50700-55-5

Basic information

• Product Name: 1-Methyl-2-nitro-1H-iMidazole-5-carboxylic acid
• Synonyms: 1-Methyl-2-nitro-1H-iMidazole-5-carboxylic acid;1H-IMidazole-5-carboxylic acid, 1-Methyl-2-nitro-;1-Methyl-2-nitro-1H-iMidazole-5-carboxylic acid-6;EOS-61726
• CAS NO: 50700-55-5
• Molecular Formula: C₅H₅N₃O₄
• Molecular Weight: 171.1109
• Mol File: 50700-55-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 493.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.72±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.44±0.26(Predicted)
• CAS DataBase Reference: 1-Methyl-2-nitro-1H-iMidazole-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-2-nitro-1H-iMidazole-5-carboxylic acid(50700-55-5)
• EPA Substance Registry System: 1-Methyl-2-nitro-1H-iMidazole-5-carboxylic acid(50700-55-5)

Safety Data

• Hazardous Substances Data: 50700-55-5(Hazardous Substances Data)

Usage

General Description

1-Methyl-2-nitro-1H-imidazole-5-carboxylic acid is a chemical compound with the molecular formula C7H6N4O4. It is an organic compound that contains a nitro group, imidazole ring, and carboxylic acid group. 1-Methyl-2-nitro-1H-iMidazole-5-carboxylic acid is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used in the manufacturing of dyes, pigments, and other organic compounds. The chemical has potential applications in the medical and agricultural industries due to its unique structure and properties. Additionally, it is important to handle this compound with caution, as it may pose health and environmental risks if not properly managed.

Upstream product

• 40361-79-3 1-methyl-2-nitro-1H-imidazole-5-carboxylic acid methyl ester 
• 40361-77-1 2-amino-1-methyl-1H-imidazole-5-carboxylic acid methyl ester 
• 39070-13-8 ethyl 1-N-methyl-2-nitro-1H-imidazole-5-carboxylate 

Downstream Products

• 304015-66-5 (1-methyl-2-nitro-1H-imidazol-5-yl)methyl (4-(hydroxymethyl)phenyl)carbamate 
• 304016-33-9 (1-methyl-2-nitro-1H-imidazol-5-yl)methyl (4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl)carbamate 
• 39928-74-0 1-methyl-2-nitro-1H-imidazole-5-carbaldehyde 
• 246536-87-8 (1-methyl-2-nitro-1H-imidazol-5-yl)methyl (4-nitrophenyl) carbonate 
• 39070-14-9 1-methyl-2-nitro-5-hydroxymethylimidazole 
• 67855-45-2 (6R)-3-methyl-7t-(3-methyl-2-nitro-3H-imidazole-4-carbonylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Relevant articles and documents

Rational Design for Nitroreductase (NTR)-Responsive Proteolysis Targeting Chimeras (PROTACs) Selectively Targeting Tumor Tissues

The catalytic properties of proteolysis targeting chimeras (PROTACs) may lead to uncontrolled off-tissue target degradation that causes potential toxicity, limiting their clinical applications. The precise control of this technology in a tissue-selective manner can minimize the potential toxicity. Hypoxia is a hallmark of most solid tumors, accompanied by elevated levels of nitroreductase (NTR). Based on this character, we presented a type of NTR-responsive PROTACs to selectively degrade proteins of interest (POI) in tumor tissues. Compound 17-1 was the first NTR-responsive PROTAC synthesized by incorporating the caging group on the Von Hippel-Lindau (VHL) E3 ubiquitin ligase ligand. It could be activated by NTR to release the active PROTAC 17 to efficiently degrade the EGFR protein and subsequently exert antitumor efficacy. Thus, a general strategy for the precise control of PROTAC to induce POI degradation in tumor tissues by NTR was established, which provided a generalizable platform for the development of NTR-controlled PROTACs to achieve selective degradation.

TH-302 SOLID FORMS AND METHODS RELATED THERETO

The present invention provides a new method for making TH-302 and solid forms thereof. The compound in its solid form is an effective anti-cancer agent and may be used in various pharmaceutical compositions, and are particularly effective for the treatment of cancer. The invention also provides a method for preparing such compounds and forms and for treating cancer in a mammal comprising the step of administering a therapeutically effective amount of a solid form of TH-302 thereof.

Design, synthesis and evaluation of imidazolylmethyl carbamate prodrugs of alkylating agents

Two approaches to prodrugs of alkylating agents based on an imidazolylmethyl carbamate nucleus were explored. A 2-azido analogue (3) of the bis-carbamate carmethizole (1) displayed similar aerobic cytotoxicity to 1 in a panel of human and murine cell lines. Approaches to the 2-amino and 2- carbamoyl analogues are described. In the second approach an imidazolylmethanol was used as a 'trigger' linked via a carbamate to the alkylating agent N,N-bis(2-chlorethyl)amine (BCEA). Nitroimidazole and methylsulphinylimidazole carbamate prodrugs 6-8 were 5-20-fold less toxic than BCEA. Despite this deactivation in the prodrug form, little increase in cytotoxicity was observed under hypoxia. The data suggest that BCEA released on bioreduction is not sufficiently potent to contribute significant additional cytotoxicity. (C) 2000 Elsevier Science Ltd.