Category: 22813-32-7

Oxazolidine Formation, or Loss of Acid, from Attempted Fluorination of Amide Side-Chain in 2-Nitroimidazoles was written by Baird, Ian R.;Patrick, Brian O.;Skov, Kirsten A.;James, Brian R.. And the article was included in Journal of Heterocyclic Chemistry in 2018.Formula: C5H5N3O4 This article mentions the following:

Reaction of Etanidazole (a 2-nitroimidazole derivative with an amide side-chain containing a hydroxyethyl group) with triflic anhydride gives, depending on conditions, a trifluoromethyl(sulfonyl)oxazolidine via a cyclization reaction, or a fluorine-free formate derivative; reaction with tosyl chloride gives only a chloroethyl derivative An attempt to replace a Br-atom in a related propyl-containing amide side-chain by a F-atom forms instead a propylene derivative via loss of HBr. The studies stem from interest in use of 2-nitroimidazoles with fluorine-containing amide side-chains as hypoxia markers. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Formula: C5H5N3O4).

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) 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 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.Formula: C5H5N3O4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Radiosensitizing, toxicological, and pharmacokinetic properties of hydroxamate analogs of nitroimidazoles as bifunctional radiosensitizers/chemical modifiers was written by Nagasawa, Hideko;Bando, Masahiro;Hori, Hitoshi;Satoh, Tetsuo;Tada, Takuhito;Onoyama, Yasuto;Inayama, Seiichi. And the article was included in International Journal of Radiation Oncology, Biology, Physics in 1992.Category: imidazoles-derivatives This article mentions the following:

The pharmacokinetics were examined of KIH-802, potassium 2-nitroimidazole-1-acetohydroxamate, using its radioisotope-labeled compound and the acute toxicity in mice. The concentration of KIH-802 was very low in the brain and its LD₅₀ was nearly half the value of that of MISO. Here, new 2-nitroimidazole radiosensitizers/chem. modifiers (KIN-804, 811, 831, 841, 844, 821, 823 and 824) were designed to enhance their sensitizing ability intensely by substituting various biol. active groups, such as hydroxamic acids and oximes, with moderate lipophilicity to the aromatic ring, if necessary, through some spacers. The sensitizing effects of all compounds were estimated to be almost equal to or better than that of MISO. The results of their toxicities shows that new hydroxamates KIN-804 and 831 are less toxic than KIH-802 and MISO. Their in vitro enhancement ratios are 2.00 and 1.75, resp., compared with those of KIH-802, MISO and SR-2508, 1.77, 1.72 and 1.72, resp., at each dose of 1 mM for EMT6/KU single cell. It is concluded that they hydroxamic acid analogs to KIH-802 may be superior radiosensitizers. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Category: imidazoles-derivatives).

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A Three-In-One Assembled Nanoparticle Containing Peptide-Radio-Sensitizer Conjugate and TLR7/8 Agonist Can Initiate the Cancer-Immunity Cycle to Trigger Antitumor Immune Response was written by Zhu, Xueqin;Wang, Xiaoxi;Li, Bingyu;Zhang, Yun;Chen, Yalan;Zhang, Wenyan;Wang, Yan;Zhai, Wenjie;Liu, Zimai;Liu, Sijia;Sun, Jiaxin;Chen, Zhenzhen;Gao, Yanfeng. And the article was included in Small in 2022.Application In Synthesis of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid This article mentions the following:

