Ben-Ishai, Ruth et al. published their research in Archives of Biochemistry and Biophysics in 1951 | CAS: 26832-08-6

1H-Imidazole-4-carboxamide (cas: 26832-08-6) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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. Reference of 26832-08-6

4-Aminoimidazole-5-carboxamide, precursor of the purines in E. coli was written by Ben-Ishai, Ruth;Volcani, Benjamin;Bergmann, Ernst D.. And the article was included in Archives of Biochemistry and Biophysics in 1951.Reference of 26832-08-6 This article mentions the following:

In the presence of only 4 γ/cc. of any of the purine bases, which by themselves gave only 30% growth, 4-aminoimidazole-5-carboxamide (I) (30γ) gave full growth. p-Aminobenzoic acid (0.1 γ/cc.) and 0.005 γ/cc. folic acid had no effect on the rate at which I was utilized but B12 (0.0002 γ/cc.) increased the rate of utilization. B12 had no effect in media containing adenine or other purine bases. The formyl derivative of I was more effective than I. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Reference of 26832-08-6).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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. Reference of 26832-08-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Matuszek, Karolina et al. published their research in Molecules in 2020 | CAS: 35487-17-3

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Synthetic Route of C4H7ClN2

Studies on the solubility of terephthalic acid in ionic liquids was written by Matuszek, Karolina;Pankalla, Ewa;Grymel, Aleksander;Latos, Piotr;Chrobok, Anna. And the article was included in Molecules in 2020.Synthetic Route of C4H7ClN2 This article mentions the following:

Low solubility of terephthalic acid in common solvents makes its industrial production very difficult and not environmentally benign. Ionic liquids are known for their extraordinary solvent properties, with capability to dissolve a wide variety of materials, from common solvents to cellulose, opening new possibilities to find more suitable solvents for terephthalic acid. This work presents studies on the solubility of terephthalic acid in ionic liquids, and demonstrates that terephthalic acid is soluble in ionic liquids, such as 1-ethyl-3-methylimidazolium diethylphosphate, 1-butyl-3-methylimidazolium acetate, and dialkylimidazolium chlorides up to four times higher than in DMSO. Addnl., the temperature effect and correlation of ionic liquid structure with solubility efficiency are discussed. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Synthetic Route of C4H7ClN2).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Synthetic Route of C4H7ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Boulmier, Amandine et al. published their research in Inorganic Chemistry in 2017 | CAS: 21252-69-7

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Application In Synthesis of 1-Octyl-1H-imidazole

Anticancer Activity of Polyoxometalate-Bisphosphonate Complexes: Synthesis, Characterization, In Vitro and In Vivo Results was written by Boulmier, Amandine;Feng, Xinxin;Oms, Olivier;Mialane, Pierre;Riviere, Eric;Shin, Christopher J.;Yao, Jiaqi;Kubo, Tadahiko;Furuta, Taisuke;Oldfield, Eric;Dolbecq, Anne. And the article was included in Inorganic Chemistry in 2017.Application In Synthesis of 1-Octyl-1H-imidazole This article mentions the following:

The authors synthesized a series of polyoxometalate-bisphosphonate complexes containing MoVIO6 octahedra, zoledronate, or an N-alkyl (n-C6 or n-C8) zoledronate analog, and in two cases, Mn as a heterometal. Mo6L2 (L = Zol, ZolC6, ZolC8) and Mo4L2Mn (L = Zol, ZolC8) were characterized by using single-crystal x-ray crystallog. and/or IR spectroscopy, elemental and energy dispersive x-ray anal. and 31P NMR. The authors found promising activity against human non-small cell lung cancer (NCI-H460) cells with IC50 values for growth inhibition of ∼5 μM per bisphosphonate ligand. The effects of bisphosphonate complexation on IC50 decreased with increasing bisphosphonate chain length: C0 ≈ 6.1×, C6 ≈ 3.4×, and C8 ≈ 1.1×. The authors then determined the activity of one of the most potent compounds in the series, Mo4Zol2Mn(III), against SK-ES-1 sarcoma cells in a mouse xenograft system finding a ∼5× decrease in tumor volume than found with the parent compound zoledronate at the same compound dosing (5 μg/mouse). Overall, the results are of interest since the authors show for the first time that heteropolyoxomolybdate-bisphosphonate hybrids kill tumor cells in vitro and significantly decrease tumor growth, in vivo, opening up new possibilities for targeting both Ras as well as epidermal growth factor receptor driven cancers. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Application In Synthesis of 1-Octyl-1H-imidazole).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Application In Synthesis of 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Shabanov, P. D. et al. published their research in Vestnik Akademii Meditsinskikh Nauk SSSR in 1985 | CAS: 26832-08-6

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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 based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Name: 1H-Imidazole-4-carboxamide

Experimental memory disorders and their pharmacological correction was written by Shabanov, P. D.. And the article was included in Vestnik Akademii Meditsinskikh Nauk SSSR in 1985.Name: 1H-Imidazole-4-carboxamide This article mentions the following:

The antiamnesic action of a variety of neurotropic drugs on 2 models of memory disorders (electronconvulsive shock and mech. brain injury) was studied in rats. GABA (200 mg/kg) and 1-methyl-3,4-di-(N-methylcarbamoyl)-pyrazole (10 μg/kg) were the most potent drugs inhibiting amnesia for passive avoidance. Piracetam (100 mg/kg) and etimazole (1.5 mg/kg) were compared for effects on learning and memory of the drinking conditioned reflex under conditions of RNA synthesis inhibition by actinomycin D. Neither compound affected learning but facilitated it after actinomycin D administration. Both drugs also increased memory retention. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Name: 1H-Imidazole-4-carboxamide).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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 based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Name: 1H-Imidazole-4-carboxamide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Urban, Milan et al. published their research in Biochemistry in 2009 | CAS: 4887-83-6

7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) 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.Related Products of 4887-83-6

Herpes Simplex Virus-1 DNA Primase: A Remarkably Inaccurate yet Selective Polymerase was written by Urban, Milan;Joubert, Nicolas;Hocek, Michal;Alexander, Richard E.;Kuchta, Robert D.. And the article was included in Biochemistry in 2009.Related Products of 4887-83-6 This article mentions the following:

Herpes simplex virus-1 primase misincorporates the natural NTPs at frequencies of around one error per 30 NTPs polymerized, making it one of the least accurate polymerases known. We used a series of nucleotide analogs to further test the hypothesis that primase requires Watson-Crick hydrogen bond formation to efficiently polymerize a NTP. Primase could not generate base pairs containing a complete set of hydrogen bonds in an altered arrangement (isoguanine/isocytosine) and did not efficiently polymerize dNTPs completely incapable of forming Watson-Crick hydrogen bonds opposite templating bases incapable of forming Watson-Crick hydrogen bonds. Similarly, primase did not incorporate most NTPs containing hydrophobic bases incapable of Watson-Crick hydrogen bonding opposite natural template bases. However, 2-pyridone NTP and 4-methyl-2-pyridone NTP provided striking exceptions to this rule. The effects of removing single Watson-Crick hydrogen bonding groups from either the NTP or templating bases varied from almost no effect to completely blocking polymerization depending both on the parental base pair (G/C vs. A/T/U) and which base pair of the growing primer (second, third, or fourth) was examined Thus, primase does not absolutely need to form Watson-Crick hydrogen bonds to efficiently polymerize a NTP. Addnl., we found that herpes primase can misincorporate nucleotides both by misreading the template and by a primer-template slippage mechanism. The mechanistic and biol. implications of these results are discussed. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Related Products of 4887-83-6).

7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) 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.Related Products of 4887-83-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Sadowsky, Jack D. et al. published their research in Bioconjugate Chemistry in 2017 | CAS: 64038-64-8

Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8) 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. 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. Formula: C6H8N2O2S

Development of Efficient Chemistry to Generate Site-Specific Disulfide-Linked Protein- and Peptide-Payload Conjugates: Application to THIOMAB Antibody-Drug Conjugates was written by Sadowsky, Jack D.;Pillow, Thomas H.;Chen, Jinhua;Fan, Fang;He, Changrong;Wang, Yanli;Yan, Gang;Yao, Hui;Xu, Zijin;Martin, Shanique;Zhang, Donglu;Chu, Phillip;dela Cruz-Chuh, Josefa;ODonohue, Aimee;Li, Guangmin;Del Rosario, Geoffrey;He, Jintang;Liu, Luna;Ng, Carl;Su, Dian;Lewis Phillips, Gail D.;Kozak, Katherine R.;Yu, Shang-Fan;Xu, Keyang;Leipold, Douglas;Wai, John. And the article was included in Bioconjugate Chemistry in 2017.Formula: C6H8N2O2S This article mentions the following:

Conjugation of small mol. payloads to specific cysteine residues on proteins via a disulfide bond represents an attractive strategy to generate redox-sensitive bioconjugates, which have value as potential diagnostic reagents or therapeutics. Advancement of such “direct-disulfide” bioconjugates to the clinic necessitates chem. methods to form disulfide connections efficiently, without byproducts. The disulfide connection must also be resistant to premature cleavage by thiols prior to arrival at the targeted tissue. We show here that commonly-employed methods to generate direct disulfide-linked bioconjugates are inadequate for addressing these challenges. We describe our efforts to optimize direct-disulfide conjugation chem., focusing on the generation of conjugates between cytotoxic payloads and cysteine-engineered antibodies (i.e., THIOMAB antibody-drug conjugates, or TDCs). This work culminates in the development of novel, high-yielding conjugation chem. for creating direct payload disulfide connections to any of several Cys mutation sites in THIOMAB antibodies or to Cys sites in other biomols. (e.g., human serum albumin and cell-penetrating peptides). We conclude by demonstrating that hindered direct disulfide TDCs with two Me groups adjacent to the disulfide, which have heretofore not been described for any bioconjugate, are more stable and more efficacious in mouse tumor xenograft studies than less hindered analogs. In the experiment, the researchers used many compounds, for example, Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8Formula: C6H8N2O2S).

Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8) 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. 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. Formula: C6H8N2O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Chen, Zhichao et al. published their research in Langmuir in 2020 | CAS: 21252-69-7

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Electric Literature of C11H20N2

Protic Imidazolium Cation-Based Ionic Liquids Show Unexpected Interfacial Properties was written by Chen, Zhichao;Morales-Collazo, Oscar;Brennecke, Joan F.. And the article was included in Langmuir in 2020.Electric Literature of C11H20N2 This article mentions the following:

Virtually, every investigation and application of ionic liquids (ILs) involves gas-liquid, liquid-liquid, and liquid-solid interactions. Therefore, understanding the behavior of ILs at those interfaces is critical In this work, we studied the interfacial properties of protic and aprotic ILs with N-alkylimidazolium and 1-alkyl-3-methylimidazolium as cations and bis(trifluoromethylsulfonyl)imide, methanesulfonate, and trifluoromethanesulfonate as anions. The surface tension of these ILs is measured with the pendant drop method in a temperature range of 293.15-343.15 K and at atm. pressure. The contact angle measurements are performed at 293.15 K on three solid substrates: polytetrafluoroethylene, glassy carbon, and platinum. Dispersive and nondispersive components of the IL surface energy are determined from the exptl. data using Fowkes theory. The most interesting result is that the protic ILs have lower surface tension and smaller contact angles than the equivalent aprotic ILs, despite the presence of high charge d. on the proton associated with one of the nitrogens of the cation. Higher charge d. on the anion results in a higher surface tension, and decreasing surface tension and contact angles are observed for increasing alkyl chain length on the cation. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Electric Literature of C11H20N2).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Electric Literature of C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Zhang, Xin et al. published their research in ACS Applied Materials & Interfaces in 2022 | CAS: 21252-69-7

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Electric Literature of C11H20N2

Irreversible Humidity-Responsive Phosphorescence Materials from Cellulose for Advanced Anti-Counterfeiting and Environmental Monitoring was written by Zhang, Xin;Cheng, Yaohui;You, Jingxuan;Zhang, Jinming;Wang, Yirong;Zhang, Jun. And the article was included in ACS Applied Materials & Interfaces in 2022.Electric Literature of C11H20N2 This article mentions the following:

Organic phosphorescence materials have many unique advantages, such as a large Stokes shift, high signal-to-noise ratio, and no interference from background fluorescence and scattered light. But, they generally lack responsiveness. Herein, we developed a new type of biopolymer-based phosphorescence materials with excellent processability and irreversible humidity-responsiveness, via introducing the imidazolium cation to cellulose chain. In the resultant cellulose derivatives, the imidazolium cation promotes the intersystem crossing, meanwhile the cation, chloride anion, and hydroxyl group form multiple hydrogen bonding interactions and electrostatic attraction interactions, which successfully inhibit the nonradiative transitions. As a result, the ionic cellulose derivatives exhibit green phosphorescence at room temperature and can be processed into phosphorescent films, coatings, and patterns. More interestingly, their phosphorescence emission changes when the different processing solvents are used. The ionic cellulose derivatives processed with acetone have a negligible phosphorescence, while they give an irreversible humidity-responsive phosphorescence, which means that the ionic cellulose derivatives processed with acetone exhibit significantly enhanced phosphorescence once they meet water vapor. Such novel irreversible responsive phosphorescence materials have huge potential in advanced anticounterfeiting, information encryption, mol. logic gates, smart tags, and process monitoring. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Electric Literature of C11H20N2).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Electric Literature of C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Sharhan, Olla et al. published their research in Inorganica Chimica Acta in 2020 | CAS: 1632-83-3

1-Methylbenzimidazole (cas: 1632-83-3) 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.Computed Properties of C8H8N2

Benzimidazolium-acridine-based silver N-heterocyclic carbene complexes as potential anti-bacterial and anti-cancer drug was written by Sharhan, Olla;Heidelberg, Thorsten;Hashim, Najihah Mohd.;Al-Madhagi, Wafa M.;Ali, Hapipah Mohd.. And the article was included in Inorganica Chimica Acta in 2020.Computed Properties of C8H8N2 This article mentions the following:

A series of N-alkylated benzimidazolium salts based on 9-substituted acridine has been synthesized and subsequently converted into the corresponding Ag(I) carbene complexes. The compounds were characterized by IR, 1H and 13C NMR spectroscopy. Identity and purity were confirmed by HRMS and elemental anal., resp. Both, ligands and complexes, were evaluated on their antibacterial and anticancer potential. All complexes exhibited higher activity against both Gram pos. and Gram neg. bacterial strains than the corresponding ligands. Human cell line experiments indicated low in-vitro cytotoxicity, while some of the complexes showed promising activity against breast cancer cells. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Computed Properties of C8H8N2).

1-Methylbenzimidazole (cas: 1632-83-3) 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.Computed Properties of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Cosar, Charles et al. published their research in Arzneimittel-Forschung in 1966 | CAS: 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 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.Application of 3034-41-1

Nitroimidazoles was written by Cosar, Charles;Crisan, Cornel;Horclois, Raymond;Jacob, Robert M.;Robert, Jacques;Tchelitcheff, Serge;Vaupre, Roger. And the article was included in Arzneimittel-Forschung in 1966.Application of 3034-41-1 This article mentions the following:

2-Alkyl 2-(4 or 5)nitroimidazoles were synthesized. Thus, 380 g. 2-methylimidazole was dissolved in 926 ml. 10N H2SO4, to obtain 2-methylimidazole acid sulfate (red oil) which was nitrated by treating with 550 ml. HNO3 (d. 1.38) and then 160 ml. HNO3 (d. 1.49) and 640 ml. H2SO4 (d. 1.83) with cooling at 18° to give 39% 2-methyl-4(5)-nitroimidazole (I, R = Me), m. 255°. Similarly were prepared the following I (R, m.p., and % yield given): H, 306° (2.5N HCl), 64; Et, 158° (H2O), 29; iso-Pr, 180° (H2O), 31. II were prepared from I by alternate methods. Method A: 38.1 g. I (R = Me) was mixed with 25.2 g. EtOK (18% in EtOH) and 100 ml. HCONMe2, EtOH was distilled, the residue was diluted with 200 ml. HCONMe2 and 37.8 g. Me2SO4 added dropwise, and the mixture heated 3 hrs. at 100° to give 62% 1,2-dimethyl-4-nitroimidazole, m. 183° (iso-PrOH). Method B: 13 g. Et2SO4 was added dropwise to a mixture of 17 g. 4-nitroimidazole, 90 ml. 2.5N NaOH, and heated 20 min. at 45°; after cooling a new addition of 90 ml. NaOH and 13 g. Et2SO4 was made, and the mixture heated 45 min. at 45°. Extraction with CHCl3 gave 27% 5.8 g. 1-ethyl-4-nitroimidazole, m. 40°. Method C: By heating 2 hrs. at 140-5° a mixture of 12.7 g. I and 22.6 g. PhCH2Cl, there was obtained 57% 1-benzyl-2-methyl-4-nitroimidazole, m. 106°. Similarly were prepared the II in the first table. [TABLE OMITTED] 2-Methyl-5-nitroimidazole (635 g.) and 3.22 kg. HO-CH2CH2Cl was refluxed 24 hrs. to yield 41% 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole, m. 160°. Similarly were prepared the III in the 2nd table. Esters of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole (IV) were prepared by reaction of acid chloride and C5H5N with the IV (R = H). Thus were prepared the following IV (R, m.p., and % yield given): Ac, 74°, 60; COCHCl2 87°, 51; COCMe3, 39°, 26; palmitoyl, 55°, 68; stearoyl, 51°, 34; CO-(CH2)2CO2H, 109°, 89; neutral succinate, 129°, 39; COCH:CHPh, 100°, 44; Bz, 102°, 89; COC6H4Cl-o, 104°, 61; COC6H4-OH-o, 154°, 15; COC6H4OMe-p, 102°, 56; COC6H2(OMe)3-3,4,5, 116°, 45; COC6H4NO2-p, 166°, 22; neutral phthalate, 130°, 13. Derivatives of 2-nitroimidazole were prepared: 1-methyl-2-nitroimidazole, m. 105°, and 1-(2-hydroxyethyl)-2-nitroimidazole, m. 116°. The NO2 in position 4 or 5 was studied by ir spectroscopy. The influence of the position of the nitro group and the nature of the other substituents on the antitrichomonas activity was studied. The 5-nitro derivatives were always found to be more active than derivatives of 4-nitroimidazole. In the 5-nitroimidazole series, the best products are those carrying a Me group in the 2-position and in the 1-position; a short saturated aliphatic chain being optionally substituted, and the presence of a hydroxy group decreasing considerably the toxicity of the product. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Application of 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 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.Application of 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem