Author: Jessica.F

Dichlorophenylacrylonitriles as AhR Ligands That Display Selective Breast Cancer Cytotoxicity in vitro was written by Baker, Jennifer R.;Gilbert, Jayne;Paula, Stefan;Zhu, Xiao;Sakoff, Jennette A.;McCluskey, Adam. And the article was included in ChemMedChem in 2018.Category: imidazoles-derivatives This article mentions the following:

Knoevenagel condensation of 3,4-dichloro- and 2,6-dichlorophenylacetonitriles gave a library of dichlorophenylacrylonitriles. Our leads (Z)-2-(3,4-dichlorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile (5) and (Z)-2-(3,4-dichlorophenyl)-3-(4-nitrophenyl)acrylonitrile (6) displayed 0.56±0.03 and 0.127±0.04 μM growth inhibition (GI₅₀) and 260-fold selectivity for the MCF-7 breast cancer cell line. A 2,6-dichlorophenyl moiety saw a 10-fold decrease in potency; addnl. nitrogen moieties (-NO₂) enhanced activity (Z)-2-(2,6-dichloro-3-nitrophenyl)-3-(2-nitrophenyl)acrylonitrile (26) and (Z)-2-(2,6-dichloro-3-nitrophenyl)-3-(3-nitrophenyl)acrylonitrile (27), with the corresponding -NH₂ analogs (Z)-2-(3-amino-2,6-dichlorophenyl)-3-(2-aminophenyl)acrylonitrile (29) and (Z)-2-(3-amino-2,6-dichlorophenyl)-3-(3-aminophenyl)acrylonitrile (30) being more potent. Despite this, both 29 (2.8±0.03 μM) and 30 (2.8±0.03 μM) were found to be 10-fold less cytotoxic than 6. A bromine moiety effected a 3-fold enhancement in solubility with (Z)-3-(5-bromo-1H-pyrrol-2-yl)-2-(3,4-dichlorophenyl)acrylonitrile 18 relative to 5 at 211 μg mL^-1. Modeling-guided synthesis saw the introduction of 4-aminophenyl substituents (Z)-3-(4-aminophenyl)-2-(3,4-dichlorophenyl)acrylonitrile (35) and (Z)-N-(4-(2-cyano-2-(3,4-dichlorophenyl)vinyl)phenyl)acetamide (38), with resp. GI₅₀ values of 0.030±0.014 and 0.034±0.01 μM. Other analogs such as 35 and 36 were found to have sub-micromolar potency against our panel of cancer cell lines (HT29, colon; U87 and SJ-G2, glioblastoma; A2780, ovarian; H460, lung; A431, skin; Du145, prostate; BE2-C, neuroblastoma; MIA, pancreas; and SMA, murine glioblastoma), except compound 38 against the U87 cell line. A more extensive evaluation of 38 ((Z)-N-(4-(2-cyano-2-(3,4-dichlorophenyl)vinyl)phenyl)acetamide) in a panel of drug-resistant breast carcinoma cell lines showed 10-206 nM potency against MDAMB468, T47D, ZR-75-1, SKBR3, and BT474. Mol. Operating Environment docking scores showed a good correlation between predicted binding efficiencies and observed MCF-7 cytotoxicity. This supports the use of this model in the development of breast-cancer-specific drugs. In the experiment, the researchers used many compounds, for example, 1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4Category: imidazoles-derivatives).

1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4) 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–C6) is higher than in water and generally decreases with a 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.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

NMR Quantification of Halogen-Bonding Ability To Evaluate Catalyst Activity was written by Chang, Yun-Pu;Tang, Teresa;Jagannathan, Jake R.;Hirbawi, Nadia;Sun, Shaoming;Brown, Jonah;Franz, Annaliese K.. And the article was included in Organic Letters in 2020.Safety of 1-Methylbenzimidazole This article mentions the following:

Quantification of halogen-bonding abilities is described for a series of benzimidazolium-, imidazolium- and bis(imidazolium) halogen-bond donors (XBDs) using ³¹P NMR spectroscopy. The measured Δδ(³¹P) values correlate with calculated activation free energy ΔG^{â€?/sup> and catalytic activity for a Friedel-Crafts indole addition This rapid method also serves as a sensitive indicator for Bronsted acid impurities. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Safety of 1-Methylbenzimidazole).}

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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Safety of 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Polarographic investigations in the imidazole and thiazole series. Nitro derivatives, aldehydes, and halogen derivatives was written by Laviron, E.. And the article was included in Abhandl. Deut. Akad. Wiss. Berlin, Kl. Chem., Geol. Biol. in 1964.Application of 3034-41-1 This article mentions the following:

4-(5)-Nitroimidazole,-2-nitroimidazole, 4-nitro- and 5-nitro-l-methylimidazole, and 4-(5)nitro-1,3-dimethylimidazolium iodide (I) are reduced in 2 steps, but the 2nd step is not equally sharp in all cases. Ε_1/2 is a linear function of pH for 2- nitroimidazole and I but not for the other compounds The diffusion current of 2-nitroimidazole is diminished at low pH. This is also true of the 5-nitro derivatives of thiazole (with NH₂, NHAc, Cl, Br, or OH substituted in position 2). 4(5)-Imidazolecarboxaldehyde and thiazolecarboxaldehyde in buffered aqueous and in absolute EtOH and MeOH solutions, acidified with H₂SO₄ or buffered with acetate and HOAc, show a marked lowering of the diffusion current in acid medium. This was ascribed to a polarographically irreducible hydrate of the imidazolium or thiazolium ion in acid, a hypothesis that was further supported by uv spectra. Of numerous halogen derivatives investigated, all compounds in the thiazol series are very easily reducible, while only the 2-iodo and 2,4,5-triiodo compounds give well defined waves in the imidazole series. At the extremes of pH, the Ε_1/2 of the halogen derivatives are independent of pH, while a more or less linear dependence on pH (with varying slope) is found for intermediate values of pH. 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 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.Application of 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Metalation and metal-halogen exchange reactions of imidazoles was written by Iddon, Brian;Lim, Bee Lan. And the article was included in Journal of the Chemical Society, Chemical Communications in 1981.Application In Synthesis of 4-Bromo-1-methylimidazole This article mentions the following:

Imidazoles I (R = SPh, R¹ = H, R² = H, MeS) underwent lithiation and sulfuration to give thioimidazoles. E.g., I (R = SPh, R¹ = R² = H) was treated with BuLi in THF at -78° followed by addition of (PhS)₂ to give I (R = R² = SPh, R¹ = H) quant. Similar treatment of I (R-R² = Br) gave 67% I (R = SPh, R¹ = R² = Br). In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Application In Synthesis of 4-Bromo-1-methylimidazole).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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 4-Bromo-1-methylimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Chlorocuprate(I) ionic liquid as an efficient and stable Cu-based catalyst for hydrochlorination of acetylene was written by Ren, Yanfei;Wu, Botao;Wang, Fumin;Li, Hang;Lv, Guojun;Sun, Mingshuai;Zhang, Xubin. And the article was included in Catalysis Science & Technology in 2019.Reference of 35487-17-3 This article mentions the following:

The gas-liquid reaction process for acetylene hydrochlorination, especially using ionic liquids (ILs) as homogeneous reaction media, has gained much attention because it can effectively avoid the deactivation caused by hot spots and carbon deposition. However, the relatively low activity and high price of the currently used ILs limit their practical applications. Herein, we synthesize a series of chlorocuprate(I) ILs to explore an efficient and stable Cu-based catalyst for acetylene hydrochlorination. The N-methylpyrrolidonium hydrochloride-0.60CuCl ([Hnmpo]Cl-0.60CuCl) IL exhibits the best catalytic performance, showing an acetylene conversion of 86% over 150 h under the conditions of 180°C and 50 h^-1 GHSV. In addition, the [Hnmpo]Cl-0.60CuCl IL has the capacity to effectively activate HCl, which is directly observed by in situ FTIR. By combining the exptl. results and theor. calculations, we propose the reaction mechanism and find that the catalytic performance of chlorocuprate(I) ILs is pos. correlated with the adsorption of HCl. The strong interaction with HCl is identified as the key characteristic of the [Hnmpo]Cl-CuCl IL, which endows it with excellent catalytic performance. Briefly, this study shows that the cost-effective [Hnmpo]Cl-CuCl IL can be a viable alternative to the com. heterogeneous HgCl₂/AC catalyst for acetylene hydrochlorination. 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. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Reference of 35487-17-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Silver(I) Ion Induced Monolayer Formation of 2-Substituted Benzimidazoles at the Air/Water Interface was written by Liu, Minghua;Kira, Akira;Nakahara, Hiroo. And the article was included in Langmuir in 1997.COA of Formula: C15H22N2 This article mentions the following:

The monolayer formation of a series of 2-substituted benzimidazoles at the air/water interface was studied by the measurements of surface pressure-area isotherms. Concentrated silver(I) ion in the subphase can induce the monolayer formation of 2-alkylbenzimidazole derivatives (BzCn) with the alkyl chain equal to or greater than C5 although the derivatives cannot form monolayers on pure water surface except BzC17. Similar behavior of monolayer formation of 2-phenylbenzimidazole was also observed The measurements of UV spectra and XPS anal. of the transferred films suggested that such monolayer formation was fulfilled through an in situ formation of a polymeric silver(I)-benzimidazole complex at the air/water interface. In the experiment, the researchers used many compounds, for example, 2-Octylbenzimidazole (cas: 13060-24-7COA of Formula: C15H22N2).

2-Octylbenzimidazole (cas: 13060-24-7) 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.COA of Formula: C15H22N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Effect of some imidazole derivatives on adenosine 3′,5′-monophosphoric acid phosphodiesterase activity was written by Lunts, V. Ya.. And the article was included in Byulleten Eksperimental’noi Biologii i Meditsiny in 1976.Recommanded Product: 3034-41-1 This article mentions the following:

The effect of 24 imidazole derivatives on the activity of phosphodiesterase EC 3.1.4.1. [9025-82-5] was studied in experiments with homogenates of rat brain and of Rana temporaria skeletal muscle. Imidazole [288-32-4] derivatives produced both activating and inhibitory influences on the enzyme. Imidazole and 7 of its alkyl substituted derivatives activated the phosphodiesterase. Tetrachloro-2-trifluoromethylbenzimidazole [2338-29-6] produced the greatest effect among the inhibitors on the phosphodiesterase activity. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 3034-41-1).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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).Recommanded Product: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Group contribution and parachor analysis of experimental data on density and surface tension for members of the homologous series of 1-C_n-3-methylimidazolium chlorides was written by Souckova, Monika;Klomfar, Jaroslav;Patek, Jaroslav. And the article was included in Fluid Phase Equilibria in 2017.Application In Synthesis of 1-Methyl-3-propylimidazolium Chloride This article mentions the following:

The d. and surface tension values are presented that represent the best current knowledge of these properties for members of the homologous series of 1-C_n-3-methylimidazolium chlorides. To identify these values, a method was used based on the consistency requirement between selected background exptl. data and group contribution models of known best achievable accuracy. The models have been developed using our own and other authors data. For this purpose 64 and 119 new exptl. data on the d. and surface tension, resp., have been measured for [C₁IM][Cl] and [C_nMIM][Cl] with n = 2, 3, 4, 6, and 10 at temperatures from (263 to 365) K and at the pressure of 0.1 MPa. The d. was measured using the buoyancy method while the surface tension was measured by the Wilhelmy plate and du Nouy ring method in parallel. The resp. expanded combined uncertainties at the 0.95 confidence level of the resultant means of sets of individual measurements performed at a given temperature do not exceed 1 kg·m^-3, 0.07 mN·m^-1 and 1 mN·m^-1. The estimated maximum deviations of the obtained recommended values from the true d. and surface tension values are 0.1 kg·m^-3 and 0.15 mN·m^-1, resp. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Application In Synthesis of 1-Methyl-3-propylimidazolium Chloride).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) 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.Application In Synthesis of 1-Methyl-3-propylimidazolium Chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nickel-catalysed asymmetric heteroarylative cyclotelomerization of isoprene was written by Zhang, Gong;Zhao, Chao-Yang;Min, Xiang-Ting;Li, Ying;Zhang, Xiang-Xin;Liu, Heng;Ji, Ding-Wei;Hu, Yan-Cheng;Chen, Qing-An. And the article was included in Nature Catalysis in 2022.Application of 1632-83-3 This article mentions the following:

Monoterpenoids are a class of isoprenoids produced from geranyl diphosphate by various monoterpene synthases. Nature has evolved over millions of years to produce various cyclic monoterpenoids. Herein, authors present a serendipitous creation of an unnatural monoterpene skeleton through heteroarylative telomerization of isoprene with heterocycles. Under nickel catalysis, a series of cyclic monoterpene derivatives bearing quaternary carbon stereocentre are constructed with up to 98% yield and 97% enantiomeric excess. Preliminary mechanistic studies suggest this atom-economic reaction proceeds through an enantioselective dimerization of isoprene and a sequential C-H alkylation of heterocycles pathway. This work not only contributes an efficient enantioselective transformation of bulk chem. isoprene, but also provides a guide to create an unnatural monoterpene framework that may exhibit different biol. activities. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Application of 1632-83-3).

1-Methylbenzimidazole (cas: 1632-83-3) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Application of 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nitroimidazoles. VI. Partition coefficients and tautomerism of simple nitroimidazoles was written by Suwinski, Jerzy;Salwinska, Ewa;Watras, Jan;Widel, Maria. And the article was included in Acta Poloniae Pharmaceutica in 1985.Electric Literature of C4H5N3O2 This article mentions the following:

Octanol-water partition coefficients (P) were determined for 42 simple nitroimidazoles with Me, Cl, Br, MeO, NH₂, and NO₂ substituents. Correlation between log P and the substituent constants π_X of Hansch and f_X of Nys-Rekker was derived. For the N-methylated compounds, the average value of π_N-CH3 was calculated to be -0.30. Significance of log P measurement in estimating the tautomeric equilibrium in 4(5)-nitroimidazoles is discussed in detail. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Electric Literature of C4H5N3O2).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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.Electric Literature of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem