Tag: M.W=250-300

Stones, Duane published the artcileModular solid-phase synthetic approach to optimize structural and electronic properties of oligo-boronic acid receptors and sensors for the aqueous recognition of oligosaccharides, COA of Formula: C12H16BBrO2, the publication is Chemistry – A European Journal (2004), 10(1), 92-100, database is CAplus and MEDLINE.

This article describes the design and optimization of the first entirely modular, parallel solid-phase synthetic approach for the generation of well-defined polyamine oligo-boronic acid receptors and fluorescence sensors for complex oligosaccharides. The synthetic approach allows an effective building of the receptor polyamine backbone, followed by the controlled diversification of the amine benzylic side chains. This approach enabled the testing, in a modular fashion, of the effect of different aryl-boronic acid units substituted with un-encumbering para electron-withdrawing or electron-donating groups. The feasibility of this approach toward automated synthesis was also investigated with the assembly of a sub-library of receptors by means of the Irori MiniKan technol. Several sub-libraries of anthracene-capped sensors containing two or three aryl-boronic acids were synthesized, and their binding to a series of model disaccharides was examined in neutral aqueous media. The calculation of association constants by fluorescence titrations confirmed that subtle changes in the structures of the inter-amine spacers in the polyamine backbone can have a significant effect on the stability of the resulting complexes. Most importantly, this study led to the determination of the preferred electronic characteristics for the aryl-boronate units, and suggests that a new generation of receptors containing very electron-poor aryl-boronic acids could lead to a significant improvement of binding affinities.

Chemistry – A European Journal published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C7H5Br2F, COA of Formula: C12H16BBrO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Lambert, Joseph B. published the artcileInductive enhancement of aryl participation, Related Products of bromides-buliding-blocks, the publication is Journal of the American Chemical Society (1977), 99(9), 3059-67, database is CAplus.

Enhanced participation by an aryl group in solvolysis could be achieved by placing an electron-withdrawing substituent vicinal to the leaving group. Acetolysis of meso-1,4-diaryl-2,3-butanediyl ditosylates and of 1,4-diaryl-2-butyl tosylates, in which the aryl groups were substituted with p-OMe, p-Me, H, p-Cl, m-CF3 and p-NO2, was examined The 2nd tosylate group provided the inductive stimulus for increased aryl participation. Comparison of the monotosylate with the ditosylate showed that the proportion of aryl participation increased from 93-9% for p-OMe, from 66-99% for p-Me, from 35-94% for H, and from 0-68% for p-Cl. Thus an electron-withdrawing substituent vicinal to the leaving group made the aryl-participation pathway essentially exclusive for aryl groups with substituents with σ ≥0. Even for a substituent with a small neg. σ value, such as p-Cl, participation could be quite significant in the ditosylate series, while completely lacking in the monotosylate series.

Journal of the American Chemical Society published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Camp, David published the artcileDevelopment of a Synthetic Process towards a Hepatitis C Polymerase Inhibitor, SDS of cas: 76283-09-5, the publication is Organic Process Research & Development (2006), 10(4), 814-821, database is CAplus.

The synthesis of clin. candidate 2-(4-{2-[(2R)-2-Cyclopentyl-5-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-2-fluoro-phenyl)-2-methyl-propionitrile (I) on multikilogram scale is described. Initial synthesis of I, clin. candidate for inhibition of the hepatitis C viral polymerase (HCVP) protein, was executed via a racemic synthetic route coupled with chiral HPLC separation Due to the achiral route and instability of key intermediates, the initial route was determined to be unsuitable for large-scale manufacture An alternate route was developed utilizing a convergent Heck coupling, resolution of a carboxylic acid via diastereomeric salt formation, and an efficient chem. recycling of the undesired enantiomer.

Organic Process Research & Development published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, SDS of cas: 76283-09-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Yuan-Xiang published the artcileDesign and syntheses of novel phthalazin-1(2H)-one derivatives as acetohydroxyacid synthase inhibitors, Formula: C7H5Br2F, the publication is Journal of Agricultural and Food Chemistry (2006), 54(24), 9135-9139, database is CAplus and MEDLINE.

A series of 2-substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives were designed via ortho-substituent cyclization to discover a new herbicidal lead structure. These compounds were synthesized by a seven-step route using 3-hydroxy-acetophenone as a starting material. Determination of the K_i values against wild-type A. thaliana acetohydroxyacid synthase (AHAS) (EC 4.1.3.18) indicated that some of the compounds displayed good enzyme inhibition activity comparable to that of KIH-6127. Bioassay data on weeds showed that the synthesized compounds exhibited the typical injury symptoms of AHAS-inhibiting herbicides, and some of them showed broad-spectrum and high herbicidal activities in postemergence treatments against Echinochloa crusgalli, Digitaria sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus, and Chenopodium album, at an application rate of 150 g/ha. To our knowledge, this is the first report of methylphthalazin-1-one derivatives as AHAS inhibitors.

Journal of Agricultural and Food Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Formula: C7H5Br2F.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Yuqiang published the artcileReaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki-Miyaura cross-coupling, Formula: C9H8BrF3, the publication is Nature Communications (2020), 11(1), 417, database is CAplus and MEDLINE.

In this work, a Ni-catalyzed migratory Suzuki-Miyaura cross-coupling featuring high benzylic or allylic selectivity has been developed. With this method, unactivated alkyl electrophiles and aryl or vinyl boronic acids can be efficiently transferred to diarylalkane or allylbenzene derivatives under mild conditions. Importantly, unactivated alkyl chlorides can also be successfully used as the coupling partners. To demonstrate the applicability of this method, showcase that this strategy can serve as a platform for the synthesis of terminal, partially deuterium-labeled mols. from readily accessible starting materials. Exptl. studies suggest that migratory cross-coupling products are generated from Ni(0/II) catalytic cycle. Theor. calculations indicate that the chain-walking occurs at a neutral nickel complex rather than a cationic one. In addition, the original-site cross-coupling products can be obtained by alternating the ligand, wherein the formation of the products has been rationalized by a radical chain process.

Nature Communications published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Formula: C9H8BrF3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Gao, Xiu-zheng published the artcileDesign, synthesis and in vitro anticancer research of novel tetrandrine and fangchinoline derivatives, Related Products of bromides-buliding-blocks, the publication is Bioorganic Chemistry (2021), 104694, database is CAplus and MEDLINE.

Cancer treatment is one of the major public health issues in the world. Tetrandrine (Tet) and fangchinoline (d-Tet) are two bis-benzyl isoquinoline alkaloids extracted from Stephania tetrandra S. Moore, and their antitumor activities have been confirmed. However, the ED of Tet and d-Tet were much higher than that of the pos. control and failed to meet clin. standards Therefore, in this study, as a continuation of our previous work to study and develop high-efficiency and low-toxic antitumor lead compounds, twenty new Tet and d-Tet derivatives were designed, synthesized and evaluated as antitumor agents against six cancer cell lines (H460, H520, HeLa, HepG-2, MCF-7, SW480 cell lines) and BEAS-2B normal cells by CCK-8 anal. Ten derivatives showed better cytotoxic effects than the parent fangchinoline, of which I showed the strongest cell growth inhibitory activity with an IC₅₀ value of 0.59μM against A549 cells. Subsequently, the antitumor mechanism of I was studied by flow cytometry, Hoechst 33258, JC-1 staining, cell scratch, transwell migration, and Western blotting assays. These results showed that compound I could inhibit A549 cell proliferation by arresting the G2/M cell cycle and inhibiting cell migration and invasion by reducing MMP-2 and MMP-9 expression. Meanwhile, I could induce apoptosis of A549 cells through the intrinsic pathway regulated by mitochondria. In addition, compound I inhibited the phosphorylation of PI3K, Akt and mTOR, suggesting a correlation between blocking the PI3K/Akt/mTOR pathway and the above antitumor activities. These results suggest that compound I may be a future drug for the development of new potential drug candidates against lung cancer.

Bioorganic Chemistry published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C8H6BrF3S, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Gunathilake, Samodha S. published the artcileSynthesis and characterization of novel semiconducting polymers containing pyrimidine, Safety of 2-Bromo-3-(2-ethylhexyl)thiophene, the publication is Polymer Chemistry (2013), 4(20), 5216-5219, database is CAplus.

The acidic Me protons of 4,6-dimethylpyrimidines can be easily deprotonated with a base to generate a resonance stabilized carbanion which can be used as a substrate for aldol condensation reactions. A series of novel conjugated polymers were synthesized by the aldol condensation reaction of 2-decyloxy-4,6-dimethylpyrimidine with various aromatic dialdehydes.

Polymer Chemistry published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C12H19BrS, Safety of 2-Bromo-3-(2-ethylhexyl)thiophene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Yuan-Xiang published the artcileDesign and syntheses of novel phthalazin-1(2H)-one derivatives as acetohydroxyacid synthase inhibitors, Formula: C7H5Br2F, the publication is Journal of Agricultural and Food Chemistry (2006), 54(24), 9135-9139, database is CAplus and MEDLINE.

A series of 2-substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives were designed via ortho-substituent cyclization to discover a new herbicidal lead structure. These compounds were synthesized by a seven-step route using 3-hydroxy-acetophenone as a starting material. Determination of the K_i values against wild-type A. thaliana acetohydroxyacid synthase (AHAS) (EC 4.1.3.18) indicated that some of the compounds displayed good enzyme inhibition activity comparable to that of KIH-6127. Bioassay data on weeds showed that the synthesized compounds exhibited the typical injury symptoms of AHAS-inhibiting herbicides, and some of them showed broad-spectrum and high herbicidal activities in postemergence treatments against Echinochloa crusgalli, Digitaria sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus, and Chenopodium album, at an application rate of 150 g/ha. To our knowledge, this is the first report of methylphthalazin-1-one derivatives as AHAS inhibitors.

Journal of Agricultural and Food Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Formula: C7H5Br2F.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Yuqiang published the artcileReaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki-Miyaura cross-coupling, Formula: C9H8BrF3, the publication is Nature Communications (2020), 11(1), 417, database is CAplus and MEDLINE.

In this work, a Ni-catalyzed migratory Suzuki-Miyaura cross-coupling featuring high benzylic or allylic selectivity has been developed. With this method, unactivated alkyl electrophiles and aryl or vinyl boronic acids can be efficiently transferred to diarylalkane or allylbenzene derivatives under mild conditions. Importantly, unactivated alkyl chlorides can also be successfully used as the coupling partners. To demonstrate the applicability of this method, showcase that this strategy can serve as a platform for the synthesis of terminal, partially deuterium-labeled mols. from readily accessible starting materials. Exptl. studies suggest that migratory cross-coupling products are generated from Ni(0/II) catalytic cycle. Theor. calculations indicate that the chain-walking occurs at a neutral nickel complex rather than a cationic one. In addition, the original-site cross-coupling products can be obtained by alternating the ligand, wherein the formation of the products has been rationalized by a radical chain process.

Nature Communications published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Formula: C9H8BrF3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Gao, Xiu-zheng published the artcileDesign, synthesis and in vitro anticancer research of novel tetrandrine and fangchinoline derivatives, Related Products of bromides-buliding-blocks, the publication is Bioorganic Chemistry (2021), 104694, database is CAplus and MEDLINE.

Cancer treatment is one of the major public health issues in the world. Tetrandrine (Tet) and fangchinoline (d-Tet) are two bis-benzyl isoquinoline alkaloids extracted from Stephania tetrandra S. Moore, and their antitumor activities have been confirmed. However, the ED of Tet and d-Tet were much higher than that of the pos. control and failed to meet clin. standards Therefore, in this study, as a continuation of our previous work to study and develop high-efficiency and low-toxic antitumor lead compounds, twenty new Tet and d-Tet derivatives were designed, synthesized and evaluated as antitumor agents against six cancer cell lines (H460, H520, HeLa, HepG-2, MCF-7, SW480 cell lines) and BEAS-2B normal cells by CCK-8 anal. Ten derivatives showed better cytotoxic effects than the parent fangchinoline, of which I showed the strongest cell growth inhibitory activity with an IC₅₀ value of 0.59μM against A549 cells. Subsequently, the antitumor mechanism of I was studied by flow cytometry, Hoechst 33258, JC-1 staining, cell scratch, transwell migration, and Western blotting assays. These results showed that compound I could inhibit A549 cell proliferation by arresting the G2/M cell cycle and inhibiting cell migration and invasion by reducing MMP-2 and MMP-9 expression. Meanwhile, I could induce apoptosis of A549 cells through the intrinsic pathway regulated by mitochondria. In addition, compound I inhibited the phosphorylation of PI3K, Akt and mTOR, suggesting a correlation between blocking the PI3K/Akt/mTOR pathway and the above antitumor activities. These results suggest that compound I may be a future drug for the development of new potential drug candidates against lung cancer.

Bioorganic Chemistry published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C8H6BrF3S, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary