Month: October 2022

Umekubo, Nariyoshi; Iwata, Ryohei; Hayashi, Yujiro published the artcile< One-pot Synthesis of Chiral cis-Hydrindanes via Diphenylprolinol Silyl Ether Mediated Domino Reaction and Aldol Condensation>, Category: bromides-buliding-blocks, the main research area is hydrindane preparation enantioselective; cyclopentanone enantioselective preparation aldol condensation acid catalyst; unsaturated aldehyde hexene dione domino Michael ether mediated.

Substituted chiral hydrindanes I [R = CO2Et, Ph, 2-BrC6H4, eyc.] were synthesized as single isomers in almost enantiopure forms through a one-pot process that proceeded via the diphenylprolinol silyl ether mediated-domino Michael/Michael reaction of α,β-unsaturated aldehydes and 3-hexene-2,5-dione, and a subsequent intramol. aldol condensation of the generated cyclopentanone intermediate.

Chemistry Letters published new progress about Aldol condensation catalysts, stereoselective. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Deyang; Zhang, Zelong; Yu, Jiang; Chen, Haihong; Lin, Xuan; Li, Ming; Wen, Lirong; Guo, Weisi published the artcile< Site-selective electrochemical thiocyanation of benzylic C-H bonds>, Safety of 1-Bromo-3-ethylbenzene, the main research area is alkylarene trimethylsilyl isothiocyanate electrochem regioselective thiocyanation; aralkyl thiocyanate preparation.

An electrochem. protocol for site-selective benzylic C(sp3)-H thiocyanation under mild reaction conditions was reported. The reaction demonstrated broad substrate scope and unique benzylic C-H site selectivity (2° > 3° > 1°) over the existing methods. Preliminary mechanistic studies indicated that the reaction probably underwent a radical-polar crossover process. This method was also successfully used for follow-up transformation and late-stage thiocyanation of bioactive mols.

Organic Chemistry Frontiers published new progress about Alkylarenes Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 2725-82-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H9Br, Safety of 1-Bromo-3-ethylbenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Trauner, Florian; Reiners, Felix; Apaloo-Messan, Kodjo-Edmond; Nissl, Benedikt; Shahbaz, Muhammad; Jiang, Dongfang; Aicher, Julian; Didier, Dorian published the artcile< Strain-release arylations for the bis-functionalization of azetidines>, Quality Control of 401-78-5, the main research area is azetidine preparation; organometallic compound azabicyclobutane arylation nucleophilic substitution Buchwald Hartwig coupling.

The addition of nucleophilic organometallic species onto in situ generated azabicyclobutanes enables the selective formation of 3-arylated azetidine intermediates through strain-release. Single pot strategies were further developed for the N-arylation of resulting azetidines, employing either SNAr reactions or Buchwald-Hartwig couplings.

Chemical Communications (Cambridge, United Kingdom) published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Quality Control of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Armani, Elisabetta; Rizzi, Andrea; Capaldi, Carmelida; De Fanti, Renato; Delcanale, Maurizio; Villetti, Gino; Marchini, Gessica; Pisano, Anna Rita; Pitozzi, Vanessa; Pittelli, Maria Gloria; Trevisani, Marcello; Salvadori, Michela; Cenacchi, Valentina; Puccini, Paola; Amadei, Francesco; Pappani, Alice; Civelli, Maurizio; Patacchini, Riccardo; Baker-Glenn, Charles A. G.; Van de Poel, Herve; Blackaby, Wesley P.; Nash, Kevin; Amari, Gabriele published the artcile< Discovery of M3 Antagonist-PDE4 Inhibitor Dual Pharmacology Molecules for the Treatment of Chronic Obstructive Pulmonary Disease>, Quality Control of 85070-57-1, the main research area is M3 antagonist PDE4 inhibitor chronic obstructive pulmonary disease.

In this paper, we report the discovery of dual M3 antagonist-PDE4 inhibitor (MAPI) compounds for the inhaled treatment of pulmonary diseases. The identification of dual compounds was enabled by the intuition that the fusion of a PDE4 scaffold derived from our CHF-6001 series with a muscarinic scaffold through a common linking ring could generate compounds active vs. both the transmembrane M3 receptor and the intracellular PDE4 enzyme. Two chem. series characterized by two different muscarinic scaffolds were investigated. SAR optimization was aimed at obtaining M3 nanomolar affinity coupled with nanomolar PDE4 inhibition, which translated into anti-bronchospastic efficacy ex vivo (inhibition of rat trachea contraction) and into anti-inflammatory efficacy in vitro (inhibition of TNFα release). Among the best compounds, compound 92a achieved the goal of demonstrating in vivo efficacy and duration of action in both the bronchoconstriction and inflammation assays in rat after intratracheal administration.

Journal of Medicinal Chemistry published new progress about Anti-inflammatory agents. 85070-57-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8BrFO2, Quality Control of 85070-57-1.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Song, Bo; Bai, Tianwen; Xu, Xiaotian; Chen, Xu; Liu, Dongming; Guo, Jiali; Qin, Anjun; Ling, Jun; Tang, Ben Zhong published the artcile< Multifunctional Linear and Hyperbranched Five-Membered Cyclic Carbonate-Based Polymers Directly Generated from CO2 and Alkyne-Based Three-Component Polymerization>, Application of C26H18Br2, the main research area is multifunctional linear hyperbranched cyclic carbonate polymer; carbon dioxide alkyne aryl halide polymerization.

Fixing carbon dioxide (CO2) into polymeric materials is a subject of enduring interest but limited to few efficient polymerizations In this work, a facile Pd(OAc)2/LiOtBu-catalyzed one-pot, three-component polymerization of CO2, bis(propargylic alc.)s, and aryl dihalides under atm. pressure is developed. Linear and hyperbranched multifunctional five-membered cyclic carbonate (5CC)-based polymers with well-defined structures, high weight-average mol. weights (Mw up to 42500), and versatile properties such as aggregation-induced emission and chiral and porous properties are successfully produced in excellent yields (up to 96%). The reaction mechanism was well studied via the d. functional theory calculation and in situ Fourier transform IR spectroscopy, both indicating that there is synergistic reaction effect among CO2, bis(propargylic alc.)s, and aryl dihalides. The polymers could be postfunctionalized by amines via catalyst-free regioselective ring-opening reaction with 100% grafting ratio. Thus, this work not only develops a new way to directly fix CO2 into polymeric materials but also provides the 5CC-based polymers with versatile properties, showing great potentials in diverse areas.

Macromolecules (Washington, DC, United States) published new progress about Aggregation-induced emission. 184239-35-8 belongs to class bromides-buliding-blocks, and the molecular formula is C26H18Br2, Application of C26H18Br2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Zhao-Ming; Shuai, Bin; Ma, Cong; Fang, Ping; Mei, Tian-Sheng published the artcile< Nickel-Catalyzed Electroreductive Syntheses of Triphenylenes Using ortho-Dihalobenzene-Derived Benzynes>, Product Details of C7H7BrO2, the main research area is triphenylene preparation regioselective; bromobenzene electroreductive reaction nickel catalyst.

Electrochem. nickel-catalyzed syntheses of triphenylenes e.g., I, by a reductive trimerization of ortho-dibromobenzenes e.g.., 5,6-dibromoindane or ortho-bromoarylsulfurofluoridates e.g., 2-bromo-4-fluorophenyl sulfurofluoridate, or by reductive cross-coupling of ortho-dibromobenzenes to 2,2′-diiodobiphenyls, were described. The former provides a practical means for the construction of triphenylene derivatives e.g., ,I in up to 87% isolated yield at room temperature For 1,2-dihalo-3-methylbenzenes and related ortho-trisubstituted substrates, trimerizations proceed with high substrate-controlled regioselectivity for the non-C3h sym. triphenylene isomer.

Chinese Journal of Chemistry published new progress about Cross-coupling reaction. 135999-16-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2, Product Details of C7H7BrO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Xin; Ang, Esther Cai Xia; Yang, Ziqi; Kee, Choon Wee; Tan, Choon-Hong published the artcile< Synthesis of chiral sulfinate esters by asymmetric condensation>, Application of C7H7BrO2S, the main research area is alc sulfinate pentanidium catalyst enantioselective condensation; sulfinate ester preparation.

Here a straightforward access to enantioenriched sulfinate esters via asym. condensation of prochiral sulfinates and alcs. using pentanidium as an organocatalyst was reported. This study successfully coupled a wide range of sulfinates and bioactive alcs. stereoselectively. The initial sulfinates was prepared from existing sulfone and sulfonamide drugs and the resulting sulfinate esters were versatile for transformations to diverse chiral sulfur pharmacophores. Through late-stage diversification 11,12 of celecoxib and other drug derivatives, was demonstrate the viability of this unified approach towards sulfur stereogenic centers.

Nature (London, United Kingdom) published new progress about Condensation reaction catalysts (stereoselective). 5751-83-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2S, Application of C7H7BrO2S.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wu, Jing; Zheng, Chunming; Li, Bryan; Hawkins, Joel M.; Scott, Susannah L. published the artcile< Efficient, continuous N-Boc deprotection of amines using solid acid catalysts>, Name: 4-Bromobenzylamine, the main research area is amine preparation; tert butyloxycarbonyl amine deprotection solid acid catalyst.

The use of simple solid Bronsted acid catalysts to achieve continuous N-Boc deprotection of amines, e.g., tert-Bu 2-oxopiperidine-1-carboxylate without addnl. workup steps has been described. Using THF as the solvent, H-BEA zeolite affords high yields of a variety of aromatic and aliphatic amines, e.g., 2-piperidinone often in residence times of less than a minute at 140°C. The same catalyst/solvent combination is ineffective in batch conditions, due to the much lower temperature of refluxing THF. Boc-protected p-chloroaniline was deprotected with a throughput of 18 mmol p-chloroaniline per h per gcat, sustained over 9 h. The active sites of the zeolite do not appear to be directly associated with the Al framework substitution in the micropores, since partially ion-exchanged Na/H-BEA shows activity similar to H-BEA. The strong Bronsted acid sites (framework [Si(OH)Al]), are likely poisoned by the amine product. Moderate Bronsted acid sites associated with silanol defects near Al on or near the external surface (and not susceptible to Na+-exchange) are presumably the active sites, since they are not poisoned even by more basic aliphatic amines.

Reaction Chemistry & Engineering published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Name: 4-Bromobenzylamine.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tang, Kai-Wei; Hsu, Wen-Li; Chen, Cheng-Ru; Tsai, Ming-Hsien; Yen, Chia-Jung; Tseng, Chih-Hua published the artcile< Discovery of triazolyl thalidomide derivatives as anti-fibrosis agents>, Name: 4-(2-Bromoacetyl)benzoic acid, the main research area is triazolyl thalidomide derivative preparation antifibrosis activity.

Fibrosis with excessive accumulation of extracellular matrix (ECM) often causes progressive organ dysfunction and results in many inflammatory and metabolic diseases, including systemic sclerosis, pulmonary fibrosis, advanced liver disease and advanced kidney disease. The store-operated calcium entry (SOCE) pathway and the related signaling pathway were both found to be the important routes for fibrogenesis. Our aim in this study was to discover novel compounds to inhibit fibrogenesis. A number of triazolyl thalidomide derivatives were synthesized and evaluated for their anti-fibrosis activities. Compounds inhibited intracellular Ca2+ activation and showed no cytotoxicity. Among them, 6-{4-[(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}hexanoic acid ( I ) with the most potent inhibitory effect was chosen for further examination The results revealed that compound I, a SOCE inhibitor, reversed the migratory ability of TGF-β1-induced myofibroblasts, dedifferentiated myofibroblasts to fibroblasts due to cytoskeleton remodeling, and restrained myofibroblast activation by targeting Orai1 and TGF-β1/SMAD2/3 signaling pathways. The in silico study indicated that compound I, with the appropriate lipophilic carbon chain and carboxylic acid, showed a good drug-likeness model score. Conclusively, the SOCE inhibitor, compound I, is used as a promising lead compound for the development of a new treatment for fibrosis.

New Journal of Chemistry published new progress about Antifibrotic agents. 20099-90-5 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO3, Name: 4-(2-Bromoacetyl)benzoic acid.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Qing; Meng, Liuwei; Zhou, Siru; Deng, Xiaoyan; Wang, Na; Ji, Yi; Peng, Yichun; Xing, Junhao; Yao, Gongmei published the artcile< Rapid generation of novel benzoic acid-based xanthine derivatives as highly potent, selective and long acting DPP-4 inhibitors: scaffold-hopping and prodrug study>, Electric Literature of 337536-14-8, the main research area is diabetes antidiabetes DPP 4 benzoic acid xanthine prodrug pharmacokinetics; Benzoic acid; DPP-4 inhibitor; Prodrug; Scaffold-hopping; Xanthine derivatives.

A series of novel xanthine derivatives 2a-l incorporating benzoic acid moieties were rapidly generated by using strategy of scaffold-hopping from our previously reported scaffold uracil to xanthine, a scaffold of approved drug linagliptin. After systematic structure-activity relationship (SAR) study around benzoic acid moieties, 5 novel DPP-4 inhibitors with low picomolar potency range (IC50 < 1 nM) and excellent selectivity against various DPP-4 homologues were identified, in which the best one, compound 2f(I), with the IC50 value of 0.1 nM for DPP-4, showed 22-fold improvement in inhibitory activity compared to lead compound uracil 1, its activity was 45-fold more potent than alogliptin. 2E, I, 2i(II) and 2k were selected for pharmacokinetic evaluation, and I and II showed the better pharmacokinetic profiles after iv administration, but poor oral bioavailability. To improve the oral pharmacokinetic profile, prodrug design approach was performed around I and II. Esters of I and II were synthesized and evaluated for stability, toxicity and pharmacokinetics. Compound 3e(III), the Me ester of compound I, was identified to demonstrate good stability, low toxicity and improved oral bioavailability, with 3-fold higher blood concentration compared to I in rats. The following in vivo evaluations revealed III provided a sustained pharmacodynamics effect for 48h, and robustly improved glucose tolerance in normal ICR and db/db mice in dose-dependent manner. Chronic treatments investigations demonstrated that III achieved more beneficial effects on fasting blood glucose levels and glucose tolerance than alogliptin in type 2 diabetic db/db mice. The overall results have shown that compound III has the potential to efficacious, safety and long-acting treatment for T2DM. European Journal of Medicinal Chemistry published new progress about Antidiabetic agents. 337536-14-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8Br2O2, Electric Literature of 337536-14-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary