Tag: 100-200

Adjacent lone pair (ALP) effects in heteroaromatic systems. 1. Isotope exchange of ring hydrogens in alkylimidazoles was written by Takeuchi, Yoshio;Yeh, Herman J. C.;Kirk, Kenneth L.;Cohen, Louis A.. And the article was included in Journal of Organic Chemistry in 1978.Related Products of 3034-41-1 This article mentions the following:

Solvent D isotope exchange (D₂O, 50°) is readily observed above pD 5 at C-2 in imidazole and its C– or N-alkyl derivatives The intermediate is an ylide, formed by base-catalyzed abstraction of H-2 from the imidazolium ion (path Y-2). A similar, but much slower, exchange is observed at C-4 (Y-4) or at C-5 (Y-5) at 100°. In strongly alk. media, NH imidazoles exchange more rapidly at C-4 or C-5 via a carbanion pathway (C) involving C-proton abstraction from the neutral mol.; in N-alkylimidazoles, however, only H-5 exchanges via the C pathway (C-5). The resistance to carbanion formation at C-4 is ascribed to the adjacent lone pair (ALP) effect, a significant electrostatic repulsion between lone pairs in the coplanar, sp² orbitals at N-3 and C-4. The partial contributions of the ylide and carbanion pathways are evaluated from kinetic data at pD 10-11 and in 1 N NaOD, resp. For 1-methylimidazole (1 N NaOD, 100°C), C-5 exchange occurs 15 times faster than Y-5 and 3 times faster than Y-4. NMR signals for H-4 and H-5 are assigned on the basis of (1) spin-decoupling experiments, (2) nuclear Overhauser enhancements, (3) chem. transformations of 1-methylimidazole-d₂, and (4) Δδ values. Ring protons adjacent to N-Me can be differentiated from other ring protons by a characteristic shift in δ with variation of solvent (Δδ); furthermore, relative to H-4, H-5 appears at higher field in nonpolar solvents and lower field in polar ones. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Related Products of 3034-41-1).

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 This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Related Products of 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer was written by Puleo, Thomas R.;Klaus, Danielle R.;Bandar, Jeffrey S.. And the article was included in Journal of the American Chemical Society in 2021.Computed Properties of C8H8N2 This article mentions the following:

A general protocol for the direct C-H etherification of N-heteroarenes is reported. Potassium tert-butoxide catalyzes halogen transfer from 2-halothiophenes to N-heteroarenes to form N-heteroaryl halide intermediates that undergo tandem base-promoted alc. substitution. Thus, the simple inclusion of inexpensive 2-halothiophenes enables regioselective oxidative coupling of alcs. with 1,3-azoles, pyridines, diazines, and polyazines under basic reaction conditions. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Computed Properties of C8H8N2).

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–C6) 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.Computed Properties of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reductive cyclization of o-phenylenediamine with CO₂ and BH₃NH₃ to synthesize 1H-benzoimidazole derivatives was written by Li, Xiao;Zhang, Junhua;Yang, Yue;Hong, Hailong;Han, Limin;Zhu, Ning. And the article was included in Journal of Organometallic Chemistry in 2021.Quality Control of 1-Methylbenzimidazole This article mentions the following:

A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO₂ and BH₃NH₃ to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH₃NH₃ promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramol. nucleophilic addition-elimination for the formation of target product. In this process, BH₃NH₃ served multifunctional roles, acting as a reducing agent and a formylation catalyst. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Quality Control of 1-Methylbenzimidazole).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Discovery and characterization of benzyloxy piperidine based dopamine 4 receptor antagonists was written by Tolentino, Kirsten T.;Mashinson, Viktoriya;Vadukoot, Anish K.;Hopkins, Corey R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2022.SDS of cas: 58442-17-4 This article mentions the following:

The dopamine receptor 4 (D4R) is highly expressed in both motor, associative and limbic subdivisions of the cortico-basal ganglia network. Due to the distribution in the brain, there is mounting evidence pointing to a role for the D4R in the modulation of this network and its subsequent involvement in L-DOPA induced dyskinesias in Parkinson′s disease. As part of our continued effort in the discovery of novel D4R antagonists, we report the discovery and characterization of a new 3- or 4-benzyloxypiperidine scaffold as D4R antagonists. We report several D4R selective compounds (>30-fold vs. other dopamine receptor subtypes) with improved in vitro and in vivo stability over previously reported D4R antagonists. In the experiment, the researchers used many compounds, for example, 1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4SDS of cas: 58442-17-4).

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. 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. SDS of cas: 58442-17-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and characterization of some new polyhydrazides by direct polycondensation in ionic liquid was written by Adbolmaleki, Amir. And the article was included in Iranian Polymer Journal in 2007.Quality Control of 1-Methyl-3-propylimidazolium Chloride This article mentions the following:

A series of new polyhydrazides were obtained by direct polycondensation of 4,4′-diphenyl sulfone dicarboxylic acid with dihydrazides in ionic liquids (ILs) as a new class of solvents which have interesting properties such as nonvolatility, high ionic concentration, good thermal stability and non-flammability. Direct polycondensation is successfully proceeded in ILs and tri-Ph phosphite (condensing agent), without any addnl. components, such as LiCl and pyridine. Therefore IL can act as both solvent and catalyst. In this investigation high mol. weight polyhydrazides have been synthesized and their properties such as solubility, and thermal stability were studied. The resulting hydrazide containing polymers exhibited inherent viscosities in 0.26-0.73 dL/g range. All polymers were soluble in polar solvents such as N-Me pyrrolidone and DMSO. The polyhydrazides had glass-transition temperatures (T_g) between 165-210°C. They could be thermally converted into the corresponding poly(1,3,4-oxadiazole)s approx. in the region of 210-330°C, as evidenced by the TGA thermograms. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Quality Control of 1-Methyl-3-propylimidazolium Chloride).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Chemo-Immunotherapeutic Antimalarials Targeting Isoprenoid Biosynthesis was written by Zhang, Yonghui;Zhu, Wei;Liu, Yi-Liang;Wang, Hong;Wang, Ke;Li, Kai;No, Joo Hwan;Ayong, Lawrence;Gulati, Anmol;Pang, Ran;Freitas-Junior, Lucio;Morita, Craig T.;Oldfield, Eric. And the article was included in ACS Medicinal Chemistry Letters in 2013.Computed Properties of C11H20N2 This article mentions the following:

We synthesized 30 lipophilic bisphosphonates and tested them in malaria parasite killing (targeting parasite geranylgeranyl diphosphate synthase, GGPPS) and human γδ T cell activation (targeting human farnesyl diphosphate synthase, FPPS). Similar patterns of activity were seen in inhibiting human FPPS and Plasmodium GGPPS, with short to medium chain-length species having most activity. In cells, shorter chain-length species had low activity, due to poor membrane permeability, and longer chain length species were poor enzyme inhibitors. Optimal activity was thus seen with ∼C₁₀ side-chains, which have the best combination of enzyme inhibition and cell penetration. We also solved the crystal structure of one potent inhibitor, bound to FPPS. The results are of interest since they suggest the possibility of a combined chemo/immuno-therapeutic approach to antimalarial development in which both direct parasite killing and γδ T cell activation can be achieved with a single compound In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Computed Properties of C11H20N2).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 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.Computed Properties of C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Tunable Cysteine-Targeting Electrophilic Heteroaromatic Warheads Induce Ferroptosis was written by Karaj, Endri;Sindi, Shaimaa H.;Kuganesan, Nishanth;Perera, Lalith;Taylor, William;Tillekeratne, L. M. Viranga. And the article was included in Journal of Medicinal Chemistry in 2022.Synthetic Route of C8H8N2 This article mentions the following:

Once considered potential liabilities, the modern era witnesses a renaissance of interest in covalent inhibitors in drug discovery. The available toolbox of electrophilic warheads is limited by constraints on tuning reactivity and selectivity. Following our work on a class of ferroptotic agents termed CETZOLEs, we discovered new tunable heterocyclic electrophiles which are capable of inducing ferroptosis. The biol. evaluation demonstrated that thiazoles with an alkyne electrophile at the 2-position selectively induce ferroptosis with high potency. D. functional theory calculations and NMR kinetic studies demonstrated the ability of our heterocycles to undergo thiol addition, an apparent prerequisite for cytotoxicity. Chemoproteomic anal. indicated several potential targets, the most prominent among them being GPX4 protein. These results were further validated by western blot anal. and the cellular thermal shift assay. Incorporation of these heterocycles into appropriate pharmacophores generated highly cytotoxic agents such as the analog BCP-T.A (I), with low nM IC₅₀ values in ferroptosis-sensitive cell lines. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Synthetic Route of C8H8N2).

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–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.Synthetic Route of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Alkyl-imidazolium glycosides: non-ionic-cationic hybrid surfactants from renewable resources was written by Salman, Abbas Abdulameer;Tabandeh, Mojtaba;Heidelberg, Thorsten;Hussen, Rusnah Syahila Duali;Ali, Hapipah Mohd. And the article was included in Carbohydrate Research in 2015.Category: imidazoles-derivatives This article mentions the following:

A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large mol. surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized mol. assemblies slightly and reduced the surface tension of surfactant solutions considerably. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Category: imidazoles-derivatives).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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. 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. Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Blend membranes based on N1-alkyl-substituted imidazolium functionalized polymers and aromatic polyethers: influence of N1-alkyl substituent on properties and alkaline stability was written by Tsagdi, A.;Dimitriou, M.;Druvari, D.;Deimede, V.. And the article was included in Polymer Bulletin (Heidelberg, Germany) in 2022.Category: imidazoles-derivatives This article mentions the following:

N1-alkyl (octyl and dodecyl)-substituted imidazolium-based PVBC homopolymers have been synthesized via N-quaternization reaction of N1-alkyl imidazole and PVBC precursor homopolymer bearing reactive benzyl chloride moieties. Due to their poor film forming properties and water solubility, these homopolymers were blended with aromatic polyethers bearing main chain pyridine units at different compositions in order to study the effect of alkyl chain length on morphol., water uptake, swelling ability and chem. stability of the prepared membranes. The B2 blend membrane with the highest N1-dodecyl-substituted imidazolium PVBC content (65 wt%) exhibited the highest water uptake (54%) despite its lower IEC value compared to the corresponding one containing N1-octyl-substituted imidazolium PVBC, low swelling ratio and a phase separated morphol. Evaluation of the chem. stability in 3.6 M KOH solution at 80°C for 7 days revealed the degradation of imidazolium via ring opening, as evidenced by ATR-FT-IR spectroscopy. Therefore, new blends having as second constituent, the N1-alkyl-substituted imidazolium functionalized poly(PVBC-co-AA₂₀) copolymers containing acrylic acid units were fabricated targeting to the improvement of chem. stability via ionic cross linking. The prepared D1 and D2 blend membranes containing 60 and 65 wt% dodecyl-imidazolium functionalized poly(PVBC-co-AA₂₀) copolymer content, resp., were flexible, exhibited moderate IECs (1.47-1.60 meq/g) and sufficient water uptakes (up to 30%). D2 blend membrane showed excellent chem. stability after testing in 3.6 M KOH solution at 80°C for 30 days, as confirmed by ATR-FT-IR spectroscopy and TGA anal. The excellent chem. stability can probably be attributed to the steric hindrance effect of N1 dodecyl substituent which effectively protects the C2 position of imidazolium from hydroxide attack as well as to the formation of a dense, ionic crosslinked structure that hinders hydroxide penetration. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Category: imidazoles-derivatives).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Theoretical elucidation of the multi-functional synthetic methodology for switchable Ni(0)-catalyzed C-H allylations, alkenylations and dienylations with allenes was written by Liu, Yuxia;Wang, Kaifeng;Ling, Baoping;Chen, Guang;Li, Yulin;Liu, Lingjun;Bi, Siwei. And the article was included in Catalysis Science & Technology in 2020.Quality Control of 1-Methylbenzimidazole This article mentions the following:

The Ni(0)-catalyzed coupling of benzimidazole with 1,1-disubstituted allenes represents a new strategy for achieving controllable C-H allylations, alkenylations and dienylations. To understand the detailed mechanisms and origins of the switchable selectivities, d. functional theory (DFT) calculations were conducted. The results using a tBu-substituted allene demonstrate that the formation of the allylated product involves a Ni-catalyzed C-H activation mechanism through ligand-to-ligand-hydrogen transfer (LLHT) under base-free conditions. In contrast, a Ni/NaOtBu co-promoted C-H activation mechanism is newly proposed in the presence of NaOtBu, which is remarkably different from the previously reported literature. The novel mechanism emphasizes that NaOtBu abstracts the Ni-activated heterocyclic (ipso-C)H atom followed by turnover limiting Ni slippage, and subsequently the allylated product is generated after alkene insertion and protonation. The strong electrostatic attraction between Ni and heterocyclic ipso-C in the Ni slippage pre-intermediate is critical for facilitating the Ni slippage. Once formed, the allylated product, assisted by NaOtBu, further evolves into a more stable alkenylated isomer. Employing a (tert-butyldimethylsilyl)-ether substituted allene as the substrate, the NaOtBu-induced chemoselectivity for dienylation vs. alkenylation was also probed and it was found that the O(tBu)-H···O(Si) hydrogen bonding interaction in the C-O(Si) cleavage pre-intermediate remarkably weakens the adjacent C-O(Si) σ-bond, thereby resulting in an exclusive C-O(Si) cleaved dienylation product. Further theor. predictions suggest that the chemoselectivity might be reversed by replacing tBu in NaOtBu by the withdrawing C(CF₃)₃ group. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Quality Control of 1-Methylbenzimidazole).

1-Methylbenzimidazole (cas: 1632-83-3) 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 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.Quality Control of 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem