounds as potential IDO1 inhibitors by attaching various fragments or ligands to indole or phenylimidazole scaffolds to improve binding to IDO1. The compounds were synthesized and their inhibitory activities against IDO1 and tryptophan 2,3-dioxygenase were evaluated. The cytotoxicities of the compounds against two tumor cell lines were also determined. Two compounds with a phenylimidazole scaffold (DX-03-12 and DX-03-13) showed potent IDO1 inhibition with IC50 values of 0.3–0.5 μM. These two IDO1 inhibitors showed low cell cytotoxicity, which indicated that they may exert their anti-tumor effect via immune modulation. Compound DX-03-12 was investigated further by determining the in vivo pharmacokinetic profile and anti-tumor efficacy. The pharmacokinetic study revealed that DX-03-12 had satisfactory properties in mice, with rapid absorption, moderate plasma clearance (～36% of hepatic blood flow), acceptable half-life (～4.6 h), and high oral bioavailability (～96%). Daily oral administration of 60 mg/kg of compound DX-03-12 decreased tumor growth by 72.2% after 19 days in a mouse melanoma cell B16-F10 xenograft model compared with the untreated control. Moreover, there was no obvious weight loss in DX-03-12-treated mice. In conclusion, compound DX-03-12 is a potent lead compound for developing IDO1 inhibitors and anti-tumor agents.

5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

NEW SUBSTITUTED ARYLSULPHONYLGLYCINES, THE PREPARATION THEREOF AND THE USE THEREOF AS PHARMACEUTICAL COMPOSITIONS

The present invention relates to substituted arylsulphonylglycines of general formula (I) wherein R, X, Y and Z are defined as in claim 1, the tautomers, enantiomers, diastereomers, mixtures thereof and salts thereof, which have valuable pharmacological properties, particularly the suppression of the interaction of glycogen phosphorylase a with the GL subunit of glycogen-associated protein phosphatase 1 (PP1 ), and their use as pharmaceutical compositions.