Tag: M.W=150-200

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

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

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

Noumir, A. published the artcileModeling of Isobaric Vapor-Liquid Equilibrium Data for Ionic Liquid-Containing Ternary Systems, HPLC of Formula: 79917-90-1, the publication is Russian Journal of Physical Chemistry A (2022), 96(1), 27-35, database is CAplus.

The object of this work focuses, on the one hand, on the development of the Wilson model for electrolytes, temperature-dependent parameters, and, on the other, tests the model and its accuracy in the prediction of ternary VLE data from few exptl. data points. The exptl. data reported in the literature are used to determine the model parameters proposed in this work for the ethanol-water binary system. The obtained interaction parameters are then used for the correlation and prediction of VLE data for five ternary systems composed of ethanol, water and different ionic liquids with different percentages at atm. pressure (101.32 kPa). We have made the prediction of ternary VLE data, ionic liquid-containing ternary systems, from temperature-dependent binary interaction parameters, adjusted by using some ternary VLE data coupled with binary VLE data. The obtained results are in good agreement with the data reported in the literature.

Russian Journal of Physical Chemistry A 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 C8H15ClN2, HPLC of Formula: 79917-90-1.

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

Li, Shasha published the artcileMerging Late-Stage Diversification with Solid-Phase Peptide Synthesis Enabled by High-Throughput On-Resin Reaction Screening, HPLC of Formula: 913835-63-9, the publication is ACS Catalysis (2022), 12(5), 3201-3210, database is CAplus.

An integrated workflow is described that combines micromole-scale high-throughput experimentation (HTE) reaction screening and solid-phase peptide synthesis (SPPS) to enable rapid synthetic method development for on-resin peptide diversification. Using this new approach, we have identified several sets of robust Suzuki-Miyaura coupling conditions with complementary scope that collectively display broad coverage with respect to both resin-bound peptide substrates containing aryl halide side chains and (hetero)arylboronic acid coupling partners. We have also demonstrated the utility of this integrated SPPS/chem. diversification method by synthesizing a multidimensional library of diverse peptides in high yields.

ACS Catalysis published new progress about 913835-63-9. 913835-63-9 belongs to imidazoles-derivatives, auxiliary class Other Aromatic Heterocyclic,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Imidazo[1,2-a]pyridine-6-boronic acid, and the molecular formula is C7H7BN2O2, HPLC of Formula: 913835-63-9.

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

Zubenko, A. A. published the artcileStudies of unsaturated azole derivatives. VIII. Novel syntheses of 2-ethynylbenzimidazoles, Formula: C9H9ClN2, the publication is Khimiya Geterotsiklicheskikh Soedinenii (1978), 1111-14, database is CAplus.

Ethynylbenzimidazole I (R = Me, R¹ = CCH) was obtained in 38-45% yields from I (R = CH:CH₂) by bromination, dehydrobromination to give 80% I (R¹ = CBr:CH₂), and further dehydrobromination, or in 25% yield by methylation of I (R = H, R¹ = CCH). Similarly, I (R = H, R¹ = CHO) treated with Ph₃:CBrCO₂Me gave 62% I (R¹ = CH:CBrCO₂Me), which was dehydrobrominated and decarboxylated to give 80% I (R = H, R¹ = CCH).

Khimiya Geterotsiklicheskikh Soedinenii 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 C6H12O2, Formula: C9H9ClN2.

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

Zakharova, N. A. published the artcileImidazole derivatives. X. Acylation of 2-hydroxymethylbenzimidazole and the products of its methylation, Quality Control of 7467-35-8, the publication is Zhurnal Obshchei Khimii (1953), 1225-30, database is CAplus.

cf. ibid. 957-63. Acylation of 2-(hydroxymethyl)benzimidazole (I) occurs primarily at the HO group and only later does the formation of diacyl derivatives take place, where the 2nd acyl group is bound to the hetero-N atom. The N-Me compounds yield only monoacyl derivatives at the HO group. Hydrolysis of 2-(chloromethyl)benzimidazole gave 65-73.6% I. I (5 g.), 5.6 ml. MeI, and 5 ml. MeOH heated in sealed tube 5 hrs. at 70-90° gave 6.35 g. solid 1-methyl-2-hydroxymethylbenzimidazole-HI and 1-methyl-2-(hydroxymethyl)benzimidazole methiodide. Treated with cold aqueous NH₄OH and extraction of the residue with dry C₆H₆ left behind 1.3 g. 1-methyl-2-hydroxymethylbenzimidazole methiodide (IA), m. 187-8° (from absolute EtOH). The solution after evaporation was treated with aqueous NH₄OH and C₆H₆ to obtain addnl. amounts IA (total yield 20.35%). The C₆H₆ extracts gave 20.1% 1-methyl-2-hydroxymethylbenzimidazole, m. 146-7° (from C₆H₆); HCl salt, m. 189-90°; HI salt, solid without definite m.p. Methylation of I at 150° gave 1,2-dimethylbenzimidazole methiodide, m. 258-9°, which is also obtained from 2-methylbenzimidazole under similar conditions. I (7 g.) heated on a steam bath with 9.45 ml. Ac₂O and 10 ml. AcOH 30-40 min. gave 98.7% crude O-acetyl derivative (IB) of I, m. 163-4° (from C₆H₆ or H₂O); I is regenerated by refluxing with 0.1N HCl or NaOH; heating with AcOH causes no change, but refluxing 30 min. with Ac₂O gave the O,1-diacetyl derivative (IC) of I, m. 97-8°. IB in EtOH treated with aqueous AgNO₃ gave the Ag salt, C₁₀H₉.O₂N₂Ag. I (0.5 g.) in 150 ml. hot H₂O, was chilled and treated with 4 ml. 25% NaOH followed by 52.1 ml. 0.1N iodine in KI yielding a precipitate of 0.82 g. 1-iodo-O-acetyl derivative of I, m. 164° (it is readily analyzed by treatment with 10% KI in 2N HCl, warming and titrating the liberated iodine). I heated 20 min. to 100° with AcONa-Ac₂O gave 84% IC, m. 98-9.5° (from C₆H₆-petr. ether), which boiled with H₂O 10 min. gave 100% IB. The 1-Me derivative (II) of I heated 1 hr. at 100° with excess Ac₂O and AcOH gave 63% of the 1-methyl-O-acetyl derivative of I, m. 76-8°. IA similarly heated with Ac₂O-AcOH 1.5 hrs. gave a red solid, while the filtrate diluted with dry Et₂O gave a yellow oil, which with Et₂O-CHCl₃ gave colorless solid, decompose 256-8°, containing 43.1% iodine. The red solid treated with CHCl₃ gave more of the above product, m. 256°; the evaporated solution after treatment with thiosulfate gave the IB, m. 164-5° (from absolute EtOH). Treatment of powd. I.HCl in PhCl at reflux with 20% excess BzCl gave 57.7% 2-(benzoyloxymethyl)benzimidazole (III) HCl salt (IIIA) and 14.5% of the more soluble 1-benzoyl-2-(benzoyloxymethyl)benzimidazole (IV). The former gave III, m. 146-7° (from dilute EtOH), which is stable in hot mineral acids (dilute) and in hot HCl forms the HCl salt, m. 233-5° (from EtOH or H₂O); heating with 4N H₂SO₄ gave the acid sulfate, C₁₅H₁₄O₆N₂S, m. 207-10° (from dilute H₂SO₄. Treatment with AgNO₃ as above gave the Ag salt, colorless solid of III. IV, m. 89-91°, is decomposed in hot mineral acids yielding salts of the III. The yellow oil observed in the above benzoylation treated with 4N HCl yields IIIA, with liberation of BzCl and BzOH; similar decomposition occurs on standing or heating to 80-100°; the oil contained 5.3% N. II with 20% excess BzCl in C₆H₆ gave after 1 hr. reflux 81-5% 1-methyl-2-(benzoyloxymethyl)benzimidazole-HCl, m. 195-7° (from dilute HCl), which on drying partly loses its HCl content; with NH₄OH this yields the free base, m. 144-6° (from H₂O). IA does not undergo the benzoylation reaction.

Zhurnal Obshchei Khimii 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 C26H41N5O7S, Quality Control of 7467-35-8.

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

Bednyagina, N. P. published the artcileHydrolytic cleavage of some sulfones of heterocyclic series. VI. Synthesis and properties of p-nitrophenylsulfonyl-N-methylbenzimidazolylmethane and p-nitrophen ylsulfonylbenzothiazolylmethane, COA of Formula: C9H10N2O, the publication is Zhurnal Obshchei Khimii (1960), 3193-6, database is CAplus.

cf. CA 51, 5086a; 53, 21971c; 54, 509i. 2-(Hydroxymethyl)benzimidazole and MeI in aqueous alc. NaOH gave 60-5% 1-methyl-2-(hydroxymethyl)benzimidazole, m. 125-30°, which with SOCl₂ gave 100% 1-methyl-2-(chloromethyl)benzimidazole-HCl, m. 195-6°; base m. 94°. This with p-O₂NC₆H₄SNa in EtOH gave p-nitrophenyl 2-(1-methylbenzimidazolyl)methyl sulfide, m. 154-5°; p-nitrophenyl 2-benzimidazolyl sulfide prepared similarly, m. 214-17°, yielded the above sulfide after treatment with MeI as above. The sulfide and KMnO₄ in AcOH gave the sulfone, m. 223-5°. 2-(Chloromethyl)benzothiazole and p-O₂NC₆H₄SNa gave p-nitrophenyl 2-benzothiazolylmethyl sulfide, m. 129-30°, which with KMnO₄ in AcOH gave the sulfone, m. 210-12°. Both the sulfones were unaffected by hot 2N HCl in 2 hrs.

Zhurnal Obshchei Khimii 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, COA of Formula: C9H10N2O.

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

Dubey, P. K. published the artcileA facile solvent-free synthesis of 1-alkyl/aralkyl-2-(1-arylsulfonylalkyl) benzimidazoles using “TBAB” as surface catalyst, Safety of 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is Journal of Heterocyclic Chemistry (2010), 47(6), 1317-1322, database is CAplus.

Reaction of 2-(α-chloroalkyl)benzimidazoles with Na arylsulfinates (I) under solvent-free conditions in the presence of Bu₄NBr as surface catalyst, by simple phys. grinding using mortar and pestle, gave 2(1H)-[α-(arylsulfonyl)alkyl]benzimidazoles. Subsequent treatment with alkylating agents under solvent-free conditions resulted in 1-alkyl/aralkyl-2-[α-(arylsulfonyl)alkyl]benzimidazoles. Alternatively, the latter were also prepared directly from 1-alkyl/aralkyl-2-(α-chloroalkyl)benzimidazoles by reaction with I. All the reactions were free from organic solvents.

Journal of Heterocyclic Chemistry 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, Safety of 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole.

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

Dubey, P. K. published the artcileSynthesis of 1-alkyl/aralkyl-2-[1-(arylsulfonyl)alkyl]benzimidazoles under phase-transfer catalysis (PTC) conditions, Related Products of imidazoles-derivatives, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2007), 46B(3), 488-491, database is CAplus.

Reaction of 2-(1-chloroalkyl)benzimidazoles (I) with Na arylsulfinates in CH₃CN under PTC conditions gives 2-[1-(arylsulfonyl)alkyl]benzimidazoles, alkylation of which by di-Me or di-Et sulfate or benzyl chloride gives the title compounds, e.g., II. These final products can also be prepared by reaction of Na arylsulfinates with 1-alkyl/aralkyl-2-(1-chloroalkyl)benzimidazoles (obtained by phase-transfer alkylation of I) in MeCN using benzyltriethylammonium chloride as phase-transfer catalyst.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry 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, Related Products of imidazoles-derivatives.

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