4750-57-6

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-5-NITRO-1H-IMIDAZOLE-2-CARBALDEHYDE is used as an intermediate in the synthesis of various pharmaceuticals for its role in creating biologically active molecules. Its anti-inflammatory and antimicrobial properties contribute to the development of new drugs that can address a range of health conditions.
Used in Organic Chemistry:
In the realm of organic chemistry, 1-METHYL-5-NITRO-1H-IMIDAZOLE-2-CARBALDEHYDE is used as a building block for the preparation of heterocyclic compounds, which are essential components in many pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatility in forming complex structures makes it a valuable compound in this field.
Used as a Reagent in Chemical Reactions:
1-METHYL-5-NITRO-1H-IMIDAZOLE-2-CARBALDEHYDE is also used as a reagent in the synthesis of coordination complexes, which have applications in areas such as catalysis, materials science, and supramolecular chemistry. Its ability to participate in various chemical reactions makes it an indispensable tool for researchers and chemists.

InChI:InChI=1/C5H5N3O3/c1-7-4(3-9)6-2-5(7)8(10)11/h2-3H,1H3

Upstream product

• 551-92-8 dimetridazole 
• 3034-38-6 5-nitro-1H-imidazole 
• 936-05-0 1-methyl-2-hydroxymethyl-5-nitroimidazole 
• 57434-36-3 5-nitro-1-methyl-2-(2-dimethylaminovinyl)-imidazole 

Downstream Products

• 31435-31-1 6-acetoxy-2-(1-methyl-5-nitro-1H-imidazol-2-ylmethylene)-benzofuran-3-one 
• 31435-32-2 6-hydroxy-2-(1-methyl-5-nitro-1H-imidazol-2-ylmethylene)-benzofuran-3-one 
• 53409-75-9 azanidazole 
• 129661-56-9 methyl-1 (isoxazolidinone-3 imino-4 methyl)-2 nitro-5 imidazole 
• 129661-59-2 methyl-1 hydroxy-4' phenyliminomethyl-2 nitro-5 imidazole 
• 129661-57-0 methyl-1 methyl-4' phenyliminomethyl-2 nitro-5 imidazole 
• 129661-60-5 methyl-1 methoxy-4' phenyliminomethyl-2 nitro-5 imidazole 
• 129661-55-8 methyl-1 phenyliminomethyl-2 nitro-5 imidazole 
• 91017-58-2 Abunidazole 

Relevant academic research and scientific papers

Preparation, antimicrobial evaluation and mutagenicity of differently substituted [2-hydroxyaryl]-[1-methyl-5-nitro-1H-2-imidazolyl]methanols

An efficient preparation of the titled compounds is described, their antimicrobial activity and mutagenic properties being evaluated. Some of the studied compounds are non mutagenic and present a MIC as low as some of the usual standards in the field.

Design, Synthesis, and Trypanocidal Activity of Novel 5-Nitroimidazolyl O-Benzyloxime Ethers

In this paper, we describe the synthesis and the action against of the trypomastigote form of Trypanosoma cruzi of a new class of nitroimidazole-2-carbaldehyde O-benzyloximes. These derivatives were designed through the application of molecular hybridization concept between two potent antiprotozoal compounds, the 5-nitrothiophene-2-carbaldehyde O-oxime 6 and the trypanocidal piperidinyl-4-carbaldehyde O-benzyloxime 7 with the intention of reaching two distinct molecular targets of T.?cruzi. The activity of these benzyl ether derivatives was tested against the infective trypomastigote forms of T.?cruzi, and the derivative (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-nitrobenzyl) oxime (1) presented moderate trypanocidal activity (IC50?=?12.7?μM) when compared with the standard drug benznidazole, which showed to be a good starting point for the design of more effective trypanocide agents.

Identification of novel functionalized carbohydrazonamides designed as chagas disease drug candidates

Background: Although several research efforts have been made worldwide to discover novel drug candidates for the treatment of Chagas disease, the nitroimidazole drug benznidazol remains the only therapeutic alternative in the control of this disease. However, this drug presents reduced efficacy in the chronic form of the disease and limited safety after long periods of admini-stration, making it necessary to search for new, more potent and safe prototypes. Objective: We described herein the synthesis and the trypanocidalaction of new functionalized carbohydrazonamides (2-10) against trypomastigote forms of Trypanosoma cruzi. Methods: These compounds were designed through the application of molecular hybridization concept between two potent anti-T. cruzi prototypes, the nitroimidazole derivative megazol (1) and the cinnamyl N-acylhydrazone derivative (14) which have been shown to be twice as potent in vitro as benznidazole. Results: The most active compounds were the (Z)-N'-((E)-3-(4-nitrophenyl)-acryloyl)-1-methyl-5-nitro-1H-imidazol-2-carbohydrazonamide (6) (IC50 =9.50 μM) and the (Z)-N'-((E)-3-(4-hydroxyphe-nyl)-acryloyl)-1-methyl-5-nitro-1H-imidazol-2-carbohydrazonamide (8) (IC50 =12.85 μM), which were almost equipotent to benznidazole (IC50 =10.26 μM) used as standard drug. The removal of the amine group attached to the imine subunit in the corresponding N-acylhydrazone derivatives (11-13) resulted in less potent or inactive compounds. The para-hydroxyphenyl derivative (8) presented also a good selectivity index (SI = 32.94) when tested against mammalian cells from Swiss mice. Conclusion: The promising trypanocidal profile of new carbohydrazonamide derivatives (6) and (8) was characterized. These compounds have proved to be a good starting point for the design of more effective trypanocidal drug candidates.

Compound and its as L-type calcium channel blocker or/and application of acetylcholine esterase inhibitors

Disclosed in this invention are compounds and the uses as L-type calcium channel blocker and/or acetylcholinesterase inhibitor thereof. The uses of said compounds in the manufactures of a medicament for the treatment of cardiovascular diseases, apoplexy or senile dementia are also disclosed in the present invention.

Synthesis and antiproliferative activity evaluation of imidazole-based indeno[1,2-b]quinoline-9,11-dione derivatives

A series of new imidazole substituted indeno[1,2-b]quinoline-9,11-dione derivatives were synthesized and evaluated for their antiproliferative effects on HeLa, LS180, MCF-7 and Jurkat human cancer cell lines. Antiproliferative effects were evaluated using MTT assay. Prepared compounds exhibited weak to good antiproliferative activity in evaluated cell lines. Prepared compounds were more potent in Jurkat cell line when compared to LS180, HeLa and MCF-7 cell lines. Compounds 29 (IC16 = 0.7 μM) and 31 (IC16 = 1.7 μM) and 33 (IC16 = 1.7 μM) were found to be the most potent molecules on Jurkat cell lines. Moreover; it was found that some of the tested compounds bearing imidazole-2-yl moiety on the C11-position of dihydropyridine ring exhibited superior antiproliferative activity in comparison to cis-platin especially in Jurkat cell line (compounds 29, 31, and 33). It seemed that the introduction of electron-withdrawing groups on the imidazole ring enhanced the antiproliferative potential of these compounds (compounds 27, 29 and 31). The results of this study proposed that some of the imidazole substituted indeno[1,2-b]quinoline-9,11-dione compounds may act as efficient anticancer agents in vitro, emphasizing their potential role as a source for rational design of potent antiproliferative agents.

5-Nitroimidazole-based 1,3,4-Thiadiazoles: Heterocyclic analogs of metronidazole as anti-helicobacter pylori agents

A series of 5-nitroimidazole-based 1,3,4-thiadiazoles were prepared and tested for antibacterial activity against Helicobacter pylori. The anti-H. pylori activity of target compounds along with the commercially available antimicrobial metronidazole was evaluated by comparing the inhibition-zone diameters determined by the paper disc diffusion bioassay. From our bioassay results against 20 clinical isolates it is evident that piperazinyl, 4-methylpiperazinyl, 3-methylpiperazinyl, and 3,5-dimethylpiperazinyl analogs (6a, 6b, 6e, and 6f, respectively) and pyrrolidine derivative 7 had strong activity at 0.5 μg/disc (average of inhibition zone >20 mm) while metronidazole had no activity at this dose. Compound 6f containing the 3,5-dimethylpiperazinyl moiety at the 2-position of the 5-(1-methyl-5-nitro-1H- imidazol-2-yl)-1,3,4-thiadiazole skeleton was the most potent compound tested at low concentrations.

Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead

As part of our efforts to develop new compounds aimed at the therapy of parasitic infections, we synthesized and assayed analogues of a lead compound megazol, 5-(1-methyl-5-nitro-1H-2-imidazolyl)-1,3,4-thiadiazol-2-amine, CAS no. 19622-55-0), in vitro. We first developed a new route for the synthesis of megazol. Subsequently several structural changes were introduced, including substitutions on the two rings of the basic nucleus, replacement of the thiadiazole by an oxadiazole, replacement of the nitroimidazole part by a nitrofurane or a nitrothiophene, and substitutions on the exocyclic nitrogen atom for evaluation of an improved import by the glucose or the purine transporters. Assays of the series of compounds on the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, as either extracellular cells or infected macrophages, indicated that megazol was more active than the derivatives. Megazol was then evaluated on primates infected with Trypanosoma brucei gambiense, including late-stage central nervous system infections in combination with suramin. Full recovery was observed in five monkeys in the study with no relapse of parasitemia within a 2 year follow-up. Because there is a lack of efficacious treatments for sleeping sickness in Africa and Chagas disease in South America, megazol is proposed as a potential alternative. The mutagenicity of this compound is at present being reevaluated, and metabolism is also under investigation prior to possible further developments.

Synthesis and evaluation of nitroheterocyclic phosphoramidates as hypoxia-selective alkylating agents

A series of novel nitroheterocyclic phosphoramidates has been prepared, and the cytotoxicity of these compounds has been evaluated in clonogenic assays against B16, wild-type and cyclophosphamide-resistant MCF-7, and HT-29 cells under aerobic conditions and HT-29 cells under hypoxic conditions. All compounds were comparable in toxicity to wild-type and resistant MCF-7 cells and were also selectively toxic to HT-29 cells under hypoxic conditions (selectivity ratios 1.7 to > 20). Analogues lacking the nitro group were not cytotoxic. Electron-withdrawing substituents increased cytotoxicity under aerobic conditions and thereby decreased hypoxic selectivity. In contrast, an electron-donating substituent markedly decreased both aerobic and hypoxic cytotoxicity but enhanced hypoxic selectivity. Chemical reduction of the nitro group resulted in rapid expulsion of the cytotoxic phosphoramide mustard. The most potent of these compounds show significant cytotoxicity under both aerobic and hypoxic conditions.

Preparation, antimicrobial evaluation, and mutagenicity of [2- hydroxyaryl]-[1-methyl-5-nitro-1H-2-imidazolyl]methanols, [5-tert-butyl-2- methylaminophenyl]-[1-methyl-5-nitro-1H-2-imidazolyl] methanol, and [2- hydroxyaryl]-[1-methyl-5-nitro-1H-2-imidazolyl] ketones

Efficient preparations of the titled compounds are described, their antimicrobial activity and mutagenic properties being evaluated. Some of the studied compounds are nonmutagenic and present a MIC as low as some of the usual standards in the field.