Month: October 2022

Kong, Xiang-Fei; Guo, Xiu-Yun; Gu, Zi-Yu; Wei, Lin-Su; Liu, Lu-Lu; Mo, Dong-Liang; Pan, Cheng-Xue; Su, Gui-Fa published the artcile< Silver(I)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles>, Category: bromides-buliding-blocks, the main research area is quinazoline fuse oxygen nitrogen heterocycle preparation antiiflammation.

A silver-catalyzed hydroalkoxylation of C2-alkynyl quinazolinones to prepare a series of novel quinazolinone-fused eight-membered N,O-heterocycles I [X = O, N; R1 = H, 12-Me, 12-MeO, etc; R2 = H, 2-MeO, 2-Br, etc; R3=R4 = H, Me, etc; R5 = H, n-pentyl, Ph, etc] in good-to-excellent yields through a selective 8-endo-dig cyclization. Mechanistic studies revealed that the silver catalyst might aid bidentate coordination of an imine group and alkyne to facilitate 8-endo-dig cyclization to afford eight-membered N,O-heterocycles I. Also, the proposed bimetal silver intermediates might promote hydroalkoxylation rapidly for quinazolinones bearing terminal alkynes at the C2-position. Biol. evaluations revealed that most of the designed quinazolinone-fused eight-membered N,O-heterocycles I inhibited nitric-oxide generation significantly in lipopolysaccharide-stimulated RAW264.7 cells and displayed their bioactivity as potentially good anti-inflammatory agents.

Organic Chemistry Frontiers published new progress about Alkoxylation catalysts, reductive (regioselective). 20776-50-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6BrNO2, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mfuh, Adelphe M.; Doyle, John D.; Chhetri, Bhuwan; Arman, Hadi D.; Larionov, Oleg V. published the artcile< Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts>, Related Products of 2252-45-1, the main research area is photoinduced borylation haloarene hydroxydiboron agent; boronic acid ester aryl preparation; cyanophenyl boronic acid preparation crystal structure; mol structure cyanophenyl boronic acid; aryl ammonium salt photoinduced borylation hydroxydiboron agent.

We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.

Journal of the American Chemical Society published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent) (haloarenes). 2252-45-1 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3S, Related Products of 2252-45-1.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Larson, Peter G.; Ferguson, David M. published the artcile< 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline>, Quality Control of 20776-50-5, the main research area is thaizoloquinoline preparation; carbonylation palladium catalyst.

4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6-C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in arriving at the thiazoloquinoline-5N-oxide intermediate using electron deficient aromatic systems. Here, authors demonstrate a synthetic route to obtain substituted thiazoloquinolines with electron-withdrawing groups at the C7 position. The target compound, 4-amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline, is obtained in eight steps using a 7-bromo surrogate as a precursor to the successful generation of the N-oxide intermediate, and final transformation via Pd-mediated C7-acylation.

Molbank published new progress about Carbonylation. 20776-50-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6BrNO2, Quality Control of 20776-50-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Karaboga, Husna; Huang, Wentao; Srivastava, Shivangi; Widmann, Scott; Addanki, Sridevi; Gamage, Kasuni Thawalama; Mazhar, Zahra; Ebalunode, Jerry O.; Briggs, James M.; Gustafsson, Jan-Ake; Filgueira, Carly S.; Gilbertson, Scott R.; Lin, Chin-Yo published the artcile< Screening of Focused Compound Library Targeting Liver X Receptors in Pancreatic Cancer Identified Ligands with Inverse Agonist and Degrader Activity>, Category: bromides-buliding-blocks, the main research area is library screening liver X receptor agonist preparation pancreatic cancer.

Pancreatic ductal adenocarcinoma (PDAC) is the predominant form of pancreatic cancer. PDACs harbor oncogenic mutations in the KRAS gene, and ongoing efforts to directly target its mutant protein product to inhibit tumor growth are a priority not only in pancreatic cancer but in other malignancies such as lung and colorectal cancers where KRAS is also commonly mutated. An alternative strategy to directly targeting KRAS is to identify and target druggable receptors involved in dysregulated cancer hallmarks downstream of KRAS dysregulation. Liver X receptors (LXRs) are members of the nuclear receptor family of ligand-modulated transcription factors and are involved in the regulation of genes which function in key cancer-related processes, including cholesterol transport, lipid and glucose metabolism, and inflammatory and immune responses. Modulation of LXRs via small mol. ligands has emerged as a promising approach for directly targeting tumor cells or the stromal and immune cells within the tumor microenvironment. We have previously shown that only one of the two LXR subtypes (LXRβ) is expressed in pancreatic cancer cells, and targeting LXR with available synthetic ligands blocked the proliferation of PDAC cells and tumor formation. In a screen of a focused library of drug-like small mols. predicted to dock in the ligand-binding pocket of LXRβ, we identified two novel LXR ligands with more potent antitumor activity than current LXR agonists used in our published studies. Characterization of the two lead compounds (GAC0001E5 and GAC0003A4) indicates that they function as LXR inverse agonists which inhibit their transcriptional activity. Prolonged treatments with novel ligands further revealed their function as LXR “”degraders”” which significantly reduced LXR protein levels in all three PDAC cell lines tested. These findings support the utility of these novel inhibitors in basic research on ligand design, allosteric mechanisms, and LXR functions and their potential application as treatments for advanced pancreatic cancer and other recalcitrant malignancies.

ACS Chemical Biology published new progress about Allosterism. 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Butkevich, Alexey N. published the artcile< Modular Synthetic Approach to Silicon-Rhodamine Homologues and Analogues via Bis-aryllanthanum Reagents>, COA of Formula: C8H3BrO3, the main research area is silicon rhodamine homolog analog preparation modular fluorophore fluorescent label; regioselective double nucleophilic addition aryllanthanum ester anhydride lactone.

A modular synthetic approach toward diverse analogs of the far-red fluorophore silicon-rhodamine (SiR), based on a regioselective double nucleophilic addition of aryllanthanum reagents to esters, anhydrides, and lactones, is proposed. The reaction has improved functional group tolerance and represents a unified strategy toward cell-permeant, spontaneously blinking, and photoactivatable SiR fluorescent labels. In tandem with Pd-catalyzed hydroxy- or aminocarbonylation, it serves a streamlined synthetic pathway to a series of validated live-cell-compatible fluorescent dyes.

Organic Letters published new progress about Acidity. 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, COA of Formula: C8H3BrO3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Jin; Wang, Yue; Zhang, Yuting; Liu, Ting; Fang, Shuai; Wang, Ruihong; Ma, Yangmin; Fang, Ran; Szostak, Roman; Szostak, Michal published the artcile< Application of Indazolin-3-ylidenes in Catalysis: Steric Tuning of Nonclassical Formally Normal N-Heterocyclic Carbenes with Dual Electronic Character for Catalysis>, Recommanded Product: 2,4,6-Trimethylbromobenzene, the main research area is gold indazolinylidene complex preparation catalyst hydroamination hydrohydrazination reaction alkyne; crystal structure gold indazolinylidene complexes; mol structure gold indazolinylidene complexes; imine preparation; hydrazide preparation; potential energy surface gold catalyzed hydroamination alkyne DFT.

N-Heterocyclic carbenes (NHCs) are pivotal ligands in chem. and catalysis, providing essential tools for the reactivity of metal centers. In particular, the development of nonclassical less heteroatom-stabilized N-heterocyclic carbenes (NHCs) has attracted tremendous attention owing to higher ligand basicity. However, research on the catalytic activity of nonclassical NHCs was challenging due to restrictions in modifying steric environment crucial for catalysis. Herein, the authors report a new class of indazolin-3-ylidene ligands derived from readily available indazole that feature steric differentiation around the metal center. Compared to classical imidazol-2-ylidenes, these ligands feature strongly enhanced σ-donation resulting from re-positioning of one of the N atoms. Simultaneously, the presence of the fused aromatic ring results in strongly enhanced π-accepting properties. The % Vbur is higher than the classic imidazol-2-ylidene IMes ligand. When used as ligands, the sterically differentiated coordination environment of indazolin-3-ylidenes efficiently promote the hydroamination reaction of alkynes to give valuable N-containing motifs, out competing the classical imidazol-2-ylidenes. This protocol also was applied to the challenging hydrohydrazination of alkynes and applied to the late-stage diversification. Comprehensive characterization, coordination chem., as well as the evaluation of steric, σ-donating, and π-accepting properties are demonstrated. Computational studies to gain insight into the reaction mechanism are reported. The authors anticipate that sterically differentiated nonclassical indazolin-3-ylidenes will accelerate the development of well-defined less heteroatom-stabilized N-heterocyclic carbene ligands in transition-metal catalysis.

Organometallics published new progress about Alkylidenes Role: CAT (Catalyst Use), PRP (Properties), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation) (gold indazolinylidene complexes). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Recommanded Product: 2,4,6-Trimethylbromobenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rotbergs, J.; Cema, G.; Oskaja, V. published the artcile< Condensation dicarboxylic acid anhydrides with compounds containing active methylene groups. V. 3-Bromophthalic anhydride condensation with some β-dicarbonyl compounds>, Computed Properties of 82-73-5, the main research area is INDANS VIA PHTHALIC ANHYDRIDE; BENZALINDANS VIA PHTHALIC ANHYDRIDE.

Condensation of 4.54 g. 3-bromophthalic anhydride (I) with 2.6 g. Et acetoacetate in 10 g. Ac2O and 4 g. Et3N at room temperature and treatment on the following day with 20 g. ice and 10 ml. concentrated HCl yielded 5.1 g. product, which after dissolving in a mixture of 750 ml. hot H2O and 150 ml. concentrated HCl gave 2.5 g. 4-bromoindan-1,3-dione (II), decomposed 158-9°; dioxime decomposed 285°. Boiling a mixture of 0.44 g. II, 0.21 g. BzH, 10 ml. EtOH, and 0.05 ml. piperidine gave, after addition of 0.2 ml. AcOH, 0.6 g. 4-bromo-2-benzalindan-1,3-dione, m. 144-6° (EtOH). Similarly prepared was 78% 4-bromo-2-(p-nitrobenzal)indan-1,3-dione, m. 283-4° (AcOH). Reaction of 2.27 g. I with 1 g. Ac2CH2, 5 g. Ac2O, and 1 g. Et3N for 24 hrs. gave 0.82 g. III, m. 165-6° (MeOH). Similarly were prepared: 41% IV (with BzCH2Ac), m. 182-3° (EtOH); 53% V (with Bz2CH2), m. 186-7° (EtOAc); 66% VI (with di-Et malonate), m. 126-7° (MeOH). Unlike the condensation product of I with Et acetoacetate, III-VI are stable when refluxed with dilute HCl.

Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija published new progress about Carbonyl compounds (organic) Role: RCT (Reactant), RACT (Reactant or Reagent). 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, Computed Properties of 82-73-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Qin, Pengjin; Wang, Li-An; O’Connor, Joseph M.; Baldridge, Kim K.; Li, Yifan; Tufekci, Burak; Chen, Jiyue; Rheingold, Arnold L. published the artcile< Transition-Metal Catalysis of Triene 6π Electrocyclization: The π-Complexation Strategy Realized>, Application of C21H22BrP, the main research area is triene electrocyclization transition metal pi complexation catalysis; catalysis; cycloaromatization; electrocyclization; transition metals; triene.

Triene 6π electrocyclization, wherein a conjugated triene undergoes a concerted stereospecific cycloisomerization to a cyclohexadiene, is a reaction of great historical and practical significance. In order to circumvent limitations imposed by the normally harsh reaction conditions, chemists have long sought to develop catalytic variants based upon the activating power of metal-alkene coordination. Herein, we demonstrate the first successful implementation of such a strategy by utilizing [(C5H5)Ru(NCMe)3]PF6 as a precatalyst for the disrotatory 6π electrocyclization of highly substituted trienes that are resistant to thermal cyclization. Mechanistic and computational studies implicate hexahapto transition-metal coordination as responsible for lowering the energetic barrier to ring closure. This work establishes a foundation for the development of new catalysts for stereoselective electrocyclizations.

Angewandte Chemie, International Edition published new progress about Alkatrienes Role: PEP (Physical, Engineering or Chemical Process), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), PROC (Process), RACT (Reactant or Reagent), PREP (Preparation). 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Application of C21H22BrP.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary