Month: November 2022

Recsei, Carl published the artcileSynthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy, Computed Properties of 401-55-8, the publication is Beilstein Journal of Organic Chemistry (2021), 813-818, database is CAplus and MEDLINE.

A simple and new procedure was developed for the construction of a bis(aryloxy)fluoromethane moiety I and ROCH(F)OR [R = 4-O₂NC₆H₄, 2,5-di-ClC₆H₄], for which no existing method was available.

Beilstein Journal of Organic Chemistry published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, Computed Properties of 401-55-8.

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

Antoniak, Damian published the artcileAlkylation of Nitropyridines via Vicarious Nucleophilic Substitution, SDS of cas: 111-83-1, the publication is Organic Letters (2022), 24(2), 516-519, database is CAplus and MEDLINE.

Electrophilic nitropyridines reacted with sulfonyl-stabilized carbanions gave alkylated nitropyridins I [R = H, Me, n-octyl, etc.; R¹ = Me, Et, n-octyl, etc.; R² = H, OMe, SPh, etc.] products of C-H alkylation via vicarious nucleophilic substitution was reported. The process consisted of formation of the Meisenheimer-type adduct, followed by base-induced β-elimination of the sulfinic acid (e.g., PhSO₂H).

Organic Letters published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, SDS of cas: 111-83-1.

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

Picard, Franck published the artcileSynthesis and Evaluation of 2′-Substituted 4-(4′-Carboxy- or 4′-carboxymethylbenzylidene)-N-acylpiperidines: Highly Potent and in Vivo Active Steroid 5α-Reductase Type 2 Inhibitors, Formula: C7H5Br2F, the publication is Journal of Medicinal Chemistry (2002), 45(16), 3406-3417, database is CAplus and MEDLINE.

Sixteen N-acylpiperidines I (R¹ = Ph₂CH, Ph₂CHCH₂, dicyclohexylmethyl, 1-adamantyl; R² = H, F, MeO; R³ = H, HO₂C; R⁴ = H, HO₂C, HO₂CCH₂) and II (R⁵ = Ph₂CH, Ph₂N, Me₃CO, 1-adamantyl), bearing carboxylic acid moieties, were synthesized and evaluated for inhibition of rat and human steroid 5α-reductase isoenzymes types 1 and 2. In the dicyclohexylacetyl series (R¹ = dicyclohexylmethyl), fluorination in the 2-position of the benzene nucleus, exchange of the carboxy group by a carboxymethyl moiety, and combination of both structural modifications led to highly active inhibitors of the human type 2 isoenzyme [IC₅₀ values: I [R² = F, R³ = H, R⁴ = HO₂C; (III)], 11 nM; I (R² = R³ = H, R⁴ = HO₂CCH₂), 6 nM; I (R² = F, R³ = H, R⁴ = HO₂CCH₂), 7 nM; finasteride, 5 nM]. In vivo all compounds tested markedly reduced the prostate weights in castrated testosterone-treated rats. Oral activity was shown for compound I (R¹ = dicyclohexylmethyl, R² = R³ = H, R⁴ = HO₂C). From the finding that III is active in the rat, although it is a rather poor inhibitor of the rat enzyme and is a strong inhibitor of the human enzyme, it is concluded that it should be highly potent in men.

Journal of Medicinal 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

Hubbard, Robert D. published the artcilePyrazolo[3,4-d]pyrimidines as potent inhibitors of the insulin-like growth factor receptor (IGF-IR), Category: bromides-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(19), 5406-5409, database is CAplus and MEDLINE.

A high throughput screen of Abbott’s compound repository revealed that the pyrazolo[3,4-d]pyrimidine class of kinase inhibitors, e.g., I, possessed moderate potency for IGF-IR, a promising target for cancer chemotherapy. The synthesis and subsequent optimization of this class of compounds led to the discovery of I that possesses in vivo IGF-IR inhibitory activity.

Bioorganic & Medicinal Chemistry Letters published new progress about 53484-26-7. 53484-26-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Nitro Compound,Amine,Benzene, name is 4-Bromo-N-methyl-2-nitroaniline, and the molecular formula is C7H7BrN2O2, Category: bromides-buliding-blocks.

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

Decroos, Christophe published the artcileToward Stable Electron Paramagnetic Resonance Oximetry Probes: Synthesis, Characterization, and Metabolic Evaluation of New Ester Derivatives of a Tris-(para-carboxyltetrathiaaryl)methyl (TAM) Radical, Computed Properties of 55788-44-8, the publication is Chemical Research in Toxicology (2013), 26(10), 1561-1569, database is CAplus and MEDLINE.

Tris-(p-carboxyltetrathiaaryl)-Me (TAM) radicals, such as 1a (“Finland” radical), are useful EPR probes for oximetry. However, they are rapidly metabolized by liver microsomes in the presence of NADPH, with the formation of diamagnetic quinone-methide metabolites resulting from an oxidative decarboxylation of one of their carboxylate substituents. In an effort to obtain TAM derivatives potentially more metabolically stable in vivo, the authors synthesized four new TAM radicals in which the carboxylate substituents of 1a have been replaced with esters groups bearing various alkyl chains designed to render them water-soluble The new compounds were completely characterized by UV-visible and EPR spectroscopies, high resolution mass spectrometry (HRMS), and electrochem. Two of them were water-soluble enough to undergo detailed microsomal metabolic studies in comparison with 1a. They are stable in the presence of the esterases present in rat liver microsomes and cytosol, and, contrary to 1a, stable to oxidation in the presence of NADPH-supplemented microsomes. A careful study of their possible microsomal reduction under anaerobic or aerobic conditions showed that they were more easily reduced than 1a, in agreement with their higher reduction potentials. They were reduced into the corresponding anions not only under anaerobic conditions but also in the presence of dioxygen. These anions were much more stable than that of 1a and could be characterized by UV-visible spectroscopy, MS, and at the level of their protonated product. However, they were oxidized by O₂, giving back to the starting ester radicals and catalyzing a futile cycle of O₂ reduction Such reactions should be considered in the design of future stable EPR probes for oximetry in vivo.

Chemical Research in Toxicology published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C3H6BrNaO3S, Computed Properties of 55788-44-8.

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

Stoelevik, Reidar published the artcileConformational analysis of 1,2-dihalotetramethylethanes and 1,2-dihalotetramethyldisilanes by molecular mechanics calculations, Computed Properties of 594-81-0, the publication is Journal of Molecular Structure (1989), 131-5, database is CAplus.

By using nonbonding atom···atom interaction potentials derived from gas-phase data on related haloalkanes, torsional potentials of the title mols. are calculated These mols. have stable anti and gauche conformations. In all mols. the anti has a lower energy than the gauche. The rotational barrier heights corresponding to a transition from gauche to anti are 0.5-1.5 kcal mol^-1 in the disilanes and 3.5-5.5 kcal mol^-1 in the ethanes. Calculated results are compared with the gas-phase observations on the disilanes.

Journal of Molecular Structure published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C10H16O2, Computed Properties of 594-81-0.

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

Wei, Changyong published the artcileDevelopment of GLUT4-selective antagonists for multiple myeloma therapy, Application In Synthesis of 1997-80-4, the publication is European Journal of Medicinal Chemistry (2017), 573-586, database is CAplus and MEDLINE.

Cancer cells consume more glucose to fuel metabolic programs fundamental to sustaining their survival, growth and proliferation. Among the fourteen SLC2A family members, GLUTs 1 and 4 are high-affinity glucose transporters. GLUT4 (SLC2A4) is highly expressed in muscle and adipose tissue. Basally retained within the cell, GLUT4 traffics to the plasma membrane (PM) in response to insulin and exercise-stimulation. The plasma cell malignancy multiple myeloma (MM) exhibits increased constitutive expression of GLUT4 on the PM, co-opting use of GLUT4 for survival and proliferation. GLUT4 inhibition by knockdown or treatment with the FDA-approved HIV protease inhibitor ritonavir leads to cytostatic and/or cytotoxic and chemosensitizing effects in tumor cells both in vitro and in vivo. We recently reported our generation of GLUT4 homol. models and virtual high-throughput screening (vHTS) to identify multiple series of novel GLUT4 antagonists. In this report, we describe our initial hit-to-lead optimization to synthesize new analogs with improved potency and selectivity for GLUT4, and the biol. characterization of these compounds in a variety of assays. We show that our lead compound (compound 20) decreases glucose uptake and cell proliferation as well as inhibits the expression of pro-survival MCL-1 in MM similar to the effect observed via knockdown of GLUT4 expression. Compound 20 is also effective at chemosensitizing multiple myeloma cell lines and patient samples to venetoclax, dexamethasone and melphalan. In sum, we report development of selective GLUT4 inhibitors lacking inhibitory activity against GLUT1 and GLUT8. We show that selective pharmacol. inhibition of GLUT4 is feasible and this may represent a novel strategy for the treatment and chemosensitization of multiple myeloma to standard therapeutics.

European Journal of Medicinal Chemistry 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 C13H10O2, Application In Synthesis of 1997-80-4.

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

He, Rong-De published the artcileReductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis, Product Details of C8H17Br, the publication is Angewandte Chemie, International Edition (2022), 61(4), e202114556, database is CAplus and MEDLINE.

Herein a cross-electrophile reaction of alkenyl acetates with alkyl bromides was reported. This work has enabled a new method for the synthesis of aliphatic alkenes from alkenyl acetates to be established that was used to add more structural complexity and mol. diversity with enhanced functionality tolerance. The method allows for a gram-scale reaction and modification of biol. active mols., and it affords access to useful building blocks. Preliminary mechanistic studies revealed that the Ni(I) species plays an essential role for the success of the coupling of these two reactivity-mismatched electrophiles.

Angewandte Chemie, International Edition published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Product Details of C8H17Br.

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

Gao, Feng published the artcileDipolar HCP materials as alternatives to DMF solvent for azide-based synthesis, Application of 4-Bromo-1-(bromomethyl)-2-fluorobenzene, the publication is Green Chemistry (2021), 23(19), 7499-7505, database is CAplus.

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO₃H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN₃ to benzylic azides and 1,2,3-triazoles in EtOH (95%), resp., avoiding the use of risky DMF and improving the separation processes of the products.

Green 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, Application of 4-Bromo-1-(bromomethyl)-2-fluorobenzene.

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

Chen, Fengli published the artcileA comparative study of C₂H₂ adsorption properties in five isomeric copper-based MOFs based on naphthalene-derived diisophthalates, Recommanded Product: 1,3-Dibromonaphthalene, the publication is Dalton Transactions (2017), 46(34), 11469-11478, database is CAplus and MEDLINE.

Five positional isomeric ligands consisting of two peripheral isophthalate moieties attached to the central naphthyl core in different ways, namely, 5,5′-(naphthyl-1,3-diyl)diisophthalate (H₄L1), 5,5′-(naphthyl-1,4-diyl)diisophthalate (H₄L2), 5,5′-(naphthyl-1,5-diyl)diisophthalate (H₄L3), 5,5′-(naphthyl-1,6-diyl)diisophthalate (H₄L4) and 5,5′-(naphthyl-2,6-diyl)diisophthalate (H₄L5), were used to generate five Cu-based MOF isomers. As revealed by single-crystal x-ray diffraction studies, they adopted two different types of topologies depending on the organic ligands: ssa topol. for the MOFs ZJNU-71 and ZJNU-74 based on the ligands H₄L1 and H₄L4, resp., and nbo topol. for the MOFs ZJNU-72, ZJNU-73 and NOTT-103 derived from the ligands H₄L2, H₄L3 and H₄L5, resp. Also, their C₂H₂ adsorption properties were systematically studied, revealing that their different C₂H₂ uptake capacities can be mainly related to their different pore sizes since they possess the same chem. compositions and gravimetric densities of open metal sites. In particular, among these five MOF compounds studied, ZJNU-71 exhibits the highest gravimetric C₂H₂ uptake of 208.1 cm³ (STP) g^-1 at 295 K and 1 atm. The value is also among the highest reported for MOF compounds under the same conditions. This work provides a fundamental understanding of the impact of the positional isomerism of the organic ligands on the structures as well as gas adsorption properties of the resulting MOFs.

Dalton Transactions 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, Recommanded Product: 1,3-Dibromonaphthalene.

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