Month: November 2022

Nagano, Masanobu published the artcileIn vivo programming of endogenous antibodies via oral administration of adaptor ligands, HPLC of Formula: 359860-27-8, the publication is Bioorganic & Medicinal Chemistry (2017), 25(21), 5952-5961, database is CAplus and MEDLINE.

Vaccination is a reliable method of prophylaxis and a crucial measure for public health. However, the majority of vaccines cannot be administered orally due to their degradation in the harsh gut environment or inability to cross the GI tract. In this study, we report the first proof-of-concept study of orally producible chem. programmed antibodies via specific conjugation of adaptor ligands to endogenous antibodies, in vivo. Pre-immunization with 2,4-dinitrophenyl (DNP), or the reactive hapten, 1,3-diketone (DK), or a novel reactive hapten, vinyl sulfone (VS) in mice, followed by oral administration of adaptor ligands composed of the hapten and biotin to the pre-immunized mice resulted in successful in vivo formation of the biotin-hapten-antibody complexes within 2 h. Pharmacokinetic evaluations revealed that apparent serum concentrations of programmed antibodies were up to 144 nM and that the serum half-lives reached up to 34.4 h. These findings show promise for the future development of orally bioavailable drug-hapten-antibody complexes as a strategy to quickly and easily modulate immune targets for aggressive pathogens as well as cancer.

Bioorganic & Medicinal 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, HPLC of Formula: 359860-27-8.

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

Pierce, Michael E. published the artcilePractical synthesis and regioselective alkylation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate to give DuP 532, a potent angiotensin II antagonist, Application of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, the publication is Journal of Organic Chemistry (1993), 58(17), 4642-5, database is CAplus.

(Hydroxymethyl)[(tetrazolylbiphenyl)methyl]imidazole, DuP 532 (I), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes. One route, which is more practical for large-scale synthesis, required the preparation of Me 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (II, R = C₂F₅). This imidazole was synthesized in five steps from com. available 2-propyl-4(5)-(hydroxymethyl)imidazole in 32% overall yield. Alternate perfluoroalkylation methods of the iodoimidazole precursor II (R = iodo) are presented. II (R = C₂F₅) (III) is remarkably stable to basic conditions and is alkylated by 2-[N-(triphenylmethyl)tetrazol-5-yl]-4′-(bromomethyl)-1′,1′-biphenyl (IV), giving only the desired regioisomer. A comparison of the alkylation of the trisubstituted precursors and analogs to III with IV indicate that even under mildly basic conditions (K₂CO₃/DMF), the mechanism is S_E2cB (anionic), except for 2-propyl-4(5)-(hydroxymethyl)imidazole which alkylates as a neutral species (S_E2′).

Journal of Organic 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, Application of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol.

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

Redondo, Jordi published the artcileHost-guest complexation of omeprazole, pantoprazole and rabeprazole sodium salts with cyclodextrins: an NMR study on solution structures and enantiodiscrimination power, Application In Synthesis of 161796-78-7, the publication is Journal of Inclusion Phenomena and Macrocyclic Chemistry (2012), 73(1-4), 225-236, database is CAplus.

The application of different cyclodextrins (CDs) as NMR chiral solvating agents (CSAs) for the sodium salts of the proton-pump inhibitors omeprazole, pantoprazole (sesquihydrate) and rabeprazole was investigated. It was proved that the formation of diastereomeric host-guest complexes in D₂O solution between the CDs and those substrates permitted the direct ¹H NMR discrimination of the enantiomers of the sodium salts of these compounds without the need of previous working-up. Rotating frame nuclear overhauser effect spectroscopy (ROESY) was used to ascertain the solution geometries of the host-guest complexes. The results suggested a preferential binding of the benzimidazole moiety of the guest mols. within the macrocyclic cavity of α-CD, whereas the higher dimensions of β- and γ-CD also permitted the inclusion of the highly substituted pyridine moieties. Moreover, the solution stoichiometries and the binding constants of the complexes formed with pantoprazole at room temperature were determined by ¹H and ¹⁹F NMR titration Diffusion-filtered Spectroscopy was applied to obtain clean spectra without the interference of the HOD signal.

Journal of Inclusion Phenomena and Macrocyclic Chemistry 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, Application In Synthesis of 161796-78-7.

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

Xia, Shumei published the artcileNickel-Catalyzed Stereoselective Alkenylation of Ketones Mediated by Hydrazine, Synthetic Route of 258278-25-0, the publication is JACS Au (2022), 2(8), 1929-1934, database is CAplus.

The direct conversion of naturally abundant carbonyl compounds provides a powerful platform for the efficient synthesis of valuable chems. In particular, the conversion of ketones to alkenes is a commonly encountered chem. transformation, often achieved via the multistep Shapiro reaction with tosylhydrazone and over stoichiometric organolithium or Grignard reagent. Herein, authors report an earth abundant nickel-catalyzed alkenylation of naturally abundant methylene ketones to afford a wide range of alkene derivatives, mediated by hydrazine. The protocol features a broad substrate scope (including alkyl ketones, aryl ketones, and aldehydes), good functional group compatibility, mild reaction conditions, water tolerance, and only environmentally friendly N₂, H₂, and H₂O as theor. byproducts. Moreover, gram-scale synthesis with good yield and generation of pharmaceutical intermediates highlighted its practical applicability.

JACS Au published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C6H8N2, Synthetic Route of 258278-25-0.

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

Van Santvliet, L. published the artcilePhysicochemical properties, NMR spectroscopy and tolerance of inclusion complexes of antazoline and tetracaine with hydroxypropyl-β-cyclodextrin, Related Products of imidazoles-derivatives, the publication is International Journal of Pharmaceutics (1998), 171(2), 147-156, database is CAplus.

To improve the tolerance of antazoline and tetracaine ophthalmic solutions, inclusion complexes of the free bases of both drugs with hydroxypropyl-β-cyclodextrin (HP-β-CD) were prepared The physicochem. properties of the drug:HP-β-CD solutions were determined and the inclusion complexes were characterized by ¹H and ¹³C NMR spectroscopy. The apparent complex constants were calculated from the phase-solubility diagram and were estimated at 403 M^-1 and 1308 M^-1 for the antazoline:HP-β-CD complex and tetracaine:HP-β-CD complex, resp. NMR anal. showed that in the 1:1 complexes the total antazoline fraction was present as an inclusion complex, whereas tetracaine was only partly included in spite of a similar phase solubility diagram. NMR spectroscopy also revealed the site of interaction of the drugs with the HP-β-CD mol. A solution acceptability test was carried out on volunteers. A relationship between the surface tension of the solutions and the tolerance was observed

International Journal of Pharmaceutics 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 C10H10O2, Related Products of imidazoles-derivatives.

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

Yang, Fei published the artcilePerformances comparison of enantiomeric separation materials prepared from shrimp and crab shells, Quality Control of 161796-78-7, the publication is Carbohydrate Polymers (2019), 238-246, database is CAplus and MEDLINE.

Previously reported studies demonstrate that many chitin/chitosan derivatives are promising for enantioseparation of chiral compounds The aim of the present study is to study influence of the chitin sources on performances of the chitosan type enantiomeric separation materials. Therefore, the chitosans were prepared from crab and shrimp shells, from which two sets of chiral selector, i.e. chitosan bis(3,5-dimethylphenylcarbamate)-(octanamide)s and chitosan bis(3,5-dichlorophenylcarbamate)-(octanamide)s were synthesized. The chitosan bis(3,5-dimethylphenylcarbamate)-(octanamide)s, resp., derived from crab and shrimp shells were close in swelling capacity and enantioseparation capability, and the same feature was found for the other two chiral selectors of chitosan bis(3,5-dichlorophenylcarbamate)-(octanamide). However, although most of the chiral analytes were eluted out in the same elution order, there were two analytes were in reversed elution orders when separated by the two chiral stationary phases of chitosan bis(3,5-dichlorophenylcarbamate)-(octanamide). Based on the observed results, enantiomeric separation materials may be developed either with shrimp chitin or crab chitin, depending on the source accessibility.

Carbohydrate Polymers 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 C8H11NO, Quality Control of 161796-78-7.

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

Remillard, David published the artcileDual Inhibition of TAF1 and BET Bromodomains from the BI-2536 Kinase Inhibitor Scaffold, 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 ACS Medicinal Chemistry Letters (2019), 10(10), 1443-1449, database is CAplus and MEDLINE.

Recent reports have highlighted the dual bromodomains of TAF1 (TAF1(1,2)) as synergistic with BET inhibition in cellular cancer models, engendering interest in TAF/BET polypharmacol. Here, we examine structure activity relationships within the BI-2536 PLK1 kinase inhibitor scaffold, previously reported to bind BRD4. We examine binding by this ligand to TAF1(2) and apply structure guided design strategies to discriminate binding to both the PLK1 kinase and BRD4(1) bromodomain while retaining activity on TAF1(2). Through this effort we discover potent dual inhibitors of TAF1(2)/BRD4(1), as well as biased derivatives showing marked TAF1 selectivity. We resolve X-ray crystallog. data sets to examine the mechanisms of the observed TAF1 selectivity and to provide a resource for further development of this scaffold.

ACS Medicinal Chemistry Letters 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, 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

Remillard, David published the artcileDegradation of the BAF Complex Factor BRD9 by Heterobifunctional Ligands, COA of Formula: C18H34N4O5S, the publication is Angewandte Chemie, International Edition (2017), 56(21), 5738-5743, database is CAplus and MEDLINE.

The bromodomain-containing protein BRD9, a subunit of the human BAF (SWI/SNF) nucleosome remodeling complex, has emerged as an attractive therapeutic target in cancer. Despite the development of chem. probes targeting the BRD9 bromodomain, there is a limited understanding of BRD9 function beyond acetyl-lysine recognition. We have therefore created the first BRD9-directed chem. degraders, through iterative design and testing of heterobifunctional ligands that bridge the BRD9 bromodomain and the cereblon E3 ubiquitin ligase complex. Degraders of BRD9 exhibit markedly enhanced potency compared to parental ligands (10- to 100-fold). Parallel study of degraders with divergent BRD9-binding chemotypes in models of acute myeloid leukemia resolves bromodomain polypharmacol. in this emerging drug class. Together, these findings reveal the tractability of non-BET bromodomain containing proteins to chem. degradation, and highlight lead compound dBRD9 as a tool for the study of BRD9.

Angewandte Chemie, International Edition 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, COA of Formula: C18H34N4O5S.

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

Steck, Edgar A. published the artcileBenzimidazole derivatives, Computed Properties of 4760-35-4, the publication is Organic Preparations and Procedures International (1975), 7(1), 6-11, database is CAplus.

1-(Aminomethyl)benzimidazoles [I, R = Me, NR2 = 3-carbamoyl-1-piperidinyl, 3-(diethylcarbamoyl-1-piperidinyl, 4-(2-hydroxyethyl)-1-piperazinyl, 4-(ethoxycarbonyl)-1-piperazinyl, R1 = 5-Cl, 6Cl, or 5,6-Cl2] were prepared by Mannich reaction of the appropriate benzimidazole and amine; o-C6H4(NH2)2 or 4-chloro-o-phenylenediamine reacted with 2-deoxy-D-glucose in the presence of Cu(I) acetate to give the corresponding 2-(D-arabino-2,3,4,5-tetrahydroxypentyl)benzimidazole; 2-(chloromethyl)-1-methyl-2-benzimidazole was treated with piperazine and tropine to give 1,4-bis(1-methyl-2-benzimidazolylmethyl)piperazine and 8-(1-methyl-2-benzimidazolyl)methyltropinium chloride resp.

Organic Preparations and Procedures International 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 C6H17NO3Si, Computed Properties of 4760-35-4.

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

Benhassine, Anfel published the artcileCobalt(II) complexes based on (1-methyl-1H-benzo[d]imidazol-2-yl) methanol derivative: synthesis, crystal structure, spectroscopy, DFT calculations, and antioxidant activity, SDS of cas: 7467-35-8, the publication is Journal of Coordination Chemistry (2018), 71(2), 311-328, database is CAplus.

The authors present a combined exptl. and computational study of two new cobalt(II) complexes as [Co(Hmbm)₂(OAc)₂] and [Co(Hmbm)₂(H₂O)₂]Cl₂ (Hmbm = (1-methyl-1H-benzo[d]imidazol-2-yl)methanol). Both complexes were characterized by FTIR and UV-visible spectroscopy, elemental anal., and single-crystal x-ray crystallog. The mol. geometries, electronic transitions, and vibrational frequencies of the two complexes and the ligand (Hmbm) in the ground state were calculated using global hybrid (B3LYP) and range-separated hybrid (CAM-B3LYP) d. functional. Qual. description of excited states and charge transfer character of electronic transitions states were carried out by plotting the Natural Transition Orbitals (NTOs) for main states, and were assigned to LMCT. The ligand and its Co(II) complexes were evaluated for their potential as DPPH radical scavengers.

Journal of Coordination 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 C9H10N2O, SDS of cas: 7467-35-8.

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