Category: 3034-41-1

NMR Chemical Shift and Methylation of 4-Nitroimidazole: Experiment and Theory* was written by Backler, Frederick;Sani, Marc Antoine;Separovic, Frances;Vasilyev, Vladislav;Wang, Feng. And the article was included in Australian Journal of Chemistry in 2021.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:

Nitroimidazoles and derivatives are a class of active pharmaceutical ingredients (APIs) first introduced sixty years ago. As anti-infection agents, the structure-activity relationships of nitroimidazole compounds have been particularly difficult to study due to their low reduction potentials and unique electronic structures. In this study, we combine dynamic nuclear polarization (DNP)-enhanced solid-state (100K), solid-state (298K), and ¹H-¹³C heteronuclear single quantum coherence (HSQC) solution-state NMR techniques (303K) with d. functional theory (DFT) to study the 1H, 13C, and 15N chem. shifts of 4-nitroimidazole (4-NI) and 1-methyl-4-nitroimidazole (CH₃-4NI). The 4-NI chem. shifts were observed at 119.4, 136.4, and 144.7ppm for 13C, and at 181.5, 237.4, and 363.0ppm for 15N. The measurements revealed that methylation (deprotonation) of the amino nitrogen N(1) of 4-NI had less effect (Δδ=-4.8ppm) on the N(1) chem. shift but was compensated by shielding of the N(3) (Δδ=11.6ppm) in CH₃-4NI. The calculated chem. shifts using DFT for 4-NI and CH₃-4NI agreed well with the exptl. values (within 2%) for the imidazole carbons. However, larger discrepancies (up to 13%) were observed between the calculated and measured 15N NMR chem. shifts for the imidazole nitrogen atoms of both mols., which indicate that effects such as imidazole ring resonant structures and mol. dynamics may also contribute to the nitrogen chem. environment. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Safety of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Safety of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The synthesis of heterocycles via addition-elimination reactions of 4- and 5-aminoimidazoles was written by Al-Shaar, Adnan H. M.;Chambers, Robert K.;Gilmour, David W.;Lythgoe, David J.;McClenaghan, Ian;Ramsden, Christopher A.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1992.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:

4-Aminoimidazoles, e.g. I (R = H, R¹ = H, Me, CH₂Ph; R² = H, Me, Et, CHMe₂), undergo addition elimination reactions with electrophilic reagents to give exclusively N-adducts, which are useful intermediates for further synthetic transformations to novel heterocyclic systems. Thus, di-Et ethoxymethylenemalonate (II) and 4-amino-1-benzylimidazole give the adduct I [R = HC:C(CO₂Et)₂, R¹ = CH₂Ph, R² = H], and subsequent acid-catalyzed cyclization gives the imidazo[4,5-b]pyridine III and a heterocyclic mesomeric betaine, which undergoes 1,3-dipolar cycloaddition with di-Me acetylenedicarboxylate to give two products. When the 2-alkyl-4-aminoimidazoles I (R = R¹ = H, R² = Me, Et, CHMe₂) are generated in situ in the presence of II, 5,5′-diimidazoles are significant products; a mechanism for this novel transformation is proposed. 4-Amino-3-cyanoimidazo[1,5-a]pyrimidines IV (R = H, Me) are formed by cyclization of the N-adduct of I (R = R¹ = R² = H) and CR³(OEt):C(CN)₂ (R³ = H, Me). The use of X:NCN [V; X = CH(OEt), CMe(OEt), C(SMe)₂] leads to novel 4-aminoimidazo[1,5-a]-1,3,5-triazine derivatives VI (R¹ = H, Me, SMe; R² = H, Me), whose chem. reactions with both electrophilic and nucleophilic reagents are reported. 5-Aminoimidazoles, e.g., VII (R = H, R¹ = Me, CH₂CH₂OH; R² = Me, CHMe₂), undergo addition-elimination reactions with the electrophilic reagents, e.g. II and V, to give N-adducts and/or C-adducts, depending upon the structure of the reagent. These stable addition-elimination products are usually obtained in good yield and are useful intermediates for further synthesis. Reaction of the amines VII with II gives mainly N-adducts VII [R = HC:C(CO₂Et)₂], which can be cyclized using phosphoryl chloride to give the versatile 7-chloroimidazo[4,5-b]pyridines VIII. With ethoxymethylenemalononitrile, the amines VII give C-adducts, which undergo thermal cyclization to give 5-amino-6-cyanoimidazo[4,5-b]pyridines IX, which are further transformed into novel heterocyclic systems, including the tricyclic imidazo[4′,5′:5,6]pyrido[2,3-d]pyrimidines X (R = H, Ph) and XI (R = H, Bu, CH₂Ph, CH₂CH₂OH). Cyclization of the adducts obtained using V provides new synthetic route to aminopurine derivatives, e.g. XII (R³ = H, NH₂, SMe), and hypoxanthines. The preference of electrophilic reagents for N– or C-addition to VII is rationalized using Frontier MO theory. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Safety of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Safety of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

CNDO/S method interpretation of ultraviolet spectra of 4-nitro and 5-nitroimidazoles was written by Crozet, M. P.;Vanelle, P.;Bouscasse, L.;Avignon, T.. And the article was included in Spectroscopy Letters in 1986.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:

The UV spectra of several nitroimidazoles are reported. These exptl. results are interpreted using CNDO/S method (CNDO for Spectroscopy). Observed transitions are π → π^* type transitions. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Safety of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Safety of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Effect of the rat liver S-9 fraction on the mutagenicity of azathioprine in the Salmonella/mammalian microsome assay was written by Nepomnaschy, I.;Sommer, S. E.;Nagel, R.. And the article was included in Experientia in 1984.Recommanded Product: 3034-41-1 This article mentions the following:

Azathioprine (I) [446-86-6] is a direct acting mutagen in S. typhimurium TA 100 and 1535. The addition of rat liver S-9 fraction with or without cofactors, or GSH  [70-18-8], decreased the mutagenicity of I in TA 100 and increased in TA 1535, indicating the effect of SH groups. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 3034-41-1).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Recommanded Product: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Molten-state nitration of substituted imidazoles: new synthetic approaches to the novel melt-cast energetic material, 1-methyl-2,4,5-trinitroimidazole was written by Duddu, Raja;Zhang, Mao-Xi;Damavarapu, Reddy;Gelber, Nathaniel. And the article was included in Synthesis in 2011.Synthetic Route of C4H5N3O2 This article mentions the following:

Novel, one-step synthetic routes for the preparation of 1-methyl-2,4,5-trinitroimidazole (MTNI) are described. In addition, a new, molten-state nitration method for the synthesis of 1-methyl-2,4,5-trinitroimidazole is developed. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Synthetic Route of C4H5N3O2).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Synthetic Route of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem