39070-14-9

Basic information

• Product Name: (3-METHYL-2-NITRO-3H-IMIDAZOL-4-YL)-METHANOL
• Synonyms: (3-METHYL-2-NITRO-3H-IMIDAZOL-4-YL)-METHANOL;1H-Imidazole-5-methanol, 1-methyl-2-nitro- (9CI);Nsc307224;(1-Methyl-2-nitro-1H-iMidazol-5-yl)Methanol;1H-IMidazole-5-Methanol, 1-Methyl-2-nitro-;(3-Methyl-2-nitro-3H-iMidazol-4-yl);1-Methyl-2-nitroiMidazole-5-Methanol;(3-METHYL-2-NITRO-3H-IMIDAZOL-4-YL)-METHANOL hcl
• CAS NO: 39070-14-9
• Molecular Formula: C₅H₇N₃O₃
• Molecular Weight: 157.13
• Product Categories: ALDEHYDE
• Mol File: 39070-14-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 422.221 °C at 760 mmHg
• Flash Point: 209.152 °C
• Appearance: /
• Density: 1.545 g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.80±0.10(Predicted)
• CAS DataBase Reference: (3-METHYL-2-NITRO-3H-IMIDAZOL-4-YL)-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (3-METHYL-2-NITRO-3H-IMIDAZOL-4-YL)-METHANOL(39070-14-9)
• EPA Substance Registry System: (3-METHYL-2-NITRO-3H-IMIDAZOL-4-YL)-METHANOL(39070-14-9)

Safety Data

• Hazardous Substances Data: 39070-14-9(Hazardous Substances Data)

Usage

Description

(3-METHYL-2-NITRO-3H-IMIDAZOL-4-YL)-METHANOL is a chemical reagent characterized by its yellow to orange crystalline powder form. It is primarily utilized in the synthesis of prodrugs, particularly those targeting hypoxic tissues.

Uses

Used in Pharmaceutical Industry:
(3-METHYL-2-NITRO-3H-IMIDAZOL-4-YL)-METHANOL is used as a chemical reagent for the synthesis of prodrugs targeting hypoxic tissues. Its application in this field is due to its ability to contribute to the development of drugs that can specifically target and treat hypoxic regions within the body, such as those found in certain types of cancers.

Upstream product

• 39070-12-7 C₇H₁₁N₃O₂*(x)ClH 
• 885281-27-6 (2-amino-1-methyl-1H-imidazol-5-yl)methanol 
• 127056-47-7 5-(tert-butyldimethylsilanyloxymethyl)-1-methyl-1H-imidazole 
• 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 
• 39928-74-0 1-methyl-2-nitro-1H-imidazole-5-carbaldehyde 
• 39070-12-7 2-amino-5-carbethoxy-1-methylimidazole hydrochloride 
• 50700-55-5 1-methyl-2-nitro-1H-imidazole-5-carboxylic acid 
• 39070-13-8 ethyl 1-N-methyl-2-nitro-1H-imidazole-5-carboxylate 
• 177760-04-2 ethyl 2-amino-1-N-methyl-1H-imidazole-5-carboxylate 

Downstream Products

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

Relevant articles and documents

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Hypoxia-activated pro-drugs of the KDAC inhibitor vorinostat (SAHA)

Hypoxia (lower than normal oxygen) is a characteristic of most solid tumours that results in poor cancer patient prognosis. The difference in cellular environment between normoxia (21percent oxygen) or physoxia (4–7.5percent oxygen) and hypoxia (2.0percent oxygen) causes increased resistance to radio- and chemotherapy, but also provides the opportunity to selectively release hypoxia-activated pro-drugs. This approach potentially allows targeting of chemotherapies, including lysine deacetylase (KDAC) inhibitors, to the hypoxic fraction of cells. Here, we report initial work on the development of KDAC inhibitors that are selectively released in hypoxic conditions. We have shown that the addition of a 4-nitrobenzyl (NB) or 1-methyl-2-nitroimidazole (NI) bioreductive group onto the hydroxamic acid moiety of SAHA, giving NB-SAHA and NI-SAHA, abolishes KDAC inhibition activity. Both NB-SAHA and NI-SAHA undergo enzyme-mediated bioreduction, in a hypoxia-dependent manner, to release SAHA selectively in 0.1percent oxygen. This work provides an important foundation for further investigations into the targeted release of KDAC inhibitors in hypoxic tumours.

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.