Category: bromides-buliding-blocks

Estrada, Carl D.; Ang, Hwee Ting; Vetter, Kim-Marie; Ponich, Ashley A.; Hall, Dennis G. published the artcile< Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning>, COA of Formula: C10H11BrO2, the main research area is diol benzyl halide boron acid catalyst enantioselective alkylation desymmetrization; alc preparation.

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chair-like six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed “”methyl blocker”” on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodol. affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Journal of the American Chemical Society published new progress about Alcohols, chiral Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, COA of Formula: C10H11BrO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Feng, Xin; Cui, Hai-Lei; Xu, Shi; Wu, Li; Chen, Ying-Chun published the artcile< Organocatalytic Direct Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactam to α,β-Unsaturated Aldehydes and an Illustration to Scaffold Diversity Synthesis [Erratum to document cited in CA153:600892]>, Reference of 3893-18-3, the main research area is erratum alkyl butyrolactam stereoselective preparation; unsaturated butyrolactam aldehyde Michael addition erratum; enantioselective diastereoselective regioselective chemoselective Michael addition erratum; alkaloid stereoselective preparation erratum; butyrolactam reductive amination intramol aza Michael addition erratum; diastereoselective reductive radical conjugate addition cyclization erratum.

On pages S11, S65, and S68 of the Supporting Information, data for compound 9k and its diastereomer 9k’ were mismatched; the corrected Supporting information is given.

Chemistry – A European Journal published new progress about Alkaloids Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Reference of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Wenwu; Wu, Limeng; Li, Deping; Huang, Yaoguang; Liu, Mingyue; Liu, Wenjie; Tian, Caizhi; Liu, Xin; Jiang, Xiaowen; Hu, Xiaolong; Gao, Xudong; Xu, Zihua; Lu, Hongyuan; Zhao, Qingchun published the artcile< Discovery of novel tacrine derivatives as potent antiproliferative agents with CDKs inhibitory property>, Application In Synthesis of 20776-50-5, the main research area is human colon lung cancer CDK9 antiproliferative anticancer tacrine derivative; AChE; CDK2; CDK9; Cancer therapeutics; Tacrine.

Tacrine was the first approved drug by the FDA for the treatment of Alzheimer′s disease (AD) but was withdrawn from the market due to its dose-dependent hepatotoxicity. Herein, we describe our efforts toward the discovery of a novel series of tacrine derivatives for cancer therapeutics. Intensive structural modifications of tacrine led to the identification of N-(4-{9-[(3S)-3-aminopyrrolidin-1-yl]-5,6,7,8-tetrahydroacridin-2-yl}pyridin-2-yl)cyclopropanecarboxamide hydrochloride ((S)-45, ZLWT-37) as a potent antiproliferative agent (GI50 = 0.029 μM for HCT116). In addition, ZLWT-37 exhibited lower inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) compared to tacrine. The in vitro studies demonstrated that ZLWT-37 could significantly induce apoptosis and arrest the cell cycle in the G2/M phase in HCT116 cells. The in vivo studies revealed that compound ZLWT-37 showed excellent antitumor efficacy in HCT116 xenograft tumor model and favorable pharmacokinetics profiles (F% = 28.70%) as well as low toxicity in the acute toxicity test with a median LD (LD50) of 380.3 mg/kg. Encouragingly, ZLWT-37 had no obvious hepatotoxicity, nephrotoxicity, and hematol. toxicity. Kinase assay suggested that ZLWT-37 possessed potent cyclin-dependent kinase 9 (CDK9) inhibitory activity (IC50 = 0.002 μM) and good selectivity over CDK2 (IC50 = 0.054 μM). Collectively, these findings indicate that compound ZLWT-37 is a promising anti-cancer agent that deserves further preclin. evaluation.

Bioorganic Chemistry published new progress about Antiproliferative agents. 20776-50-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6BrNO2, Application In Synthesis of 20776-50-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Capel, Estefania; Luis-Barrera, Javier; Sorazu, Ana; Uria, Uxue; Prieto, Liher; Reyes, Efraim; Carrillo, Luisa; Vicario, Jose L. published the artcile< Transannular Approach to 2,3-Dihydropyrrolo[1,2-b]isoquinolin-5(1H)-ones through Bronsted Acid-Catalyzed Amidohalogenation>, HPLC of Formula: 6942-39-8, the main research area is pyrroloisoquinolinone preparation; benzo fused ene lactam amidohalogenation elimination Bronsted acid catalyst.

A transannular approach has been developed for the construction of pyrrolo[1,2-b]isoquinolinones I (R1 = H, F, Cl, Me, OMe, etc.; R2 = H, F, etc.; R3 = H, Me, etc.; R4 = H, F) starting from benzo-fused nine-membered enelactams II. This process takes place in the presence of a halogenating agent and under Bronsted acid catalysis and proceeds via a transannular amidohalogenation, followed by elimination. The reaction has been found to be wide in scope, enabling the formation of a variety of tricyclic products I in good overall yield, regardless of the substitution pattern in the initial lactam substrate. The reaction has also been applied to the total synthesis of a reported topoisomerase I inhibitor and to the formal synthesis of rosettacin. Further extension of this methodol. allows the preparation of 10-iodopyrrolo[1,2-b]isoquinolinones III (R1 = H, Me; R2 = H, F; R3 = H, F, Me, OMe) by using an excess of halogenating agent and these compounds can be further manipulated through standard Suzuki coupling chem. into a variety of 10-aryl-substituted pyrrolo[1,2-b]isoquinolinones IV.

Journal of Organic Chemistry published new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 6942-39-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H6BrFO2, HPLC of Formula: 6942-39-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Lei; Hu, Xile published the artcile< Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds>, Formula: C7H4BrF3, the main research area is toluene aryl bromide nickel catayst electrochem arylation; arylmethylbenzene preparation.

Convergent paired electrosynthesis is an energy-efficient approach in organic synthesis; however, it is limited by the difficulty to match the innate redox properties of reaction partners. Here we use nickel catalysis to cross-couple the two intermediates generated at the two opposite electrodes of an electrochem. cell, achieving direct arylation of benzylic C-H bonds. This method yields a diverse set of diarylmethanes, which are important structural motifs in medicinal and materials chem. Preliminary mechanistic study suggests oxidation of a benzylic C-H bond, Ni-catalyzed C-C coupling, and reduction of a Ni intermediate as key elements of the catalytic cycle.

Chemical Science published new progress about Alkylarenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Formula: C7H4BrF3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Menzel, Karsten; Dimichele, Lisa; Mills, Paul; Frantz, Doug E.; Nelson, Todd D.; Kress, Michael H. published the artcile< Regioselective halogen-metal exchange reaction of 3-substituted 1,2-dibromo arenes: the synthesis of 2-substituted 5-bromobenzoic acids>, Formula: C8H3BrO3, the main research area is substituted dibromoarene isopropylmagnesium chloride regioselective halogen metal exchange; bromoarene substituted preparation; bromobenzoic acid substituted preparation; regioselective halogen metal exchange reagent isopropylmagnesium chloride.

Regioselective halogen-metal exchange reactions using isopropylmagnesium chloride were carried out on 3-substituted 1,2-dibromo arenes, e.g., I. When the 3-substituent was either electron-withdrawing and/or possessed lone pair electrons that enabled chelation of isopropylmagnesium chloride, a high regioselectivity for the halogen-metal exchange adjacent to the 3-substituents resulted.

Synlett published new progress about Aromatic carboxylic acids Role: SPN (Synthetic Preparation), PREP (Preparation) (bromo-). 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, Formula: C8H3BrO3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jana, Amit Kumar; Singh, Jyotsana; Ganesher, Asha; Kumar, Amit; Banerjee, Arpita; Kumar, Deepak; Verma, Sarvesh Kumar; Sharma, Ashok Kumar; Bhatta, Rabi Sankar; Konwar, Rituraj; Panda, Gautam published the artcile< Tyrosine-Derived Novel Benzoxazine Active in a Rat Syngenic Mammary Tumor Model of Breast Cancer>, Reference of 81107-97-3, the main research area is benzoxazine derivative anticancer breast cancer apoptosis.

In continuing efforts of improving benzoxazepine derivatives as an anti-breast cancer agent, a new chem. entity, benzoxazine, was designed from scaffold morphing. Structure-activity relationship studies revealed that H, -OMe, -CF3, and -F were well tolerated on R1 and R2 positions of ring A, and R2 as -CH2CH2N(CH2)4 (N-Et pyrrolidine) and -CH2CH2N(CH2)5 (N-Et piperidine) chains on ring D increased activities (Series B, Figure 3). 13d selected as a lead compound (IC50: 0.20 to 0.65 μM) induces apoptosis, cell cycle arrest, and loss of mitochondrial membrane potential in breast cancer cells. Compound 13d was formulated into 13d-f using cyclodextrin to improve its solubility for a pharmacokinetic, in vivo efficacy study. Both 13d and 13d-f regressed tumor growth at concentrations of 5 and 20 mg/kg better than tamoxifen without any mortality in a rat syngenic mammary tumor model. Collectively, our data suggest that tyrosine-derived novel benzoxazine 13d could be a potential lead for the treatment of breast cancer and hence deserve further in-depth studies.

Journal of Medicinal Chemistry published new progress about Antiproliferative agents. 81107-97-3 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3O, Reference of 81107-97-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Chang; Zhang, Chao; Lu, Tong-Bu published the artcile< Graphdiyne anchored ultrafine Ag nanoparticles for highly efficient and solvent-free catalysis of CO2 cycloaddition>, Synthetic Route of 3959-07-7, the main research area is silver nanoparticle carbon dioxide cycloaddition graphdiyne.

Apart from photo-/electro-catalytic CO2 reduction, an important alternative route to CO2 utilization is to use this inert mol. as a C1 source to synthesize value-added chems.; however, the practical application is limited by the low conversion efficiency. Herein, we reported a composite catalyst of 3D sponge-like pyrenyl-graphdiyne (Pyr-GDY) anchored ultrafine Ag nanoparticles (Ag/Pyr-GDY), with the average size of Ag NPs of only 1.6 nm. The porous 3D Pyr-GDY component can not only anchor and stabilize the capping agent free ultrafine Ag NPs by virtue of the strong affinity between alkynyl groups and Ag, but also enhance the local concentration of CO2 due to the porous nature of 3D Pyr-GDY. As a result, the optimized Ag/Pyr-GDY catalyst displays a record-high activity towards the catalysis of CO2 cycloaddition with propargylamines under ambient temperature and pressure, with a TON of 20 488 and a yield of 83%, and is 15.3 times more active than the most efficient catalyst Ag27-MOF (TON = 1333, yield = 34%). Moreover, our catalysis was performed in a solvent-free system, which provides an economic, green and practical avenue for carbon capture, utilization and storage (CCUS).

Materials Chemistry Frontiers published new progress about Concentration (process). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Synthetic Route of 3959-07-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhao, Gui-Ling; Rios, Ramon; Vesely, Jan; Eriksson, Lars; Cordova, Armando published the artcile< Organocatalytic enantioselective aminosulfenylation of α,β-unsaturated aldehydes>, Formula: C9H7BrO, the main research area is unsaturated aldehyde alkylthio succinimide chiral organocatalyst aminosulfenylation; sucnimido mercaptoaldehyde stereoselective preparation.

A simple, highly enantioselective organocatalytic aminosulfenylation of α,β-unsaturated aldehydes affords orthogonally protected β-amino-α-mercaptoaldehydes in high yields and 93 to > 99% ee. Notably, the catalytic transformation shows that it is possible to efficiently employ all components of an electrophile, which includes a nucleofuge, in organocatalytic domino reactions of enals.

Angewandte Chemie, International Edition published new progress about Addition reaction (aminosulfenylation, stereoselective). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Formula: C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jimenez-Almarza, Alicia; Lopez-Magano, Alberto; Mas-Balleste, Ruben; Aleman, Jose published the artcile< Tuning the Activity-Stability Balance of Photocatalytic Organic Materials for Oxidative Coupling Reactions>, Quality Control of 3959-07-7, the main research area is imine preparation; amine oxidative coupling photocatalytic; amines; imines; organic materials; oxidative coupling; photocatalysis.

In the series of materials reported herein, the triazine-based material shows the optimal compromise between activity and stability when studied for the oxidative coupling of amines, achieving imine products. Accordingly, while significant leaching of mol. active fragments was ruled out for triazine-based polymers, other materials of the series show a significant chem. erosion as a result of the reaction with the amine substrates. Consequently, only a triazine-based material allowed performing several catalytic cycles (up to seven) with yields higher than 80%. The applicability of this heterogeneous catalyst had been proven with a variety of substrates, confirming its stability and obtaining diverse imine coupling products with excellent yields.

ACS Applied Materials & Interfaces published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Quality Control of 3959-07-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary