Category: imidazoles-derivatives

Ye, Chen-Xi published the artcileStereocontrolled 1,3-nitrogen migration to access chiral α-amino acids, COA of Formula: C9H9ClN2, the publication is Nature Chemistry (2022), 14(5), 566-573, database is CAplus and MEDLINE.

Here a protocol for the economical and practical synthesis of optically active α-amino acids RNHC(R¹)(R²)C(O)OH (R = Ts, Ms, C(O)OMe, (2,2,2-trichloroethoxy)carbonyl; R¹ = H, Me; R² = pent-2-yn-1-yl, 4-methylphenyl, 2H-1,3-benzodioxol-5-yl, etc.) based on an unprecedented stereocontrolled 1,3-nitrogen shift was reported. The method employs abundant and easily accessible carboxylic acids R¹CH(R²)C(O)OH as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalyzed C(sp³)-H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.

Nature 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 C7H7BrFN, COA of Formula: C9H9ClN2.

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

Gohil, Vishal M. published the artcileNutrient-sensitized screening for drugs that shift energy metabolism from mitochondrial respiration to glycolysis, HPLC of Formula: 2508-72-7, the publication is Nature Biotechnology (2010), 28(3), 249-255, database is CAplus and MEDLINE.

Most cells have the inherent capacity to shift their reliance on glycolysis relative to oxidative metabolism, and studies in model systems have shown that targeting such shifts may be useful in treating or preventing a variety of diseases ranging from cancer to ischemic injury. However, we currently have a limited number of mechanistically distinct classes of drugs that alter the relative activities of these two pathways. We screen for such compounds by scoring the ability of >3500 small mols. to selectively impair growth and viability of human fibroblasts in media containing either galactose or glucose as the sole sugar source. We identify several clin. used drugs never linked to energy metabolism, including the antiemetic meclizine, which attenuates mitochondrial respiration through a mechanism distinct from that of canonical inhibitors. We further show that meclizine pretreatment confers cardioprotection and neuroprotection against ischemia-reperfusion injury in murine models. Nutrient-sensitized screening may provide a useful framework for understanding gene function and drug action within the context of energy metabolism

Nature Biotechnology 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

Suter, Scott R. published the artcileStructure-Guided Control of siRNA Off-Target Effects, Recommanded Product: (2-Methyl-1H-imidazol-4-yl)methanol, the publication is Journal of the American Chemical Society (2016), 138(28), 8667-8669, database is CAplus and MEDLINE.

Short interfering RNAs (siRNAs) are promising therapeutics that make use of the RNA interference (RNAi) pathway, but liabilities arising from the native RNA structure necessitate chem. modification for drug development. Advances in the structural characterization of components of the human RNAi pathway have enabled structure-guided optimization of siRNA properties. Here the authors report the 2.3 Å resolution crystal structure of human Argonaute 2 (hAgo2), a key nuclease in the RNAi pathway, bound to an siRNA guide strand bearing an unnatural triazolyl nucleotide at position 1 (g1). Unlike natural nucleotides, this analog inserts deeply into hAgo2’s central RNA binding cleft and thus is able to modulate pairing between guide and target RNAs. The affinity of the hAgo2-siRNA complex for a seed-only matched target was significantly reduced by the triazolyl modification, while the affinity for a fully matched target was unchanged. In addition, siRNA potency for off-target repression was reduced (4-fold increase in IC₅₀) by the modification, while on-target knockdown was improved (2-fold reduction in IC₅₀). Controlling siRNA on-target vs. microRNA (miRNA)-like off-target potency by projection of substituent groups into the hAgo2 central cleft from g1 is a new approach to enhance siRNA selectivity with a strong structural rationale.

Journal of the American Chemical Society published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C4H7BrO, Recommanded Product: (2-Methyl-1H-imidazol-4-yl)methanol.

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

Sambasivarao, K. published the artcileEffect of some antihistamines on the uterine response to estrogen in the rat, Synthetic Route of 2508-72-7, the publication is Indian Journal of Physiology and Pharmacology (1977), 21(3), 207-8, database is CAplus and MEDLINE.

Water imbibition by rat uterus induced by estradiol dipropionate (I dipropionate) [113-38-2] (10 μg/day for 5 days, i.p.) was not decreased by antihistamines, but was augmented by 1 of them, viz. antazoline-HCl [2508-72-7]. Thus, previously observed prolongation of the estrous cycle by antihistamines may not be due to blockade of uterine hyperemia or edema induced by estrogens.

Indian Journal of Physiology and Pharmacology 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

Sambasivarao, K. published the artcileEffect of some antihistaminic drugs on the estrous cycle of rats, COA of Formula: C17H20ClN3, the publication is Indian Journal of Physiology and Pharmacology (1977), 21(2), 156-8, database is CAplus and MEDLINE.

The effect of some antihistaminic drugs namely antazoline-HCl [2508-72-7], diphenhydramine-HCl [147-24-0] and mepyramine maleate [59-33-6] has been investigated on the estrous cycle in albino rats. On daily i.p. administrationfor 6 days, all 3 drugs (10 mg/kg) significantly prolonged the duration of the estrous cycle. The duration of subsequent cycles returned to near normal.

Indian Journal of Physiology and Pharmacology 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, COA of Formula: C17H20ClN3.

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

Dessouky, Y. M. published the artcileDetermination of some pharmaceutical amines by sodium dioctyl sulfosuccinate, Recommanded Product: N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, the publication is Bulletin of the Faculty of Pharmacy (Cairo University) (1979), 16(1), 67-74, database is CAplus.

The conditions of diphasic titration of amines, based on ion-pair formation, were modified and applied to the determination of 7 pharmaceutical amines, e.g., aminopyrine (I) [58-15-1] and promethazine-HCl [58-33-3]. Acetate buffer of pH 0.91 or 0.65 and dimethylyellow screened with methylene blue as indicator were used. The stoichiometry (1:1) of the reaction between Na dioctyl sulfosuccinate [577-11-7] and the amines was determined; this made it unnecessary the need for the side-by-side titration of an authentic sample of the amine. Amounts as low as 0.30 mg could be determined by the modified procedure as against 10 mg by the unmodified procedure. The results obtained with the modified procedure are compared with those of British pharmacopeia(1973) and European pharmacopeia(1971) methods.

Bulletin of the Faculty of Pharmacy (Cairo University) 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, Recommanded Product: N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride.

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

Beleslin, D. B. published the artcileAnalysis of the gross behavioral changes induced by tetraethylammonium and a comparison with other substances affecting the autonomic and central nervous system after intraventricular injections to conscious cats, Application In Synthesis of 2508-72-7, the publication is Neuropharmacology (1974), 13(12), 1171-7, database is CAplus and MEDLINE.

Tetraethylammonium chloride (TEA) [56-34-8] (0.2-3.0 mg, intraventricularly) caused emotional behavior, autonomic changes, motor phenomena, and convulsions in cats. Other drugs which affect the autonomic or central nervous system did not block the effects of TEA. Of the drugs tested for behavioral effects, 7 caused behavioral changes similar to TEA, 2 caused autonomic and motor phenomena followed by sedation and sleep, and 2 caused depressant behavior. The emotional behavior caused by TEA appears to involve central muscarinic cholinoceptive sites, while the autonomic changes, motor phenomena, and convulsions appeared to result from direct actions on the nerve cells.

Neuropharmacology 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, Application In Synthesis of 2508-72-7.

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

Gortinskaya, T. V. published the artcileSome derivatives of 4,4′-dihydrazinodiphenyl sulfone and 4-hydrazinophenyl 2-acetamido-5-thiazolyl sulfone, SDS of cas: 45533-87-7, the publication is Zhurnal Obshchei Khimii (1957), 1960-4, database is CAplus.

Heating 1.4 g. opianic acid in 50 ml. EtOH with 1 g. (p-HCl.H₂NNHC₆H₄)₂SO₂ in 10 ml. H₂O gave a precipitate of 2.2 g. {4-[2,3,4-HO₂C(MeO)₂C₆H₂CH:NNH]C₆H₄}₂SO₂ (I), m. 268-9°. If the reaction is run in H₂O there is formed yellow II, m. 258-60°, which changes to I on heating with ROH or alc. H₂SO₄. Hydrogenation of 4-nitrophenyl-2-amino-5-thiazolyl sulfone in EtOH over Raney Ni gave 87% 4-H₂NC₆H₄ analog, m. 217-19°. Hydrogenation of 4-nitrophenyl-2-acetamido-5-thiazolyl sulfone over Raney Ni in H₂O gave the 4-H₂NC₆H₄ analog, m. 268-9°. This (5.4 g.), 42 ml. AcOH, 21 ml. concentrated HCl, and 10.5 ml. H₂O diazotized with 1.1 g. NaNO₂ at 0° and the solution treated with 7.85 g. SnCl₂ in 38.5 ml. HCl, and kept 2 days at room temperature gave 0.3 g. p-H₂NNHC₆H₄ analog HCl salt, m. 222°; the filtrate treated with H₂S and filtered gave with NH₄OH 1.6 g. free base (IIA), m. 243-5°. The following hydrazones are reported: from (p-H₂NNHC₆H₄)₂SO₂ (III) and p-HOC₆H₄CHO, m. 238-40°; from III and p-AcNHC₆H₄CHO, m. 262-5°; from III and 3,4-MeO(HO)C₆H₃CHO, m. 250-2°; from 4-hydrazinophenyl-2-acetamido-5-thiazolyl sulfone (IV) and p-AcNHC₆H₄CHO, m. 221-3°; from IV and 3,4-MeO(HO)C₆H₃CHO, m. 238-40°; from IV and opianic acid, m. 263-4°. III showed some in vitro activity against human and avian tuberculosis and acid-fast saprophytic sp., Microsporon sp., Trichophyton sp., Achorion sp., and actinomyces sp. Some activity was found for III hydrazone, p-HOC₆H₄CHO, and IIA.

Zhurnal Obshchei Khimii published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, SDS of cas: 45533-87-7.

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

Moore, Terry W. published the artcileSynthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy, Recommanded Product: 4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine, the publication is ACS Medicinal Chemistry Letters (2013), 4(8), 762-767, database is CAplus and MEDLINE.

Targeting host cell factors required for virus replication provides an alternative to targeting pathogen components and represents a promising approach to develop broad-spectrum antiviral therapeutics. High-throughput screening (HTS) identified two classes of inhibitors with broad-spectrum antiviral activity against ortho- and paramyxoviruses including influenza A virus (IAV), measles virus (MeV), respiratory syncytial virus (RSV), and human parainfluenza virus type 3 (HPIV3). Hit-to-lead optimization delivered inhibitor N-methyl-N-((1-methyl-4,5-diphenyl-1H-imidazol-2-yl)methyl)aniline, with EC₅₀ values of 0.88 and 0.81 μM against IAV strain WSN and MeV strain Edmonston, resp. It was also found that N-methyl-N-((1-methyl-4,5-diphenyl-1H-imidazol-2-yl)methyl)aniline delivers good stability in human liver S9 fractions with a half-life of 165 min. These data establish N-methyl-N-((1-methyl-4,5-diphenyl-1H-imidazol-2-yl)methyl)aniline as a promising lead for antiviral therapy through a host-directed mechanism.

ACS Medicinal Chemistry Letters 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 C9H7N5O, Recommanded Product: 4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine.

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

Martinez-Alanis, Paulina R. published the artcileCopper Versus Thioether-Centered Oxidation: Mechanistic Insights into the Non-Innocent Redox Behavior of Tripodal Benzimidazolylaminothioether Ligands, SDS of cas: 4760-35-4, the publication is Chemistry – A European Journal (2013), 19(19), 6067-6079, database is CAplus and MEDLINE.

A series of Cu⁺ complexes with ligands that feature varying numbers of benzimidazole/thioether donors and methylene or ethylene linkers between the central nitrogen atom and the thioether sulfur atoms have been spectroscopically and electrochem. characterized. Cyclic voltammetry measurements indicated that the highest Cu²⁺/Cu⁺ redox potentials correspond to sulfur-rich coordination environments, with values decreasing as the thioether donors are replaced by nitrogen-donating benzimidazoles. Both Cu²⁺ and Cu⁺ complexes were studied by DFT. Their electronic properties were determined by analyzing their frontier orbitals, relative energies, and the contributions to the orbitals involved in redox processes, which revealed that the HOMOs of the more sulfur-rich copper complexes, particularly those with methylene linkers (-N-CH₂-S-), show significant aromatic thioether character. Thus, the theor. predicted initial oxidation at the sulfur atom of the methylene-bridged ligands agrees with the exptl. determined oxidation waves in the voltammograms of the NS₃– and N₂S₂-type ligands as being ligand-based, as opposed to the copper-based processes of the ethylene-bridged Cu⁺ complexes. The electrochem. and theor. results are consistent with our previously reported mechanistic proposal for Cu²⁺-promoted oxidative C-S bond cleavage, which in this work resulted in the isolation and complete characterization (including by X-ray crystallog.) of the decomposition products of two ligands employed, further supporting the novel reactivity pathway invoked. The combined results raise the possibility that the reactions of copper-thioether complexes in chem. and biochem. systems occur with redox participation of the sulfur atom.

Chemistry – A European Journal 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, SDS of cas: 4760-35-4.

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