Month: February 2023

Facile access to N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones was written by Huang, Hsin-Yi;Lin, Xiu-Yi;Yen, Shih-Yao;Liang, Chien-Fu. And the article was included in Organic & Biomolecular Chemistry in 2020.Reference of 1632-83-3 This article mentions the following:

N-Formamides e.g., N-benzylformamide synthesis using N-formyl imide RC(O)NHC(O)H (R = Ph, tert-Bu, pyridin-4-yl, thiophen-2-yl, etc.) with primary and secondary amines e.g., benzylamine with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH路H₂O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines RC(O)N=CHN(CH₃)₂ with TsOH路H₂O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole I (R¹ = H, Me; R² = H, Me, F, CN, etc.; R³ = H, Me, Cl; R⁴ = H, Me, Bn, Ts; R²R³ = -CH=CH-CH=CH-) and quinazolinone derivs II (R⁵ = H, Pr, Ph, cyclopentyl, etc.). Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- and metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Reference of 1632-83-3).

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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Reference of 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Discovery of small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase was written by Kaur, Supreet;Nieto, Nicholas S.;McDonald, Peter;Beck, Josh R.;Honzatko, Richard B.;Roy, Anuradha;Nelson, Scott W.. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2022.Application of 145040-37-5 This article mentions the following:

Malaria is caused by infection with protozoan parasites of the Plasmodium genus, which is part of the phylum Apicomplexa. Most organisms in this phylum contain a relic plastid called the apicoplast. The apicoplast genome is replicated by a single DNA polymerase (apPOL), which is an attractive target for anti-malarial drugs. We screened small-mol. libraries (206,504 compounds) using a fluorescence-based high-throughput DNA polymerase assay. Dose/response anal. and counter-screening identified 186 specific apPOL inhibitors. Toxicity screening against human HepaRG human cells removed 84 compounds and the remaining were subjected to parasite killing assays using chloroquine resistant P. falciparum parasites. Nine compounds were potent inhibitors of parasite growth and may serve as lead compounds in efforts to discover novel malaria drugs. 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: 145040-37-5Application of 145040-37-5).

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. 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.Application of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and evaluation of 2-(4-[4-acetylpiperazine-1-carbonyl] phenyl)-1H-benzo[d]imidazole-4-carboxamide derivatives as potential PARP-1 inhibitors and preliminary study on structure-activity relationship was written by Chen, Miaojia;Huang, Honglin;Wu, Kaiyue;Liu, Yunfan;Jiang, Lizhi;Li, Yang;Tang, Guotao;Peng, Junmei;Cao, Xuan. And the article was included in Drug Development Research in 2022.Category: imidazoles-derivatives This article mentions the following:

A series of 2-(4-[4-substitutedpiperazine-1-carbonyl]phenyl)-1H-benzo[d]imidazole-4-carboxamide derivatives I [R = Me, Ph, 2-furyl, etc.] was designed, synthesized and successful characterization as novel and effective poly ADP-ribose polymerases (PARP)-1 inhibitors to improve the structure-activity relationships about the substituents in the hydrophobic pocket. These derivatives were evaluated for their PARP-1 inhibitory activity and cellular inhibitory against BRCA-1 deficient cells (MDA-MB-436) and wild cells (MCF-7) using PARP kit assay and MTT method. The results indicated that compared with other heterocyclic compounds, furan ring-substituted derivatives I [R = 2-furyl, 3-methyl-2-furyl, 5-bromo-2-furyl, 5-chloro-2-furyl] showed better PARP-1 inhibitory activity. Among this derivatives, compound I [R = 5-bromo-2-furyl] displayed the strongest inhibitory effects on PARP-1 enzyme (IC₅₀ = 0.023渭M), which was close to that of Olaparib. The compounds I [R = 5-bromo-2-furyl] (IC₅₀ = 43.56 卤 0.69渭M) and I [R = 5-chloro-2-furyl] (IC₅₀ = 36.69 卤 0.83渭M) displayed good antiproliferation activity on MDA-MB-436 cells and inactivity on MCF-7 cells, indicating that they had high selectivity and targeting. The mol. docking method was used to explore the binding mode of compound I [R = 5-bromo-2-furyl] and PARP-1, and implied that the formation of hydrogen bond was essential for PARP-1 inhibition activities. This study also showed that in the hydrophobic pocket (AD binding sites), the introduction of strong electroneg. groups (furan ring, e.g.) or halogen atoms in the side chain of benzimidazole might improve its inhibitory activity and this strategy could be applied in further research. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Category: imidazoles-derivatives).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Understanding effect of molecular structure of imidazole-based ionic liquids on catalytic performance for biomass inulin hydrolysis was written by Lu, Peng;Zhao, Zhi-Ping;Wang, Xing-Ya;Lan, Gong-Jia;Wang, Xiao-Lan. And the article was included in Molecular Catalysis in 2017.Reference of 35487-17-3 This article mentions the following:

Developing a green hydrolysis process of biomass for the production of the value-added compounds has been widely concerned. This article aimed at elucidating the structure-property relationship of ionic liquids (ILs) as catalysts, i.e., effect of the chem. structures of anion and cation of ILs on their acidity and catalytic properties of inulin hydrolysis. Twenty kinds of imidazole-based ILs and one kind of quaternary ammonium ILs were synthesized. Inulin hydrolysis for the reducing sugar production was investigated with a series of functionalized ILs under moderate temperature (75 掳C) and atm. pressure. The chem. structure, acidity and catalytic property of ILs were exptl. characterized and theor. analyzed. The possible catalytic hydrolysis mechanisms of polysaccharide or lignocellulose by ILs were detailedly analyzed. This work demonstrated that the catalytic performance of catalysts depends not only on its acidity, but also on the chem. structure. It was revealed that imidazole-based ILs showed better catalytic performance than quaternary ammonium ILs in the inulin hydrolysis system, and SO₃H-functionalized sulfonate ILs obtained more efficient catalytic property because the hydrolysis reaction was catalyzed by the synergy of anion and cation, compared with the sulfuric acid with stronger acidity, which can cause serious equipment corrosion in biomass hydrolysis process. In all these tested ILs, (1-(4-sulfonic acid)-butyl-3-ethylimidazolium hydrogen sulfate) ([C₂MIM-PS][HSO^–₄]) exhibited the best catalytic performance, and the yield of reducing sugar was 100%. Understanding the structure-property relationship of ILs will be helpful to design the covalent immobilization strategy of ILs to improve its reusability and eliminate the potential harmfulness to the environment. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Reference of 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. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Reference of 35487-17-3

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

Lewis acid / base-free strategy for the synthesis of 2-arylthio and selenyl benzothiazole / thiazole and imidazole was written by Balakishan, Guniganti;Kumaraswamy, Gullapalli;Narayanarao, Vykunthapu;Shankaraiah, Pagilla. And the article was included in Heterocyclic Communications in 2021.Related Products of 1632-83-3 This article mentions the following:

A Cu(II)-catalyzed Csp²-Se and Csp²-sulfur bond formation was achieved with moderate to good yields without the aid of Lewis acid and base. The reaction was compatible with a wide range of heterocycles such as benzothiazole, thiazole and imidazole. Also, this typical protocol was found to be active in thio-selenation via S-H activation. Addnl., a plausible mechanistic pathway involving Cu(III) putative intermediate was proposed. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Related Products of 1632-83-3).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3鈥揅6) is higher than in water and generally decreases with a This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Related Products of 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Sustainable Cascades to Difluoroalkylated Polycyclic Imidazoles was written by Lin, Sheng-Nan;Chen, Yu;Luo, Xiao-Dong;Li, Yi. And the article was included in European Journal of Organic Chemistry in 2021.Quality Control of 7-Methyl-1H-benzo[d]imidazole This article mentions the following:

Herein a visible light promoted difluoroalkylated cascade of imidazoles and alkenes e.g., I to afford highly functionalized polycyclic imidazoles e.g., II was reported. This method features a direct radical cyclization of imidazoles with alkenes e.g., I using BrCF₂R (R = C(O)OEt, N-cyclohexylcarbamoyl, (thiomorpholin-4-yl)carbonyl, etc.) as radical sources. The reaction conditions tolerate a wide range of substrate scope and afford the desired products e.g., II with up to 95% isolated yield under mild conditions. Radical-trapping and light-on/off experiments indicated a photocatalytic radical mechanism. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Quality Control of 7-Methyl-1H-benzo[d]imidazole).

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. 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.Quality Control of 7-Methyl-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A library of novel hydroxamic acids targeting the metallo-protease family: Design, parallel synthesis and screening was written by Flipo, Marion;Beghyn, Terence;Charton, Julie;Leroux, Virginie A.;Deprez, Benoit P.;Deprez-Poulain, Rebecca F.. And the article was included in Bioorganic & Medicinal Chemistry in 2007.Synthetic Route of C9H8N2O This article mentions the following:

The authors report here the design and parallel synthesis of 217 compounds based on a malonic-hydroxamic acid template. These compounds are obtained via a two-step solution-phase procedure. The set of diverse building-blocks used makes this strategy suitable for the search of inhibitors of various metallo-proteases and for the investigation of the biol. role of new metallo-proteases. As a proof of concept, the authors screened this library on neutral aminopeptidase (APN; E.C. 3.4.11.2), the prototypal enzyme of the M1 family. Several submicromolar inhibitors were identified. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Synthetic Route of C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Synthetic Route of C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Probing the free-state solution behavior of drugs and their tendencies to self-aggregate into nano-entities was written by LaPlante, Steven R.;Roux, Valerie;Shahout, Fatma;LaPlante, Gabriela;Woo, Simon;Denk, Maria M.;Larda, Sacha T.;Ayotte, Yann. And the article was included in Nature Protocols in 2021.HPLC of Formula: 145040-37-5 This article mentions the following:

The free-state solution behaviors of drugs profoundly affect their properties. Therefore, it is critical to properly evaluate a drug’s unique multiphase equilibrium when in an aqueous environment, which can comprise lone mols., self-associating aggregate states and solid phases. To date, the full range of nano-entities that drugs can adopt has been a largely unexplored phenomenon. This protocol describes how to monitor the solution behavior of drugs, revealing the nano-entities formed as a result of self-associations The procedure begins with a simple NMR 1H assay, and depending on the observations, subsequent NMR dilution, NMR T2-CPMG (spin-spin relaxation Carr-Purcell-Meiboom-Gill) and NMR detergent assays are used to distinguish between the existence of fast-tumbling lone drug mols., small drug aggregates and slow-tumbling colloids. Three orthogonal techniques (dynamic light scattering, transmission electron microscopy and confocal laser scanning microscopy) are also described that can be used to further characterize any large colloids. The protocol can take a non-specialist between minutes to a few hours; thus, libraries of compounds can be evaluated within days. 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: 145040-37-5HPLC of Formula: 145040-37-5).

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. 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.HPLC of Formula: 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Hidden signatures: new reagents for developing latent fingerprints was written by Plater, M. John;Barnes, Paul;McDonald, Lauren K.;Wallace, Sandy;Archer, Nia;Gelbrich, Thomas;Horton, Peter N.;Hursthouse, Michael B.. And the article was included in Organic & Biomolecular Chemistry in 2009.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

Aldehydes substituted with a quaternized pyridinium or quinolinium ring have been investigated for the development of latent fingerprints. Two routes were developed to a novel in situ formed azacyanine dye. This dye might form in the fingerprint where reagents are concentrated but does not form appreciably in solution experiments as evidenced by the lack of an absorption band at 600 nm. N-Alkyl and N-aryl substituted benzimidazole-2-carboxaldehydes give stable fluorescent fingerprints. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem