Category: imidazoles-derivatives

Grunberg, E.; Titsworth, E. published an article in 1965, the title of the article was Toxicity and antitrichomonad activity of 2-nitroimidazole and 2-nitrobenzimidazole derivatives.Formula: C7H5N3O2 And the article contains the following content:

2-Nitroimidazole, 2-nitrobenzimidazole, and their alkyl, alkoxy, and chloro derivatives were generally moderately to highly toxic in mice. Only 1,4,5-trimethyl-2-nitroimidazole and 5,6-dimethyl-2-nitrobenzimidazole were relatively atoxic. 2-Nitroimidazole and certain of its Me derivatives were active orally against Trichomonas foetus infection in mice as well as subcutaneously against local T. vaginalis infection in mice. The 1-allyl derivative was inactive orally against T. foetus, but did show activity by both the subcutaneous and oral routes against T. vaginalis. 2-Nitrobenzimidazole and its alkyl, alkoxy, and chloro derivatives were without oral activity against either T. vaginalis or T. foetus. The majority of the 2-nitrobenzimidazole derivatives tested showed slight to moderate activity subcutaneously against local T. vaginalis infection of mice. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Formula: C7H5N3O2

2-Nitro-1H-benzo[d]imidazole(cas:5709-67-1) belongs to imidazoles. It 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. Formula: C7H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Beaman, Alden G.; Tautz, William; Gabriel, Thomas; Keller, Oscar; Loome, Voldemar; Duschinsky, Robert published an article in 1965, the title of the article was Studies in the Nitroimidazole series. I. Synthesis of azomycin and related compounds.Reference of 2-Nitro-1H-benzo[d]imidazole And the article contains the following content:

Azomycin (2-nitroimidazole) was synthesized in 50% yield by treatment of 2-aminoimidazole with HONO in the presence of CuSO4 (Jones and Robins, CA 55, 559c). Synthetic azomycin was identified with natural azomycin by mixed m.p., by Pka, by uv and ir and by its in vitro anti-bacterial spectrum against 19 microorganisms. The method was also applied to the preparation of alkyl-2-aminoimidazoles and to 2-aminobenzimidazoles. The resulting 2-nitro compounds were then alkylated in the 1-position. When treated with alkali, the 1-alkyl-2-nitroimidazoles were more stable than the 1-alkyl-2-nitrobenzimidazoles which were transformed into 2-benzimidazolinones. The compounds were tested microbiol. by agar diffusion-cup plate employing a complex nitrogenous medium. Growth inhibition characteristics for the various compounds against a number of bacteria were given. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Reference of 2-Nitro-1H-benzo[d]imidazole

2-Nitro-1H-benzo[d]imidazole(cas:5709-67-1) belongs to imidazoles. It 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. Reference of 2-Nitro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On April 20, 1966, Fitzmaurice, Colin published a patent.Reference of 2-Nitro-1H-benzo[d]imidazole The title of the patent was Nitroimidazoles. And the patent contained the following:

Nitroimidazole derivatives (I) in which R = H or an alkyl group with 1-3 C atoms and X = an alkoxy or acyloxy group with 1-4 C atoms are prepared to be used in pharmaceutical preparations for the treatment of protozoal infections. Thus, 10 g. 4-nitroimidazole (II) and 12 ml. ClCH2OMe was heated 3 hrs. in a sealed tube at 100°, the cooled solution was taken up in H2O, made alk. with Na2CO3, and extracted with CHCl3 to give 6.3 g.I (R= H, X = OMe),m. 66.5-67° (C6H6). In the same way, 2.5 g. 2-methyl-4-nitroimidazole, and 5 ml. ClCH2OMe gave 1.4 g. I (R = Me, X = OMe), m. 71.5-2.5° (Et2O). II (1.7 g.) and 4 ml. ClCH2OAc was heated 1 hr. at 140°, the mixture was cooled overnight, treated with H2O and Na2CO3, and extracted with CHCl3. The residual oil of the evaporated (in vacuo) CHCl3 extract was triturated with Et2O and the precipitate recrystallized from EtOAc, giving 1.5 g. I (R = H, X = CH2OAc) (III), m. 83.5-4.5°. III, m. 88-8.5°, was also prepared in 6.2-g. yield by refluxing 5 g. II, 5 ml. AcOCH2Cl, and 3.5 g. K2CO3 4 hrs. in 50 ml. Me2CO, evaporating the filtered solution in vacuo, and extracting the residue with EtOAc, boiling the extract with C, and precipitating it with petroleum ether. II (6 g.) and 7.5 ml. EtCO2CH2Cl (IV) was refluxed 3 hrs. and cooled overnight, the excess IV was distilled in vacuo, and the residue treated in H2O with Na2CO3, extracted with CHCl3, giving I (R = H, X = EtCO2CH2), m. 61-2° (Et2O-petroleum ether). The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Reference of 2-Nitro-1H-benzo[d]imidazole

2-Nitro-1H-benzo[d]imidazole(cas:5709-67-1) belongs to imidazoles. It 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. Reference of 2-Nitro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On May 18, 1966, there was a patent named 2-Nitroimidazoles.Computed Properties of 5709-67-1. And the patent contained the following:

Substituted 2-nitroimidazoles were prepared for use against protozoa, bacteria, and pathogenic fungi. 2-(p-Bromobenzeneazo)imidazole (50 g.) in EtOH hydrogenated over Raney Ni, and the red-brown oily product treated in 75 cc. H2O with 10 cc. concentrated H2SO4 and then 12 hrs. with 400 cc. absolute MeOH yielded crude 2-aminoimidazole sulfate (I), m. 255°, beginning to decompose at 278°, which recrystallized from boiling 3:1 H2O-EtOH gave I, m. 280° (decomposition). H2NCH2CH(OEt)2 (100 g.) and 162 cc. H2O treated 48 hrs. at room temperature with methylisourea sulfate and evaporated, and the viscous oily residue crystallized from 1100 cc. Me2CO yielded N-(2,2-diethoxyethyl)guanidine sulfate, m. 150-3° (MeOH-Me2CO); a 76.6-g. portion added during 15 min. with stirring into 750 cc. boiling H2O and 4.8 cc. concentrated H2SO4 and refluxed 15 min. gave I, m. 280° (decomposition) (H2O). I (15.7 g.), 41 g. NaNO2, and 297 g. CuSO4.5H2O in 18,000 cc. H2O kept 16 hrs. at room temperature, adjusted with dilute HNO3 to about pH 2.0, and extracted with AcOEt yielded the yellow 2-nitroimidazole (II) which was sublimed at 175°/0.5-1.0 mm. I (660 mg.), 1.6 g. NaNO2, and 40 cc. H2O kept 1 hr. at room temperature gave similarly II. 2-(p-Bromobenzeneazo)-4-methylimidazole (8.58 g.) in 200 cc. EtOH hydrogenated 4 hrs. at 14-21 atm./50° over 2 g. Raney Ni, and the crude product in H2O neutralized with 2.7 cc. 12N H2SO4 gave the 4-Me derivative (III) of I, m. 229-31° (1:10 H2O-EtOH); a 0.146-g. portion in I cc. H2O treated 21 hrs. at room temperature with 2.5 g. CuSO4.5H2O and 0.35 g. NaNO2 in 360 cc. H2O and adjusted with 1.5 cc. dilute HCl to pH 2.0 gave III. I (6.7 g.), 12.7 g. CuSO4.5H2O, and 460 cc. 12N H2SO4 treated at -20° with 69 g. NaNO2 in 80 cc. H2O (introduced under the surface of the mixture), kept 24 hrs. at room temperature, and adjusted with concentrated NH4OH to pH 0.5 gave II. CuSO4.5H2O (150 g.) in 2000 cc. H2O and then 79.2 g. I in 1000 cc. H2O added at 0° to 1600 cc. 12N H2SO4, cooled to -20°, treated (under the surface) with 828 g. NaNO2 in 3000 cc. H2O during 1 hr., kept 40 hrs. at room temperature, adjusted at -10° to pH 1.0 with about 5000 cc. concentrated NH4OH, and stirred 1-2 hrs. at 0° yielded II, m. 289° (decomposition). 1-Methyl-2-aminoimidazole-HCl (6.7 g.), 12.5 g. CuSO4.5H2O, and 800 cc. 12N H2SO4 treated at -20° with 69 g. NaNO2 in 160 cc. H2O and kept 40 hrs. at room temperature yielded 1-Me derivative of II, m. 102-3° (isoPrOH). 4,5-Dimethyl derivative of I gave similarly during 12 hrs. the 4,5-dimethyl derivative of II, which was sublimed at 100-10°/ 0.05 mm. 2-Aminobenzimidazole (13.3 g.) in 110 cc. 1.0N H2SO4 and 25 g. CuSO4.5H2O treated dropwise with stirring during 55 min. with 34.5 g. NANO2 in 100 cc. H2O at 0°, stirred 18 hrs. at room temperature, treated dropwise with cooling and stirring with 33 cc. 18N H2SO4, stirred 1.5 hrs. at room temperature, and extracted with 1000 cc. Et2O yielded 2-nitrobenzimidazole (IV), m. 261-2° (decomposition). IV (3.22 g.) in 10 cc. 2.5N NaOH and 20 cc. H2O treated dropwise with stirring at 55° with 3.0 cc. Me2SO4, stirred 1.5 hrs. at room temperature, and kept 12 hrs. gave the 1-Me derivative of IV, m. 166-8° (aqueous EtOH). 2-Amino-5,6-dimethylbenzimidazole (16.1 g.) in 100 cc. 1.0N H2SO4 and 25 g. CuSO4.5H2O treated dropwise with stirring at 0° with 34.5 g. NaNO2 in 100 cc. H2O gave similarly the 5,6-dimethyl derivative of IV, m. 244-5° (aqueous EtOH). Examples for the formulation of IV and some of its derivatives in tablets, capsules, suppositories, and injection solutions are given. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Computed Properties of 5709-67-1

2-Nitro-1H-benzo[d]imidazole(cas:5709-67-1) belongs to imidazoles. It 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. Computed Properties of 5709-67-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On January 8, 1966, Lebedev, O. V.; Epishina, L. V.; Sevost’yanova, V. V.; Novikova, T. S.; Khmel’nitskii, L. I.; Novikov, S. S.; Prikhod’ko, A. S. published a patent.Application In Synthesis of 2-Nitro-1H-benzo[d]imidazole The title of the patent was 2-Nitroimidazoles. And the patent contained the following:

The title compounds are prepared by treating 2-amino derivatives of imidazole with an aqueous solution of Cu(NO2)2 and NaNO2 at a temperature of ∼60°. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Application In Synthesis of 2-Nitro-1H-benzo[d]imidazole

2-Nitro-1H-benzo[d]imidazole(cas:5709-67-1) belongs to imidazoles. It 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. Application In Synthesis of 2-Nitro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On October 31, 2021, Li, Xuwen; Zhang, Zijian; Luo, Xinlong; Schrier, Jacob; Yang, Andrew D.; Wu, Tao P. published an article.Application In Synthesis of N-Methyl-7H-purin-6-amine The title of the article was The exploration of N6-deoxyadenosine methylation in mammalian genomes. And the article contained the following:

A review. N6-methyladenine (N6-mA, m6dA, or 6mA), a prevalent DNA modification in prokaryotes, has recently been identified in higher eukaryotes, including mammals. Although 6mA has been well-studied in prokaryotes, the function and regulatory mechanism of 6mA in eukaryotes are still poorly understood. Recent studies indicate that 6mA can serve as an epigenetic mark and play critical roles in various biol. processes, from transposable-element suppression to environmental stress response. Here, we review the significant advances in methodol. for 6mA detection and major progress in understanding the regulation and function of this non-canonical DNA methylation in eukaryotes, predominantly mammals. The experimental process involved the reaction of N-Methyl-7H-purin-6-amine(cas: 443-72-1).Application In Synthesis of N-Methyl-7H-purin-6-amine

The Article related to review dna methylation mammalian genome, dna n6-methyladenine (6ma), mammalian dna modification, non-canonical mammalian dna methylation, Biochemical Genetics: Reviews and other aspects.Application In Synthesis of N-Methyl-7H-purin-6-amine

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Yang, Siqian; Wang, Yaoxin; Chen, Ying; Dai, Qi published an article in 2020, the title of the article was MASQC: next generation sequencing assists third generation sequencing for quality control in N6-methyladenine DNA identification.Formula: C6H7N5 And the article contains the following content:

DNA N6-methyladenine (6mA) modification has been discovered as the most prevalent DNA modification in prokaryotes and eukaryotes, involving gene expression, DNA replication and repair, and host-pathogen interactions. Single-mol. real-time sequencing (SMRT-seq) can detect 6mA events in prokaryotic and eukaryotic genomes at the single-nucleotide level. However, there are no strict and economical quality control methods for high false-pos. 6mA events in eukaryotic genomes. Therefore, by analyzing the distribution of 6mA in eukaryotic and prokaryotes, we proposed a method named MASQC (MeDIP-seq assists SMRT-seq for quality control in 6mA identification), which can identify 6mA events without doing the whole genome amplification (WGA) sequencing. The proposed MASQC method was assessed on two eukaryotic genomes and six bacterial genomes, our results demonstrate that MASQC performs well in quality control of false pos. 6mA identification for both eukaryotic and prokaryotic genomes. The experimental process involved the reaction of N-Methyl-7H-purin-6-amine(cas: 443-72-1).Formula: C6H7N5

The Article related to methyladenine prokaryote eukaryote next generation dna sequencing, dna n6-methyladenine, medip-seq, smrt-seq, eukaryotes, prokaryotes, Biochemical Genetics: Methods and other aspects.Formula: C6H7N5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On April 20, 1993, Palejwala, Vaseem A.; Rzepka, Robert W.; Simha, Devendranath; Humayun, M. Zafri published an article.Recommanded Product: 55662-66-3 The title of the article was Quantitative multiplex sequence analysis of mutational hot spots. Frequency and specificity of mutations induced by a site-specific ethenocytosine in M13 viral DNA. And the article contained the following:

An assay is described for determining the frequency and specificity of mutations occurring at hot spots within a population of DNA mols. The procedure consists of (a) annealing the DNA population with a labeled oligonucleotide designed to prime DNA synthesis at the mutational hot spot; (b) DNA elongation in the presence of a single dideoxynucleoside triphosphate together with 1-3 deoxynucleoside triphosphates, and (c) quantitation of all limit elongation products by high-resolution gel electrophoresis followed by autoradiog. and computing densitometry. Derivation of mutational frequency and specificity over a wide range of values is demonstrated for M13 viral DNA mixtures containing defined proportions of wild-type and mutant DNAs, as well as for M13 viral DNA populations obtained by transfection of DNA bearing a defined site-specific ethenocytosine lesion. The assay is shown to yield results similar to those obtained by laborious clone-by-clone sequencing of viral progeny. The method is not affected significantly by several tested variables and appears to be suitable for use as a quant. assay for sequence microheterogeneity at defined positions within DNA populations. Application of the methodol. demonstrates that ethenocytosine, an exocyclic DNA lesion induced by carcinogens such as vinyl chloride and urethane, is a highly efficient mutagenic lesion with a mutational specificity expected for noninstructive lesions. The experimental process involved the reaction of Imidazo[1,2-c]pyrimidin-5(6H)-one(cas: 55662-66-3).Recommanded Product: 55662-66-3

The Article related to mutation hot spot multiplex sequence analysis, m13 virus dna mutation ethenocytosine specificity, Biochemical Genetics: Methods and other aspects.Recommanded Product: 55662-66-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On October 31, 2012, WOJTASIAK-WYPART, M.; Soma, L. R.; Rudy, J. A.; Uboh, C. E.; Boston, R. C.; Driessen, B. published an article.Safety of N-(2-Bromo-6-fluorophenyl)-4,5-dihydro-1H-imidazol-2-amine hydrochloride The title of the article was Pharmacokinetic profile and pharmacodynamic effects of romifidine hydrochloride in the horse. And the article contained the following:

Romifidine HCl (romifidine) is an α2-agonist commonly used in horses. This study was undertaken to investigate the pharmacokinetics (PK) of romifidine following i.v. (i.v.) administration and describe the relationship between PK parameters and simultaneously recorded pharmacodynamic (PD) parameters. Romifidine (80 μg/kg) was administered by i.v. infusion over 2 min to six adult Thoroughbred horses, and plasma samples were collected and analyzed using liquid chromatog.-mass spectrometry. Limit of quantification was <0.1 ng/mL. PD parameters and arterial blood gases were measured for 300 min following romifidine administration. Statistical PD data anal. included mixed-effect modeling. After i.v. administration of romifidine, the plasma concentration-vs.-time curve was best described by a two-compartmental model. Terminal elimination half-life (t1/2β) was 138.2 (104.6-171.0) min and volumes for central (Vc) and peripheral (V2) compartments were 1.89 (0.93-2.39) and 2.57 (1.71-4.19) L/kg, resp. Maximum plasma concentration (Cmax) was 51.9 ± 13.1 ng/mL measured at 4 min following commencement of drug administration. Systemic clearance (Cl) was 32.4 (25.5-38.4) mL·min/kg. Romifidine caused a significant reduction in heart rate and cardiac index and an increase in mean arterial pressure (P < 0.05). Sedation score and head height values were significantly different from the baseline values for 120 min (P < 0.05). The decline in cardiovascular and sedative effects correlated with the decline in plasma romifidine concentration (P < 0.05). In conclusion, a highly sensitive anal. technique for the detection of romifidine in equine plasma allowed detailed description of its PK profile. The drug produces long-lasting sedation in horses that corresponds with the long terminal elimination half-life of the drug. The experimental process involved the reaction of N-(2-Bromo-6-fluorophenyl)-4,5-dihydro-1H-imidazol-2-amine hydrochloride(cas: 65896-14-2).Safety of N-(2-Bromo-6-fluorophenyl)-4,5-dihydro-1H-imidazol-2-amine hydrochloride

The Article related to sedivet pharmacodynamics pharmacokinetics sedative equus heart rate blood pressure, Pharmacology: Drug Metabolism and other aspects.Safety of N-(2-Bromo-6-fluorophenyl)-4,5-dihydro-1H-imidazol-2-amine hydrochloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On June 30, 2020, Spingardi, Paolo; Kriaucionis, Skirmantas published an article.Application of 443-72-1 The title of the article was How m6A sneaks into DNA. And the article contained the following:

A review. The biol. function and origin of N6-methyladenine (m6A) in DNA have been widely debated. A new study demonstrates that the majority of m6A in DNA originates from RNA catabolism via a nucleotide salvage pathway. The experimental process involved the reaction of N-Methyl-7H-purin-6-amine(cas: 443-72-1).Application of 443-72-1

The Article related to review dna n6 methyladenine rna catabolism nucleotide salvage pathway, General Biochemistry: Reviews and other aspects.Application of 443-72-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem