Month: November 2022

Akiyama, Sota published the artcileA Copper(I)-Catalyzed Radical-Relay Reaction Enabling the Intermolecular 1,2-Alkylborylation of Unactivated Olefins, Recommanded Product: Ethylbromofluoroacetate, the publication is Journal of the American Chemical Society (2021), 143(13), 5260-5268, database is CAplus and MEDLINE.

The 1st catalytic intermol. 1,2-alkylborylation reaction via a radical-relay mechanism between unactivated olefins, bis(pinacolato)diboron, and an alkyl electrophile is reported. Successful implementation of this method requires that the competing boryl substitution of the alkyl electrophile is retarded to facilitate the radical relay. This challenge was overcome using electronically or sterically demanding alkyl electrophiles, which results in the simultaneous and highly regioselective introduction of a gem-difluoro, monofluoro, tertiary, or secondary alkyl group and a boryl group across the C:C double bond.

Journal of the American Chemical Society 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, Recommanded Product: Ethylbromofluoroacetate.

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

Okuda, Shogo published the artcileSupramolecular Helical Assemblies of Dirhodium(II) Paddlewheels with 1,4-Diazabicyclo[2.2.2]octane: A Remarkable Substituent Effect on the Helical Sense Preference and Amplification of the Helical Handedness Excess of Metallo-Supramolecular Helical Polymers, Product Details of C12H25Br, the publication is Journal of the American Chemical Society (2022), 144(6), 2775-2792, database is CAplus and MEDLINE.

Authors report unique coordination-driven supramol. helical assemblies of a series of dirhodium(II) tetracarboxylate paddlewheels bearing chiral Ph or Me substituted amide-bound m-terphenyl residues with triethylene glycol monomethyl ether (TEG) or n-dodecyl tails through a 1:1 complexation with 1,4-diazabicyclo[2.2.2]octane (DABCO). The chiral dirhodiums with DABCO in CHCl₃/n-hexane (1/1) form one-handed helical coordination polymers with a controlled propeller chirality at the m-terphenyl groups stabilized by intermol. hydrogen-bonding networks between the adjacent amide groups at the periphery mainly via a cooperative nucleation/elongation mechanism as supported by CD and vibrational CD along with variable-temperature (VT) absorption and CD anal. The VT visible-absorption titrations revealed the temperature-dependent changes in the degree of polymerizations The columnar supramol. helical structures were elucidated by x-ray diffraction and at. force microscopy. The helix-sense of the homopolymer carrying the bulky Ph and n-dodecyl substituents is opposite to those of other chiral homopolymers despite the same absolute configuration at the pendants. A remarkably strong “sergeants and soldiers” (S&S) effect was observed in most of the chiral/achiral copolymers, while the copolymers with the chiral bulky phenyl-substituted dirhodiums with n-dodecyl chains displayed an “abnormal” S&S effect accompanied by inversion of the helix-sense, which can be switched to a “normal” S&S effect by changing the solvent composition A nonracemic dirhodium complex of 20% enantiomeric excess bearing the less bulky chiral Me substituents with n-dodecyl chains assembled with DABCO to form an almost one-handed helix (the “majority rule” (MR) effect), whereas the three other nonracemic copolymers showed a weak MR effect.

Journal of the American Chemical Society published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C12H25Br, Product Details of C12H25Br.

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

Suzuki, Takayoshi published the artcileRapid Discovery of Highly Potent and Selective Inhibitors of Histone Deacetylase 8 Using Click Chemistry to Generate Candidate Libraries, Application In Synthesis of 1997-80-4, the publication is Journal of Medicinal Chemistry (2012), 55(22), 9562-9575, database is CAplus and MEDLINE.

To find HDAC8-selective inhibitors, we designed a library of HDAC inhibitor candidates, each containing a zinc-binding group that coordinates with the active-site zinc ion, linked via a triazole moiety to a capping structure that interacts with residues on the rim of the active site. These compounds were synthesized by using click chem. Screening identified HDAC8-selective inhibitors including (I) (IC₅₀ = 0.070 μM), which was more potent than PCI-34058 (IC₅₀ = 0.31 μM), a known HDAC8 inhibitor. Mol. modeling suggested that the phenylthiomethyl group of I binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin in cells and exerted growth-inhibitory effects on T-cell lymphoma and neuroblastoma cells (GI₅₀ = 3-80 μM). These findings suggest that HDAC8-selective inhibitors have potential as anticancer agents.

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 C9H9BrO2, Application In Synthesis of 1997-80-4.

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

Zin, Nor Farah Hani Md published the artcileCytotoxicity of asymmetric mononuclear silver(I)-N-heterocyclic carbene complexes against human cervical cancer: Synthesis, crystal structure, DFT calculations and effect of substituents, Synthetic Route of 143-15-7, the publication is Journal of Organometallic Chemistry (2022), 122439, database is CAplus.

A new series of asym. N,N’-disubstituted benzimidazolium derived N-heterocyclic carbene (NHC) ligands and their mononuclear silver(I)-NHC complexes are reported. The ligands were prepared from N-alkylation of 1-methylbenzimidazole with alkyl bromides (n = 10-18 in even parity), non-fluorinated or fluorinated benzyl bromides. In situ deprotonation of the ligands with silver oxide, followed by metathesis reaction with potassium hexafluorophosphate facilitated the formation of the mononuclear silver(I)-NHC complexes. Chem. structures of all the compounds were elucidated using Fourier transform IR, ¹H and ¹³C NMR (NMR) spectroscopy, and CHN elemental microanal. The coordination mode of the Ag(I)-NHC complexes was confirmed by single crystal XRD anal. Single crystal anal. of ortho-fluorinated benzyl-containing complex showed that each complex consisted of one Ag(I) ion coordinated with two NHC ligands in a linear geometry in the presence of one PF^–₆ anion in the lattice. Cytotoxic effects of the NHC ligands and their silver(I) complexes against human cervical cancer cells (HeLa) and normal human skin fibroblasts (Hs27) were investigated using the MTT assay. Cytotoxicity of these compounds was dependent on the N-substituents in the benzimidazolium moiety and the presence of silver ions. Benzylated ligands were non-active while their dialkylated analogs showed weak to excellent cytotoxic effects on HeLa cells. The incorporation of silver ions and elongation of alkyl chains significantly enhanced cytotoxicity. D. functional theory revealed that Ag-C bond strength was insensitive to the NHC ligand design, and about one-third of the overall complex binding enthalpy was contributed by the non-covalent interaction between the long alkyl chains. Long-chain ligands (n = 16-18) and all silver(I)-NHC complexes exhibited superior cytotoxicity against HeLa cells (IC₅₀ ranged between 1.18μM-9.38μM) as compared to that of the anticancer drug, Etoposide (IC₅₀ = 25.67μM).

Journal of Organometallic Chemistry published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C13H19Br2ClN2O, Synthetic Route of 143-15-7.

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

Bendale, Pravin published the artcileSecond Generation Tetrahydroquinoline-Based Protein Farnesyltransferase Inhibitors as Antimalarials, Product Details of C3H7BrO2S, the publication is Journal of Medicinal Chemistry (2007), 50(19), 4585-4605, database is CAplus and MEDLINE.

Substituted tetrahydroquinolines (THQs) have been previously identified as inhibitors of mammalian protein farnesyltransferase (PFT). Previously it was shown that blocking PFT in the malaria parasite led to cell death and that THQ-based inhibitors are the most potent among several structural classes of PFT inhibitors (PFTIs). THQ-based PFTIs, e.g., I, were synthesized and several compounds were discovered that inhibit the malarial enzyme in the sub- to low-nanomolar range and that block the growth of the parasite (P. falciparum) in the low-nanomolar range. This body of structure-activity data can be rationalized in most cases by consideration of the X-ray structure of one of the THQs bound to mammalian PFT together with a homol. structural model of the malarial enzyme. The results of this study provide the basis for selection of antimalarial PFTIs for further evaluation in preclin. drug discovery assays.

Journal of Medicinal Chemistry published new progress about 16523-02-7. 16523-02-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Sulfone,Aliphatic hydrocarbon chain, name is 2-Bromoethyl Methyl Sulfone, and the molecular formula is C3H7BrO2S, Product Details of C3H7BrO2S.

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

Pokorny, Jan published the artcileSubstituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters, Application In Synthesis of 76283-09-5, the publication is European Journal of Medicinal Chemistry (2021), 113706, database is CAplus and MEDLINE.

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Four compounds had IC₅₀ below 5μmol/L; I and II were selected for studies of the mechanism of action. Cell cycle anal. revealed an increase in the number of apoptotic cells at 5 x IC₅₀ concentration, where activation of irreversible changes leading to cell death can be expected. Both I and II led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 x IC₅₀ and almost complete inhibition at 5 x IC₅₀. Interestingly, compound II at 5 x IC₅₀ caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds I and II trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacol. parameters of derivative I were superior to II, therefore I was the finally selected candidate for the development of anticancer drug.

European 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, Application In Synthesis of 76283-09-5.

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

Kakinami, Takaaki published the artcileHalogenation using quaternary ammonium polyhalides. XXV. Bromination of acetanilides with benzyltrimethylammonium tribromide-zinc chloride system, Formula: C10H16Br3N, the publication is Nippon Kagaku Kaishi (1990), 705-8, database is CAplus.

The reaction of acetanilides with equimolar amounts of PhCH₂N⁺Me₃ Br₃^– and ZnCl₂ in AcOH under mild conditions gave the bromo-substituted acetanilides in good yields. E.g., AcNHC₆H₃Me₂-3,5 gave 99% AcNHC₆HBr₂Me₂-2,4,3,5.

Nippon Kagaku Kaishi published new progress about 111865-47-5. 111865-47-5 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, and the molecular formula is C10H16Br3N, Formula: C10H16Br3N.

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

Miura, Yozo published the artcileSyntheses and Characterization of Poly(1,3-phenylene-2-amino-1,3-phenylene)s and Dimer and Tetramer Model Compounds, HPLC of Formula: 111865-47-5, the publication is Macromolecules (1998), 31(7), 2041-2046, database is CAplus.

The Pd-catalyzed cross-coupling polycondensation of 2,6-dibromoaniline or 2,6-dibromo-4-tert-butylaniline with 1,3-phenylenebis(trimethylene boronate) in benzene-water in the presence of K₂CO₃ and Bu₄NCl gave poly(1,3-phenylene-2-amino-1,3-phenylene)s in 56-86% yields. The number average mol. weights of the poly(1,3-phenylene)s determined by GPC using styrene standards are 2500-5720, which correspond to the d.p. of 15.0-25.6. The thermal stabilities of the polyphenylenes were evaluated by thermal gravimetry. The corresponding dimer and tetramer model compounds of poly(1,3-phenylene-2-amino-1,3-phenylene)s were prepared, and their properties were compared with those of the poly(1,3-phenylene)s.

Macromolecules published new progress about 111865-47-5. 111865-47-5 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, and the molecular formula is C10H16Br3N, HPLC of Formula: 111865-47-5.

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

Herberich, Gerhard E. published the artcileDerivatives of borole. V. Synthesis of [1-(diisopropylamino)borole]metal complexes and the Diels-Alder dimer of 1-(diisopropylamino)borole, Category: bromides-buliding-blocks, the publication is Chemische Berichte (1985), 118(11), 4303-13, database is CAplus.

Oxidation of Li [1-(diisopropylamino)borolenediide] (I) with SnCl₂ forms the Diels-Alder dimer II. I is a versatile reagent for the formation of [1-(diisopropylamino)borole]metal complexes. Suitable substrates are metal halides (CoBr₃·DME, NiCl₂·DME), organometallic metal halides, and simple metal halides in the presence of CO. Thermal reactions of II with carbonyl compounds may also give borole complexes. Fifteen compounds of Cr, Mn, Fe, Co, Ni, Ru, and Rh, including triple-decked complexes, are described.

Chemische Berichte published new progress about 18346-57-1. 18346-57-1 belongs to bromides-buliding-blocks, auxiliary class Cobalt, name is Cobalt(II) dibromo(1,2-dimethoxyethane), and the molecular formula is C4H10Br2CoO2, Category: bromides-buliding-blocks.

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

Kitagawara, Yumina published the artcileNovel bioactivation pathway of benzbromarone mediated by cytochrome P450, Application of Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, the publication is Drug Metabolism & Disposition (2015), 43(9), 1303-1306, database is CAplus and MEDLINE.

Benzbromarone (BBR) is a hepatotoxic drug, but the detailed mechanism of its toxicity remains unknown. We identified 2,6-dibromohydroquinone (DBH) and mono-debrominated catechol (2-ethyl-3-(3-bromo-4,5-dihydroxybenzoyl)benzofuran; CAT) as novel metabolites of BBR in rat and human liver microsomal systems by comparison with chem. synthesized authentic compounds, and we also elucidated that DBH is formed by cytochrome P 450 2C9 and that CAT is formed mainly by CYP1A1, 2D6, 2E1, and 3A4. Furthermore, CAT, DBH, and the oxidized form of DBH are highly cytotoxic in HepG2 compared with BBR. Taken together, our data demonstrate that DBH, a novel reactive metabolite, may be relevant to BBR-induced hepatotoxicity.

Drug Metabolism & Disposition published new progress about 111865-47-5. 111865-47-5 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, and the molecular formula is C10H16Br3N, Application of Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide.

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