Month: December 2022

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

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

Narla, Divya published the artcileSimultaneous estimation of aceclofenac and esomeprazole sodium in bulk by RP-HPLC, COA of Formula: C17H18N3NaO3S, the publication is American Journal of PharmTech Research (2016), 6(2), 493-502, database is CAplus.

A simple, accurate, precise and specific RP-HPLC method has been developed for the simultaneous estimation of Aceclofenac and Esomeprazole Sodium in bulk. Chromatog. anal. was carried out on C18 column (250mm × 4.6mm, 5μm). Mobile phase used is a homogenous mixture of ACN: Methanol in the ratio of 50:50 volume/volume The detection was carried out at 285nm. The retention times were found to be 3.00 and 4.41 min for Aceclofenac and Esomeprazole Na resp. Both the drugs showed linearity in the range of 30 – 70mcg/mL. The correlation coefficient was found to be 0.99 and 0.992 for Aceclofenac and Esomeprazole Na resp. The developed method was validated as per ICH guidelines.

American Journal of PharmTech Research 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 C17H18N3NaO3S, COA of Formula: C17H18N3NaO3S.

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

Dutt, Manesh Chandra published the artcileIdentification of basic drugs by the thin-layer chromatographic profiles of their ninhydrin complexes, Synthetic Route of 2508-72-7, the publication is Journal of Chromatography (1981), 206(2), 267-77, database is CAplus.

Fifty-two common basic drugs produce various colors when spotted with ninhydrin [485-47-2] on plastic thin-layer plates and heated. When the plate is then developed in a suitable solvent each of the colored spots separates into a variety of addnl. colored spots and patches, the number of which depends on the temperature of heating. The relative intensity and spatial arrangement form a profile that is highly characteristic of the compounds The formation of such profiles was investigated at 100 and 160°C.

Journal of Chromatography published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C17H20ClN3, Synthetic Route of 2508-72-7.

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

Dutt, Manesh Chandra published the artcileUse of ninhydrin as a spray reagent for the detection of some basic drugs on thin-layer chromatograms, HPLC of Formula: 2508-72-7, the publication is Journal of Chromatography (1980), 195(1), 133-8, database is CAplus.

In a study aimed at exploring the potential of ninhydrin [485-47-2] to produce colored spots on thin-layer chromatog. plates, a wide variety of colors, on a white background, were produced by 52 of the 56 bases studied. In most instances different colors were produced at each of the selected temperatures (80, 120, and 160°), e.g., with amphetamine sulfate [60-13-9] the colors produced were pink-violet, grey-brown, and red-brown, resp. The response of the compounds to this method varied from 20 μg at room temperature to 1 μg at 160°.

Journal of Chromatography published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C17H20ClN3, HPLC of Formula: 2508-72-7.

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

Vidic, Jasmina published the artcileGold Surface Functionalization and Patterning for Specific Immobilization of Olfactory Receptors Carried by Nanosomes, Recommanded Product: 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 Analytical Chemistry (Washington, DC, United States) (2007), 79(9), 3280-3290, database is CAplus and MEDLINE.

There is substantial interest in engineering solid supports to achieve functional immobilization of membrane receptors both for investigation of their biol. function and for the development of novel biosensors. Three simple and practical strategies for immobilization of a human olfactory receptor carried by nanosomes are presented. The basis of the functionalization of solid gold surfaces is a self-assembled monolayer (SAM) containing biotinyl groups. Biotinyl groups are subsequently used to attach neutravidin and then biotinylated monoclonal antibody directed against the receptor to allow its specific grafting. Surface plasmon resonance technique is implemented for real-time monitoring of step-by-step surface functionalization and, in addition, for testing the functional response of immobilized olfactory receptors. The authors show that OR1740 is functional when immobilized via a tag attached to its C-terminus, but not via its N-terminus. Finally, the authors demonstrate that gold surfaces can be patterned by the SAMs tested using microcontact printing. AFM images of immobilized nanosomes onto a patterned surface suggest that small nanosomes flatten and fuse into larger vesicles but do not merge into a continuous layer. The whole study emphasizes the outstanding performances of the BAT/PEGAT SAM, which could be useful for developing on-a-chip sensor formats for membrane receptor investigations and use.

Analytical Chemistry (Washington, DC, United States) 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 C10H10O2, Recommanded Product: 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

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

Sergievskii, A. V. published the artcileReactions of methyl 4-aminofurazan-3-carboximidate with nitrogen-containing nucleophiles, Synthetic Route of 332026-86-5, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2001), 37(5), 717-720, database is CAplus.

Me 4-aminofurazan-3-carboximidate reacts with aromatic amines and hydrazines to give the corresponding amidines and amidrazones. The reaction of the title compound with o-phenylenediamine yields 3-amino-4-(2-benzimidazoyl)furazan, and with acylhydrazines N²-acyl-4-aminofurazan-3-carbohydrazides are formed. The latter undergo thermal intramol. cyclization with formation of 3-amino-4-(1,2,4-triazol-3-yl)furazan derivatives containing various substituents in position 5 of the triazole ring.

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) published new progress about 332026-86-5. 332026-86-5 belongs to imidazoles-derivatives, auxiliary class Oxadiazole,Amine,Benzimidazole, name is 4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine, and the molecular formula is C10H14O, Synthetic Route of 332026-86-5.

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

Keni, Shubham published the artcileBenzimidazole: a propitious scaffold with multifarious therapeutic potential, Recommanded Product: 1,2-Diphenyl-1H-benzo[d]imidazole, the publication is European Journal of Biomedical and Pharmaceutical Sciences (2018), 5(11), 483-488, database is CAplus.

A review is presented on the antibacterial, antifungal, antiviral, antiinflammatory, antihypertensive activity of benzimidazole derivatives as drug. Most of the drugs and pharmacol. active moieties possess heterocyclic ring structure and presence of hetero atoms or groupings evinces privileged specificities in their pharmacol. targets. Among the heterocyclic compounds, benzimidazole has emerged as cardinal construction motif, which plays pivotal role in drug development. Benzimidazole scaffold is known to possess some prime pharmacol. activities like anti- mycobacterial, antimicrobial, anti-viral, antioxidant, antiinflammatory, antihypertensive, etc. This broad spectrum of biol. and biochem. activities was further assisted by the synthetic flexibility of benzimidazole, which permits development of large no of structurally diverse derivatives Therefore, it is necessary to compile the latest information along with earlier information to understand present status of benzimidazole nucleus in drug discovery. In the present review, various derivatives of benzimidazole possessing anti-mycobacterial, antimicrobial, analgesic and antiinflammatory potential are brought into limelight and their activity was elucidated in accordance with structure activity relation studies.

European Journal of Biomedical and Pharmaceutical Sciences 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, Recommanded Product: 1,2-Diphenyl-1H-benzo[d]imidazole.

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

Jankowska-Anyszka, Marzena published the artcileSynthesis of a new class of ribose functionalized dinucleotide cap analogs for biophysical studies on interaction of cap-binding proteins with the 5′ end of mRNA, Synthetic Route of 359860-27-8, the publication is Organic & Biomolecular Chemistry (2011), 9(15), 5564-5572, database is CAplus and MEDLINE.

MRNAs of primitive eukaryotes such as Caenorhabditis elegans and Ascaris summ possess two different caps at their 5′ terminus. They have either a typical cap which consists of 7-methylguanosine linked via a 5′,5′-triphosphate bridge to the first transcribed nucleotide (MMG cap) or an atypical hypermethylated form with two addnl. Me groups at the N2 position (TMG cap). Studies on interaction between the 5′ end of mRNA and proteins that specifically recognize its structure have been carried out for several years and they often require chem. modified cap analogs. Here, we present the synthesis of five novel dinucleotide MMG and TMG cap analogs designed for binding studies using biophys. methods such as ESR and surface plasmon resonance. New analogs were prepared by derivatization of the 2′,3′-cis diol of the second nucleotide in the cap structure with levulinic acid, and coupling of the obtained acetal through its carboxylic group with 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino TEMPO), ethylenediamine (EDA) or (+)-biotinyl-3,6,9-trioxaundecanediamine (amine-PEO₃-biotin).

Organic & Biomolecular 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 C18H34N4O5S, Synthetic Route of 359860-27-8.

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