Month: November 2022

《Development of pyrazolo[3,4-d]pyrimidine-6-amine-based TRAP1 inhibitors that demonstrate in vivo anticancer activity in mouse xenograft models》 was written by Kim, Darong; Kim, So-Yeon; Kim, Dongyoung; Yoon, Nam Gu; Yun, Jisu; Hong, Ki Bum; Lee, Changwook; Lee, Ji Hoon; Kang, Byoung Heon; Kang, Soosung. Quality Control of 4-Bromo-1-(bromomethyl)-2-fluorobenzene And the article was included in Bioorganic Chemistry on August 31 ,2020. The article conveys some information:

TNF Receptor Associated Protein 1 (TRAP1) is a mitochondrial paralog of Hsp90 related to the promotion of tumorigenesis in various cancers via maintaining mitochondrial integrity, reducing the production of reactive oxygen species, and reprogramming cellular metabolism Consequently, Hsp90 and TRAP1 have been targeted to develop cancer therapeutics. Herein, we report a series of pyrazolo[3,4-d]pyrimidine derivatives that are mitochondria-permeable TRAP1 inhibitors. Structure-based drug design guided the optimization of potency, leading to the identification of compounds 47 and 48 as potent TRAP1 and Hsp90 inhibitors with good metabolic and plasma stability as well as acceptable CYP and hERG inhibition. X-ray co-crystallization studies confirmed both 47 and 48 interact with the ATP binding pocket in the TRAP1 protein. Compounds 47 and 48 demonstrated excellent anticancer efficiency in various cancer cells, with limited toxicity over normal hepatocyte and prostate cells. Mouse PC3 xenograft studies showed 47 and 48 significantly reduced tumor growth. The experimental process involved the reaction of 4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5Quality Control of 4-Bromo-1-(bromomethyl)-2-fluorobenzene)

4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Organobromine compounds are produced naturally by marine creatures (sponges, corals, sea slugs, tunicates, sea fans) and seaweed, plants, fungi, lichen, algae, bacteria, microbes, and some mammals. Quality Control of 4-Bromo-1-(bromomethyl)-2-fluorobenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Improved HDAC inhibition, stronger cytotoxic effect and higher selectivity against leukemias and lymphomas of novel, tricyclic vorinostat analogues》 was written by Bieszczad, Bartosz; Garbicz, Damian; Switalska, Marta; Dudek, Marta K.; Warszycki, Dawid; Wietrzyk, Joanna; Grzesiuk, Elzbieta; Mieczkowski, Adam. COA of Formula: C5H9BrO2This research focused ontricyclic vorinostat analog lymphoma leukemia HDAC inhibition cytotoxic effect; HDAC inhibitors; Vorinostat; dibenzodiazocines; histone deacetylase; hydroxamic acid; selectivity. The article conveys some information:

Histone deacetylase (HDAC) inhibitors are a class of drugs used in the cancer treatment. Here, we developed a library of 19 analogs of Vorinostat, an HDAC inhibitor used in lymphomas treatment. In Vorinostat, we replaced the hydrophobic Ph group with various tricyclic ′caps′ possessing a central, eight-membered, heterocyclic ring, and investigated the HDAC activity and cytotoxic effect on the cancer and normal cell lines. We found that 3 out of the 19 compounds, based on dibenzo[b,f]azocin-6(5H)-one, 11,12-dihydrodibenzo[b,f]azocin-6(5H)-one, and benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)-dione scaffolds, showed better HDACs inhibition than the referenced Vorinostat. In leukemic cell line MV4-11 and in the lymphoma cell line Daudi, three compounds showed lower IC50 values than Vorinostat. These compounds had higher activity and selectivity against MV4-11 and Daudi cell lines than reference Vorinostat. We also observed a strong correlation between HDACs inhibition and the cytotoxic effect. Cell lines derived from solid tumors: A549 (lung carcinoma) and MCF-7 (breast adenocarcinoma) as well as reference BALB/3T3 (normal murine fibroblasts) were less susceptible to compounds tested. Developed derivatives show improved properties than Vorinostat, thus they could be considered as possible agents for leukemia and lymphoma treatment. The experimental part of the paper was very detailed, including the reaction process of Ethyl 3-bromopropanoate(cas: 539-74-2COA of Formula: C5H9BrO2)

Ethyl 3-bromopropanoate(cas: 539-74-2) 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. COA of Formula: C5H9BrO2 In contrast, terrestrial plants account only for a few bromine-containing compounds.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of C6H4BBrF3KOn May 1, 2020 ,《Deacetylative Aryl Migration of Diaryliodonium Salts with C(sp2)-N Bond Formation toward ortho-Iodo N-Aryl Sulfonamides》 appeared in Organic Letters. The author of the article were Chen, Huangguan; Wang, Limin; Han, Jianwei. The article conveys some information:

An unprecedented approach of metal-free C(sp2)-N bond formation via deacetylation/intramol. aryl migration is demonstrated with novel N-sulfonamide substituted diaryliodonium salts. The reaction provides a variety of ortho-iodo N-aryl sulfonamides. The products were employed in several coupling reactions to afford useful diarylamine scaffolds. Furthermore, the key intermediates of zwitterionic iodoniums in the reaction were isolated and verified by the X-ray crystallog. anal., which showcased unambiguous mechanistic insight into the reactivity of the reaction cascade. In the experiment, the researchers used many compounds, for example, potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8Electric Literature of C6H4BBrF3K)

potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Electric Literature of C6H4BBrF3K Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Formula: C4H6BrFO2On May 6, 2022 ,《Synthesis of α-Fluorinated Areneacetates through Photoredox/Copper Dual Catalysis》 appeared in Organic Letters. The author of the article were Levitre, Guillaume; Granados, Albert; Cabrera-Afonso, Maria Jesus; Molander, Gary A.. The article conveys some information:

A metallaphotoredox method for the preparation of α-fluorinated areneacetates R-R1 [R = 4-MeC6H4, 3-FC6H4, 4-BrC6H4, etc.; R1 = CFC(O)OEt, CF2C(O)OEt, CF2P(O)OEt2] based on the synergistic combination of Ir/Cu dual catalysis from boronic acids was reported. The mild conditions allowed broad functional group tolerance, including substrates containing aldehydes, free phenols and N-Boc-protected amines. Mechanistic investigations support a process proceeding via photoredox/copper dual catalysis. The experimental part of the paper was very detailed, including the reaction process of Ethylbromofluoroacetate(cas: 401-55-8Formula: C4H6BrFO2)

Ethylbromofluoroacetate(cas: 401-55-8) is a member of organofluorine compounds. Organofluorine compounds, which have carbon-fluorine bonds, show unique features such as high thermal and chemical stability, high surface activity, no light-absorbing ability, high pharmacological effect, and so on. Owing to their specific characters, they are indispensable chemicals for industry and our daily lives.Formula: C4H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Battistuzzi, Gianfranco; Cacchi, Sandro; Fabrizi, Giancarlo; Bernini, Roberta published an article in Synlett. The title of the article was 《3-Arylpropanoate esters through the palladium-catalyzed reaction of aryl halides with acrolein diethyl acetal》.Category: bromides-buliding-blocks The author mentioned the following in the article:

The reaction of aryl halides with acrolein di-Et acetal in the presence of Pd(OAc)2, n-Bu3N, and n-Bu4NCl in DMF at 90° affords Et 3-arylpropanoates. A variety of functional groups are tolerated in the aryl halides, including ether, aldehyde, ketone, ester, nitrile, and nitro groups. Ortho-substituents do not hamper the reaction. 3-Arylpropanoate esters were isolated in good to excellent yields with many neutral, electron-rich and electron-poor aryl iodides and electron-poor aryl bromide. Neutral and electron-rich aryl bromides gave the desired ester in moderate yields. After reading the article, we found that the author used Ethyl 3-(2-bromophenyl)propanoate(cas: 135613-33-1Category: bromides-buliding-blocks)

Ethyl 3-(2-bromophenyl)propanoate(cas: 135613-33-1) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Baudet, Karine; Kale, Vishal; Mirzakhani, Mohsen; Babel, Lucille; Naseri, Soroush; Besnard, Celine; Nozary, Homayoun; Piguet, Claude published an article on January 6 ,2020. The article was titled 《Neutral Heteroleptic Lanthanide Complexes for Unravelling Host-Guest Assemblies in Organic Solvents: The Law of Mass Action Revisited》, and you may find the article in Inorganic Chemistry.Related Products of 583-69-7 The information in the text is summarized as follows:

The binding of lanthanide containers [Ln(β-diketonate)3dig] [dig = 1-methoxy-2-(2-methoxyethoxy)ethane] to aromatic tridentate N-donor ligands (L) in dichloromethane produces neutral nine-coordinate heteroleptic [LLn(β-diketonate)3] complexes, the equilibrium reaction quotients of which vary with the total concentrations of the reacting partners. This problematic drift prevents the determination of both reliable thermodn. stability constants and intrinsic host-guest affinities. The classical solution theory assigns this behavior to changes in the activity coefficients of the various partners in nonideal solutions, and a phenomenol. approach attempts to quant. attribute this effect to some partition of the solvent mols. between bulk-innocent and contact-noninnocent contributors to the chem. potential. This assumption eventually predicts an empirical linear dependence of the equilibrium reaction quotient on the concentration of the formed [LLn(β-diketonate)3] complexes, a trend exptl. supported in this contribution for various ligands L differing in lipophilicity and nuclearity and for lanthanide containers grafted with diverse β-diketonate coligands. Even if the origin of the latter linear dependence is still the subject of debate, this work demonstrates that this approach can be exploited by experimentalists for extracting reliable thermodn. constants suitable for analyzing and comparing host-guest affinities in organic solvents. In the experiment, the researchers used many compounds, for example, 2-Bromobenzene-1,4-diol(cas: 583-69-7Related Products of 583-69-7)

2-Bromobenzene-1,4-diol(cas: 583-69-7) 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. Related Products of 583-69-7 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

Cheng, Xinyi; Liu, Xingchen; Wang, Shengchun; Hu, Ying; Hu, Binjing; Lei, Aiwen; Li, Jie published their research in Nature Communications on December 31 ,2021. The article was titled 《Organozinc pivalates for cobalt-catalyzed difluoroalkylarylation of alkenes》.Application In Synthesis of Ethylbromofluoroacetate The article contains the following contents:

A cobalt-catalyzed regioselective difluoroalkylarylation of both activated and unactivated alkenes with solid arylzinc pivalates and difluoroalkyl bromides through a cascade Csp3-Csp3/Csp3-Csp2 bond formation under mild reaction conditions. Indeed, a wide range of functional groups on difluoroalkyl bromides, olefins, 1,3-dienes as well as (hetero)arylzinc pivalates are well tolerated by the cobalt-catalyst, thus furnished three-component coupling products in good yields and with high regio- and diastereoselectivity. Kinetic experiments compared arylzinc pivalates and conventional arylzinc halides highlighted the unique reactivity of these organozinc pivalates. Mechanistic studies strongly supported that the reaction involved direct halogen atom abstraction via single electron transfer to difluoroalkyl bromides from the in-situ formed cobalt(I) species, thus realized a Co(I)/Co(II)/Co(III) catalytic cycle. In the experiment, the researchers used Ethylbromofluoroacetate(cas: 401-55-8Application In Synthesis of Ethylbromofluoroacetate)

Ethylbromofluoroacetate(cas: 401-55-8) is a member of organofluorine compounds. Organofluorine compounds, which have carbon-fluorine bonds, show unique features such as high thermal and chemical stability, high surface activity, no light-absorbing ability, high pharmacological effect, and so on. Owing to their specific characters, they are indispensable chemicals for industry and our daily lives.Application In Synthesis of Ethylbromofluoroacetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nakayama, Yoshiki; Ando, Gaku; Abe, Manabu; Koike, Takashi; Akita, Munetaka published an article in ACS Catalysis. The title of the article was 《Keto-Difluoromethylation of Aromatic Alkenes by Photoredox Catalysis: Step-Economical Synthesis of α-CF2H-Substituted Ketones in Flow》.Synthetic Route of C10H16Br3N The author mentioned the following in the article:

A step-economical method for synthesis of α-CF2H-substituted ketones from readily available alkene feedstocks was developed. Radical difluoromethylation of aromatic alkenes combining DMSO oxidation and photoredox catalysis is a key to the successful transformation. Electrochem. anal., laser flash photolysis (LFP), and d. functional theory (DFT) calculations reveal that N-tosyl-S-difluoromethyl-S-phenylsulfoximine serves as the best CF2H radical source among analogous sulfone-based CF2H reagents. The present photocatalytic keto-difluoromethylation was applied to flow synthesis and easily scaled up to gram-scale synthesis within a reasonable reaction time. Furthermore, potentials of the α-CF2H-substituted ketones for useful synthetic intermediates are shown; e.g., synthesis of the CF2H-containing α-hydroxyamide with the same carbon skeleton as that of the anticonvulsant active CF3-analog, is disclosed. Addnl., mechanistic studies are also discussed. In addition to this study using Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, there are many other studies that have used Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide(cas: 111865-47-5Synthetic Route of C10H16Br3N) was used in this study.

Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide(cas: 111865-47-5) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Synthetic Route of C10H16Br3NSome of these compounds are identical to man-made organobromine compounds, such as methyl bromide, bromoform, and bromophenols, but many others are entirely new moleclar entities, often possessing extraordinary and important biological properties.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Biphenylyl-1,2,4-oxadiazole based liquid crystals – synthesis, mesomorphism, effect of lateral monofluorination》 were Fouad, Farid S.; Ness, Todd; Wang, Kunlun; Ruth, Christopher E.; Britton, Sonia; Twieg, Robert J.. And the article was published in Liquid Crystals in 2019. Safety of 1-Bromo-4-ethoxy-2-fluorobenzene The author mentioned the following in the article:

Aiming at developing a new type of materials for functional applications, three series of new compounds were prepared, 3-(biphenylyl)-1,2,4-oxadiazoles, Series I; laterally mono-fluorinated 3-(biphenylyl)-1,2,4-oxadiazoles, Series II; and 5-(biphenylyl)-1,2,4-oxadiazoles, Series III. Liquid crystalline properties of these compounds were studied using differential scanning calorimetry and polarizing optical microscopy. Ten of the thirteen compounds in Series I are mesogenic forming either N or SmA phases depending on the length-to-width mol. ratio. Mesogens of the positional isomers, Series III are both N and SmA. Monofluorination of the biphenylyl group at either the central or the terminal phenylene rings, Series III, resulted in the formation of nematic mesogens with low phase transition temperatures and broad nematic phase range. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-ethoxy-2-fluorobenzene(cas: 107713-66-6Safety of 1-Bromo-4-ethoxy-2-fluorobenzene)

1-Bromo-4-ethoxy-2-fluorobenzene(cas: 107713-66-6) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Safety of 1-Bromo-4-ethoxy-2-fluorobenzene Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Synthesis of 18F-difluoromethylarenes using arylboronic acids, ethyl bromofluoroacetate and [18F]fluoride》 were Sap, Jeroen B. I.; Wilson, Thomas C.; Kee, Choon Wee; Straathof, Natan J. W.; am Ende, Christopher W.; Mukherjee, Paramita; Zhang, Lei; Genicot, Christophe; Gouverneur, Veronique. And the article was published in Chemical Science in 2019. Application of 401-55-8 The author mentioned the following in the article:

Herein, the radiosynthesis of 18F-difluoromethylarenes RCHF18F (R = 4-C2H5, 4-OC6H5, 3,5-CH3, etc.) via the assembly of three components, a boron reagent, Et bromofluoroacetate, and cyclotron-produced non-carrier added [18F]fluoride was reported. The two key steps are a copper-catalyzed cross-coupling reaction, and a Mn-mediated 18F-fluorodecarboxylation. In the experiment, the researchers used many compounds, for example, Ethylbromofluoroacetate(cas: 401-55-8Application of 401-55-8)

Ethylbromofluoroacetate(cas: 401-55-8) is a member of organofluorine compounds. Organofluorine compounds, which have carbon-fluorine bonds, show unique features such as high thermal and chemical stability, high surface activity, no light-absorbing ability, high pharmacological effect, and so on. Owing to their specific characters, they are indispensable chemicals for industry and our daily lives.Application of 401-55-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary