Month: December 2022

Talsi, Evgenii P. published the artcileIsoinversion Behavior in the Enantioselective Oxidations of Pyridylmethylthiobenzimidazoles to Chiral Proton Pump Inhibitors on Titanium Salalen Complexes, Formula: C17H18N3NaO3S, the publication is ACS Catalysis (2015), 5(8), 4673-4679, database is CAplus.

The oxidation of two pyridylmethylthiobenzimidazoles to proton pump inhibitors (S)-omeprazole and (R)-lansoprazole, and to their enantiomers, with H₂O₂ is achieved by using chiral titanium salalen complexes as catalysts. The latter ensure high enantioselectivities (up to 96% ee) and efficiencies (TN 200-300), with high sulfoxide yields (up to >96%). The oxidation enantioselectivities vary with temperature in a nonmonotonic manner, demonstrating isoinversion behavior. Maximum enantioselectivity is attained at 273···283 K, which temperature region may be recommended for preparative oxidations Kinetic peculiarities and the oxidation mechanism are discussed.

ACS Catalysis published new progress about 161796-78-7. 161796-78-7 belongs to imidazoles-derivatives, auxiliary class Membrane Transporter/Ion Channel,Proton Pump, name is Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide, and the molecular formula is C8H11BO2, Formula: C17H18N3NaO3S.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Topcu, Mehmet Ali published the artcileGold Leaching from Copper Anode Slime with 1-Butly-3-Methyl Imidazolium Chloride, Name: 3-Butyl-1-methyl-1H-imidazol-3-ium chloride, the publication is JOM (2022), 74(5), 2120-2128, database is CAplus.

The aim of this study was to realize gold leaching from copper anode slime (CAS) with ionic liquid treatment. A novel medium, 1-Bu -3-methyl-imidazolium chloride (BmimCl), was used as the leaching reagent. The effects of ionic liquid concentration, temperature, time ,and solid/liquid ratio (S/L) on the leaching efficiency were investigated by Taguchi optimization and ANOVA methods. The results showed that 61.20% of gold leaching efficiency was achieved from CAS, under the optimum leaching conditions which were determined as %80 ionic liquid concentration, 50°C temperature, 1 h time and 1/20 g/mL solid/liquid ratio. The statistical results of the experiments revealed that the effects of each parameter on the gold leaching with BmimCl were in the following order: temperature > time > solid/liquid ratio > ionic liquid concentration

JOM published new progress about 79917-90-1. 79917-90-1 belongs to imidazoles-derivatives, auxiliary class Ionic Liquid,Ionic Liquid, name is 3-Butyl-1-methyl-1H-imidazol-3-ium chloride, and the molecular formula is C6H12O2, Name: 3-Butyl-1-methyl-1H-imidazol-3-ium chloride.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Valdez-Padilla, David published the artcileSynthesis and antiprotozoal activity of novel 1-methylbenzimidazole derivatives, Category: imidazoles-derivatives, the publication is Bioorganic & Medicinal Chemistry (2009), 17(4), 1724-1730, database is CAplus and MEDLINE.

In this paper are reported the synthesis and antiprotozoal activity in vitro of 24 1-methylbenzimidazole derivatives (13-36) substituted at position 2 with aminocarbonyl, N-methylaminocarbonyl, N,N-dimethylaminocarbonyl, ethoxycarbonyl, 1-hydroxyethyl and acetyl groups, some of them with chlorine atoms at the benzenoid ring. Compounds 13-36 were more active than metronidazole, the choice drug against Giardia intestinalis and most of them against Trichomonas vaginalis. The most active group of compounds for both parasites was that with a 2-ethoxycarbonyl group (16, 22, 28, 34), independently of the substitution pattern at the benzenoid ring.

Bioorganic & Medicinal Chemistry published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C13H10F2, Category: imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Taldone, Tony published the artcileSynthesis and evaluation of cell-permeable biotinylated PU-H71 derivatives as tumor Hsp90 probes, Name: N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, the publication is Beilstein Journal of Organic Chemistry (2013), 544-556, database is CAplus and MEDLINE.

The attachment of biotin to a small mol. provides a powerful tool in biol. Here, we present a systematic approach to identify biotinylated analogs of the Hsp90 inhibitor PU-H71 that are capable of permeating cell membranes so as to enable the investigation of Hsp90 complexes in live cells. The identified derivative 2g can isolate Hsp90 through affinity purification and, as we show, represents a unique and useful tool to probe tumor Hsp90 biol. in live cells by affinity capture, flow cytometry and confocal microscopy. To our knowledge, 2g is the only reported biotinylated Hsp90 probe to have such combined characteristics.

Beilstein Journal of Organic Chemistry published new progress about 359860-27-8. 359860-27-8 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Chiral,Amine,Amide,Ether,Inhibitor, name is N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C3H5BN2O2, Name: N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Kumar, Manoranjan published the artcileIron(III) Chloride-Catalyzed Decarboxylative-Deaminative Functionalization of Phenylglycine: A Tandem Synthesis of Quinazolinones and Benzimidazoles, Quality Control of 2622-67-5, the publication is Advanced Synthesis & Catalysis (2015), 357(13), 2862-2868, database is CAplus.

The first iron(III) chloride-catalyzed decarboxylative-deaminative functionalization of phenylglycine with o-substituted nitroarenes was achieved for the synthesis of 4(3H)-quinazolinones and benzimidazoles. The reaction of 2-nitrobenzonitrile/2-nitro-N,N-diphenylamine with phenylglycine at 120 C in the presence of potassium carbonate as a base in toluene generated the products in 45-87% yields. Various functional groups like nitro, fluoride, chloride and trifluoromethyl were well tolerated under the present reaction conditions. In this tandem approach, involvement of transfer hydrogenation of the nitro functionality with in situ generated ammonia, imination, nitrile hydration to amide and oxidative cyclization sequences have been established. The process avoids the use of an external hydrogen source, costly catalysts as well as the isolation of amine and amide intermediates.

Advanced Synthesis & Catalysis published new progress about 2622-67-5. 2622-67-5 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Benzene,Benzimidazole, name is 1,2-Diphenyl-1H-benzo[d]imidazole, and the molecular formula is C19H14N2, Quality Control of 2622-67-5.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Agelis, George published the artcileRational design, efficient syntheses and biological evaluation of N,N’-symmetrically bis-substituted butylimidazole analogs as a new class of potent Angiotensin II receptor blockers, Category: imidazoles-derivatives, the publication is European Journal of Medicinal Chemistry (2013), 352-370, database is CAplus and MEDLINE.

A series of sym. bis-substituted imidazole analogs bearing at the N-1 and N-3 positions two biphenyl moieties ortho substituted either with tetrazole or carboxylate functional groups was designed based on docking studies and utilizing for the first time an extra hydrophobic binding cleft of the AT1 receptor. The synthesized analogs were evaluated for their in vitro antagonistic activities (pA₂ values) and binding affinities (-logIC₅₀ values) to the Angiotensin II AT1 receptor. Among them, the dipotassium (-logIC₅₀ = 9.04) and the disodium (-logIC₅₀ = 8.54) salts of 4-butyl-N,N’-bis{[2′-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl}imidazolium bromide (I) as well as the bis-ortho-carboxylic acid derivative (-logIC₅₀ = 9.46) and 4-butyl-2-hydroxymethyl-N,N’-bis{[2′-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl}imidazolium bromide (-logIC₅₀ = 8.37, pA₂ = 8.58) showed high binding affinity to the AT1 receptor and high antagonistic activity (potency). The potency was similar or even superior to that of Losartan (-logIC₅₀ = 8.25, pA₂ = 8.25). On the contrary, 2-butyl-N,N’-bis{[2′-[2H-tetrazol-5-yl]biphenyl-4-yl]methyl}imidazolium bromide (-logIC₅₀ = 5.77) and 2-butyl-4-chloro-5-hydroxymethyl-N,N’-bis{[2′-[2H-tetrazol-5-yl]biphenyl-4-yl]methyl}imidazolium bromide (-logIC₅₀ = 6.38) displayed very low binding affinity indicating that the orientation of the Bu group is of primary importance. Docking studies of the representative highly active I·2Na clearly showed that this mol. has an extra hydrophobic binding feature compared to prototype drug Losartan and it fits to the extra hydrophobic cavity. These results may contribute to the discovery and development of a new class of biol. active mols. through bis-alkylation of the imidazole ring by a convenient and cost effective synthetic strategy.

European Journal of Medicinal Chemistry published new progress about 79047-41-9. 79047-41-9 belongs to imidazoles-derivatives, auxiliary class Imidazole,Chloride,Alcohol, name is (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, and the molecular formula is C8H13ClN2O, Category: imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Bovy, Philippe R. published the artcileNonpeptide angiotensin II antagonists: N-phenyl-1H-pyrrole derivatives are angiotensin II receptor antagonists, Synthetic Route of 79047-41-9, the publication is Journal of Medicinal Chemistry (1993), 36(1), 101-10, database is CAplus and MEDLINE.

A series of 5-[1-[4-[(4,5-disubstituted-1H-imidazol-1-yl)methyl]-substituted]-1H-pyrrol-2-yl]-1H-tetrazoles and 5-[1-[4-[(3,5-dibutyl-1H-1,2,4-triazol-1-yl)methyl]-substituted]-1H-pyrrol-2-yl]-1H-tetrazoles were investigated as novel AT₁-selective angiotensin II receptor antagonists. Computer-assisted modeling techniques were used to evaluate structural parameters in comparison to the related biphenyl system. New synthetic procedures were developed to prepare the novel compounds The best antagonists in this series had IC₅₀ values (rat uterine membrane receptor binding) in the 10^-8 M range and corresponding pA₂ in isolated organ assay (rabbit aorta rings). Structure-activity relationships indicate some similarities with the finding in the biphenyl system. Substitution on the pyrrole ring modulates activity. Compound I antagonized angiotensin-induced blood pressure increase when administered to conscious rat at 30 mg/kg per os.

Journal of Medicinal Chemistry published new progress about 79047-41-9. 79047-41-9 belongs to imidazoles-derivatives, auxiliary class Imidazole,Chloride,Alcohol, name is (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, and the molecular formula is C8H13ClN2O, Synthetic Route of 79047-41-9.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Singh, Rajeeva published the artcileAntibody-Drug Conjugates with Indolinobenzodiazepine Dimer Payloads: DNA-Binding Mechanism of Indolinobenzodiazepine Dimer Catabolites in Target Cancer Cells, Product Details of C18H34N4O5S, the publication is Molecular Pharmaceutics (2020), 17(1), 50-58, database is CAplus and MEDLINE.

DNA-targeting indolinobenzodiazepine dimer (IGN) payloads are used in several clin.-stage antibody-drug conjugates. IGN drugs alkylate DNA through the single imine moiety present in the dimer in contrast to the pyrrolobenzodiazepine dimer drugs, such as talirine and tesirine, which contain two imine moieties per dimer and cross-link DNA. This study explored the mechanism of binding of IGN to DNA in cells and to synthetic duplex and hairpin oligonucleotides. New, highly sensitive IGN-DNA binding ELISA methods were developed using biotinylated IGN analogs (monoimine, diimine, and diamine IGNs) and digoxigenin-labeled duplex oligonucleotides, which allowed the measurement of drug-DNA adducts in viable cells at concentrations below IC₅₀. Furthermore, the release of free drug from the IGN-DNA adduct upon treatment with nuclease ex vivo was tested under physiol. conditions. The monoimine IGN drug formed a highly stable adduct with DNA in cells, with stability similar to that of the diimine drug analog. Both monoimine and diimine IGN-DNA adducts released free drugs upon DNA cleavage by nuclease at 37°C, although more free drug was released from the monoimine compared to the diimine adduct, which presumably was partly cross-linked. The strong binding of the monoimine IGN drug to duplex DNA results from both the noncovalent IGN-DNA interaction and the covalent bond formation between the 2-amino group of a guanine residue and the imine moiety in IGN.

Molecular Pharmaceutics published new progress about 359860-27-8. 359860-27-8 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Chiral,Amine,Amide,Ether,Inhibitor, name is N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C12H16N2O2, Product Details of C18H34N4O5S.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Dubey, P. K. published the artcileAlternate method for the synthesis of N-alkyl/aralkyl-2-(α-hydroxyalkyl/aralkyl)benzimidazoles via regiospecific acetylation, Name: (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Synthetic Communications (2007), 37(10), 1675-1681, database is CAplus.

Acetylation of 1H-2-(α-hydroxyalkyl/aryl)benzimidazoles with Ac₂O results in the regiospecific formation of O-acetoxy derivative, which on alkylation with alkylating agents in nonaqueous media under phase-transfer catalytic conditions affords N-alkyl derivatives The latter, on hydrolysis in an aqueous basic medium, results in the title compounds in good yields in high purity. Alternatively, the title compounds was also obtained by reduction of 1-substituted-2-acetyl/benzoylbenzimidazoles using NaBH₄.

Synthetic Communications published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C9H10N2O, Name: (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Rao, S. Srinivas published the artcileSynthesis of N,N¹-disubstituted bisbenzimidazole sulphides of potential pharmacological interest, Computed Properties of 4760-35-4, the publication is Journal of Chemical and Pharmaceutical Research (2014), 6(3), 1199-1204, 6 pp., database is CAplus.

A series of N,N¹-disubstituted bisbenzimidazole sulfides I (R = R¹ = H, Me, Et, Bn, n-Bu) were prepared by condensation followed by alkylation using DMF as solvent and K₂CO₃ as a base and tetra-n-butylammonium bromide (TBAB) as phase transfer catalyst.

Journal of Chemical and Pharmaceutical Research published new progress about 4760-35-4. 4760-35-4 belongs to imidazoles-derivatives, auxiliary class Chloride,Benzimidazole, name is 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, and the molecular formula is C9H9ClN2, Computed Properties of 4760-35-4.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem