Author: Jessica.F

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

Boardman, Larry D. published the artcileMetal promoted cyclization. 5. Mechanistic duality in cycloalkylation of alkenylmetal derivatives, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of the American Chemical Society (1984), 106(20), 6105-7, database is CAplus.

Cycloalkylation of ω-halo-1-alkenylmetals can proceed by either a σ- or a π-type cyclization process. The σ-process, observed with alkenyllithium derivatives, is applicable to the formation of four- through seven-membered cycloalkenes. It does not require the second metal, e.g., Si, but requires the cis relationship between Li and the cyclizing moiety, and is regiospecific. The required (Z)-1-iodo-ω-bromo-1-alkenes may conveniently be prepared via carbometalation of alkynes with alkenylmetals followed by iodinolysis, treatment with (Me₂CHCH₂)₃Al-Cl₂ZrCp₂, and brominolysis with NBS. On the other hand, the π-process, observed with 1,1-dimetallo-ω-halo-1-alkenes (I, M¹ = Al, Zn, Zr, Si; M² = Si, Zn, Al, Zr; R = H, alkyl; X = halo) has been applied to the synthesis of three-, four-, and six-membered cycloalkenes, the relative ease of cyclization being 3, 4 ≫ 5 < 6. This process seems to require two metals, but the alkene geometry is unimportant. It can be regioselective but nonregiospecific.

Journal of the American Chemical Society published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Alonso, Diego A. published the artcile3,5-Bis(trifluoromethyl)phenyl sulfones in the synthesis of 3,5-disubstituted cyclopent-2-enones, Category: bromides-buliding-blocks, the publication is ARKIVOC (Gainesville, FL, United States) (2007), 243-262, database is CAplus.

3,5-Bis(trifluoromethyl)phenyl sulfones {BTFP sulfones; 3,5-(CF₃)₂C₆H₃S(O)₂CH₂R; R = Ph, C₆H₄NO₂-4, CO₂ⁱPr, CN, P(O)(OEt)₂; 1a–e}, easily synthesized from 3,5-bis(trifluoromethyl)benzenethiol, react under PTC with (Z)-1,4-dichloro-2-butene to afford the cyclopentenyl sulfones {3; 4-(3,5-(CF₃)₂C₆H₃S(O)₂)-4-Rcyclopentene}, which suffer further diastereoselective alkene epoxidation with MCPBA giving BTFP sulfonyl cyclopentene oxides with the dominant isomer having the sulfonyl away from the oxygen bridge in good yields. These epoxides are convenient precursors of 3,5-disubstituted cyclopent-2-enones (e.g. 5-bromo-3-phenyl-2-cyclopenten-1-one), which result from epoxide ring-opening with different nucleophiles and final successive oxidation-BTFP sulfinate elimination.

ARKIVOC (Gainesville, FL, United States) published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Category: bromides-buliding-blocks.

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

Mashat, Khlood H. published the artcileSynthesis, structures, DNA-binding and anticancer activities of some copper(I)-phosphine complexes, Recommanded Product: Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I), the publication is Polyhedron (2019), 164-172, database is CAplus.

Copper(I) complexes with a phenanthroline-phosphine set of ligands were synthesized by refluxing methanolic solutions of CuBr₂ with at least a four fold molar excess of the phosphine ligands, followed by the treatment of the formed {CuBr(PR₃)₃ complexes [R = Ph (1a), 4-fluorophenyl (1b), cyclohexyl (1c) or 4-methoxyphenyl (1d)]} with 1 molar equivalent of 1,10-phenanthroline in DCM. The tris(4-methoxyphenyl)phosphine ligand afforded [Cu(P[C₆H₄-4-OMe]₃)₂(phen)]Br (2d), while the other phosphines produced complexes CuBr(PR₃)(phen) [R = Ph (2a), 4-fluorophenyl (2b) or cyclohexyl (2c)]. The new complexes were characterized by elemental anal., ³¹P NMR spectroscopy and mass spectrometry. Addnl. confirmation of the structures of 1b, 2b, 2c and 2d were determined by single crystal x-ray diffraction. A DNA-binding study of the complexes 2a–2d against ct-DNA showed binding constant values that correspond to the intercalation mode of binding. The notable variations in the binding constants of the complexes suggest some contribution from the phosphine ligands. The lipophilicity of the complexes was evaluated theor. and the calculated log P value of complex 2d is pos. and high, being in the same range of relatively easy membrane penetrating drugs. The calculated log P values of complexes 2a–2c are neg., indicating a low membrane permeability. Complexes 2a–2d were examined against four different cancer cell lines. The choice of the phosphine ligand appears to influence the copper(I)-phosphine anticancer activities against the different cancer cell lines. The data suggested that complexes 2a and 2d show potential anticancer activity against prostate and breast cancers. The four copper complexes were docked against four different proteins associated with prostate or breast cancers activities, highlighting some of the structural-DNA interactions.

Polyhedron published new progress about 25753-84-8. 25753-84-8 belongs to bromides-buliding-blocks, auxiliary class Copper, name is Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I), and the molecular formula is C30H24BrCuN2P, Recommanded Product: Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I).

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

Wang, Kai published the artcileSolvent Annealing Effects in Dithieno[3,2-b:2′,3′-d]pyrrole-5,6-Difluorobenzo[c][1,2,5]thiadiazole Small Molecule Donors for Bulk-Heterojunction Solar Cells, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene, the publication is Chemistry of Materials (2016), 28(15), 5415-5425, database is CAplus.

Low-bandgap small mol. (SM) donors that can be solution-processed with fullerene acceptors (e.g., PC₆₁/₇₁BM) are proving to be particularly promising in bulk-heterojunction (BHJ) solar cells. Compared to their π-conjugated polymer counterparts, SM donors are well-defined (monodisperse) and more synthetically modular, with relatively wide ranges of bandgaps that can be achieved in stepwise couplings of various donor and acceptor motifs. However, the optimization of SM-fullerene morphologies and BHJ device efficiencies relies more specifically on the use of processing additives, postprocessing thermal, or solvent vapor annealing (SVA) approaches, and achieving adequate interpenetrating networks and structural order in BHJ thin films can be challenging. In this report, we examine the correlated effects of mol. structure and postprocessing SVA on the BHJ solar cell performance of a set of π-extended SM donors composed of dithieno[3,2-b:2′,3′-d]pyrrole (DTP) and 5,6-difluorobenzo[c][1,2,5]thiadiazole ([2F]BT) units. In these systems (SM1-SM3), the introduction of addnl. alkyl substituents and unsubstituted thiophene rings on the peripheral unit groups critically impacts the effects of SVA steps on BHJ solar cell efficiency. We show that the more π-extended and alkyl-substituted analog SM3 stands out, with BHJ device efficiencies of ∼6% obtained from SVA with CS₂, while SVA-treated SM3-based active layers also show the most favorable ordering and carrier mobility patterns. However, unlike numbers of SM donors reported in recent years, DTP-[2F]BT SM analogs are in general not prone to dramatic performance variations in BHJ thin films cast with processing additives. Our results indicate that the role of SVA steps is not independent of the mol. structure of the SM donors used in the BHJ solar cells.

Chemistry of Materials 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 C3H5F3O, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene.

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

Zhang, Yanbing published the artcileNear-Infrared Fluorescent Thienothiadiazole Dyes with Large Stokes Shifts and High Photostability, Formula: C4Br2N2O4S, the publication is Journal of Organic Chemistry (2017), 82(11), 5597-5606, database is CAplus and MEDLINE.

A series of near-IR (NIR) organic emissive materials were synthesized and the photophys. properties analyzed. The donor-acceptor-donor materials were designed with thienopyrazine and thienothiadiazole acceptor groups with thiophene-, furan-, and triphenylamine-based donor groups. The absorption and emission spectra were found to be widely tunable on the basis of the donor and acceptor groups selected. Computational anal. confirms these materials undergo an intramol. charge-transfer event upon photoexcitation. Large Stokes shifts of ∼150 nm were observed and rationalized by computational anal. of geometry changes in the excited state. Fluorescence studies on the dye series reveal maximum peak emission wavelengths near 900 nm and a quantum yield exceeding 16% for 4,6-bis(2-thienyl)thieno[3,4-c][1,2,5]thiadiazole. Addnl., several dyes were found to have reasonable quantum yields within this NIR region (>1%), with emission wavelengths reaching 1000 nm at the emission curve onset. Photostability studies were conducted on these materials in an ambient oxygen environment, revealing excellent stability in the presence of oxygen from all the dyes studied relative to a benchmark cyanine dye (ICG) during photoexcitation with exceptional photostability from the 4,6-bis(5′-dodecyl-[2,2′-bithiophene]-5-yl)thieno[3,4-c][1,2,5]thiadiazole derivative

Journal of Organic Chemistry published new progress about 52431-30-8. 52431-30-8 belongs to bromides-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 2,5-Dibromo-3,4-dinitrothiophene, and the molecular formula is C5H10O, Formula: C4Br2N2O4S.

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

Gopalsamy, Ariamala published the artcilePF-07059013: A Noncovalent Modulator of Hemoglobin for Treatment of Sickle Cell Disease, Name: 2-Amino-5-bromo-3-fluorobenzaldehyde, the publication is Journal of Medicinal Chemistry (2021), 64(1), 326-342, database is CAplus and MEDLINE.

Sickle cell disease (SCD) is a genetic disorder caused by a single point mutation (β6 Glu → Val) on the β-chain of adult Hb (HbA) that results in sickled Hb (HbS). In the deoxygenated state, polymerization of HbS leads to sickling of red blood cells (RBC). Several downstream consequences of polymerization and RBC sickling include vaso-occlusion, hemolytic anemia, and stroke. We report the design of a noncovalent modulator of HbS, clin. candidate PF-07059013 (23). The seminal hit mol. was discovered by virtual screening and confirmed through a series of biochem. and biophys. studies. After a significant optimization effort, we arrived at 23, a compound that specifically binds to Hb with nanomolar affinity and displays strong partitioning into RBCs. In a 2-wk multiple dose study using Townes SCD mice, 23 showed a 37.8% (±9.0%) reduction in sickling compared to vehicle treated mice. 23 (PF-07059013) has advanced to phase 1 clin. trials.

Journal of Medicinal Chemistry published new progress about 906811-51-6. 906811-51-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Amine,Benzene,Aldehyde, name is 2-Amino-5-bromo-3-fluorobenzaldehyde, and the molecular formula is C7H5BrFNO, Name: 2-Amino-5-bromo-3-fluorobenzaldehyde.

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