Tag: M.W=250-300

Wang, Li-Jun published the artcileSynthesis, biological evaluation and structure-activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents, Name: 4-Bromo-1-(bromomethyl)-2-fluorobenzene, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(10), 3473-3479, database is CAplus and MEDLINE.

Fifty-seven derivatives of glycyrrhetinic acid (GA) were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Among them, sixteen compounds showed greater anti-HBV activity than GA, especially, compounds I (R = 4-iodobenzyl), I (R = 4-(trifluoromethyl)benzyl), I (R = 4-nitrobenzyl), I (R = (2-methylthiazol-4-yl)methyl) exhibited significantly inhibitory activities against HBV DNA replication with IC₅₀ values of 5.71, 5.36, 8.90 and 9.08 μM, resp. The structure-activity relationships (SARs) of GA derivatives were discussed for exploring novel anti-HBV agents.

Bioorganic & Medicinal Chemistry Letters 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 C17H18N3NaO3S, Name: 4-Bromo-1-(bromomethyl)-2-fluorobenzene.

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

Kolycheva, M. T. published the artcileFluorinated benzaldehydes in Leuckart and Rodionov reactions, Computed Properties of 21101-63-3, the publication is Zhurnal Organicheskoi Khimii (1989), 25(11), 2367-72, database is CAplus.

Difluoromethylating RCOR¹ [I; R = 2-HOC₆H₄, R¹ = Me; R = 3,4-(HO)₂C₆H₃, R¹ = H] with ClCHF₂ in Me₂CHOH containing KOH at 70° gave 27-82% I [R = 2-CHF₂OC₆H₄, 3,4-(CHF₂O)₂C₆H₃; same R¹]. These and I (R = 2-CF₃C₆H₄, 2- and 4-CHF₂OC₆H₄; R¹ = H) reacted with HCONH₂ at 150-180° to give 57-82% RCHR¹NHCHO, which were hydrolyzed with concentrated HCl in MeOH to give 25-86% RCHR¹NH₂.HCl (II), and reduced with LiAlH₄ in THF to give 30-52% RCH₂NHMe.HCl (R = 4-CHF₂OC₆H₄, 2-CF₃C₆H₄). RCH₂Br (R = 4-CF₃SC₆H₄, 4-C₂F₅OC₆H₄) reacted with urotropine in CHCl₃ and then with aqueous-alc. HCl to give the corresponding II in 25-74% yield. RCHO (R = 2- and 4-CHF₂OC₆H₄) condensed with CH₂(CO₂H)₂ in EtOH containing NH₄OAc to give 40-52% RCH(NH₂)CH₂CO₂H and 18-35% RCH:CHCO₂H. Analogous treatment of PhCOCF₃ gave 56% CF₃CPh(OH)CH₂CO₂H.

Zhurnal Organicheskoi Khimii 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, Computed Properties of 21101-63-3.

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

Armstrong, W. W. Jr. published the artcileExperimental control of lime-induced iron chlorosis in trifoliate orange seedlings by soil applications of some iron compounds, HPLC of Formula: 1997-80-4, the publication is J. Rio Grande Valley Hort. Soc. (1956), 43-8, database is CAplus.

cf. Cooper and Peynado, C.A. 49, 7793b. Trifoliate orange (Poncirus trifoliata) seedlings were used as indicator plants in an experiment to determine the effectiveness of several Fe compounds in the treatment of citrus in high-lime soils for lime-induced Fe chlorosis. Soil applications of ground FeSO₄ (I), Fe ethylenediaminetetraacetic acid (II), and Fe N-hydroxyethylethylenediaminetriacetic acid (EDTA) (III) were very effective in preventing chlorosis, while unchelated EDTA was much less effective and Fe-rich fritted glass had no apparent effect. The higher the rate of application of I or II, the more effective was the treatment. Only III exhibited toxicity, a dose equivalent to 0.5 g. Fe/sq. ft. causing wilting and death of the plants.

J. Rio Grande Valley Hort. Soc. 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, HPLC of Formula: 1997-80-4.

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

Demirtas, Ibrahim published the artcileSynthetic route to 1,3-disubstituted naphthalene derivatives, Synthetic Route of 52358-73-3, the publication is Journal of Chemical Research, Synopses (2002), 524-526, database is CAplus.

The preparation of methoxy- and cyanonaphthalene derivatives is described. The preparation of 1,3-dimethoxynaphthalene, 1-bromo-3-methoxynaphthalene, 1-methoxy-3-bromonaphthalene and 1,3-dicyanonaphthalene involves the reaction of 1,3-dibromonaphthalene with the corresponding nucleophile.

Journal of Chemical Research, Synopses published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C10H6Br2, Synthetic Route of 52358-73-3.

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

Gokalp, Faik published the artcileTheoretical study of synthesis of 1,3-dibromonaphthanlene, Quality Control of 52358-73-3, the publication is Journal of the Chemical Society of Pakistan (2018), 40(6), 1089-1092, database is CAplus.

Naphthalene derivatives have been attracted the interest for synthesis of natural products having biol. properties. Elimination reaction of tetrabromonaphthalene (1) resulted in the formation of 1,3-dibromonaphthalene (2) rather than 1,4-dibomonaphthalene (3). This phenomenon was explained by theor. investigation. The phys. properties and optimization of tetrabromonaphthalene (1), 1,3-dibromonaphthalene (2) and 1,4-dibromonaphthalene (3) were evaluated by B3lyp/6-31+G(d,p) method. Due to the HOMO-LUMO gap of 1,3-dibromonaphthalene (2) was higher than that of the 1,4-dibomonaphthalene (3), the formation of 1,3-dibromonaphthalene (2) was favorable. Moreover, Higher dipole moment of 1,3-dibromonaphthalene (2) than 1,4-dibomonaphthalene (3) supported the synthesis of 1,3-dibromonaphthalene (2) properly.

Journal of the Chemical Society of Pakistan published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C10H6Br2, Quality Control of 52358-73-3.

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

Yang, Wenqian published the artcileThe First Fluorescent Diboronic Acid Sensor Specific for Hepatocellular Carcinoma Cells Expressing Sialyl Lewis X, Safety of 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, the publication is Chemistry & Biology (2004), 11(4), 439-448, database is CAplus and MEDLINE.

Carbohydrate antigens with subterminal fucosylation have been implicated in the development and progression of several cancers, including hepatocellular carcinoma (HCC). Fluorescent sensors targeting fucosylated carbohydrate antigens could potentially be used for diagnostic and other applications. The authors have designed and synthesized a series of 26 diboronic acid compounds as potential fluorescent sensors for such carbohydrates. Among these compounds, 7q was able to fluorescently label cells expressing high levels of sLex (HEPG2) within a concentration range of 0.5 to 10 μM. This compound (7q) did not label cells expressing Lewis Y (HEP3B), nor cells without fucosylated antigens (COS7). This represents the first example of a fluorescent compound labeling cells based on cell surface carbohydrate structures.

Chemistry & Biology 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 C7H7ClN2, Safety of 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane.

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

Dokla, Eman M. E. published the artcileDevelopment of Potent Adenosine Monophosphate Activated Protein Kinase (AMPK) Activators, Product Details of C8H6BrF3S, the publication is ChemMedChem (2015), 10(11), 1915-1923, database is CAplus and MEDLINE.

Previously, the authors reported the identification of a thiazolidinedione-based adenosine monophosphate activated protein kinase (AMPK) activator, compound 1 (N-(4-((3-((1-methylcyclohexyl)methyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-4-nitro-3-(trifluoromethyl)benzenesulfonamide), which provided a proof of concept to delineate the intricate role of AMPK in regulating oncogenic signaling pathways associated with cell proliferation and epithelial-mesenchymal transition (EMT) in cancer cells. In this study, the authors used compound 1 as a scaffold to conduct lead optimization, which generated a series of derivatives Anal. of the antiproliferative and AMPK-activating activities of individual derivatives revealed a distinct structure-activity relationship and identified 59 (N-(3-nitrophenyl)-N’-(4-((3-((3,5-bis(trifluoromethyl)phenyl)methyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)urea) as the optimal agent. Relative to 1, compound 59 exhibits multifold higher potency in upregulating AMPK phosphorylation in various cell lines irresp. of their liver kinase B1 (LKB1) functional status, accompanied by parallel changes in the phosphorylation/expression levels of p70S6K, Akt, Foxo3a, and EMT-associated markers. Consistent with its predicted activity against tumors with activated Akt status, orally administered 59 was efficacious in suppressing the growth of phosphatase and tensin homolog (PTEN)-null PC-3 xenograft tumors in nude mice. Together, these findings suggest that 59 has clin. value in therapeutic strategies for PTEN-neg. cancer and warrants continued investigation in this regard.

ChemMedChem 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, Product Details of C8H6BrF3S.

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

Guo, Pu published the artcileCompound shape effects in minor groove binding affinity and specificity for mixed sequence DNA, Name: 4-Bromo-N-butyl-2-nitroaniline, the publication is Journal of the American Chemical Society (2018), 140(44), 14761-14769, database is CAplus and MEDLINE.

AT-specific heterocyclic cations that bind in the DNA duplex minor groove have had major successes as cell and nuclear stains and as therapeutic agents which can effectively enter human cells. Expanding the DNA sequence recognition capability of the minor groove compounds could also expand their therapeutic targets and have an impact in many areas, such as modulation of transcription factor biol. activity. 2268681509. Success in the design of mixed sequence binding compounds has been achieved with N-methylbenzimidazole (N-MeBI) thiophenes which are preorganized to fit the shape of the DNA minor groove and H-bond to the -NH of G·C base pairs that projects into the minor groove. Initial compounds bound strongly to a single G·C base pair in an AT context with a specificity ratio of 50 (K_d AT-GC/K_d AT) or less and this was somewhat low for biol. use. We felt that modifications of compound shape could be used to probe local DNA microstructure in target mixed base-pair sequences of DNA and potentially improve the compound binding selectivity. Modifications were made by increasing the size of the benzimidazole N-substituent, e.g., by using N-iso-Bu instead of N-Me, and by changing the mol. twist by introducing substitutions at specific positions on the aromatic core of the compounds In both cases, we were able to achieve a dramatic increase in binding specificity, including no detectable binding to pure AT sequences, without a significant loss in affinity to mixed base-pair target sequences.

Journal of the American Chemical Society published new progress about 1036461-93-4. 1036461-93-4 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is 4-Bromo-N-butyl-2-nitroaniline, and the molecular formula is C10H13BrN2O2, Name: 4-Bromo-N-butyl-2-nitroaniline.

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

Rene, Olivier published the artcileDiscovery of oxa-sultams as RORc inverse agonists showing reduced lipophilicity, improved selectivity and favorable ADME properties, Computed Properties of 76283-09-5, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(18), 4455-4461, database is CAplus and MEDLINE.

Modification of the δ-sultam ring of RORc inverse agonist 2 led to the discovery of more polar oxa-sultam 65. The less lipophilic inverse agonist (65) displayed high potency in a biochem. assay, which translated into inhibition of IL-17 production in human peripheral blood mononuclear cells. The successful reduction of lipophilicity of this new analog gave rise to addnl. improvements in ROR selectivity and aqueous kinetic solubility, as well as reduction in plasma protein binding, while maintaining high cellular permeability.

Bioorganic & Medicinal Chemistry Letters 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, Computed Properties of 76283-09-5.

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

Touaibia, Mohamed published the artcileStructure-Activity Relationship Studies of New Sinapic Acid Phenethyl Ester Analogues Targeting the Biosynthesis of 5-Lipoxygenase Products: The Role of Phenolic Moiety, Ester Function, and Bioisosterism, HPLC of Formula: 1997-80-4, the publication is Journal of Natural Products (2022), 85(1), 225-236, database is CAplus and MEDLINE.

Sinapic acid is found in many edible plants and fruits, such as rapeseed, where it is the predominant phenolic compound New sinapic acid phenethyl ester (SAPE) analogs were synthesized and screened as inhibitors of the biosynthesis of 5-lipoxygenase (5-LO) in stimulated HEK293 cells and polymorphonuclear leukocytes (PMNL). Inhibition of leukotriene biosynthesis catalyzed by 5-LO is a validated therapeutic strategy against certain inflammatory diseases and allergies. Unfortunately, the only inhibitor approved to date has limited clin. use because of its poor pharmacokinetic profile and liver toxicity. With the new analogs synthesized in this study, the role of the phenolic moiety, ester function, and bioisosterism was investigated. Several of the 34 compounds inhibited the biosynthesis of 5-LO products, and 20 compounds were 2-11 times more potent than zileuton in PMNL, which are important producers of 5-LO products. Compounds 5i (I)(IC₅₀: 0.20 μM), 5l (II) (IC₅₀: 0.20 μM), and 5o (III)(IC₅₀: 0.21 μM) bearing 4-trifluoromethyl, Me, or methoxy substituent at meta-position of the phenethyl moiety were 1.5 and 11.5 times more potent than SAPE (IC₅₀: 0.30 μM) and zileuton (IC₅₀: 2.31 μM), resp. Addnl., compound 9 (IC₅₀: 0.27 μM), which was obtained after acetylation of the 4-hydroxyl of SAPE, was equivalent to SAPE and 8 times more active than zileuton. Furthermore, compound 20b (IV) (IC₅₀: 0.27 μM) obtained after the bioisosteric replacement of the ester function of SAPE by the 1,2,4-oxadiazole heterocycle was equivalent to SAPE and 8 times more active than zileuton. Thus, this study provides a basis for the rational design of new mols. that could be developed further as anti 5-LO therapeutics.

Journal of Natural Products 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 C10H2F12NiO4, HPLC of Formula: 1997-80-4.

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