Radiotherapy (RT) has been shown to cause immunogenic cell death (ICD) of cancer cells, which promote the release of tumor-associated antigens, and trigger the cancer-immunity cycle (CIC). However, ICD induced by RT usually does not occur in hypoxic tumor cells due to their resistance to radiation. Moreover, RT also induces programmed death ligand 1 (PD-L1) upregulation on tumor cells, which has an inhibitory effect on T lymphocytes. Therefore, therapy based on CIC must selectively target the restricted steps of antitumor immunity. Herein, the authors design a versatile three-in-one assembling nanoparticle that can simultaneously execute these obstacles. The amphiphilic peptide drug conjugate NIA-D1, containing the hydrophobic radio-sensitizer 2-(2-nitroimidazol-1-yl) acetic acid (NIA), a peptide substrate of matrix metalloproteinase-2, and a hydrophilic PD-L1 antagonist DPPA-1, is constructed and co-assembled with hydrophobic Toll-like receptor (TLR) 7/8 agonist R848 to form nanoparticle NIA-D1@R848. The NIA-D1@R848 nanoparticles combined with RT can trigger the apoptosis of tumor cells and initiate the CIC. In the presence of R848, it promotes the maturation of dendritic cells, which together with protein programmed cell death protein 1 (PD-1) and its ligand PD-L1 blockade to relieve T cell suppression, and amplify the antitumor immune cycle. In conclusion, a functionalized three-in-one nanoparticle NIA-D1@R848 is successfully constructed, which can induce strong systemic antitumor immune response. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Application In Synthesis of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid).

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) 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 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.Application In Synthesis of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nitroimidazoles with a halogen-containing side-chain was written by Baird, Ian R.;Patrick, Brian O.;Skov, Kirsten A.;James, Brian R.. And the article was included in Canadian Journal of Chemistry in 2018.Formula: C5H5N3O4 This article mentions the following:

Syntheses are reported for: nine 2-nitroimidazoles, five 2-methyl-5-nitroimidazoles, and five 2-methyl-4-nitroimidazoles. The nitroimidazoles all have an amide side-chain at the N1 atom of the imidazole, with 17 of them containing one to five halogen atoms. The aim is to study compounds for comparison with EF5 (I), a previously reported, pentafluoropropylacetamide derivative of 2-nitroimidazole that is currently used as a hypoxia marker drug to detect cancerous tumors. The new compounds are characterized by standard methods, including X-ray structural data. Intra- and inter-mol. H-bonding is seen in the solid state structures, likely an important property in biol. use; another key property of the nitroimidazoles is their reduction potentials, and the measured CV data confirm that 2-nitroimidazole compounds with longer side-chains and more F-atoms (like I) are worth investigating for possible activity as hypoxia-selective, bioreductive agents. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Formula: C5H5N3O4).

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) 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.Formula: C5H5N3O4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of nitroimidazole substituted 3,3,9,9-tetramethyl-4,8-diazaundecane-2,10-dione dioximes (propylene amine oximes, PnAOs): ligands for technetium-99m complexes with potential for imaging hypoxic tissue was written by Ramalingam, Kondareddiar;Raju, Natarajan;Nanjappan, Palaniappa;Nowotnik, David P.. And the article was included in Tetrahedron in 1995.COA of Formula: C5H5N3O4 This article mentions the following:

A series of 2-substituted-1,3-diaminopropanes have been synthesized as precursors to nitroimidazole-substituted 3,3,9,9-tetramethyl-4,8-diazaundecane-2,10-dione dioxime (propylene amine oxime, PnAO) ligands. 3-Chloro-3-methyl-1-(2- or 4-nitro-1H-imidazol-1-yl)-2-nitrosobutanes required for the syntheses of nitroimidazole substituted PnAO ligands were prepared from the corresponding dimethylallylnitroimidazoles by the addition of nitrosyl chloride. A number of nitroimidazole derivatized PnAO ligands possessing potential for either electrostatic, hydrophobic, or hydrophilic interactions were synthesized as precursors to technetium-99m complexes under investigation as potential imaging agents of hypoxia. Derivatives of PnAO, substituted at carbon one, were prepared using the 3-chloro-3-methyl-1-(2- or 4-nitro-1H-imidazol-1-yl)-2-nitrosobutanes. Three PnAOs derivatized at the central carbon atom were prepared using 3-bromo-3-methylbutan-2-one. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7COA of Formula: C5H5N3O4).

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. COA of Formula: C5H5N3O4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem