Month: October 2022

Brandstatter, Marco; Huwyler, Nikolas; Carreira, Erick M. published the artcile< Gold(I)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade>, COA of Formula: C21H22BrP, the main research area is bicyclooctenone preparation diastereoselective enantioselective; enyne aldehyde propargylic acetate preparation cyclization tandem gold catalyst.

Stereoselective synthesis of bicyclo[3.3.0]octenones I (R = Ph, naphthalen-2-yl, i-Pr, etc.) from chiral 1,3-enyne aldehydes bearing propargylic acetates (R,E/Z)-CH3CH(OC(O)CH3)CCC(R)=CH(CH2)2CHO is described. The method is based on a Au(I)-catalyzed domino sequence with concomitant transfer of chirality involving 1,3-acyloxy migration followed by Nazarov cyclization and an unprecedented aldol addition The method furnishes densely functionalized bicyclic structures in high yields, with up to 97% ee and good diastereoselectivity.

Chemical Science published new progress about Aldol addition catalysts, stereoselective. 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, COA of Formula: C21H22BrP.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Cao, Feng-Xia; Zhao, Li-Ming published the artcile< Cyclization of 1,4-dihydroxyanthraquinone with α,β-unsaturated aldehyde: a new strategy for the synthesis of cyclopentanoids>, Category: bromides-buliding-blocks, the main research area is cyclopentanoid preparation dihydroxyanthraquinone cyclization alpha beta unsaturated aldehyde.

A cascade cyclization strategy was developed for the synthesis of cyclopentane-fused anthraquinones through the condensation of 1,4-dihydroxyanthraquinone with α,β-unsaturated aldehydes in the presence of common inorganic base NaOH. These fused-tetracyclic anthraquinone products are formed in a single step from readily accessible starting materials under very mild conditions without the use of any expensive or complex reagents. This method represents an unprecedented example of a base-promoted protocol to access five-membered carbocyclic rings in a single step. Moreover, this chem. also provides useful guidance for the preparation of 6,5-fused ring systems.

Tetrahedron Letters published new progress about Crystal structure. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Doerner, Bernd; Kuntner, Claudia; Bankstahl, Jens P.; Wanek, Thomas; Bankstahl, Marion; Stanek, Johann; Muellauer, Julia; Bauer, Florian; Mairinger, Severin; Loescher, Wolfgang; Miller, Donald W.; Chiba, Peter; Mueller, Markus; Erker, Thomas; Langer, Oliver published the artcile< Radiosynthesis and in vivo evaluation of 1-[18F]fluoroelacridar as a positron emission tomography tracer for P-glycoprotein and breast cancer resistance protein>, COA of Formula: C7H4BrNO4, the main research area is fluorine 18 elacridar preparation PET tumor imaging Pgp BCRP.

Aim of this study was to label the potent dual P-glycoprotein (Pgp) and breast cancer resistance protein (BCRP) inhibitor elacridar (1) with 18F to provide a positron emission tomog. (PET) radiotracer to visualize Pgp and BCRP. A series of new 1- and 2-halogen- and nitro-substituted derivatives of 1 (4a-e) was synthesized as precursor mols. and reference compounds for radiolabelling and shown to display comparable in vitro potency to 1 in increasing rhodamine 123 accumulation in a cell line overexpressing human Pgp (MDCKII-MDR1). 1-[18F]fluoroelacridar ([18F]4b) was synthesized in a decay-corrected radiochem. yield of 1.7 ± 0.9% by a 1-step no-carrier added nucleophilic aromatic 18F-substitution of 1-nitro precursor 4c. Small-animal PET imaging of [18F]4b was performed in naive rats, before and after administration of unlabeled 1 (5 mg/kg, n = 3), as well as in wild-type and Mdr1a/b (-/-) Bcrp1 (-/-) mice (n = 3). In PET experiments in rats, administration of unlabeled 1 increased brain activity uptake by a factor of 9.5 (p = 0.0002, 2-tailed Student’s t-test), whereas blood activity levels remained unchanged. In Mdr1a/b (-/-) Bcrp1 (-/-) mice, the mean brain-to-blood ratio of activity at 60 min after tracer injection was 7.6 times higher as compared to wild-type animals (p = 0.0002). HPLC anal. of rat brain tissue extracts collected at 40 min after injection of [18F]4b revealed that 93 ± 7% of total radioactivity in brain was in the form of unchanged [18F]4b. In conclusion, the in vivo behavior of [18F]4b was found to be similar to previously described [11C]1 suggesting transport of [18F]4b by Pgp and/or BCRP at the rodent BBB. However, low radiochem. yields and a significant degree of in vivo defluorination will limit the utility of [18F]4b as a PET tracer.

Bioorganic & Medicinal Chemistry published new progress about Animal gene, MDR1 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, COA of Formula: C7H4BrNO4.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhou, Bing; Hu, Jiantao; Xu, Fuming; Chen, Zhuo; Bai, Longchuan; Fernandez-Salas, Ester; Lin, Mei; Liu, Liu; Yang, Chao-Yie; Zhao, Yujun; McEachern, Donna; Przybranowski, Sally; Wen, Bo; Sun, Duxin; Wang, Shaomeng published the artcile< Discovery of a Small-Molecule Degrader of Bromodomain and Extra-Terminal (BET) Proteins with Picomolar Cellular Potencies and Capable of Achieving Tumor Regression>, SDS of cas: 337536-14-8, the main research area is preparation degrader bromodomain extra terminal protein cancer.

The bromodomain and extra-terminal (BET) family proteins, consisting of BRD2, BRD3, BRD4, and testis-specific BRDT members, are epigenetic “”readers”” and play a key role in the regulation of gene transcription. BET proteins are considered to be attractive therapeutic targets for cancer and other human diseases. Recently, heterobifunctional small-mol. BET degraders have been designed based upon the proteolysis targeting chimera (PROTAC) concept to induce BET protein degradation Herein, we present our design, synthesis, and evaluation of a new class of PROTAC BET degraders. One of the most promising compounds, 23, effectively degrades BRD4 protein at concentrations as low as 30 pM in the RS4;11 leukemia cell line, achieves an IC50 value of 51 pM in inhibition of RS4;11 cell growth and induces rapid tumor regression in vivo against RS4;11 xenograft tumors. These data establish that compound 23 (BETd-260/ZBC260) is a highly potent and efficacious BET degrader.

Journal of Medicinal Chemistry published new progress about Antiproliferative agents. 337536-14-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8Br2O2, SDS of cas: 337536-14-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Slack, Eric D.; Colacot, Thomas J. published the artcile< Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics>, Synthetic Route of 401-78-5, the main research area is iridium complex catalyzed carbon hydrogen bond borylation aromatic heteroaromatic; borane aromatic heteroaromatic derivative preparation.

A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified using catalytic amounts of H2O, alcs., etc., when B2pin2 was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]2/dtbbpy or Me4Phen.

Organic Letters published new progress about Aromatic compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Synthetic Route of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Schuisky, Peter; Federsel, Hans-Jurgen; Tian, Wei published the artcile< Regioisomerism in the Synthesis of a Chiral Aminotetralin Drug Compound: Unraveling Mechanistic Details and Diastereomer-Specific In-Depth NMR Investigations>, Recommanded Product: 2-(4-Bromo-3-methylphenyl)acetic acid, the main research area is regioisomerism synthesis chiral aminotetralin drug ARA2 unraveling mechanism.

During chem. process development of a novel 2-aminotetralin derivative(I) intended for use as an antidepressant, scrutiny of the byproduct present in the drug mol. revealed a set of regioisomers. Detailed studies showed that this impurity issue originated from an early synthetic step in which a brominated tetralone motif was generated in a ring-closing protocol. It was found that this reaction was accompanied by a migration of the aromatic bromo substituent via different bromonium species along two discrete pathways. This example of the halogen dance reaction resulted in the formation of a series of tetralone impurities with a bromine distributed across all available aromatic positions of the tetralin nucleus. Subsequently, when subjected to reductive amination conditions, each of these tetralones gave rise to pairs of aminotetralins in a diastereomeric relationship. NMR investigations revealed that the alicyclic portion of the compounds thus formed displayed very complex signal patterns, which required further in-depth studies using a variety of sophisticated techniques. As a result, a deep insight into the structural features of the current 2-aminotetralin family was obtained, which is emphasized by the definition of a novel “”0.2 ppm rule”” allowing the absolute configuration at tetralin C-2 to be determined

Journal of Organic Chemistry published new progress about Absolute configuration. 215949-57-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO2, Recommanded Product: 2-(4-Bromo-3-methylphenyl)acetic acid.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Baker, Sarah I.; Yaghoubi, Mahshid; Bidwell, Samantha L.; Pierce, Savannah L.; Hratchian, Hrant P.; Baxter, Ryan D. published the artcile< Enhanced Reactivity for Aromatic Bromination via Halogen Bonding with Lactic Acid Derivatives>, COA of Formula: C9H11Br, the main research area is arene bromination regioselective lactic acid bromosuccinimide.

Herein, a new method for regioselective aromatic bromination using lactic acid derivatives as halogen bond acceptors with N-bromosuccinimide (NBS) is reported. Several structural analogs of lactic acid affected the efficiency of aromatic brominations, presumably via Lewis acid/base halogen-bonding interactions. Rate comparisons of aromatic brominations demonstrated the reactivity enhancement available via catalytic additives capable of halogen bonding. Computational results demonstrated that Lewis basic additives interact with NBS to increase the electropos. character of bromine prior to electrophilic transfer. An optimized procedure using catalytic mandelic acid under aqueous conditions at room temperature has been developed to promote aromatic bromination on a variety of arene substrates with complete regioselectivity.

Journal of Organic Chemistry published new progress about Aryl bromides Role: SPN (Synthetic Preparation), PREP (Preparation). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, COA of Formula: C9H11Br.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Aliboni, Eraldo published the artcile< Vitamin C in human saliva>, Related Products of 82-73-5, the main research area is .

By the method of Farmer and Abt (C.A. 30, 8273.5) the vitamin C content of human saliva (50 cases) was 12-50 (average 23) γ per 100 cc., no remarkable differences being found between men and women, or normal and pathol. subjects.

Clin. odontoiat. published new progress about Saliva. 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, Related Products of 82-73-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Schmidt, Jurema; Rotter, Marco; Weiser, Tim; Wittmann, Sandra; Weizel, Lilia; Kaiser, Astrid; Heering, Jan; Goebel, Tamara; Angioni, Carlo; Wurglics, Mario; Paulke, Alexander; Geisslinger, Gerd; Kahnt, Astrid; Steinhilber, Dieter; Proschak, Ewgenij; Merk, Daniel published the artcile< A Dual Modulator of Farnesoid X Receptor and Soluble Epoxide Hydrolase To Counter Nonalcoholic Steatohepatitis>, COA of Formula: C9H8BrFO2, the main research area is benzylbenzamide dual modulator analog preparation nonalcoholic steatohepatitis; dual modulator analog FXR sEH benzylbenzamide analog pharmacokinetics.

Nonalcoholic steatohepatitis arising from Western diet and lifestyle is characterized by accumulation of fat in liver causing inflammation and fibrosis. It evolves as serious health burden with alarming incidence, but there is no satisfying pharmacol. therapy to date. Considering the disease’s multifactorial nature, modulation of multiple targets might provide superior therapeutic efficacy. In particular, farnesoid X receptor (FXR) activation that revealed antisteatotic and antifibrotic effects in clin. trials combined with inhibition of soluble epoxide hydrolase (sEH) as anti-inflammatory strategy promises synergies. To exploit this dual concept, we developed agents exerting partial FXR agonism and sEH inhibitory activity. Merging known pharmacophores and systematic exploration of the structure-activity relationship on both targets produced dual modulators with low nanomolar potency. Extensive in vitro characterization confirmed high dual efficacy in cellular context combined with low toxicity, and pilot in vivo data revealed favorable pharmacokinetics as well as engagement on both targets in vivo.

Journal of Medicinal Chemistry published new progress about Antifibrotic agents. 85070-57-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8BrFO2, COA of Formula: C9H8BrFO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Xia; Xu, Hui; Shi, Ji-Long; Hao, Huimin; Yuan, Hong; Lang, Xianjun published the artcile< Salicylic acid complexed with TiO2 for visible light-driven selective oxidation of amines into imines with air>, Recommanded Product: 4-Bromobenzylamine, the main research area is salicylic acid complexed anatase visible light selective oxidation amines; selective oxidation amine imines air.

The interplay of salicylic acid (SA) and reactive oxygen species (ROS) can modulate biotic and abiotic stress of plants, essential biol. aerobic oxidation processes. Meanwhile, ROS plays a critical role in TiO2 photocatalytic system for the degradation of organic species. Herein, we developed a system consisted of SA and TiO2 aiming at the selective oxidation of organic mols. by ROS. Interestingly, SA complexed with TiO2 leads to ligand-to-metal charge transfer (LMCT) under visible light irradiation The charge transfer from ligand (chem. adsorbed SA) to metal (conduction band of TiO2) activates O2 to ROS, superoxide (O·-2). The pos. charge located at ligand SA is connected with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) catalysis for direct two-electron oxidation of amines and later regenerated by O·2-. SA and its derivatives were screened as ligands of TiO2 for the selective aerobic oxidation of amines into imines under blue light-emitting diode (LED) irradiation in which 5-CH3O-SA (5-methoxysalicylic acid, 0.8 mol%) complexed with anatase TiO2 and coupled with TEMPO (5 mol%) confers significantly better results than the others. By this visible light LMCT route, both primary amines and secondary amines can be selectively oxidized into corresponding imines with atm. O2 as the terminal oxidant. Importantly, the desired product of N-benzylidenebenzylamine can be isolated in 92% yield.

Applied Catalysis, B: Environmental published new progress about Amines Role: PEP (Physical, Engineering or Chemical Process), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Recommanded Product: 4-Bromobenzylamine.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary