Month: October 2022

《Stannylation and Stille Coupling of Base-Sensitive Tetrahydroxanthones to Heteromeric Biaryls》 was published in Advanced Synthesis & Catalysis in 2015. These research results belong to Lindner, Stephanie; Nieger, Martin; Braese, Stefan. Safety of 3-Bromo-2-nitrobenzoic acid The article mentions the following:

Herein, the synthesis of heteromeric tetrahydroxanthone biaryls is described, a widespread core structure of many natural products. The development of both stannylation and Stille coupling procedures of base-sensitive tetrahydroxanthones enabled their coupling with benzene derivatives as well as with xanthenes. These methods provide access to structures that are analogous to parnafungin as well as to dimeric compounds similar to secalonic acid or (5R,5’R,6R,6’R,10aR,10’aR)-rel-(-)-5,5′-bis(acetyloxy)-10a,10’a-bis[(acetyloxy)methyl]-5,5′,6,6′,7,7′,10a,10’a-octahydro-1,1′,8,8′-tetrahydroxy-6,6′-dimethyl-[2,4′-Bi-9H-xanthene]-9,9′-dione [i.e., phomoxanthone]. The synthesis of the target compounds was achieved using 7-bromo-2,3,4,4a-tetrahydro-1H-xanthen-1-one, 2,3,4,4a-tetrahydro-7-iodo-1H-xanthen-1-one (1R,4aS)-rel-7-bromo-2,3,4,4a-tetrahydro-1H-xanthen-1-ol as starting materials. Key intermediates for the coupling reactions included (tributylstannyl)xanthene derivatives Dimers thsu formed included 2,2′,3,3′,4,4′,4a,4’a-octahydro-[7,7′-bi-1H-Xanthene]-1,1′-dione. In the experimental materials used by the author, we found 3-Bromo-2-nitrobenzoic acid(cas: 116529-61-4Safety of 3-Bromo-2-nitrobenzoic acid)

3-Bromo-2-nitrobenzoic acid(cas: 116529-61-4) 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. Safety of 3-Bromo-2-nitrobenzoic acid 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

Computed Properties of C4H6BrFO2On May 16, 2022 ,《Biocatalytic Asymmetric Construction of Secondary and Tertiary Fluorides from β-Fluoro-α-Ketoacids》 appeared in Angewandte Chemie, International Edition. The author of the article were Fang, Jason; Turner, Laura E.; Chang, Michelle C. Y.. The article conveys some information:

Fluorine is a critical element for the design of bioactive compounds, driving advances in selective and sustainable fluorination. However, stereogenic tertiary fluorides pose a synthetic challenge and are thus present in only a few approved drugs (fluticasone, solithromycin, and sofosbuvir). The aldol reaction of fluorinated donors provides an atom-economical approach to asym. C-F motifs via C-C bond formation. Authors report that the type II pyruvate aldolase HpcH and engineered variants perform addition of β-fluoro-α-ketoacids (including fluoropyruvate, β-fluoro-α-ketobutyrate, and β-fluoro-α-ketovalerate) to diverse aldehydes. The reactivity of HpcH towards these fluoro-donors grants access to enantiopure secondary or tertiary fluorides. In addition to representing the first synthesis of tertiary fluorides via biocatalytic carboligation, the afforded products could improve the diversity of fluorinated building blocks and enable the synthesis of fluorinated drug analogs. In the experimental materials used by the author, we found Ethylbromofluoroacetate(cas: 401-55-8Computed Properties of 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.Computed Properties of C4H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Safety of EthylbromofluoroacetateOn May 11, 2020 ,《Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives》 appeared in Angewandte Chemie, International Edition. The author of the article were Kc, Shekhar; Dhungana, Roshan K.; Khanal, Namrata; Giri, Ramesh. The article conveys some information:

The authors report a Ni-catalyzed regioselective α-carbonylalkylarylation of vinylarenes with α-halocarbonyl compounds and arylzinc reagents. The reaction works with primary, secondary, and tertiary α-halocarbonyl mols., and electronically varied arylzinc reagents. The reaction generates γ,γ-diarylcarbonyl derivatives with α-secondary, tertiary, and quaternary carbon centers. The products can be readily converted to aryltetralones, including a precursor to Zoloft, an antidepressant drug. In addition to this study using Ethylbromofluoroacetate, there are many other studies that have used Ethylbromofluoroacetate(cas: 401-55-8Safety of Ethylbromofluoroacetate) was used in this study.

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.Safety of Ethylbromofluoroacetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of C7H5Br2FOn May 13, 2021 ,《Design and Structure-Activity Relationships of Isothiocyanates as Potent and Selective N-Acylethanolamine-Hydrolyzing Acid Amidase Inhibitors》 appeared in Journal of Medicinal Chemistry. The author of the article were Malamas, Michael S.; Pavlopoulos, Spiro; Alapafuja, Shakiru O.; Farah, Shrouq I.; Zvonok, Alexander; Mohammad, Khadijah A.; West, Jay; Perry, Nicholas Thomas; Pelekoudas, Dimitrios N.; Rajarshi, Girija; Shields, Christina; Chandrashekhar, Honrao; Wood, Jodi; Makriyannis, Alexandros. The article conveys some information:

N-Acylethanolamines are signaling lipid mols. implicated in pathophysiol. conditions associated with inflammation and pain. N-Acylethanolamine acid amidase (NAAA) favorably hydrolyzes lipid palmitoylethanolamide, which plays a key role in the regulation of inflammatory and pain processes. The synthesis and structure-activity relationship studies encompassing the isothiocyanate pharmacophore have produced potent low nanomolar inhibitors for hNAAA, while exhibiting high selectivity (>100-fold) against other serine hydrolases and cysteine peptidases. We have followed a target-based structure-activity relationship approach, supported by computational methods and known cocrystals of hNAAA. We have identified systemically active inhibitors with good plasma stability (t1/2 > 2 h) and microsomal stability (t1/2 ∼ 15-30 min) as pharmacol. tools to investigate the role of NAAA in inflammation, pain, and drug addiction. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5Synthetic Route of C7H5Br2F)

4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals.Synthetic Route of C7H5Br2F Organobromine compounds have fallen under increased scrutiny for their environmental impact.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2009,Chemistry – A European Journal included an article by Andaloussi, Mounir; Lindh, Jonas; Saevmarker, Jonas; Sjoeberg, Per J. R.; Larhed, Mats. COA of Formula: C6H4BBrF3K. The article was titled 《Microwave-Promoted Palladium(II)-Catalyzed C-P Bond Formation by Using Arylboronic Acids or Aryltrifluoroborates》. The information in the text is summarized as follows:

The first PdII-catalyzed P arylation has been performed by using palladium acetate, the rigid bidentate ligand dmphen (dmphen = 2,9-dimethyl-1,10-phenanthroline), and without the addition of base or acid. Couplings of arylboronic acids or aryl trifluoroborates with H-phosphonate dialkyl esters were conducted in 30 min with controlled microwave (MW) heating under non-inert conditions. Aryl phosphites were also synthesized at room temperature with atm. air as the sole reoxidant. The arylated phosphonates were isolated in 44-90% yields. The excellent chemoselectivity of the method was illustrated in the synthesis of a Mycobacterium tuberculosis glutamine synthetase (MTB-GS) inhibitor. Online ESI-MS was used to detect cationic palladium species in ongoing reactions directly, and a catalytic cycle has been proposed based on these results. In the experiment, the researchers used many compounds, for example, potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8COA of Formula: C6H4BBrF3K)

potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8) 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. COA of Formula: C6H4BBrF3K Due to the reactivity of bromide, they are used as potential precursors or important intermediates in organic synthesis.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2009,Chemistry – A European Journal included an article by Gendrineau, Thomas; Demoulin, Nicolas; Navarre, Laure; Genet, Jean-Pierre; Darses, Sylvain. COA of Formula: C6H4BBrF3K. The article was titled 《Rhodium-Catalyzed Formation of Stereocontrolled Trisubstituted Alkenes from Baylis-Hillman Adducts》. The information in the text is summarized as follows:

Efficient and general conditions for the formation of stereodefined trisubstituted alkenes by using the rhodium-catalyzed reaction of unactivated Baylis-Hillman adducts with either organoboronic acids or potassium trifluoro(organo)borates are reported (see scheme). We report here efficient and general conditions for the formation of stereodefined trisubstituted alkenes using the rhodium-catalyzed reaction of unactivated Baylis-Hillman adducts with either organoboronic acids and potassium trifluoro(organo)borates. The use of the [{Rh(cod)OH}2] precursor gave very fast coupling reactions under low catalyst loading, very mild reaction conditions (from room temperature up to 50 °C) and without the need of addnl. phosphane ligands. Based on the new reaction conditions, the reaction, originally limited to Baylis-Hillman adducts derived from esters, could be extended to a large variety of Baylis-Hillman adducts, bearing either keto, cyano or amido functionalities. Moreover, the reaction of Baylis-Hillman adducts bearing esters functionality was improved and could be conducted at lower temperature using lower catalyst loading. In addition to this study using potassium (3-bromophenyl)trifluoroborate, there are many other studies that have used potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8COA of Formula: C6H4BBrF3K) was used in this study.

potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8) 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. In contrast, terrestrial plants account only for a few bromine-containing compounds.COA of Formula: C6H4BBrF3K

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

McNamara, Dennis J.; Berman, Ellen M.; Fry, David W.; Werbel, Leslie M. published an article in Journal of Medicinal Chemistry. The title of the article was 《Potent inhibition of thymidylate synthase by two series of nonclassical quinazolines》.Formula: C9H8BrNO4 The author mentioned the following in the article:

The synthesis and biol. activity of two series of nonclassical thymidylate synthase (TS) inhibitors are described. The first is a series of 10-propargyl-5,8-dideazafolic acid derivatives I (R = NH2; R1 = R2 = Cl, R3 = H; R1-R3 = OMe; R1 = R3 = H, R2 = Ac, F, cyano, CONH2, SO2NMe2, NO2, COCF3, OCF3) and the second is a series of 2-deamino derivatives I (R = H; R1 = R2 = Cl, R3 = H, R1-R3 = OMe; R1 = R3 = H, R4 = Ac), both bearing a more lipophilic substituent on the Ph ring than the CO-glutamate of classical antifolates. The compounds were tested for inhibition of purified L1210 TS and for inhibition of L1210 cell growth in vitro. Several of these nonclassical analogs approached the TS inhibitory potency of 10-propargyl-5,8-dideazafolic acid (II), a glutamate-containing TS inhibitor. I (R = NH2) were generally potent inhibitors of L1210 TS, with ED50s within the range of 0.51-11.5 μM for II. I (R = H) also exhibited significant, although diminished, TS inhibition. Both series were growth inhibitory to cells in tissue culture and this inhibition could be reversed by thymidine alone, indicating that the primary target was TS. None of the compounds was a potent inhibitor of dihydrofolate reductase. These studies indicate that the presence of the glutamate moiety in folate analogs is not an absolute requirement for potent inhibition of TS.Methyl 5-(bromomethyl)-2-nitrobenzoate(cas: 88071-91-4Formula: C9H8BrNO4) was used in this study.

Methyl 5-(bromomethyl)-2-nitrobenzoate(cas: 88071-91-4) 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: C9H8BrNO4 In contrast, terrestrial plants account only for a few bromine-containing compounds.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2016,Kaiser, Felix; Schmidt, Andrea; Heydenreuter, Wolfgang; Altmann, Philipp Johannes; Casini, Angela; Sieber, Stephan A.; Kuehn, Fritz Elmar published 《Self-assembled palladium and platinum coordination cages: Photophysical studies and anticancer activity》.European Journal of Inorganic Chemistry published the findings.Name: 3,5-Dibromoaniline The information in the text is summarized as follows:

Self-assembled coordination cages are interesting as drug delivery systems. Therefore, the synthesis of new ML (M = Pd, Pt) mol. cages, derived from highly fluorescent, rigid polyaromatic ligands is reported and the first PtL cage with a ligand consisting of three pyridine moieties is described. Photophys. properties were examined showing high quantum yields of up to 48% for the methoxy-functionalized ligands. Coordination of the ligands to palladium and platinum ions reduces the metallocages’ fluorescence, however. The host-guest chem. of the palladium cage with cisplatin is investigated confirming the encapsulation. The cages encapsulating cisplatin show a significantly increased cytotoxicity towards A549 (human lung adenocarcinoma) cells compared to cisplatin, and thus appear to be promising delivery vectors for the anticancer drug cisplatin. The results came from multiple reactions, including the reaction of 3,5-Dibromoaniline(cas: 626-40-4Name: 3,5-Dibromoaniline)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Name: 3,5-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2016,Isenegger, Patrick G.; Baechle, Florian; Pfaltz, Andreas published 《Asymmetric Morita-Baylis-Hillman reaction: catalyst development and mechanistic insights based on mass spectrometric back-reaction screening》.Chemistry – A European Journal published the findings.Category: bromides-buliding-blocks The information in the text is summarized as follows:

An efficient protocol for the evaluation of catalysts for the asym. Morita-Baylis-Hillman (MBH) reaction was developed. By mass spectrometric back-reaction screening of quasi-enantiomeric MBH products, an efficient bifunctional phosphine catalyst was identified that outperforms literature-known catalysts in the MBH reaction of Me acrylate with aldehydes. The close match between the selectivities measured for the forward and back reaction and kinetic measurements provided strong evidence that the aldol step and not the subsequent proton transfer is rate- and enantioselectivity-determining In the experiment, the researchers used many compounds, for example, 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Category: bromides-buliding-blocks)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) 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. Category: bromides-buliding-blocks In contrast, terrestrial plants account only for a few bromine-containing compounds.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Sun, Ying-Ji; Li, Pei; Huang, Qian-Qian; Zhang, Jian-Jun; Itoh, Shinobu published 《Dioxygenation of Flavonol Catalyzed by Copper(II) Complexes Supported by Carboxylate-Containing Ligands: Structural and Functional Models of Quercetin 2,4-Dioxygenase》.European Journal of Inorganic Chemistry published the findings.SDS of cas: 1129-28-8 The information in the text is summarized as follows:

To obtain insights into the role of the carboxylate group of Glu73 in the active site of quercetin 2,4-dioxygenase (2,4-QD), the copper(II) complexes [CuIILn(AcO)] [1 (Ln = L1), 2 (Ln = L2), 3 (Ln = L3), and 4 (Ln = L4)] supported by carboxylate-containing ligands [L1H = 2-{[bis(pyridin-2-ylmethyl)amino]methyl}benzoic acid; L2H = 3-{[bis(pyridin-2-ylmethyl)amino]methyl}benzoic acid,; L3H = 2-({bis[2-(pyridin-2-yl)ethyl]amino}methyl)benzoic acid; L4H = 3-({bis[2-(pyridin-2-yl)ethyl]amino}methyl)benzoic acid] as well as the ternary CuII flavonolate (fla-) complexes [CuIILn(fla)] [5 (Ln = L1), 6 (Ln = L2), 7 (Ln = L3), and 8 (Ln = L4)] were synthesized and characterized as structural and functional models for the active site of 2,4-QD. The ternary complexes [CuIILn(fla)] showed different reactivities in the dioxygenation of bound flavonolate to benzoic acid, salicylic acid, and N,N-dimethylbenzamide at 75-90° (single-turnover reaction) in the order 5 >> 7 > 8 ≈ 6. A similar reactivity tendency was found in the catalytic dioxygenation of the substrate flavonol (multiturnover reaction) by the binary complexes. The different reactivities of the copper complexes could be attributed to the different Lewis acidities of the copper(II) ions induced by the different coordination environments of the ligands. The results will provide important insights into the pivotal catalytic role of the carboxylate group of Glu73 in 2,4-QD (no data). In the experiment, the researchers used Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8SDS of cas: 1129-28-8)

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. Moreover, several studies demonstrate that the average proportion of bromine in drugs is significantly higher than that in natural products. SDS of cas: 1129-28-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary