Month: October 2022

In 2018,Betti, Marco; Catarzi, Daniela; Varano, Flavia; Falsini, Matteo; Varani, Katia; Vincenzi, Fabrizio; Dal Ben, Diego; Lambertucci, Catia; Colotta, Vittoria published 《The aminopyridine-3,5-dicarbonitrile core for the design of new non-nucleoside-like agonists of the human adenosine A2B receptor》.European Journal of Medicinal Chemistry published the findings.Formula: C9H9BrO2 The information in the text is summarized as follows:

A new series of amino-3,5-dicyanopyridines I (R1 = OEt, cyclopropylmethoxy, NHCOCH3, etc.; R2 = COOMe, CONH2, CONHCH3, etc.) as analogs of the adenosine hA2B receptor agonist BAY60-6583 was synthesized. All the compounds that interact with the hA2B adenosine receptor display EC50 values in the range 9-350 nM behaving as partial agonists, with the only exception being the I (R1 = NHCOCH3, R2 = CONH2) which shows a full agonist profile. Moreover, the compound I (R1 = cyclopropylmethoxy, R2 = 1H-imidazol-2-yl) turns out to be 3-fold more active than BAY60-6583 although less selective. This result can be considered a real breakthrough due to the currently limited number of non-adenosine hA2B AR agonists reported in literature. To simulate the binding mode of nucleoside and non-nucleoside agonists at the hA2B AR, mol. docking studies were performed at homol. models of this AR subtype developed by using two crystal structures of agonist-bound A2A AR as templates. These investigations allowed to represent a hypothetical binding mode of hA2B receptor agonists belonging to the amino-3,5-dicyanopyridine series and to rationalize the observed SAR. In the experiment, the researchers used Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8Formula: C9H9BrO2)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) belongs to organobromine compounds.Most of the natural organobromine compounds are produced by marine organisms , and several brominated metabolites with antibacterial , antitumor , antiviral , and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Formula: C9H9BrO2 Moreover, several studies demonstrate that the average proportion of bromine in drugs is significantly higher than that in natural products.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,Angewandte Chemie, International Edition included an article by Yi, Xiangli; Hu, Xile. Name: Ethyltriphenylphosphonium bromide. The article was titled 《Formal Aza-Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis》. The information in the text is summarized as follows:

An approach to transform electrochem. generated organic radical intermediates into neutral products e.g., I by reaction with a metal catalyst was described. This approach combines electrochem. oxidation with Cu catalysis to effect formal aza-Wacker cyclization of internal alkenes e.g., crotyl N-phenylcarbamate. The Cu catalyst is essential for transforming secondary and primary alkyl radical intermediates into alkenes. A wide range of 5-membered N-heterocycles can be prepared under mild conditions. In the experiment, the researchers used many compounds, for example, Ethyltriphenylphosphonium bromide(cas: 1530-32-1Name: Ethyltriphenylphosphonium bromide)

Ethyltriphenylphosphonium bromide(cas: 1530-32-1) is a phase transfer catalyst, used to accelerate the cure of phenolic-based epoxy resins, certain fluoroelastomer resins and thermosetting powder coatings. It is also used as catalysts in the synthesis of certain organic compounds and as a pharmaceutical intermediate.Name: Ethyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Enantioselective Construction of Quaternary All-Carbon Centers via Copper-Catalyzed Arylation of Tertiary Carbon-Centered Radicals》 were Wu, Lianqian; Wang, Fei; Chen, Pinhong; Liu, Guosheng. And the article was published in Journal of the American Chemical Society in 2019. Recommanded Product: 3,5-Dibromoaniline The author mentioned the following in the article:

An enantioselective copper-catalyzed arylation of tertiary carbon-centered radicals, leading to quaternary all-carbon stereocenters, has been developed herein. The tertiary carbon-centered radicals, including both benzylic and nonbenzylic radicals, were produced by the addition of trifluoromethyl radical to α-substituted acrylamides, and subsequently captured by chiral aryl copper(II) species to give C-Ar bonds with excellent enantioselectivity. Importantly, an acylamidyl (CONHAr) group adjacent to the tertiary carbon radical is essential for the asym. radical coupling. The reaction itself features broad substrate scope, excellent functional group compatibility and mild conditions. In addition to this study using 3,5-Dibromoaniline, there are many other studies that have used 3,5-Dibromoaniline(cas: 626-40-4Recommanded Product: 3,5-Dibromoaniline) was used in this study.

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Recommanded Product: 3,5-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Energy Transfer to Ni-Amine Complexes in Dual Catalytic, Light-Driven C-N Cross-Coupling Reactions》 were Kudisch, Max; Lim, Chern-Hooi; Thordarson, Pall; Miyake, Garret M.. And the article was published in Journal of the American Chemical Society in 2019. Application of 402-43-7 The author mentioned the following in the article:

Dual catalytic light-driven cross-coupling methodologies utilizing a Ni(II) salt with a photocatalyst (PC) have emerged as promising methodologies to forge aryl C-N bonds under mild conditions. The recent discovery that the PC can be omitted and the Ni(II) complex directly photoexcited suggests that the PC may perform energy transfer (EnT) to the Ni(II) complex, a mechanistic possibility that has recently been proposed in other systems across dual Ni photocatalysis. Here, we report the first studies in this field capable of distinguishing EnT from electron transfer (ET), and the results are consistent with Förster-type EnT from the excited state [Ru(bpy)3]Cl2 PC to Ni-amine complexes. The structure and speciation of Ni-amine complexes that are the proposed EnT acceptors were elucidated by crystallog. and spectroscopic binding studies. With the acceptors known, quant. Förster theory was utilized to predict the ratio of quenching rate constants upon changing the PC, enabling selection of an organic phenoxazine PC that proved to be more effective in catalyzing C-N cross-coupling reactions with a diverse selection of amines and aryl halides. The results came from multiple reactions, including the reaction of 1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7Application of 402-43-7)

1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Due to the reactivity of bromide, they are used as potential precursors or important intermediates in organic synthesis. Application of 402-43-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Intratumorally Injected Photothermal Agent-Loaded Photodynamic Nanocarriers for Ablation of Orthotopic Melanoma and Breast Cancer》 were Sun, Xiaodong; Zhuang, Bo; Zhang, Mengmeng; Jiang, Heliu; Jin, Yiguang. And the article was published in ACS Biomaterials Science & Engineering in 2019. Quality Control of Ethyl 4-bromobutyrate The author mentioned the following in the article:

Traditional chemotherapy of cancers may lead to serious adverse reactions due to little drug distribution in tumors. Here, a combination of photothermal therapy (PTT) and photodynamic therapy (PDT) was used for local treatment of orthotopic melanoma and breast cancer via intratumoral (i.t.) injection of photothermal agent-loaded photodynamic nanocarriers. A hydrophobic derivative of indocyanine green, DCC, was synthesized and entrapped into a pH-sensitive photosensitizer-core copolymer, PDCZP, to form DCC@PDCZP. The nanocarriers showed remarkable fluorescence, high singlet oxygen quantum yields, and a strong photothermal effect. Flow cytometry suggested that the nanocarriers were efficiently internalized by cancer cells. Near IR thermal imaging and fluorescence self-imaging showed that the i.t. injected DCC@PDCZP mainly remained in the tumors, but the i.v. (i.v.) nanocarriers were distributed a little. One i.t. injection of DCC@PDCZP was enough to ablate the orthotopic B16-F10 and 4T1 mouse tumors under 830 and 660 nm irradiation at 4 h postinjection. More importantly, no local recurrences were found, though swabs were formed at 9 days post-treatment. The major anticancer mechanisms included improvement of cancer cell necrosis due to hyperthermia, inhibition of neovascularization, and enhancement of cell apoptosis. The i.t. injection of PTT/PDT nanoformulations is thus a promising local treatment of superficial tumors. The experimental process involved the reaction of Ethyl 4-bromobutyrate(cas: 2969-81-5Quality Control of Ethyl 4-bromobutyrate)

Ethyl 4-bromobutyrate(cas: 2969-81-5) belongs to bromides. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact.Quality Control of Ethyl 4-bromobutyrate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Design, Synthesis and Biological Evaluation of Carbazole Derivatives as Antitubercular and Antibacterial Agents》 were Sellamuthu, Satheeshkumar; Bhat, Mohammad F.; Kumar, Ashok; Nath, Gopal; Singh, Sushil K.. And the article was published in Current Bioactive Compounds in 2019. Electric Literature of C6H5Br2N The author mentioned the following in the article:

Background: The neuroleptic chlorpromazine has been reported for antitubercular activity but the associated antipsychotic activity restricted its clin. presentation. Objectives: Novel derivatives of carbazole having structural similarity with chlorpromazine were designed, in an attempt to reduce the associated side effects, while retaining the antitubercular activity. Materials and Methods: The designed mols. were synthesized and screened for antitubercular and antibacterial activities. The blood-brain barrier (BBB) permeability and mammalian cell (VERO) cytotoxicity (CC50) were examined to determine the safety of compounds Results: Among the developed compounds, 14c, 15c, 16c and 17c were found to be promising against Mtb H37Rv at MIC of 1.56 mug/mL. They were also effective against S. aureus and E. coli at MIC of 0.98 and 7.81 mug/mL, resp. The BBB permeability of the compounds was found to be less than chlorpromazine. Therefore, the developed compounds are expected to have diminished antipsychotic effect. The compounds were further marked safe against mammalian VERO cells at CC50 > 90 mug/mL. Conclusion: The profound antitubercular activity with a concomitant reduction in BBB permeability of carbazole derivatives can pave new vista in the discovery of antitubercular drugs. In addition to this study using 3,5-Dibromoaniline, there are many other studies that have used 3,5-Dibromoaniline(cas: 626-40-4Electric Literature of C6H5Br2N) was used in this study.

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Electric Literature of C6H5Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Well-Designed Phosphine-Urea Ligand for Highly Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Methacrylonitrile: A Combined Experimental and Theoretical Study》 were Xiong, Yang; Du, Zhuanzhuan; Chen, Haohua; Yang, Zhao; Tan, Qiuyuan; Zhang, Changhui; Zhu, Lei; Lan, Yu; Zhang, Min. And the article was published in Journal of the American Chemical Society in 2019. Application In Synthesis of o-Bromobenzaldehyde The author mentioned the following in the article:

A novel chiral phosphine-urea bifunctional ligand has been developed for Cu-catalyzed asym. 1,3-dipolar cycloaddition of iminoesters with methacrylonitrile, a long-standing challenging substrate in asym. catalysis. Distortion-interaction energy anal. based on d. functional theory (DFT) calculations reveals that the distortion energy plays an important role in the observed enantioselectivity, which can be attributed to the steric effect between the phosphine ligand and the dipole reactant. DFT calculations also indicate that nucleophilic addition is the enantioselectivity-determining step and hydrogen bonding between the urea moiety and methacrylonitrile assists in control of the diastereo- and enantioselectivity. By a combination of metal catalysis and organocatalysis, excellent diastereo- and enantioselectivities (up to 99:1 diastereomeric ratio, 99% enantiomeric excess) as well as good yields are achieved. A wide range of substitution patterns of both iminoester and acrylonitrile is tolerated by this catalyst system, providing access to a series of highly substituted chiral cyanopyrrolidines with up to two quaternary stereogenic centers. The synthetic utility is demonstrated by enantioselective synthesis of antitumor agent ETP69 with a pivotal nitrile pharmacophore and an all-carbon quaternary stereogenic center. In the part of experimental materials, we found many familiar compounds, such as o-Bromobenzaldehyde(cas: 6630-33-7Application In Synthesis of o-Bromobenzaldehyde)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.Application In Synthesis of o-BromobenzaldehydeIt is also used in L-threonine aldolase-catalyzed enantio and diastereoselective aldol reactions. Further, it reacts with trichloromethane to prepare 1-(2-bromo-phenyl)-2,2,2-trichloro-ethanol.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Highly Selective, Amine-Derived Cannabinoid Receptor 2 Probes》 was published in Chemistry – A European Journal in 2020. These research results belong to Westphal, Matthias V.; Sarott, Roman C.; Zirwes, Elisabeth A.; Osterwald, Anja; Guba, Wolfgang; Ullmer, Christoph; Grether, Uwe; Carreira, Erick M.. Safety of 4-Bromobutanoic acid The article mentions the following:

The endocannabinoid (eCB) system is implied in various human diseases ranging from central nervous system to autoimmune disorders. Cannabinoid receptor 2 (CB2R) is an integral component of the eCB system. Yet, the downstream effects elicited by this G protein-coupled receptor upon binding of endogenous or synthetic ligands are insufficiently understood-likely due to the limited arsenal of reliable biol. and chem. tools. Herein, we report the design and synthesis of CB2R-selective cannabinoids along with their in vitro pharmacol. characterization (binding and functional studies). They combine structural features of HU-308 and AM841 to give chimeric ligands that emerge as potent CB2R agonists with high selectivity over the closely related cannabinoid receptor 1 (CB1R). The synthesis work includes convenient preparation of substituted resorcinols often found in cannabinoids. The utility of the synthetic cannabinoids in this study is showcased by preparation of the most selective high-affinity fluorescent probe for CB2R to date. The results came from multiple reactions, including the reaction of 4-Bromobutanoic acid(cas: 2623-87-2Safety of 4-Bromobutanoic acid)

4-Bromobutanoic acid(cas: 2623-87-2) belongs to carboxylic acids. The chief chemical characteristic of the carboxylic acids is their acidity. They are generally more acidic than other organic compounds containing hydroxyl groups but are generally weaker than the familiar mineral acids (e.g., hydrochloric acid, HCl, sulfuric acid, H2SO4, etc.).Safety of 4-Bromobutanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Synthesis of 2-Aminoquinazoline- and 2-Aminopyrimidine-Fused Hybrid Scaffolds by Copper-Catalyzed C(sp2)-N Coupling and Cyclization Followed by Oxidation》 was published in European Journal of Organic Chemistry in 2020. These research results belong to Kwak, Jung Pyo; Dao, Pham Duy Quang; Cho, Chan Sik. Electric Literature of C7H5BrO The article mentions the following:

2-(2-Bromoaryl)- and 2-(2-bromovinyl)-4,7-dimethoxybenzimidazoles are coupled and cyclized with cyanamide as a building block in DMF in the presence of a catalytic amount of a copper catalyst along with a base to give the corresponding 2-aminoquinazoline- and 2-aminopyrimidine-fused 4,7-dimethoxybenzimidazoles in good yields. Subsequent oxidation of such N-fused hybrid scaffolds by treatment of ceric ammonium nitrate in acetonitrile/H2O affords unprecedented 2-aminoquinazoline- and 2-aminopyrimidine-fused benzimidazolequinones. In the experimental materials used by the author, we found o-Bromobenzaldehyde(cas: 6630-33-7Electric Literature of C7H5BrO)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.Electric Literature of C7H5BrOIt is a key starting material in the total synthesis of an anticancer agent, (-)-taxol.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Diversified Transformations of Tetrahydroindolizines to Construct Chiral 3-Arylindolizines and Dicarbofunctionalized 1,5-Diketones》 was published in Journal of the American Chemical Society in 2020. These research results belong to Zhang, Dong; Su, Zhishan; He, Qianwen; Wu, Zhikun; Zhou, Yuqiao; Pan, Chenjing; Liu, Xiaohua; Feng, Xiaoming. SDS of cas: 5437-45-6 The article mentions the following:

Enantioselective diverse synthesis of a small-mol. collection with structural and functional similarities or differences in an efficient manner is an appealing but formidable challenge. Asym. preparation and branching transformations of tetrahydroindolizines in succession present a useful approach to the construction of N-heterocycle-containing scaffolds with functional group, and stereochem. diversity. Herein, we report a breakthrough toward this end via an initial diastereo- and enantioselective [3 + 2] cycloaddition between pyridinium ylides and enones, following diversified sequential transformations. Chiral N,N’-dioxide-earth metal complexes enable the generation of optically active tetrahydroindolizines in situ, across the strong background reaction for racemate-formation. In connection with deliberate sequential transformations, involving convenient rearom. oxidation, and light-active aza-Norrish II rearrangement, the tetrahydroindolizine intermediates were converted into the final library including 3-arylindolizine derivatives and dicarbofunctionalized 1,5-dicarbonyl compounds More importantly, the stereochem. of four-stereogenic centered tetrahydroindolizine intermediates could be efficiently transferred into axial chirality in 3-arylindolizines and vicinal pyridyl and aryl substituted 1,5-diketones. In addition, densely functionalized cyclopropanes and bridged cyclic compounds were also discovered depending on the nature of the pyridinium ylides. Mechanism studies were involved to explain the stereochem. during the reaction processes. After reading the article, we found that the author used Benzyl 2-bromoacetate(cas: 5437-45-6SDS of cas: 5437-45-6)

Benzyl 2-bromoacetate(cas: 5437-45-6) belongs to benzyl acetate. Benzyl acetate is a synthetic chemical produced for industry from benzyl alcohol and acetic acid, but is also naturally present in the essential oils of many plants, including jasmine and ylang ylang.SDS of cas: 5437-45-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary