Author: Jessica.F

Enantioselective Synthesis of Multisubstituted Spirocyclopentane Oxindoles Enabled by Pd/Chiral Rh(III) Complex Synergistic Catalysis was written by Wan, Qian;Chen, Liang;Li, Shiwu;Kang, Qiang;Yuan, Yaofeng;Du, Yu. And the article was included in Organic Letters in 2020.Formula: C6H8N2O This article mentions the following:

An asym. [3 + 2]-cycloaddition reaction of α,β-unsaturated 2-acyl imidazoles with spirovinylcyclopropanyl-2-oxindoles catalyzed synergistically by an achiral palladium(0) catalyst and a chiral-at-metal rhodium(III) complex has been developed. A series of biol. important 3-spirocyclopentane-2-oxindoles with four contiguous stereocenters were synthesized in high yields (up to 99%) with excellent stereoselectivities (up to 99% ee, 20:1 dr). In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Formula: C6H8N2O).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Controlling a Cohort: Use of Mirabilis-Based Purge Calculations to Understand Nitrosamine-Related Risk and Control Strategy Options was written by Burns, Michael J.;Teasdale, Andrew;Elliott, Eric;Barber, Chris G.. And the article was included in Organic Process Research & Development in 2020.Application In Synthesis of 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 This article mentions the following:

The recent discovery of nitrosamines within marketed drugs, such as Valsartan, has led to changes within the regulatory landscape. Most notably, the requirement for a risk evaluation of the presence of nitrosamines within the drug product has been extended from sartan-type tetrazole containing drugs to all marketed products. The largest inherent risks associated with a drug substance will generally arise from impurity formation and carryover in the synthetic manufacturing process. Despite the classification of nitrosamines within the cohort of concern, the understanding of their behavior based on physicochem. properties is unaffected by this status, and as such all control options laid out in ICH M7 should be considered acceptable. This communication aims to show how the use of purge calculations, utilizing the Mirabilis software, fully de-risked nitrosamine concerns related to the development of Candesartan cilexetil. Aligned to the principles of impurity control in the ICH M7 guideline, this provided a suitable strategy to determine, and subsequently demonstrate control of, the nitrosamine risk. 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 In Synthesis of 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).

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 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.Application In Synthesis of 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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Discovery of Isoindoline Amide Derivatives as Potent and Orally Bioavailable ADAMTS-4/5 Inhibitors for the Treatment of Osteoarthritis was written by Zhao, Peng;Liu, Dong;Song, Chunying;Li, Di;Zhang, Xinzhu;Horecny, Ivana;Zhang, Fengqi;Yan, Yuna;Zhuang, Linghang;Li, Jing;Liu, Suxing;Mao, Yuchang;Feng, Jun;Liu, Jian;Tao, Weikang. And the article was included in ACS Pharmacology & Translational Science in 2022.Application of 85692-37-1 This article mentions the following:

Osteoarthritis (OA) treatment is a highly unmet medical need. Development of a disease-modifying OA drug (DMOAD) is challenging with no approved drugs on the market. Inhibition of ADATMS-4/5 is a promising OA therapeutics to target cartilage degradation and potentially can reduce joint pain and restore its normal function. Starting from the reported ADAMTS-5 inhibitor GLPG1972, we applied a scaffold hopping strategy to generate a novel isoindoline amide scaffold. Representative compound I showed high potency in ADATMS-4/5 inhibition, as well as good selectivity over a panel of other metalloproteases. In addition, compound I exhibited excellent druglike properties and showed better pharmacokinetic (PK) profiles than GLPG1972 cross-species. Compound I demonstrated dose-dependent efficacy in two in vivo rat osteoarthritis models. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Application of 85692-37-1).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) 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. 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 of 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

KIO₄-mediated Selective Hydroxymethylation/Methylenation of Imidazo-Heteroarenes: A Greener Approach was written by Franco, Marcelo Straesser;Saba, Sumbal;Rafique, Jamal;Braga, Antonio Luiz. And the article was included in Angewandte Chemie, International Edition in 2021.Synthetic Route of C18H21N3 This article mentions the following:

Herein, a KIO₄-mediated, sustainable and chemoselective approach for the one-pot C(sp²)-H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction has been reported. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields. In the experiment, the researchers used many compounds, for example, N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine (cas: 106961-33-5Synthetic Route of C18H21N3).

N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine (cas: 106961-33-5) 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. 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 C18H21N3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The effects of cardiac drugs on human erythrocyte carbonic anhydrase I and II isozymes was written by Argan, Onur;Cikrikci, Kubra;Baltaci, Aybike;Gencer, Nahit. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2020.Safety of 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 This article mentions the following:

Cardiovascular diseases are the leading cause of mortality worldwide. In recent years, the relationship between carbonic anhydrase inhibitors and atherosclerosis has attracted attention. In this study, we aimed to determine the in vitro effects of 35 frequently used cardiac drugs on human carbonic anhydrase I (hCA I) and II (hCA II). The inhibitory effects of the drugs on hCA I and hCA II were determined with both the hydratase and esterase methods. The most potent inhibitors observed were propafenone (hCA I: 2.8μM and hCA II: 3.02μM) and captopril (hCA I: 1.58μM and hCA II: 6.25μM). Isosorbide mononitrate, propranolol, furosemide, and atorvastatin were also potent inhibitors. The inhibitor constant, K_i, value from the Lineweaver-Burk plot for propafenone was 2.38μM for hCA I and 2.97μM for hCA II. The tested cardiac drugs showed potent in vitro inhibition of the hCA I and II isoenzymes. Especially, in patients with atherosclerotic heart disease, these drugs may be preferred primarily due to the beneficial effects of carbonic anhydrase inhibition on atherosclerosis. 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: 145040-37-5Safety of 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).

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. 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).Safety of 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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ultrasonic chemical oxidative degradations of 1,3-dialkylimidazolium ionic liquids and their mechanistic elucidations was written by Li, Xuehui;Zhao, Jinggan;Li, Qianhe;Wang, Lefu;Tsang, Shik Chi. And the article was included in Dalton Transactions in 2007.Application In Synthesis of 1-Methyl-3-propylimidazolium Chloride This article mentions the following:

A highly efficient process for oxidative degradation of 1,3-dialkylimidazolium ionic liquids in hydrogen peroxide/acetic acid aqueous medium assisted by ultrasonic chem. irradiation is, for the first time, described. It is shown that more than 93% of the 1,3-dialkylimidazolium cation with the corresponding Cl^–, Br^–, BF₄^– and PF₆^– counter-anions at a concentration of 2.5 mM can be degraded at 50 °C within 12 h while at 72 h the conversions approach 99%. A tentative mechanism for the degradation of these ILs is for the first time proposed through a detailed kinetic anal. of several characteristic transients and/or immediate products, which are identified during the ILs degradation using GC-MS. The results clearly indicate that three hydrogen atoms in the imidazolium ring are the first sites preferably oxidized, followed by cleavage of the alkyl groups attached to the N atoms from the ring. The nature of the alkyl chain length on the imidazolium ring and the type of counter anion do not seem to affect the degradation process. Further, selective fragmentations of C-N bonds of the imidazolium or derived ring lead to ring opening, forming degraded intermediates. It is also shown that acetoxyacetic acid and biurea are the final kinetically stable degraded products from the ILs under the degradation conditions. 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. 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.Application In Synthesis of 1-Methyl-3-propylimidazolium Chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nitroimidazoles. Part X. Spectral studies on isomeric 1-substituted 4- and 5-nitroimidazoles and some 2-nitroimidazoles was written by Nagarajan, K.;Sudarsanam, V.;Parthasarathy, P. C.;Arya, V. P.;Shenoy, S. J.. And the article was included in Indian Journal of Chemistry in 1982.Quality Control of 1-Methyl-4-nitroimidazole This article mentions the following:

Chem. shifts of C-4 in I (R = H, Me, vinyl, O₂N, etc.; R¹ = H, Me, Cl, O₂N, etc.; R² = H, Cl, O₂N, etc.) fall within a narrow range of 130-3 ppm and in the isomeric II at 120-4 ppm, offering a method for distinguishing between isomeric pairs. An addnl. diagnostic method utilizes the observation that for II the signal due to C-5 has extra multiplicity due to 3-bond coupling with protons of the group on N-1, which C-4 in I does not exhibit. DMSO induced chem. shifts for C-5 H in II (δ DMSO-d₆ – δ CDCl₃) are much larger than those for C-4 H in I and are useful aids for structure assignment. Mass spectra of the 1-alkyl-5-nitroimidazoles I generally show fragments due to loss of OH, which are mostly absent in II; the loss of NO₂ is also more intense in the former than in the latter. The phenomena are traced to participation by the alkyl group at position-1. Acid and alkali induced shifts in water and EtOH UV spectra of a variety of nitroimidazoles are described and discussed. 1-Alkyl-5-nitroimidazoles undergo hypsochromic shifts in 0.1 N H₂SO₄ more readily than the 4-nitro isomers. On silica gel plates, compounds of I generally move faster than those of II. The m. ps. of the 5-nitroimidazoles are as a rule lower than those of the 4-nitro counterparts. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Quality Control of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Quality Control of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Low molecular weight gelators (LMWGs) for ionic liquids: the role of hydrogen bonding and sterics in the formation of stable low molecular weight ionic liquid gels was written by McNeice, Peter;Zhao, Yingying;Wang, Jianxun;Donnelly, Gerald F.;Marr, Patricia C.. And the article was included in Green Chemistry in 2017.Recommanded Product: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

Low mol. weight gelators capable of forming a gel with an ionic liquid are rare. We report the ability of 3 sugar based gelators from renewable resources (derived from isosorbide and mannitol) to form gels with 21 ionic liquids comprising a range of cations and anions that are commonly applied in a variety of technologies. It was found that the combined consideration of Kamlet-Taft values with ionic liquid size and shape gives a useful predictor of successful gel formation. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Recommanded Product: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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.Recommanded Product: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Surface structures of binary mixtures of imidazolium-based ionic liquids using high-resolution Rutherford backscattering spectroscopy and time of flight secondary ion mass spectroscopy was written by Nakajima, Kaoru;Miyashita, Motoki;Suzuki, Motofumi;Kimura, Kenji. And the article was included in Journal of Chemical Physics in 2013.Reference of 404001-48-5 This article mentions the following:

Surface structures of binary mixtures of imidazolium-based ionic liquids having a common anion (bis(trifluoromethanesulfonyl)imide (TFSI), namely C₂MIM_1-xC₁₀MIM_xTFSI (x = 0.5 and 0.1), were studied using high-resolution Rutherford backscattering spectroscopy (HRBS) and time of flight secondary ion mass spectroscopy (TOF-SIMS). Although both measurements show surface segregation of C₁₀MIM the degrees of the segregation are different. The surface fraction x_surf of C₁₀MIM is estimated to be 0.6 and 0.18 by HRBS for x = 0.5 and 0.1, resp. On the other hand, TOF-SIMS indicates much stronger surface segregation, namely x_surf = 0.83 and 0.42 for x = 0.5 and 0.1, resp. The observed discrepancy can be attributed to the difference in the probing depth between HRBS and TOF-SIMS. The observed surface segregation can be roughly explained in terms of surface tension. (c) 2013 American Institute of Physics. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Reference of 404001-48-5).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Reference of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Asymmetric [3 + 2] Cycloaddition Employing N,N’-Cyclic Azomethine Imines Catalyzed by Chiral-at-Metal Rhodium Complex was written by Gong, Jun;Wan, Qian;Kang, Qiang. And the article was included in Organic Letters in 2018.HPLC of Formula: 85692-37-1 This article mentions the following:

An efficient asym. 1,3-dipolar cycloaddition of α,β-unsaturated 2-acyl imidazoles with N,N’-cyclic azomethine imines catalyzed by a chiral-at-metal rhodium complex is reported. The corresponding N,N’-bicyclic pyrazolidine derivatives with three contiguous tertiary stereocenters, e.g., I, were obtained in good yields (up to 99%) with excellent stereoselectivities (>20:1 dr and >99% ee). Remarkably, as little as 0.5 mol % of a chiral Rh(III) complex can promote a gram-scale reaction with excellent yield and enantioselectivity. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1HPLC of Formula: 85692-37-1).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) 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 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.HPLC of Formula: 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem