39070-13-8

Basic information

• Product Name: Ethyl 3-Methyl-2-nitro-3H-iMidazole-4-carboxylate
• Synonyms: Ethyl 3-Methyl-2-nitro-3H-iMidazole-4-carboxylate;1H-IMidazole-5-carboxylic acid, 1-Methyl-2-nitro-, ethyl ester;Ethyl 1-Methyl-2-nitroiMidazole-5-carboxylate;Ethyl 3-Methyl-2-nitro-3H-iMidazole-4-carboxylate-5;1-methyl-2-nitro-1H-imidazole-5-carboxylate;ethyl 3-methyl-2-nitroimidazole-4-carboxylate
• CAS NO: 39070-13-8
• Molecular Formula: C₇H₉N₃O₄
• Molecular Weight: 199.16406
• EINECS: -0
• Mol File: 39070-13-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 379.2°Cat760mmHg
• Flash Point: 183.1°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 5.97E-06mmHg at 25°C
• Refractive Index: 1.584
• PKA: -1.61±0.25(Predicted)
• CAS DataBase Reference: Ethyl 3-Methyl-2-nitro-3H-iMidazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-Methyl-2-nitro-3H-iMidazole-4-carboxylate(39070-13-8)
• EPA Substance Registry System: Ethyl 3-Methyl-2-nitro-3H-iMidazole-4-carboxylate(39070-13-8)

Safety Data

• Hazardous Substances Data: 39070-13-8(Hazardous Substances Data)

Usage

General Description

Ethyl 3-Methyl-2-nitro-3H-imidazole-4-carboxylate is a chemical compound with the molecular formula C8H10N4O4. It is a derivative of imidazole and is commonly used in organic synthesis and pharmaceutical research. Ethyl 3-Methyl-2-nitro-3H-iMidazole-4-carboxylate has demonstrated potential antimicrobial and antifungal properties, making it a valuable component in drug development and disease control. Its nitro group also makes it a versatile building block for the synthesis of various pharmaceutical compounds and agrochemicals. Additionally, ethyl 3-Methyl-2-nitro-3H-imidazole-4-carboxylate may have other biological activities that could be explored in future research.

InChI:InChI=1/C7H9N3O4/c1-3-14-6(11)5-4-8-7(9(5)2)10(12)13/h4H,3H2,1-2H3

Upstream product

• 39070-12-7 C₇H₁₁N₃O₂*(x)ClH 
• 89531-66-8 ethyl 2-(N-methylformamido)acetate 
• 177760-04-2 ethyl 2-amino-1-N-methyl-1H-imidazole-5-carboxylate 
• 39070-12-7 2-amino-5-carbethoxy-1-methylimidazole hydrochloride 

Downstream Products

• 40647-83-4 1-(1-methyl-2-nitro-1H-imidazol-5-yl)ethan-1-one 
• 39928-74-0 1-methyl-2-nitro-1H-imidazole-5-carbaldehyde 
• 918633-87-1 evofosfamide 
• 246536-87-8 (1-methyl-2-nitro-1H-imidazol-5-yl)methyl (4-nitrophenyl) carbonate 

Relevant articles and documents

Development and pre-clinical testing of a novel hypoxia-activated KDAC inhibitor

Tumor hypoxia is associated with therapy resistance and poor patient prognosis. Hypoxia-activated prodrugs, designed to selectively target hypoxic cells while sparing normal tissue, represent a promising treatment strategy. We report the pre-clinical efficacy of 1-methyl-2-nitroimidazole panobinostat (NI-Pano, CH-03), a novel bioreductive version of the clinically used lysine deacetylase inhibitor, panobinostat. NI-Pano was stable in normoxic (21% O2) conditions and underwent NADPH-CYP-mediated enzymatic bioreduction to release panobinostat in hypoxia (2). Treatment of cells grown in both 2D and 3D with NI-Pano increased acetylation of histone H3 at lysine 9, induced apoptosis, and decreased clonogenic survival. Importantly, NI-Pano exhibited growth delay effects as a single agent in tumor xenografts. Pharmacokinetic analysis confirmed the presence of sub-micromolar concentrations of panobinostat in hypoxic mouse xenografts, but not in circulating plasma or kidneys. Together, our pre-clinical results provide a strong mechanistic rationale for the clinical development of NI-Pano for selective targeting of hypoxic tumors.

Compositions and methods for treating cancer

The invention provides a protected anti-neoplastic agent of the formula Hyp-N, wherein N is an anti-neoplastic agent and a protectable hydroxyl group of the anti-neoplastic is substituted with Hyp; Hyp is a moiety having the formula: wherein R 2 is hydrogen; R 3 is hydrogen or C 1 -C 6 alkyl; R 1 is C 1 -C 6 alkyl or C 1 -C 6 alkoxy, optionally substituted with one or more heteroatom-containing groups; and R 4 is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 alkoxy, optionally substituted with one or more heteroatom-containing groups.

Bioreductively activatable prodrug conjugates of phenstatin designed to target tumor hypoxia

A variety of solid tumor cancers contain significant regions of hypoxia, which provide unique challenges for targeting by potent anticancer agents. Bioreductively activatable prodrug conjugates (BAPCs) represent a promising strategy for therapeutic intervention. BAPCs are designed to be biologically inert until they come into contact with low oxygen tension, at which point reductase enzyme mediated cleavage releases the parent anticancer agent in a tumor-specific manner. Phenstatin is a potent inhibitor of tubulin polymerization, mimicking the chemical structure and biological activity of the natural product combretastatin A-4. Synthetic approaches have been established for nitrobenzyl, nitroimidazole, nitrofuranyl, and nitrothienyl prodrugs of phenstatin incorporating nor-methyl, mono-methyl, and gem-dimethyl variants of the attached nitro compounds. A series of BAPCs based on phenstatin have been prepared by chemical synthesis and evaluated against the tubulin-microtubule protein system. In a preliminary study using anaerobic conditions, the gem-dimethyl nitrothiophene and gem-dimethyl nitrofuran analogues were shown to undergo efficient enzymatic cleavage in the presence of NADPH cytochrome P450 oxidoreductase. Each of the eleven BAPCs evaluated in this study demonstrated significantly reduced inhibitory activity against tubulin in comparison to the parent anti-cancer agent phenstatin (IC50?=?1.0?μM). In fact, the majority of the BAPCs (seven of the eleven analogues) were not inhibitors of tubulin polymerization (IC50?>?20?μM), which represents an anticipated (and desirable) attribute for these prodrugs, since they are intended to be biologically inactive prior to enzyme-mediated cleavage to release phenstatin.