Tag: 100-200

Tautomerism of amidines. IV. Methylation of 4(5)-nitroglyoxaline and 4(5)-phenylglyoxaline was written by Hazeldine, C. E.;Pyman, F. L.;Winchester, John. And the article was included in Chem. Soc. in 1924.Computed Properties of C4H5N3O2 This article mentions the following:

A further study has been made of the influence of various substituents on the relative proportions of the 2 isomeric alkyl derivatives produced by the action of alkyl esters upon amidines. The NO₂ group favors the formation of the 5-O₂N-1-Me derivative as does the Br derivative but to a smaller extent. The Ph group is exceptional in that the ratio of the 4:1-Me to 5:1-Me derivative is 4.8:1, although its influence is similar to that of the NO₂ and Br groups in affecting the results of the distillation of the common methiodides of 4- and 5-substituted 1-methylglyoxalines. 4-Nitro-1-methylglyoxaline (I), m. 133-4°; HCl salt, large prisms, losing HCl at 100°. 5-Nitro derivative (II), m. 55°; HCl salt, small prisms with 2H₂O, m. 195° (decomposition); picrate, yellow, m. 153.5°, soluble in about 25 parts boiling H₂O. Nitration of 1-methyl-glyoxaline by boiling with HNO₃-H₂SO₄ 2 hrs. gave 21% I and 8% II. Methylation of 4(5)-nitroglyoxaline gave 62.3% II and 0.18% I (ratio, 350:1). Reduction of II by SnCl₂ and HCl gave NH₃, MeNH₂ and NH₂CH₂CO₂H. 4-p-Nitrophenyl-1-methylglyoxaline (III), pale yellow, m. 195°; nitrate, cream-colored needles, m. 197° (decomposition); picrate, m. 258°. III is obtained in 56% yield by nitration of 4-phenyl-1-methylglyoxaline, together with about 10% of the nitrate of the o-isomer, decomposes 182°. The 5-p-nitro derivative (IV), lemon-yellow, m. 171-2°; nitrate, m. 213° (decomposition); picrate, m. 184°. Methylation of 4-p-nitrophenylglyoxaline gave a mixture of 28% III and 2.6% IV. Nitration of III gave 90% of the 5-nitro derivative (V), faintly yellow, m. 208-9°; the HCl salt crystallines with 0.5 H₂O and loses its HCl at 100°. IV yields the 4-nitro derivative, faintly yellow, m. 187°. Methylation of 5-nitro-4-p-nitrophenylglyoxaline gave 66% of V. Reduction of V with SnCl₂ and HCl gave 5-amino-4-p-aminophenyl-1-methylglyoxaline, isolated as the di-HCl salt, needles, darken 200°, do not m. 300°; aqueous solutions give an oil with NaOH which soon darkens in color, or, with NH₃, a solution of transient indigo color. It reduces NH₄OH-AgNO₃ and gives a clear magenta solution with FeCl₃. Hydrolysis gave H₂NC₆H₄CH₂(NH₂)CO₂H, NH₂Me and NH₃. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Computed Properties of C4H5N3O2).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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.Computed Properties of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Comparative toxicokinetic/toxicodynamic study of rubber antioxidants, 2-mercaptobenzimidazole and its methyl substituted derivatives, by repeated oral administration in rats was written by Sakemi, Kazue;Ito, Rieno;Umemura, Takashi;Ohno, Yasuo;Tsuda, Mitsuhiro. And the article was included in Archives of Toxicology in 2002.HPLC of Formula: 4887-83-6 This article mentions the following:

