Category: 14062-30-7

Qiu, Han-Yue; Fu, Jiang-Yan; Yang, Min-Kai; Han, Hong-Wei; Wang, Peng-Fei; Zhang, Ya-Han; Lin, Hong-Yan; Tang, Cheng-Yi; Qi, Jin-Liang; Yang, Rong-Wu; Wang, Xiao-Ming; Zhu, Hai-Liang; Yang, Yong-Hua published the artcile< Identification of new shikonin derivatives as STAT3 inhibitors>, Related Products of 14062-30-7, the main research area is shikonin derivative PMMB187 preparation antitumor breast STAT3 inhibitor; Anti-neoplastic; Breast cancer; Napabucasin (PubChem CID: 10331844); Plumbagin (PubChem CID: 10205); STA-21 (PubChem CID: 363709); STAT3 inhibitors; Shikonin; Shikonin (PubChem CID: 479503); Structural modifications.

The signal transducer and activator of transcription 3 is a constitutively activated oncogenic protein in various human tumors and represents a valid target for anticancer drug design. In this study, the authors have achieved a new type of STAT3 inhibitors based on structural modifications on shikonin scaffold, guided by computational modeling. By tests, PMMB-187 exhibited a more outstanding profile than shikonin on a small panel of human breast cancer cells, especially for the MDA-MB-231 cells. For the cellular mechanisms research, PMMB-187 was found to induce cell apoptosis in MDA-MB-231 cells, associated with the reduction of mitochondrial membrane potential, production of ROS and alteration of the levels of apoptosis-related proteins. Furthermore, PMMB-187 inhibited constitutive/inducible STAT3 activation, transcriptional activity, nuclear translocation and downstream target genes expression in STAT3-dependent breast cancer cells MDA-MB-231. Besides, no obvious inhibitory effect on activation of STAT1 and STAT5 was observed with PMMB-187 treatment. Most notably, the in vivo studies further revealed that PMMB-187 could dramatically suppress the MDA-MB-231 cells xenografted tumor growth. The in vitro and in vivo results collectively suggest that PMMB-187 may serve as a promising lead compound for the further development of potential therapeutic anti-neoplastic agents.

Biochemical Pharmacology (Amsterdam, Netherlands) published new progress about Antiproliferative agents. 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Related Products of 14062-30-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hu, Xiao-Qian; Han, Jia-Bin; Zhang, Cheng-Pan published the artcile< Cu-Mediated Trifluoromethylation of Aromatic α-Diazo Esters with the Yagupolskii-Umemoto Reagent>, Electric Literature of 14062-30-7, the main research area is aromatic diazo ester trifluoromethylation Yagupolskii Umemoto reagent copper; trifluoromethyl arylacetic ester preparation; copper trifluoromethylation catalyst.

Reductive trifluoromethylation of aromatic α-diazo esters at room temperature with the Yagupolskii-Umemoto reagent {[Ph2SCF3][OTf]; (I)} in DMF in the presence of excess CuCl gave a variety of α-trifluoromethyl arylacetates, e.g., II, in up to 93 % yield. The prior reaction of I with CuCl before the addition of the α-diazo esters was imperative for the conversion. This initial reaction might pregenerate the key [CuICF3] intermediate, according to the results of our control experiments When the long-chain perfluoroalkyl diphenylsulfonium triflates were used instead of I, the reaction of an aromatic α-diazo ester under the same conditions followed by treatment with NaHCO3 gave a series of fluorinated α,β-unsaturated esters in good yields. This protocol gives a facile, convenient, and practical access to α-trifluoromethyl arylacetates and their analogs, implying that the “”+Rfn”” reagents are compatible with α-diazo esters in the presence of an appropriate reductant.

European Journal of Organic Chemistry published new progress about Esters Role: RCT (Reactant), RACT (Reactant or Reagent) (α-diazo). 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Electric Literature of 14062-30-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

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

Zhang, Tianyu; Yang, Zhenkun; Zhou, Dapeng; Meng, Fuliang; Han, Zhengyu; Huang, Hai published the artcile< Non-metal Lewis acid-catalyzed cross-Claisen condensation for β-keto esters>, Safety of Ethyl 2-(3-bromophenyl)acetate, the main research area is alkoxy silyl ketene acetal keto ester Lewis acid catalyst; keto alkoxy ester cehmoselective preparation Claisen condensation.

A new catalytic and highly chemoselective cross-Claisen condensation of esters was disclosed. In the presence of TBSNTf2 as a non-metal Lewis acid, various esters can undergo cross-Claisen condensation to form β-keto esters which are important building blocks. Compared with the traditional Claisen condensation, this process, employing silyl ketene acetals (SKAs) as carbonic nucleophiles to achieve cross-Claisen condensation, requires mild conditions and has good tolerance of functional groups.

Organic & Biomolecular Chemistry published new progress about 1,3-Dicarbonyl compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Safety of Ethyl 2-(3-bromophenyl)acetate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wu, Guojiao; Deng, Yifan; Wu, Chaoqiang; Zhang, Yan; Wang, Jianbo published the artcile< Synthesis of α-Aryl Esters and Nitriles: Deaminative Coupling of α-Amino-Esters and α-Aminoacetonitriles with Arylboronic Acids>, Safety of Ethyl 2-(3-bromophenyl)acetate, the main research area is nitrile benzeneacetonitrile preparation; benzeneacetic areneacetic acid ester preparation; arenes; boron; diazo compounds; nitriles; synthetic methods.

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-amino esters and α-(amino)acetonitrile derivatives, resp., as starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds (carbon-nitrogen bonds) into C(sp3)-C(sp2) bonds (carbon-carbon bonds). The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. The synthesis of the target compounds was achieved using glycine ester hydrochloride, leucine ester hydrochloride, aspartate ester hydrochloride, alanine ester hydrochloride as starting materials in a reaction with (aryl)boronic acids. The title compounds thus formed included benzeneacetic acid esters, 1-naphthaleneacetic acid ester, benzenepropanoic acid esters, α-phenyl-1H-indole-3-propanoic acid ester, benzenebutanoic acid ester and similar substances. A reaction of (aryl)boronic acids with α-(amino)acetonitrile gave α-(alkyl)benzeneacetonitrile derivatives Nitriles included α-(hexyl)benzeneacetonitrile, α-phenyl-3-thiophenepropanenitrile and similar compounds

Angewandte Chemie, International Edition published new progress about Amino acid esters Role: RCT (Reactant), RACT (Reactant or Reagent). 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Safety of Ethyl 2-(3-bromophenyl)acetate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fahandej-Sadi, Anis; Lundgren, Rylan J. published the artcile< Copper-Mediated Synthesis of Monofluoro Aryl Acetates via Decarboxylative Cross-Coupling>, Computed Properties of 14062-30-7, the main research area is fluoro oxopropanoic acid aryl boronate preparation copper decarboxylative arylation; aryl fluoroacetate preparation.

Cu-promoted oxidative cross-coupling of α-fluoromalonate half-esters and aryl boron reagents to deliver monofluoro α-aryl acetates under mild conditions (in air at room temperature) was reported. The reaction used a simple, readily available mono-fluorinated building block to generate arylated compounds with functional groups that were not easily tolerated by existing methods, such as aryl bromides, iodides, pyridines, and pyrimidines.

Synlett published new progress about Acetates Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Computed Properties of 14062-30-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rajput, Santosh; Gardner, Christopher R.; Failes, Timothy W.; Arndt, Greg M.; Black, David StC.; Kumar, Naresh published the artcile< Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones>, Quality Control of 14062-30-7, the main research area is antitumor quinolinone dihydroquinolinone preparation; Anticancer; Dihydroquinolin-4-one; Quinolin-4-one.

A series of 3-aryl-5,7-dimethoxyquinolin-4-ones I [R1 = Ph, 4-BrC6H4, 4-MeC6H4, etc.] and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones II [ R2 = Ph, 4-BrC6H4, 4-MeC6H4, etc.] were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives Biol. evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound demonstrated 85.9-99% reduction in cell viability against the cell lines tested.

Bioorganic & Medicinal Chemistry published new progress about Antitumor agents. 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Quality Control of 14062-30-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Moon, Patrick J.; Yin, Shengkang; Lundgren, Rylan J. published the artcile< Ambient Decarboxylative Arylation of Malonate Half-Esters via Oxidative Catalysis>, Related Products of 14062-30-7, the main research area is monoaryl acetate preparation; decarboxylative arylation coupling arylboron nucleophile malonic acid.

We report decarboxylative carbonyl α-arylation by coupling of arylboron nucleophiles with malonic acid derivatives This process is enabled by the merger of aerobic oxidative Cu catalysis with decarboxylative enolate interception reminiscent of malonyl-CoA reactivity in polyketide biosynthesis. This method enables the synthesis of monoaryl acetate derivatives containing electrophilic functional groups that are incompatible with existing α-arylation reactivity paradigms. The utility of the reaction is demonstrated in drug intermediate synthesis and late-stage functionalization.

Journal of the American Chemical Society published new progress about Arylation. 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Related Products of 14062-30-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Moon, Patrick J.; Fahandej-Sadi, Anis; Qian, Wenyu; Lundgren, Rylan J. published the artcile< Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters>, Application of C10H11BrO2, the main research area is aryl boronic ester arylacetate potassium copper decarboxylative benzylation catalyst; alkenyl boronic ester arylacetate potassium copper decarboxylative benzylation catalyst; copper arylacetate aryl boronic ester potassium acetate decarboxylative benzylation; diarylmethane preparation; aerobic catalysis; boron; copper; cross-coupling; decarboxylation.

The copper-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.

Angewandte Chemie, International Edition published new progress about Alkanes Role: SPN (Synthetic Preparation), PREP (Preparation) (diarylmethane). 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Application of C10H11BrO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Bookser, Brett C.; Kasibhatla, Srinivas Rao; Appleman, James R.; Erion, Mark D. published the artcile< AMP Deaminase Inhibitors. 2. Initial Discovery of a Non-Nucleotide Transition-State Inhibitor Series>, SDS of cas: 14062-30-7, the main research area is coformycin aglycon analog preparation AMPDA inhibitor; adenylate adenosine deaminase inhibitor coformycin analog.

A series of N3-substituted coformycin aglycon analogs are described that inhibit AMP deaminase (AMPDA) or adenosine deaminase (ADA). The key steps involved in the preparation of these compounds are treating the sodium salt of 6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one with an alkyl bromide or an alkyl mesylate to generate the N3-alkylated compound, and (2) reducing the N3-alkylated compound with NaBH4. Selective inhibition of AMPDA was realized when the N3-substituent contained a carboxylic acid moiety. For example, the compound which has a hexanoic acid side chain inhibited AMPDA with a Ki = 4.2 μM and ADA with a Ki = 280 μM. Substitution of large lipophilic groups α to the carboxylate provided a moderate potency increase with maintained selectivity as exemplified by the α-benzyl analog (AMPDA Ki = 0.41 μM and ADA Ki > 1000 μM). These compounds, as well as others described in this series of papers, are the first compounds suitable for testing whether selective inhibition of AMPDA can protect tissue from ischemic damage by increasing local adenosine concentrations at the site of injury and/or by minimizing adenylate loss.

Journal of Medicinal Chemistry published new progress about Structure-activity relationship, enzyme-inhibiting. 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, SDS of cas: 14062-30-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary