Tag: M.W=150-200

Doebelin, Christelle published the artcileDiscovery and Optimization of a Series of Sulfonamide Inverse Agonists for the Retinoic Acid Receptor-Related Orphan Receptor-a, SDS of cas: 13682-33-2, the publication is Medicinal Chemistry (Sharjah, United Arab Emirates) (2019), 15(6), 676-684, database is CAplus and MEDLINE.

Background: Despite a massive industry endeavor to develop RORalpha-modulators for autoimmune disorders, there has been no indication of efforts to target the close family member RORa for similar indications. This may be due to the misconception that RORa is redundant to RORalpha, or the inherent difficulty in cultivating tractable starting points for RORa. RORa-selective modulators would be useful tools to interrogate the biol. of this understudied orphan nuclear receptor. Objective: The goal of this research effort was to identify and optimize synthetic ligands for RORa starting from the known LXR agonist T0901317. Methods: Fourty-five analogs of the sulfonamide lead (1) were synthesized and evaluated for their ability to suppress the transcriptional activity of RORa, RORalpha, and LXRa in cell-based assays. Analogs were characterized by 1H-NMR, 13C-NMR, and LC-MS anal. The pharmacokinetic profile of the most selective RORa inverse agonist was evaluated in rats with i.p. (i.p.) and per oral (p.o.)dosing. Results: Structure-activity relationship studies led to potent dual RORa/RORalpha inverse agonists as well as RORa-selective inverse agonists (20, 28). LXR activity could be reduced by removing the sulfonamide nitrogen substituent. Attempts to improve the potency of these selective leads by varying substitution patterns throughout the mol. proved challenging.

Medicinal Chemistry (Sharjah, United Arab Emirates) published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C9H9N3, SDS of cas: 13682-33-2.

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

Cheng, Huan published the artcileCatalytic Performance of Pd Nanoparticles Obtained by Direct Reduction in Cellulose-Poly(ferrocenylsilane) Hybrid Sponges, Application of 3-Butyl-1-methyl-1H-imidazol-3-ium chloride, the publication is Advanced Materials Interfaces (2022), 9(6), 2101664, database is CAplus.

Cellulose-poly(ferrocenylsilane) (PFS) polyionic liquid (PIL) composite sponges are fabricated by codissoln. of cellulose and PFS-PIL, followed by solvent exchange and freeze-drying. The hybrid sponges are used to in situ produce and immobilize palladium nanoparticles (Pd NPs), leading to Pd NP-decorated porous supports. The formation of Pd NPs is confirmed by TEM and XPS measurements. The as-prepared cellulose/PFS-PIL@Pd sponges exhibit a high catalytic activity in the reduction of 4-nitrophenol (4-NiP) to 4-aminophenol (4-AmP). As a variety of metal NPs may be immobilized using this method, these sponges constitute a promising new class of catalytic porous supports.

Advanced Materials Interfaces 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, Application of 3-Butyl-1-methyl-1H-imidazol-3-ium chloride.

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

Freitas, Gabriel published the artcileImpact of magnetic ionic liquids as catalysts on the curing process of epoxy/anhydride system: Mechanistic investigation and dynamic-mechanical analysis, Quality Control of 79917-90-1, the publication is Journal of Applied Polymer Science (2022), 139(28), e52606, database is CAplus.

Cyclic acid anhydride – based hardeners provide excellent physic-mech. and thermal properties to epoxy networks. However, the curing process takes place at relatively high temperature, thus limiting the applications as coatings and free-heating devices. The present work describes for the first time the efficient catalytic action of imidazolium- and phosphonium- based ionic liquids (IL) bearing iron tetrachloride (FeCl₄) as counter anion for the curing process of epoxy prepolymer (EP)/methyl tetrahydrophthalic anhydride (MTHPA) even at room temperature Indeed, both differential scanning calorimetry and rheol. anal. revealed that the addition of 5 phr of trihexyl (tetradecyl)-phosphonium iron tetrachloride (P₆₆₆₁₄. FeCl₄) resulted in faster curing process when compared with systems cured with conventional tertiary amine. The gelation at room temperature occurred before 24 h with this magnetic IL. Moreover, the systems catalyzed by P₆₆₆₁₄. FeCl₄ presented higher glass transition temperature, higher storage modulus and higher crosslink d. as indicated by dynamic-mech. anal. (DMA). A mechanism for the curing process was proposed based on DSC and Fourier transform IR anal. These results highlight the importance of magnetic ILs as catalysts for the curing process of EP/MTHPA system and open new avenues for applications of this system as a room temperature-based curing system.

Journal of Applied Polymer Science 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, Quality Control of 79917-90-1.

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

Klock, Cornelius published the artcileDiscovery of Potent and Specific Dihydroisoxazole Inhibitors of Human Transglutaminase 2, COA of Formula: C9H10N2O, the publication is Journal of Medicinal Chemistry (2014), 57(21), 9042-9064, database is CAplus and MEDLINE.

Transglutaminase 2 (TG2) is a ubiquitously expressed enzyme that catalyzes the posttranslational modification of glutamine residues on protein or peptide substrates. A growing body of literature has implicated aberrantly regulated activity of TG2 in the pathogenesis of various human inflammatory, fibrotic, and other diseases. Taken together with the fact that TG2 knockout mice are developmentally and reproductively normal, there is growing interest in the potential use of TG2 inhibitors in the treatment of these conditions. Targeted-covalent inhibitors based on the weakly electrophilic 3-bromo-4,5-dihydroisoxazole (DHI) scaffold have been widely used to study TG2 biol. and are well tolerated in vivo, but these compounds have only modest potency, and their selectivity toward other transglutaminase homologs is largely unknown. In the present work, we first profiled the selectivity of existing inhibitors against the most pertinent TG isoforms (TG1, TG3, and FXIIIa). Significant cross-reactivity of these small mols. with TG1 was observed Structure-activity and -selectivity analyses led to the identification of modifications that improved potency and isoform selectivity. Preliminary pharmacokinetic anal. of the most promising analogs was also undertaken. Our new data provides a clear basis for the rational selection of dihydroisoxazole inhibitors as tools for in vivo biol. investigation.

Journal of 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 C9H10N2O, COA of Formula: C9H10N2O.

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

Yoshikawa, Masato published the artcileDesign and synthesis of potent and selective pyridazin-4(1H)-one-based PDE10A inhibitors interacting with Tyr683 in the PDE10A selectivity pocket, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Bioorganic & Medicinal Chemistry (2016), 24(16), 3447-3455, database is CAplus and MEDLINE.

Utilizing structure-based drug design techniques, we designed and synthesized phosphodiesterase 10A (PDE10A) inhibitors based on pyridazin-4(1H)-one. These compounds can interact with Tyr683 in the PDE10A selectivity pocket. Pyridazin-4(1H)-one derivative 1 was linked with a benzimidazole group through an alkyl spacer to interact with the OH of Tyr683 and fill the PDE10A selectivity pocket. After optimizing the linker length, we identified 1-(cyclopropylmethyl)-5-[3-(1-methyl-1H-benzimidazol-2-yl)propoxy]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (16f) as having highly potent PDE10A inhibitory activity (IC₅₀ = 0.76 nM) and perfect selectivity against other PDEs (>13,000-fold, IC₅₀ = >10,000 nM). The crystal structure of 16f bound to PDE10A revealed that the benzimidazole moiety was located deep within the PDE10A selectivity pocket and interacted with Tyr683. Addnl., a bidentate interaction existed between the 5-alkoxypyridazin-4(1H)-one moiety and the conserved Gln716 present in all PDEs.

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 C19H14N2, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

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

Miller, Ross A. published the artcileIodine as a Chemoselective Reoxidant of TEMPO: Application to the Oxidation of Alcohols to Aldehydes and Ketones, Safety of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, the publication is Organic Letters (2003), 5(3), 285-287, database is CAplus and MEDLINE.

Chemoselective alc. oxidations using catalytic TEMPO and stoichiometric iodine as the terminal oxidant were studied. Iodine was compared to other pos. halogens as the terminal oxidant and shown to be superior in cases of electron-rich and heteroaromatic rings. The new conditions were successfully applied to the oxidation of 2-butyl-5-chloro-4-imidazolemethanol to its aldehyde derivative, which is an important intermediate in the synthesis of losartan.

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

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

Anderson, Ross published the artcileSelective oxidation of alcohols to carbonyl compounds and carboxylic acids with platinum group metal catalysts, Category: imidazoles-derivatives, the publication is Advanced Synthesis & Catalysis (2003), 345(4), 517-523, database is CAplus.

The use of platinum group metal (PGM) catalysts for the selective oxidation of various primary and secondary alcs. under mild conditions is described. High throughput screening (HTS) techniques have been used to identify trends in catalyst activity and product selectivity. Using air as oxidant and water as solvent 5% Pt, 1% Bi/C has been identified as an efficient catalyst for the transformation of 2-octanol to 2-octanone and 1-octanol to octanoic acid. To improve aldehyde selectivity the promotion of Pt/Al₂O₃ and Ru/C catalysts has been investigated. The use of H₂O₂ as oxidant has been demonstrated as a suitable alternative to air.

Advanced Synthesis & Catalysis 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

Mimmi, Maria Chiara published the artcileModels for biological trinuclear copper clusters. Characterization and enantioselective catalytic oxidation of catechols by the copper(II) complexes of a chiral ligand derived from (S)-(-)-1,1′-binaphthyl-2,2′-diamine, Quality Control of 4760-35-4, the publication is Dalton Transactions (2004), 2192-2201, database is CAplus and MEDLINE.

The dinuclear and trinuclear Cu(II) complexes of an octadentate ligand (I) derived from (S)-1,1′-binaphthyl-2,2′-diamine were prepared and characterized by UV/visible, CD, EPR and NMR spectroscopy. The ligand contains two tridentate aminobis(benzimidazole) donor arms connected to a central bidentate diaminobinaphthyl linker, which hosts the chiral unit. In the dinuclear Cu complex the ligation occurs essentially within the tridentate arms of the ligand. The two Cu centers are EPR nonequivalent and noninteracting. The EPR data suggests that one of the Cu ions addnl. interacts with one of the tertiary aminonaphthyl donors. In the trinuclear complex the two aminonaphthyl donors bind the third Cu ion. The EPR spectrum of this complex shows the signal for a mononuclear Cu(II) center bound to a tridentate arm, while the remaining two Cu(II) centers are coupled through hydroxo groups. The CD spectrum shows that in the free ligand a severe reduction of the dihedral angle between the naphthyl groups from the strain free range occurs. This conformation is stabilized by ring stacking interactions with the benzimidazole groups. On complex formation this interaction is removed because the benzimidazole groups are involved in metal binding. In the dinuclear Cu complex the conformation of the binaphthyl chromophore probably approaches the strain free range, while in the trinuclear Cu complex a marked flattening of the dihedral angle between the two naphthyl rings occurs. Both complexes are active catalysts in the oxidation of L-/D-Dopa derivatives to quinones. High enantioselectivity is observed in the oxidation of L-/D-Dopa Me ester catalyzed by the dinuclear Cu complex, which exhibits strong preference for the d enantiomer. The enantioselectivity is largely lost for the trinuclear Cu complex.

Dalton Transactions 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, Quality Control of 4760-35-4.

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

Mimmi, Maria Chiara published the artcileSynthesis and conformational studies of a chiral octadentate ligand derived from (R)-1,1′-binaphthyl-2,2′-diamine and its dinuclear zinc(II) and nickel(II) complexes, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is European Journal of Inorganic Chemistry (2003), 3934-3944, database is CAplus.

The synthesis of the octadentate ligand (R)-(-)-N,N’-dimethyl-N,N’-bis{3-[bis(1-methyl-2-benzimidazolylmethyl)]-aminopropyl}-1,1′-binaphthyl-2,2′-diamine (L), containing a central 1,1′-binaphthalenediamine core connected to two aminobis(benzimidazole) arms by flexible trimethylene C chains, and its dinuclear complexes [Zn₂L](ClO₄)₄ and [Ni₂L](ClO₄)₄ is reported. The structural features of the free ligand and the metal complexes were studied by NMR, UV/Visible, CD, and computational methods, including simulated annealing-mol. mechanics and semiempirical PM3 calculations The preferred conformation of the free ligand was characterized by a relatively small dihedral angle of ∼75° between the two naphthyl rings, which is imposed by favorable stacking interactions between benzimidazole rings from different arms. In the dinuclear Zn(II) complex each metal ion is pseudotetrahedral and bound to three N donors of one aminobis(benzimidazole) arm and one N donor of the binaphthalenediamine residue. Coordination of the benzimidazole groups to the metal ions prevents the stacking interactions seen in the free ligand and, consequently, the dihedral angle between the naphthyl groups increases to the more usual ∼90°. In the dinuclear Ni(II) complex, the ligand still provides four N donors to each metal centers, but the stereochem. preference of the Ni(II) ions imposes a ligand field of tetragonal symmetry, with pseudo-octahedral metal centers, and this occurs with pronounced flattening of the dihedral angle between the naphthyl groups. The change in conformation, from L to [Zn₂L]⁴⁺ to [Ni₂L]⁴⁺, of the critical 1,1′-binaphthalenediamine residue is clearly indicated by CD spectra.

European Journal of Inorganic 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, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole.

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

Kolasa, Teodozyj published the artcileSymmetrical Bis(heteroarylmethoxyphenyl)alkylcarboxylic Acids as Inhibitors of Leukotriene Biosynthesis, SDS of cas: 4760-35-4, the publication is Journal of Medicinal Chemistry (2000), 43(17), 3322-3334, database is CAplus and MEDLINE.

Sym. bis(quinolylmethoxyphenyl)alkylcarboxylic acids were investigated as inhibitors of leukotriene biosynthesis and the sodium salt of bisquinolylmethoxyphenylpentanoic acid I met our design parameters for a drug candidate (ABT-080). I was readily synthesized in three steps from com. available diphenolic acid. Against intact human neutrophils, the sodium salt of I inhibited ionophore-stimulated LTB₄ formation with an IC₅₀ = 20 nM. In zymosan-stimulated mouse peritoneal macrophages producing both LTC₄ and PGE₂, the sodium salt of I showed 9000-fold selectivity for inhibition of LTC₄ (IC₅₀ = 0.16 nM) over PGE₂ (IC₅₀ = 1500 nM). Preliminary pharmacokinetic evaluation in rat and cynomolgus monkey demonstrated good oral bioavailability and elimination half-lives of 9 and 5 h, resp. Pharmacol. evaluation of leukotriene inhibition with oral dosing was demonstrated in a rat pleural inflammation model (ED₅₀ = 3 mg/kg) and a rat peritoneal passive anaphylaxis model (LTB₄, ED₅₀ = 2.5 mg/kg; LTE₄, ED₅₀ = 1.0 mg/kg). In a model of airway constriction induced by antigen challenge in actively sensitized guinea pigs, the sodium salt of I dosed orally blocked bronchoconstriction with an ED₅₀ = 0.4 mg/kg, the most potent activity we have observed for any leukotriene inhibitor in this model. The mode of inhibitory action of the sodium salt of I occurs at the stage of 5-lipoxygenase biosynthesis as it blocks both leukotriene pathways leading to LTB₄ and LTC₄ but not PGH₂ biosynthesis. However,the sodium salt of I does not inhibit 5-lipoxygenase catalysis in a broken cell enzyme assay; therefore the sodium salt of I likely acts as a FLAP inhibitor.

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, SDS of cas: 4760-35-4.

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