Category: imidazoles-derivatives

Solvatochromism of Heteroaromatic Compounds: XIX. Factors Affecting Quantitative Characteristics of Solvatochromism in Aprotic Inert Media was written by Turchaninov, V. K.;Vokin, A. I.;Aksamentova, T. N.;Krivoruchka, I. G.;Shulunova, A. M.;Andriyankova, L. V.. And the article was included in Russian Journal of General Chemistry (Translation of Zhurnal Obshchei Khimii) in 2003.Computed Properties of C4H5N3O2 This article mentions the following:

The effects of aprotic inert media on the electronic absorption spectra of aromatic nitro compounds p-NO₂C₆H₄R were used as evidence for the linear correlation between the slope s_a of the solvatochromism equations ν_max = ν₀ + s_aπ^* and the dipole moments of the mols. in their ground electronic state μ_g. A linear correlation was established between ν₀ and the first ionization potential of subunits PhR. A new approach to estimating the dipole moment of electronically excited mols. (μ_e) for mols. like p-NO₂C₆H₄R from the correlation μ_e = rμ_g was proposed. 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. 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.Computed Properties of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Identification of new process-related impurity in the key intermediate in the synthesis of TCV-116 was written by Testen, Ana;Plevnik, Miha;Stefane, Bogdan;Cigic, Irena Kralj. And the article was included in Acta Pharmaceutica (Warsaw, Poland) in 2019.Synthetic Route of C33H34N6O6 This article mentions the following:

Development of safe and effective drugs requires complete impurity evaluation and, therefore, knowledge about the formation and elimination of impurities is necessary. During impurity profiling of a key intermediate during synthesis of candesartan cilexetil (1-(((cyclohexyloxy)carbonyl) oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl) methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, TCV-116), a novel compound, which had not been reported previously, was observed Structural elucidation of impurity was achieved by liquid chromatog. hyphenated to different high resolution mass analyzers. Based on exact mass measurements and fragmentation pattern, a chloro alkyl carbonate ester analog of the intermediate was identified. Structure of the impurity was confirmed by mass spectro-metric and NMR analyses of the target substance. Identified impurity could represent a hazard if it is transferred to the final API stage and its presence should be kept below allowed limits. Further investigation could reveal whether bis(1-chloroethyl) carbonate is a precursor to impurity formation. Therefore, synthesis should be regulated so as to minimize impurity production Anal. of the final product indicated that the amount of impurity did not exceed 50 mg L^-1, which represents the detection limit, determined according to the signal/noise ratio. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Synthetic Route of C33H34N6O6).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) 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 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).Synthetic Route of C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

TEMPO-Mediated Synthesis of N-(Fluoroalkyl)imidazolones via Reaction of Imidazoles with Iodofluoroacetate was written by Chen, Jia-Hao;Ahmed, Wasim;Li, Ming-Hua;Li, Zhao-Dong;Cui, Zi-Ning;Tang, Ri-Yuan. And the article was included in Advanced Synthesis & Catalysis in 2020.Electric Literature of C8H8N2 This article mentions the following:

A TEMPO-mediated oxidative copper-catalyzed synthesis of N-(fluoroalkyl)imidazolones e.g., I via the radical addition of imidazoles such as 6-bromo-3-methyl-3H-imidazo[4,5-b]pyridine, 1-phenylimidazole, 5-bromo-1-methylbenzimidazole, etc. with iodofluoroacetate ICH(F)C(O)OCH₂CH₃ was reported. A possible key intermediate involving TEMPO was observed by ESI-MS. Also found that aerobic oxidation conditions were effective for the transformation in the presence of a copper catalyst, enabling access to a number of N-(fluoroalkyl)imidazolones I in moderate to good yields. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Electric Literature of C8H8N2).

1-Methylbenzimidazole (cas: 1632-83-3) 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 C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Structural, spectroscopic, and electrochemical properties of tri- and tetradentate N₃ and N₃S copper complexes with mixed benzimidazole/thioether donors was written by Castillo, Ivan;Ugalde-Saldivar, Victor M.;Rodriguez Solano, Laura A.;Sanchez Eguia, Brenda N.;Zeglio, Erica;Nordlander, Ebbe. And the article was included in Dalton Transactions in 2012.Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

Cupric and cuprous complexes of bis(2-methylbenzimidazolyl)(2-methylthiophene)amine (L¹), bis(2-methylbenzimidazolyl)benzylamine (L²), bis(2-methylbenzimidazolyl)(2,4-dimethylphenylthioethyl)amine (L³), bis(1-methyl-2-methylbenzimidazolyl)benzylamine (Me₂L²), and bis(1-methyl-2-methylbenzimidazolyl)(2,4-dimethylphenylthioethyl)amine (Me₂L³) were spectroscopically, structurally, and electrochem. characterized. The thioether-containing ligands L³ and Me₂L³ give rise to complexes with Cu-S bonds in solution and in the solid state, as evidenced by UV-visible spectroscopy and x-ray crystallog. The Cu²⁺ complexes [L¹CuCl₂] (1), [L²CuCl₂] (2) and [Me₂L³CuCl]ClO₄ (3^Me,ClO4) are monomeric in solution according to ESI mass spectrometry data, as well as in the solid state. Their Cu⁺ analogs [L¹Cu]ClO₄, [L²Cu]ClO₄, [L³Cu]ClO₄ (4–6), [BOC₂L¹Cu(NCCH₃)]ClO₄ (4^BOC), [Me₂L²Cu(NCCH₃)₂]PF₆ (5^Me) and [Me₂L³Cu]₂(ClO₄)₂ (6^Me) are also monomeric in MeCN solution, as confirmed crystallog. for 4^BOC and 5^Me. In contrast, 6^Me is dimeric in the solid state, with the thioether group of one of the ligands bound to a symmetry-related Cu⁺ ion. Cyclic voltammetry studies revealed that the bis(2-methylbenzimidazolyl)amine-Cu²⁺/Cu⁺ systems possess half-wave potentials in the range -0.16 to -0.08 V (referenced to the ferrocenium-ferrocene couple); these values are nearly 0.23 V less neg. than those reported for related bis(picolyl)amine-derived ligands. Based on these observations, the N₃ or N₃S donor set of the benzimidazole-derived ligands is analogous to previously reported chelating systems, but the electronic environment they provide is unique, and may have relevance to histidine and methionine-containing metalloenzymes. This is also reflected in the reactivity of [Me₂L²Cu(NCCH₃)₂]⁺ (5^Me) and [Me₂L³Cu]⁺ (6^Me) towards dioxygen, which gave the superoxide anion in both cases. The thioether-bound Cu⁺ center in 6^Me appears to be more selective in the generation of O₂âˆ?sup>- than 5^Me, lending evidence to the hypothesis of the modulating properties of thioether ligands in Cu-O₂ reactions. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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 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.Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Alkyl substituent effect on density, viscosity and chemical behavior of 1-alkyl-3-methylimidazolium chloride was written by Olmo, Lourdes del;Lage-Estebanez, Isabel;Lopez, Rafael;Garcia de la Vega, Jose M.. And the article was included in Journal of Molecular Modeling in 2014.Reference of 79917-89-8 This article mentions the following:

Mol. structure of the conformers of 1-C_n-3-methylimidazolium chloride (n = 1 to 4) ionic liquids has been explored and the relationships with d. and viscosity have been studied using COSMO related methodologies. Effects of the number of conformers, ionic character, anion-cation relative positions and the alkyl chain length of the cation on predictions of properties have been analyzed. The quality of the predictions has been tested by comparing with exptl. results. Moreover, COSMO polarization charge densities, σ-profiles and σ-potentials of the conformers have been analyzed. Predictions on the chem. behavior based on the values of these properties in the conformers have been used to elucidate the affinity for electrophilic and nucleophilic reagents of ionic liquids In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Reference of 79917-89-8).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ionic liquid modification of graphene oxide and its role towards controlling the porosity, and mechanical robustness of polyurethane foam was written by Mondal, Titash;Basak, Suman;Bhowmick, Anil K.. And the article was included in Polymer in 2017.Formula: C4H7ClN2 This article mentions the following:

1-Me imidazole chloride ionic liquid grafted graphene oxide (G[MIM]Cl) was synthesized and utilized as an effective agent for controlling the strength, distribution and dimension of the pores of polyurethane foam system (ILF). Polymeric foams fabricated with pristine expandable graphite (GF) and the neat polymer (PUF) demonstrated a distorted cell structure and an uneven distribution of the pores. Addnl., the mech. properties of GF and PUF were found to be inferior compared to those of ILF. The effect of surface modification of filler on the dispersion in the polyurethane matrix was also studied and compared with the dispersion of the unfunctionalized filler. The ILF exhibited higher elec. conductivity over the GF and the PUF. Compressive stress-strain behavior and dynamic mech. properties indicated that ILF demonstrated significant mech. robustness compared to GF and PUF. These findings can be readily extended to the development of complex three dimensional polymeric architecture where controlled porosity is required. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Formula: C4H7ClN2).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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 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).Formula: C4H7ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A versatile synthesis of pyrazolo[3,4-c]isoquinoline derivatives by reaction of 4-aryl-5-aminopyrazoles with aryl/heteroaryl aldehydes: the effect of the heterocycle on the reaction pathways was written by Bogza, Sergei L.;Kobrakov, Konstantin I.;Malienko, Anna A.;Perepichka, Igor F.;Sujkov, Sergei Yu.;Bryce, Martin R.;Lyubchik, Svetlana B.;Batsanov, Andrei S.;Bogdan, Natalya M.. And the article was included in Organic & Biomolecular Chemistry in 2005.Reference of 3012-80-4 This article mentions the following:

The reaction of 4-(3,4-dimethoxyphenyl)-5-aminopyrazoles I (R¹ = Me, Et, Ph, PhCH₂) with aromatic and heterocyclic aldehydes R²CHO (R² = Ph, 3-ClC₆H₄, 4-Et₂NC₆H₄, 3-pyridyl, 2-quinolinyl, 1,2,3-thiadiazol-5-yl) in strong acidic media (trifluoroacetic or formic acid) produced the intermediate pyrazolyl azomethines, which undergo cyclization, similar to the Pictet-Spengler condensation, to give, after in situ aromatization, 5-aryl(heteroaryl)-pyrazolo[3,4-c]isoquinolines II. Whereas for benzaldehyde and its derivatives this one-pot synthesis presents a convenient general route to 5-aryl-pyrazolo[3,4-c]isoquinolines II, in the case of heterocyclic aldehydes the product structure varies markedly with the structure of the aldehyde used: (i) 3-pyridyl-, 3-quinolyl-, 3-thienyl-, and 1,2,3-thiadiazolyl-5-carboxaldehydes give pyrazolo[3,4-c]isoquinolines II; (ii) 1-methylbenzimidazolyl-2-carboxaldehyde gives only intermediate azomethine, which does not cyclize; (iii) 1-R³-3-indolylcarboxaldehydes (R³ = H, Me, PhCH₂) eliminate the heteroaryl fragment resulting in 5-unsubstituted pyrazolo[3,4-c]isoquinolines II (R² = H). Thienyl-2-carboxaldehyde reacts by both pathways (i) and (iii) depending on the reaction conditions. The single crystal X-ray structures for II (R¹ = Me, R² = 2-thienyl; R¹ = PhCH₂, R² = 4-Et₂NC₆H₄; R¹ = Me, R² = H) provide confirmation of the different types of products formed in these reactions. Mechanisms which explain these transformations are presented. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Reference of 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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 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.Reference of 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

An expeditious synthesis of benzimidazole derivatives catalyzed by Lewis acids was written by Zhang, Zhan-Hui;Yin, Liang;Wang, Yong-Mei. And the article was included in Catalysis Communications in 2007.Formula: C8H8N2 This article mentions the following:

An expeditious and efficient route for the synthesis of benzimidazole derivatives by the reaction of o-phenylenediamines with orthoesters in the presence of Lewis acids was described. ZrCl₄, SnCl₄.5H₂O, TiCl₄, BF₃.Et₂O, ZrOCl₂.8H₂O and HfCl₄ exhibited high catalytic activity for this transformation. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Formula: C8H8N2).

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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Formula: C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Acetic Acid Mediated Electrochemical Synthesis of Benzazole and its Application in the Synthesis of Pharmaceutically Active Compounds was written by Ghoshal, Tanay;Patel, Tarun M.;Kotturi, Sharadsrikar. And the article was included in ChemistrySelect in 2021.Application In Synthesis of 1H-Benzimidazole-5-carbaldehyde This article mentions the following:

An acetic acid promoted electrochem. synthesis of benzazoles, benzimidazoles, benzthiazoles and benzoxazoles was reported. The method offered large substrate scope, good functional group tolerance, while using cheap electrolyte. The method use acetic acid as the electrolyte which has a better solubility in methanol, hence the reaction time was less and product formation was observed in high yield without much side product. This electrochem. method was further utilized to synthesize thiabendazole, fuberidazole, chlormidazole and advance intermediates of bilastine and clemizole in good yields. In the experiment, the researchers used many compounds, for example, 1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4Application In Synthesis of 1H-Benzimidazole-5-carbaldehyde).

1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4) 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.Application In Synthesis of 1H-Benzimidazole-5-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

(6R,8S)-(2-Benzimidazolyl)hydroxymethylpenicillanic acids as potent antibacterial agents and β-lactamase inhibitors was written by Chen, Yuhpyng L.;Hedberg, Kirk;Guarino, Karen;Retsema, James A.;Anderson, Margaret;Manousos, Mary;Barrett, John. And the article was included in Journal of Antibiotics in 1991.Electric Literature of C9H8N2O This article mentions the following:

(6R,8S)-(2-Benzimidazolyl)hydroxymethylpenicillanic acids I [R = (un)substituted alkyl, alkenyl etc.] (24 compds) are potent antibacterial agents and β-lactamase inhibitors against Gram-pos. bacteria and Haemophilus influenzae. The (6R,8R)-isomers, the 6,6-spirobenzimidazolepenam alc., (7R,9S)-(1-vinyl-2-benzimidazolyl)hydroxymethylcephalosporanic acid, and 6β-(2-benzimidazolyl)aminopenicillanic acid are much less active as antibacterials or β-lactamase inhibitors. The syntheses and structure-activity relationships of these compounds are discussed. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Electric Literature of C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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.Electric Literature of C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem