Tag: M.W=150-200

Li, Pinyi; Jia, Xiuwen; Ma, Xiaoli; Ma, Wenbo; Sheng, Yilin; Zhao, Jingwei; Zhao, Fei published the artcile< A Catalyst-Free Cascade Reaction for the Selective Assembly of 3-Hydroxyisoindolinones on Water>, Related Products of 3959-07-7, the main research area is hydroxyisoindolinone green preparation; alkynylbenzoic acid nitrogen nucleophile cascade.

A catalyst- and additive-free cascade reaction between 2-alkynylbenzoic acids and nitrogen-containing nucleophiles for the selective assembly of 3-hydroxyisoindolinones I [R1 = H, 4-Me, 6-F, etc.; R2 = H, n-Bu, Ph, etc.; R3 = n-Bu, Ph, Bn, etc.] under water was developed. This protocol featured readily available starting materials, an environmentally benign solvent, simple operation, extraordinarily broad substrate scope, good functional group tolerance, excellent selectivity, good to excellent yields, high atom- and step-economy, and high bond-forming efficiency, thus provided a convenient and highly efficient access to 3-hydroxyisoindolinones I.

Asian Journal of Organic Chemistry published new progress about Alkynes, aryl Role: RCT (Reactant), RACT (Reactant or Reagent). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Related Products of 3959-07-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Pal, Ritesh; Chakraborty, Jeet; Mukhopadhyay, Titas Kumar; Kanungo, Ajay; Saha, Rimita; Chakraborty, Amit; Patra, Dipendu; Datta, Ayan; Dutta, Sanjay published the artcile< Substituent effect of benzyl moiety in nitroquinoxaline small molecules upon DNA binding: Cumulative destacking of DNA nucleobases leading to histone eviction>, Name: 4-Bromobenzylamine, the main research area is nitroquinoxaline preparation antitumor hydrophobicity SAR DNA binding destacking; Entropically favored; Hydrogen bond disruption; Hydrophobic interaction; In-vitro nucleosome disassembly; Mammalian cell cytotoxicity; Nucleobase destacking.

Cooperative disruption of Watson-Crick hydrogen bonds, as well as base-destacking, was shown to be triggered by a quinoxaline-based small mol. consisting of an N,N-dimethylaminopropyl tether, and a para-substituted benzyl moiety. This events led to superstructure formation and DNA condensation as evident from biophys. experiments and classical mol. dynamics simulations. The DNA superstructure formation by mono-quinoxaline derivatives I [R = 1-piperidyl, [3-(dimethylamino)propylamino]; R1 = benzyl, 2-thienylmethyl, (4-iodophenyl)methyl, etc.] was highly entropically favored and predominantly driven by hydrophobic interactions. Furthermore, oversupercoiling of DNA and base-destacking cumulatively induced histone eviction from in-vitro assembled nucleosomes at lower micromolar concentrations implicating biol. relevance. The DNA structural modulation and histone eviction capacity of the benzyl para-substituents were in the order: -I > -CF3> -Br > -Me > -OMe > -OH, which was largely guided by the polarity of benzyl para-substituent and the resulting mol. topol. The most hydrophobic derivative I [R = [3-(dimethylamino)propylamino], R1 = (4-iodophenyl)methyl] with para-iodo benzyl moiety caused maximal disruption of base pairing and generation of superstructures. Both these events gradually diminished as the polarity of the benzyl para-substituent increases. On the other hand, quinoxaline derivatives I having heterocyclic ring instead of benzyl ring, or in the absence of N,N-dimethylamino head-group, was incapable of inducing any DNA structural change and histone eviction. Further, the quinoxaline compounds I displayed potent anticancer activities against different cancer cell lines which directly correlates with the hydrophobic effects of the benzyl para-substituents. Overall, the study provided new insights into the mechanistic approach of DNA structural modulation driven histone eviction guided by the hydrophobicity of synthesized compounds leading to cellular cytotoxicity towards cancer cells.

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Name: 4-Bromobenzylamine.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhou, Zhao-Zhao; Zhao, Jia-Hui; Gou, Xue-Ya; Chen, Xi-Meng; Liang, Yong-Min published the artcile< Visible-light-mediated hydrodehalogenation and Br/D exchange of inactivated aryl and alkyl halides with a palladium complex>, Product Details of C9H11Br, the main research area is aryl alkyl halide amine free radical reductive dehalogenation; dehalogenative deuteration reductive cyclization addition cycloaddition arylation.

Herein, a novel photo-induced amine-free radical reductive dehalogenation of inactivated aryl/alkyl bromides and chlorides with a palladium complex is described,. Which reveals excellent functional group compatibility and broad substrate scope. Extensional transformations for reductive cyclization, dehalogenative deuteration, and intra- and intermol. radical addition can be achieved smoothly. Mechanistic studies indicate a single-electron photoredox catalytic system with inactivated solvent as the hydrogen atom donor.

Organic Chemistry Frontiers published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Product Details of C9H11Br.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Lin, Lucy; Turner, Lewis D.; Silhar, Peter; Pellett, Sabine; Johnson, Eric A.; Janda, Kim D. published the artcile< Identification of 3-hydroxy-1,2-dimethylpyridine-4(1H)-thione as a metal-binding motif for the inhibition of botulinum neurotoxin A>, Recommanded Product: 4-Bromobenzylamine, the main research area is hydroxy dimethylpyridine dione botulinum neurotoxin inhibitor.

Botulinum neurotoxin serotype A (BoNT/A) is an important therapeutic target owing to its extremely potent nature, but also has potential use as a biowarfare agent. Currently, no therapeutic exists to reverse the long-lasting paralysis caused by BoNT/A. Herein, we describe the identification of 3-hydroxy-1,2-dimethylpyridine-4(1H)-thione (3,4-HOPTO) as a metal binding warhead for the inhibition of BoNT/A1. An initial screen of 96 metal binding fragments identified three derivatives containing the 3,4-HOPTO scaffold to inhibit the BoNT/A1 light chain (LC) at >95% at 1 mM. Addnl. screening of a 3,4-HOPTO sub-library identified structure-activity relationships (SARs) between N-substituted 3,4-HOPTO derivatives and the BoNT/A1 LC. Subsequent synthesis was conducted to improve on inhibitory potency – achieving low μM biochem. IC50 values. Representative compounds were evaluated in a cellular-based assay and showed promising μM activity.

RSC Medicinal Chemistry published new progress about Enzyme inhibitors (botulinum neurotoxin type A). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Recommanded Product: 4-Bromobenzylamine.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tien, Chieh-Hung; Trofimova, Alina; Holownia, Aleksandra; Kwak, Branden S.; Larson, Reed T.; Yudin, Andrei K. published the artcile< Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations>, Computed Properties of 576-83-0, the main research area is CO surrogate palladium catalyzed carbonylative transformation; aminocarbonylation alkoxycarbonylation Sonogashira Zuzuki Miyaura coupling catalyst; C1 building blocks; CO surrogates; carbonylation; carboxyboronates; palladium catalysis.

The application of carboxy-MIDA-boronate (MIDA=N-methyliminodiacetic acid) as an in situ CO surrogate for various palladium-catalyzed transformations is described. Carboxy-MIDA-boronate was previously shown to be a bench-stable boron-containing building block for the synthesis of borylated heterocycles. The present study demonstrates that, in addition to its utility as a precursor to heterocycle synthesis, carboxy-MIDA-boronate is an excellent in situ CO surrogate that is tolerant of reactive functionalities such as amines, alcs., and carbon-based nucleophiles. Its wide functional-group compatibility is highlighted in the palladium-catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki-Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good-to-excellent yields in a one-pot fashion.

Angewandte Chemie, International Edition published new progress about Alkoxycarbonylation. 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Computed Properties of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Berger, Florian; Plutschack, Matthew B.; Riegger, Julian; Yu, Wanwan; Speicher, Samira; Ho, Matthew; Frank, Nils; Ritter, Tobias published the artcile< Site-selective and versatile aromatic C-H functionalization by thianthrenation>, Recommanded Product: 1-Bromo-3-ethylbenzene, the main research area is arene thianthrenium salt carbon hydrogen bond functionalization regioselective thianthrenation; functionalized arene preparation.

Direct C-H functionalization can quickly increase useful structural and functional mol. complexity. Site selectivity can sometimes be achieved through appropriate directing groups or substitution patterns-in the absence of such functionality, most aromatic C-H functionalization reactions provide more than one product isomer for most substrates. Development of a C-H functionalization reaction that proceeds with high positional selectivity and installs a functional group that can serve as a synthetic linchpin for further functionalization would provide access to a large variety of well-defined arene derivatives Here we report a highly selective aromatic C-H functionalization reaction that does not require a particular directing group or substitution pattern to achieve selectivity, and provides functionalized arenes that can participate in various transformations. We introduce a persistent sulfur-based radical to functionalize complex arenes with high selectivity and obtain thianthrenium salts, e.g., I that are ready to engage in different transformations, via both transition-metal and photoredox catalysis. This transformation differs fundamentally from all previous aromatic C-H functionalization reactions in that it provides direct access to a large number of derivatives of complex small mols., quickly generating functional diversity with selectivity that is not achievable by other methods.

Nature (London, United Kingdom) published new progress about Aromatic hydrocarbons Role: 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, Recommanded Product: 1-Bromo-3-ethylbenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Huiqiong; Feng, Huangdi; Zhang, Jingxian; Van der Eycken, Erik V.; Huang, Liliang published the artcile< Synthetic Access to Secondary Propargylamines via a Copper-Catalyzed Oxidative Deamination/Alkynylation Cascade>, HPLC of Formula: 3959-07-7, the main research area is amine alkyne deaminative coupling alkynylation copper; secondary propargylamine preparation; copper deaminative coupling alkynylation catalyst.

A selective cascade reaction of primary amines and alkynes for the synthesis of the corresponding secondary propargylamines is described. This protocol proceeds with a CuBr2/TBHP system through a process of oxidative deamination of primary amines to imine and alkynylation, featuring a wide scope of substrates with good functional-group tolerance and operational simplicity. Addnl., the use of two different primary amines could also work smoothly using this protocol.

Journal of Organic Chemistry published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, HPLC of Formula: 3959-07-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Shaofei; Vayer, Marie; Noel, Florent; Vukovic, Vuk D.; Golushko, Andrei; Rezajooei, Nazanin; Rowley, Christopher N.; Leboeuf, David; Moran, Joseph published the artcile< Unlocking the Friedel-Crafts arylation of primary aliphatic alcohols and epoxides driven by hexafluoroisopropanol>, Reference of 576-83-0, the main research area is alc preparation regioselective; epoxide arene ring opening Friedel Crafts arylation Bronstedacid catalyst; arylethane preparation; aliphatic alc arene Friedel Crafts arylation Bronsted acid catalyst.

The limitations thar easily overcome using Bronsted acid catalysis in hexafluoroisopropanol (HFIP) as a solvent were reported. Electron-poor aromatic epoxides and aliphatic epoxides undergo stereospecific arylation to give alcs. RC(R1)(Ar)CH2OH/RCH(OH)CH(Ar)OH, and based on the reaction conditions, it can partake in a second nucleophilic substitution with a different arene ArH in one pot. Ph ethanols R3(CH2)2OH (R3 = Ph, 2,6-dichlorophenyl, 2,4,6-trimethylphenyl, etc.) react through a phenonium intermediate, whereas simple aliphatic alcs. e.g., cyclopentanol participate in a rare intermol. SN2 Friedel-Crafts process, delivering linear products e.g., 1,3,5-trimethyl-2-phenethylbenzene exclusively. In this work, an alternative to metal-catalyzed cross-couplings was provided for accessing important scaffolds, and widening the range of applications of the Friedel-Crafts reaction.

Chem published new progress about Aralkyl alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Reference of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Brown, Hilary M.; Doppalapudi, Karan R.; Fedick, Patrick W. published the artcile< Accelerated synthesis of energetic precursor cage compounds using confined volume systems>, Category: bromides-buliding-blocks, the main research area is glyoxal benzylamine hexabenzylhexaazaisowurtzitane microdroplet.

Confined volume systems, such as microdroplets, Leidenfrost droplets, or thin films, can accelerate chem. reactions. Acceleration occurs due to the evaporation of solvent, the increase in reactant concentration, and the higher surface-to-volume ratios amongst other phenomena. Performing reactions in confined volume systems derived from mass spectrometry ionization sources or Leidenfrost droplets allows for reaction conditions to be changed quickly for rapid screening in a time efficient and cost-saving manner. Compared to solution phase reactions, confined volume systems also reduce waste by screening reaction conditions in smaller volumes prior to scaling. Herein, the condensation of glyoxal with benzylamine (BA) to form hexabenzylhexaazaisowurtzitane (HBIW), an intermediate to the highly desired energetic compound 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20), was explored. Five confined volume systems were compared to evaluate which technique was ideal for forming this complex cage structure. Substituted amines were also explored as BA replacements to screen alternative cage structure intermediates and evaluate how these accelerated techniques could apply to novel reactions, discover alternative reagents to form the cage compound, and improve synthetic routes for the preparation of CL-20. Ultimately, reaction acceleration is ideal for predicting the success of novel reactions prior to scaling up and determining if the expected products form, all while saving time and reducing costs. Acceleration factors and conversion ratios for each reaction were assessed by comparing the amount of product formed to the traditional bulk solution phase synthesis.

Scientific Reports published new progress about Acceleration. 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Han, Xin; Wang, Chao; Qin, Chong; Xiang, Weiguo; Fernandez-Salas, Ester; Yang, Chao-Yie; Wang, Mi; Zhao, Lijie; Xu, Tianfeng; Chinnaswamy, Krishnapriya; Delproposto, James; Stuckey, Jeanne; Wang, Shaomeng published the artcile< Discovery of ARD-69 as a highly potent proteolysis targeting chimera (PROTAC) degrader of androgen receptor (AR) for the treatment of prostate cancer>, Quality Control of 3959-07-7, the main research area is prostate neoplasm antitumor proteolysis targeting chimera androgen receptor.

We report herein the discovery of highly potent PROTAC degraders of androgen receptor (AR), as exemplified by IARD-69. I induces degradation of AR protein in AR-pos. prostate cancer cell lines in a dose- and time-dependent manner. I achieves DC50 values of 0.86, 0.76, and 10.4 nM in LNCaP, VCaP, and 22Rv1 AR+ prostate cancer cell lines, resp. I is capable of reducing the AR protein level by >95% in these prostate cancer cell lines and effectively suppressing AR-regulated gene expression. I potently inhibits cell growth in these AR-pos. prostate cancer cell lines and is >100 times more potent than AR antagonists. A single dose of I effectively reduces the level of AR protein in xenograft tumor tissue in mice. Further optimization of I may ultimately lead to a new therapy for AR+, castration-resistant prostate cancer.

Journal of Medicinal Chemistry published new progress about Androgen receptor antagonists. 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