Category: imidazoles-derivatives

Mowat, Jeffrey published the artcileIdentification of the Highly Active, Species Cross-Reactive Complex I Inhibitor BAY-179, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is ACS Medicinal Chemistry Letters (2022), 13(3), 348-357, database is CAplus and MEDLINE.

Mitochondria are key regulators of energy supply and cell death. Generation of ATP within mitochondria occurs through oxidative phosphorylation (OXPHOS), a process which utilizes the four complexes (complex I-IV) of the electron transport chain and ATP synthase. Certain oncogenic mutations (e.g., LKB1 or mIDH) can further enhance the reliance of cancer cells on OXPHOS for their energetic requirements, rendering cells sensitive to complex I inhibition and highlighting the potential value of complex I as a therapeutic target. Herein, we describe the discovery of a potent, selective, and species cross-reactive complex I inhibitor. A high-throughput screen of the Bayer compound library followed by hit triaging and initial hit-to-lead activities led to a lead structure which was further optimized in a comprehensive lead optimization campaign. Focusing on balancing potency and metabolic stability, this program resulted in the identification of BAY-179, an excellent in vivo suitable tool with which to probe the biol. relevance of complex I inhibition in cancer indications.

ACS Medicinal Chemistry Letters 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, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole.

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

Kassem, A. A. published the artcileProlonged release antazoline hydrochloride tablets. Part II. Using repeated granulation technique, Product Details of C17H20ClN3, the publication is Bulletin of the Faculty of Pharmacy (Cairo University) (1976), 14(1), 187-205, database is CAplus.

Repeated granulation of antazoline-HCl (I) [2508-72-7] with 5% and 10% Et cellulose [9004-57-3] and shellac solutions, followed by release-time study of the drug from its tablets, showed no increase in the release proportional to the concentration of the former binder. However, with shellac the increase in the release time was proportional to the concentration increase. In both cases, the release of I was relatively more rapid in gastric fluid than in that observed in intestinal fluid. The effects of number of granulations and surface area of the tablet on drug release were also studied. Shellac was more effective than Et cellulose in reducing the release of the drug.

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, Product Details of C17H20ClN3.

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

Kassem, A. A. published the artcileProlonged release antazoline hydrochloride tablets. Part 1. Using insoluble substances, Category: imidazoles-derivatives, the publication is Bulletin of the Faculty of Pharmacy (Cairo University) (1976), 14(1), 85-99, database is CAplus.

Addition of Mg stearate [557-04-0] and hydrogenated castor oil to antazoline-HCl (I) [2508-72-7] tablets made with Et cellulose [9004-57-3], prolonged the drug release. The tablets containing 15% and 20% Mg stearate released I more slowly in the gastric fluid than in the intestinal fluid, the release being more pronounced with the latter. Hydrogenated castor oil (10-20%) was perferred since it caused a gradual and uniform drug release both in gastric and intestinal fluids. Of the various retarding materials studied, hydrogenated castor oil caused the least erosion of I tablets, followed by Mg stearate.

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, Category: imidazoles-derivatives.

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

Motawi, A. published the artcileAccelerated stability studies of amaranth solution in presence of some drugs and excipients, Product Details of C17H20ClN3, the publication is Scientia Pharmaceutica (1980), 48(4), 377-84, database is CAplus.

Accelerated stability studies of amaranth (FD & C Red No 2) [915-67-3] solution in the presence of some excipients commonly used in pharmaceutical formulations, namely, lactose [63-42-3], mannitol [69-65-8], syrup, gelatin, Tween 80 [9005-65-6], polyethylene glycol (PEG 6000, 4000 and 1500) [25322-68-3] and some drugs, namely, ascorbic acid [50-81-7], chlorpheniramine maleate [113-92-8], antazoline-HCl [2508-72-7], chlorpromazine-HCl [69-09-0] and diphenhydramine-HCl [147-24-0], were carried out at 60°. The dye solution itself was very stable. Lactose and mannitol did not produce marked effects on dye stability. Syrup and gelatin caused fading of the dye solution Complete discoloration of the dye solutions resulted in the presence of Tween 80, PEG 6000, 4000, and 1500 after storage of 12-48 h. Diphenhydramine-HCl, antazoline-HCl and chlorpheniramine maleate did not affect the stability of the dye. On the other hand, ascorbic acid caused fading of the dye solution within few hours. Chlorpromazine-HCl gave a faint pinkish violet colloidal solution when mixed with the dye solution

Scientia Pharmaceutica 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, Product Details of C17H20ClN3.

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

Abdellatif, Khaled R. A. published the artcileSynthesis and antimicrobial activity of novel 2-substituted-1H-benzimidazole derivatives, Application of 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is Organic Chemistry: An Indian Journal (2013), 9(3), 115-120, database is CAplus.

The reaction of chloromethyl-1-methyl-1H-benzimidazole with ethyl-4-aminobenzoate yielded the ester 2 which upon hydrazinolysis resulted in [(1-methyl-1H-benzimidazol-2-ylmethyl)amino]benzohydrazide. Condensation of [(1-methyl-1H-benzimidazol-2-ylmethyl)amino]benzohydrazide with 2-nitrobenzaldehyde afforded the arylidene derivative which was cyclized to thiazolidinone derivative Substituted benzamide and oxadiazole derivative were prepared via reacting [(1-methyl-1H-benzimidazol-2-ylmethyl)amino]benzohydrazide with phthalic anhydride and benzoic acid, resp. Reaction of [(1-methyl-1H-benzimidazol-2-ylmethyl)amino]benzohydrazide with 4-chlorophenyl isocyanate and Et isothiocyanate gave the corresponding semicarbazide and thiosemicarbazide. The thiosemicarbazide was cyclized to triazole and thiadiazole derivatives Also, reacting thiosemicarbazide with both chloroacetic acid and maleic anhydride afforded thiazolidinone derivatives The prepared compounds were evaluated for in vitro antimicrobial activity using ciprofloxacin and triflucan as standard references

Organic Chemistry: An Indian 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, Application of 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole.

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

Ayad, E. M. published the artcileSelective and indicator antazoline lactose agar medium (ALA-medium), Formula: C17H20ClN3, the publication is Egyptian Journal of Pharmaceutical Sciences (1974), 15(4), 489-94, database is CAplus.

Antazoline-HCl was incorporated into a solid agar medium in order to study the isolation and identification of certain gram-neg. bacteria from stool samples. The medium for isolation of gram-neg. bacteria from gram-pos. bacteria contained 0.625 mg/ml of antazoline-HCl (called ALA-medium A), while the medium for isolating non-lactose fermenting gram-neg. bacteria contained 0.7 mg/ml of antazoline-HCl (called ALA-medium B). A comparison was made of the inhibitory action on different microorganisms of various antazoline-HCl concentrations and MacConkey’s agar and SS agar. Non-lactose fermenters were successfully isolated from stool samples before and after enrichment in selenite broth.

Egyptian Journal of Pharmaceutical Sciences 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, Formula: C17H20ClN3.

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

Durant, Graham J. published the artcilePotential histamine H2-receptor antagonists. 3. Methylhistamines, Category: imidazoles-derivatives, the publication is Journal of Medicinal Chemistry (1976), 19(7), 923-8, database is CAplus and MEDLINE.

Syntheses are described for all mono-, and some di- and trimethylhistamines, including the novel compounds β-methyl- (I) [24160-35-8], 4,Nα-dimethyl- (II) [36376-52-0], and 4,Nα,Nα-trimethylhistamine-2HCl (III) [54732-97-7], and agonist activities reported for stimulation of histamine [51-45-6] H1 (guinea-pig ileum) and H2 (rat gastric acid secretion) receptors. H2 receptor agonist activities indicated substantial retention of receptor binding for 4-methylhistamine-2 HCl (IV) [36376-47-3] and Nα-methylhistamine-2HCl (V) [16503-22-3]. Structure in relation to potential histamine receptor antagonists was discussed.

Journal of Medicinal Chemistry 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, Category: imidazoles-derivatives.

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

Woo, Ho Bum published the artcileSynthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity, COA of Formula: C9H10N2O, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(2), 933-936, database is CAplus and MEDLINE.

A novel curcumin mimic library possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of I or II with diversely substituted benzimidazolyl-2-carbaldehydes. The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound III with IC₅₀ of 1.0 and 1.9 μM has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, resp., and that compound IV with IC₅₀ of 1.9 μM has a strong inhibitory effect on the growth of MCF-7 cancer cells.

Bioorganic & Medicinal Chemistry Letters 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 C24H12, COA of Formula: C9H10N2O.

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

Gumus, Fatma published the artcileSynthesis, Cytotoxicity, and DNA Interactions of New Cisplatin Analogues Containing Substituted Benzimidazole Ligands, Computed Properties of 4760-35-4, the publication is Journal of Medicinal Chemistry (2009), 52(5), 1345-1357, database is CAplus and MEDLINE.

Six new platinum(II) complexes (I; R = CH₂Cl, CH₂OCOMe, CH₂CH₂OH; R₁ = H, Me) were synthesized and evaluated for their reactivity against model nucleophile I^–, cellular uptake, and in vitro antiproliferative activities against the human MCF-7 breast and HeLa cervix cancer cell lines. The effect of the compounds on pBR322 plasmid DNA was studied by gel electrophoretic mobility measurements. Flow cytometric anal. was also carried out to study the effect of representative compounds bearing 2-chloromethyl or acetoxymethylbenzimidazole substituents on the cell cycle distribution of MCF-7 and HeLa cells, resp. In general, it was found that Pt(II) complexes were less cytotoxic than cisplatin and were comparable to carboplatin. The results of the plasmid DNA interaction and the restriction studies suggest that changing the chem. structure of the benzimidazole ligands may modulate DNA binding mode and the sequence selectivity. The studied compounds had no significant effect on the cell cycle profile of the cells used. However, the acetoxymethylbenzimidazole derivative induced a significant increase in the SubG1 cell population at a concentration of 20 μM.

Journal of 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, Computed Properties of 4760-35-4.

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

Addy, Partha Sarathi published the artcileA Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation, Computed Properties of 359860-27-8, the publication is Journal of the American Chemical Society (2017), 139(34), 11670-11673, database is CAplus and MEDLINE.

Chemoselective modification of complex biomols. has become a cornerstone of chem. biol. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-directed labeling, remains high. Here the authors show that 5-hydroxyindoles exhibit remarkably high reactivity toward aromatic diazonium ions and this reaction can be used to chemoselectively label proteins. The authors have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eukaryotes, enabling efficient site-specific incorporation of 5-hydroxyindole into virtually any protein. The 5-hydroxytryptophan residue was shown to allow rapid, chemoselective protein modification using the azo-coupling reaction, and the utility of this bioconjugation strategy was further illustrated by generating a functional antibody-fluorophore conjugate. Although the resulting azo-linkage is otherwise stable, the authors show that it can be efficiently cleaved upon treatment with dithionite. The work establishes a unique chemoselective “unclickable” bioconjugation strategy to site-specifically modify proteins expressed in both bacteria and eukaryotes.

Journal of the American Chemical Society 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, Computed Properties of 359860-27-8.

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