2-Mercaptobenzimidazole (MBI), a rubber antioxidant, is known to exhibit potent thyroid toxicity in rats, whereas its methylated derivatives are much less toxic. To characterize this methyl-substituent effect on the thyroid toxicity of MBI, comparative toxicokinetic analyses have been conducted in the present study. MBI and the MMBIs [4-methylated MBI (4-MMBI) and 5-methylated MBI (5-MMBI), and a 1:1 mixture of these 4- and 5-methylated isomers (MMBI mix)] suspended in corn oil were repeatedly administered (at 0.3-0.6 mmol/kg) to male Wistar rats by gavage once daily for 2 wk. After the first and last administrations, blood and urine samples were collected, and the levels of unchanged compounds and their desulfurated metabolites were determined by high performance liquid chromatog. After repeated oral administration (roa), the C_max and area under concentration-time curve (AUC) of MBI were markedly increased, while the MMBIs essentially were cleared from the blood within 10 h. After roa, the C_max and AUC of 4-MMBI decreased markedly, suggesting metabolic enzyme induction. However, the toxicokinetic parameters of 5-MMBI were not markedly altered by roa. The inhibitory potencies (IC₅₀) against lactoperoxidase of MBI, 4-MMBI, and 5-MMBI were 20.6 μM, 45.6 μM and 31.6 μM, resp. Thus, the authors suggest that the marked decrease of thyroid toxicity by Me substitution of MBI is caused mainly by a decrease in systemic exposure to the compounds and partly by a decrease in inhibition of thyroid hormone synthesis. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6HPLC of Formula: 4887-83-6).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of α-Difluoromethyl Aryl Ketones through a Photoredox Difluoromethylation of Enol Silanes was written by Selmi-Higashi, Elias;Zhang, Jinlei;Cambeiro, Xacobe C.;Arseniyadis, Stellios. And the article was included in Organic Letters in 2021.COA of Formula: C6H8N2O This article mentions the following:

An efficient and highly straightforward access to α-difluoromethylated ketones through a visible light-mediated difluoromethylation of readily available enol silanes was reported. The method, which takes advantage of the polyvalence of Hu’s reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, used here as a CHF₂ radical precursor under catalytic photoredox conditions, was practical, scalable and provided the corresponding α-CHF₂ ketones in good to excellent yields. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1COA of Formula: C6H8N2O).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.COA of Formula: C6H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and crystallization of 3-methyl-1-propyl-1,3-dihydro-1H-imidazol-2-ylidene)silver(I) chlorido(5,10,15,20-tetraphenylporphinato)cadmate(II) was written by Bruekers, J. P. J.;Elemans, J. A. A. W.;Nolte, R. J. M.;Tinnemans, P.. And the article was included in IUCrData in 2022.SDS of cas: 79917-89-8 This article mentions the following:

The structure of the title salt, [Ag(C₇H₁₂N₂)₂][CdCl(C₄₄H₂₈N₄)], at 150 K has triclinic symmetry. One of the Ph rings bonded to the porphyrin mol. and the Pr groups of both ylidene mols. coordinating to silver are disordered over two positions. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8SDS of cas: 79917-89-8).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) 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.SDS of cas: 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nitration of 2,3-dihydroimidazo[1,2-a]benzimidazole and its N⁹-substituted derivatives was written by Sochnev, Vadim S.;Kuz’menko, Tatyana A.;Morkovnik, Anatolii S.;Divaeva, Lyudmila N.;Podobina, Anastasia S.;Zubenko, Alexander A.;Chepurnoy, Pavel B.;Borodkin, Gennadii S.;Klimenko, Alexander I.. And the article was included in Mendeleev Communications in 2021.Electric Literature of C9H9N3 This article mentions the following:

7-Nitro-2,3-dihydroimidazo[1,2-a]benzimidazole and its N⁹-substituted derivatives could be conveniently synthesized by nitration of the corresponding tricyclic precursors with a nitrating mixture or with the HNO₃/CF₃COOH system. This reaction occurred fairly smoothly and with good regioselectivity. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Electric Literature of C9H9N3).

2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7) 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. 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. Electric Literature of C9H9N3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Toxicity of nitro compounds toward hypoxic mammalian cells in vitro: dependence on reduction potential was written by Adams, G. E.;Stratford, I. J.;Wallace, R. G.;Wardman, P.;Watts, M. E.. And the article was included in JNCI, Journal of the National Cancer Institute in 1980.Synthetic Route of C5H5N3O4 This article mentions the following:

Fifteen nitroarom. and nitroheterocyclic compounds that can act as radiosensitizers were tested for their cytotoxicity toward hypoxic Chinese hamster V79 cells in vitro. The cytotoxicity increased markedly as the electron affinity, measured as a one-electron reduction potential, increased. Nonnitro compounds of similar electron affinities (such as quinones) that also act as radiosensitizers did not exhibit this specific toxicity toward hypoxic cells. The implications of the presence of the nitro group as a prerequisite for the hypoxic cell toxicity are discussed, and the mechanism of the cytotoxicity was compared with that of hypoxic cell radiosensitization. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Synthetic Route of 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. 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 C5H5N3O4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A simplified synthesis of 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate was written by Wilson, Hanna. And the article was included in Journal of Labelled Compounds & Radiopharmaceuticals in 2003.Safety of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid This article mentions the following:

2-Nitro-1H-Imidazole-1-acetic acid (2,3,5,6-tetrafluorophenyl) ester was synthesized via an improved route which involves the direct coupling of 2-(2-nitroimidazol-1-yl)acetic acid with 2,3,5,6-tetrafluorophenol. This ester is an intermediate for ¹⁸F-fluorinated derivatives of 2-nitro-N-(2,3,3-trifluoropropyl)-1H-imidazole-1-acetamide or fluoroetanidazole. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Safety 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 a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Safety of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Effects of imidazo[1,2-a]benzimidazole derivatives on gastric secretion and the antiulcer action was written by Spasov, A. A.;Kovalev, G. V.;Bakumov, P. A.;Reshetov, M. E.;Anisimova, V. A.;Avdyunina, N. I.. And the article was included in Farmakologiya i Toksikologiya (Moscow) in 1990.Synthetic Route of C9H9N3 This article mentions the following:

Experiments on rats showed that of 16 studied imidazo [1,2-a] benzimidazole derivatives only the compounds with Ph at C-2 and a N-containing radical at N-9 inhibit gastric acid secretion. The binding of a methoxy group to Ph, replacement by its adamantyl, displacement of the N-containing substituent to N-1 or its substitution were found to decrease or stop the inhibiting action of these substances on gastric parietal cells. Dihydrochloride of 2-phenyl-9(β-diethylaminoethyl)imidazo[1,2-a]benzimidazole was more potent than cimetidine and omeprazole in inhibiting gastric acid secretion and pepsin output, and in exerting an antiulcer action. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Synthetic Route of C9H9N3).

2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7) 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 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.Synthetic Route of C9H9N3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer was written by Tanaka, Takafumi;Tanaka, Tsukushi;Tsuji, Taro;Yazaki, Ryo;Ohshima, Takashi. And the article was included in Organic Letters in 2018.Related Products of 85692-37-1 This article mentions the following:

A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center, e.g., I (X-rays single crystal structure shown), were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Related Products of 85692-37-1).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Related Products of 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Benzimidazoles. III was written by Montanari, F.;Passerini, R.. And the article was included in Bollettino Scientifico della Facolta di Chimica Industriale di Bologna in 1953.Application of 83741-35-9 This article mentions the following:

2,3-(O₂N)₂C₆H₃Cl (2 g., 1 equivalent) reduced with 13.5 g. (6 equivalents) SnCl₂.2H₂O and 15 mL. concentrated HCl, and the product vacuum-distilled (113°/4 mm.) gives 2,3-(H₂N)₂C₆H₃Cl (I). Refluxing 1 equivalent I.2HCl 3 h. with 2 equivalents anhydrous HCO₂Na gives 4-chlorobenzimidazole, m. 170-1°. 2,3-(H₂N)₂C₆H₃Br gives 4-bromobenzimidazole, m. 168°. 2,3-(H₂N)₂C₆H₃OMe, m. 39-40°, gives 4-methoxybenzimidazole, m. 168°. 5-Nitro benzimidazole with SnCl₂ gives the 5-amino compound, m. 164°. 2-Nitro-6-methylbenzimidazole (15 g.) suspended in 33 mL. concentrated HCl and a little EtOH with 0.21 g. Sn yields the chlorostannate which gives 4-methyl-2-phenylbenzimidazole, m. 246°. BzH with 2,3-(H₂N)₂C₆H₃R gives the following 4-R derivatives of 2-phenylbenzimidazole: Cl, m. 227-8°; MeO, m. 214-15°; O₂N, m. 194-5°. With 3,4-(H₂N)₂C₆H₃OMe, BzH gives 5-methoxy-2-phenylbenzimidazole, m. 218-19°. By reduction of 2-nitro-2′-methylbenzanilide (from ο-nitroaniline and ο-MeC₆H₄COCl) is obtained 2-ο-tolylbenzimidazole, m. 111-12°. Likewise from the corresponding benzanilides are obtained the following benzimidazoles: 2-m-tolyl, m. 112-13°; 2-(ο-methoxyphenyl), m. 179-80°; and 2-(m-methoxyphenyl), m. 205°. 18 references In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-benzoimidazole (cas: 83741-35-9Application of 83741-35-9).

4-Bromo-1H-benzoimidazole (cas: 83741-35-9) 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 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 of 83741-35-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem