Category: 939-99-1

Jing, Ke published the artcileVisible-light photoredox-catalyzed carboxylation of benzyl halides with CO₂: Mild and transition-metal-free, HPLC of Formula: 939-99-1, the publication is Chinese Journal of Catalysis (2022), 43(7), 1667-1673, database is CAplus.

The visible-light photoredox-catalyzed carboxylation of benzyl chlorides and bromides with CO₂ has been reported. With inexpensive organic dyes as photocatalysts and amines as electron donors, this carboxylation proceeds well in the absence of sensitive organometallic reagents, transition metal catalysts, or metallic reductants. A wide range of com. available and inexpensive benzyl halides undergo such carboxylation to give valuable aryl acetic acids, including several pharmaceutical mols. and drug precursors, in moderate to high yields. Moreover, this reaction features mild reaction conditions (one atm. pressure of CO₂ and room temperature), broad substrate scope, good functional group tolerance, easy scalability, and low catalyst loading, thus providing an efficient approach for the assembly of aryl acetic acids.

Chinese Journal of Catalysis published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H6ClF3, HPLC of Formula: 939-99-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Liu, Limin published the artcileDesign, synthesis and antitumor activity evaluation of trifluoromethyl-substituted pyrimidine derivatives, Application of 1-(Chloromethyl)-4-(trifluoromethyl)benzene, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 128268, database is CAplus and MEDLINE.

In order to find efficient new antitumor drugs, a series of novel trifluoromethyl-substituted pyrimidine derivatives were designed and synthesized and the bioactivity against four human tumor cells (PC-3, MGC-803, MCF-7 and H1975) was evaluated by MTT assay. Compound I displayed potent anti-proliferative activity on H1975 (IC₅₀ = 2.27 μM), which was better than the pos. control 5-FU (IC₅₀ = 9.37 μM). Further biol. evaluation studies showed that compound I apoptosis of H1975 cells and arrested the cell cycle at G2/M phase. Furthermore, compound I induced H1975 cells apoptosis through increasing the expression of pro-apoptotic proteins Bax and p53 and down-regulating the anti-apoptotic protein Bcl-2. In addition, compound I was able to be tightly embedded in the active pocket of EGFR. These results demonstrated that compound I has a potential as a lead compound for further investigation.

Bioorganic & Medicinal Chemistry Letters published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H6ClF3, Application of 1-(Chloromethyl)-4-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Li, Zhen published the artcileA tautomeric ligand enables directed C-H hydroxylation with molecular oxygen, Computed Properties of 939-99-1, the publication is Science (Washington, DC, United States) (2021), 372(6549), 1452-1457, database is CAplus and MEDLINE.

Hydroxylation of aryl carbon-hydrogen bonds with transition metal catalysts has proven challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to carboxylic acids. IR, x-ray, and computational anal. support a possible role of ligand tautomerization from mono-anionic (L,X) to neutral (L,L) coordination in the catalytic cycle of aerobic carbon-hydrogen hydroxylation reaction. The conventional site selectivity dictated by heterocycles is overturned by this catalyst, thus allowing late-stage modification of compounds of pharmaceutical interest at previously inaccessible sites.

Science (Washington, DC, United States) published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H6ClF3, Computed Properties of 939-99-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Zhang, Xiao published the artcileDesign, Synthesis, and Synergistic Activity of Eight-Membered Oxabridge Neonicotinoid Analogues, Safety of 1-(Chloromethyl)-4-(trifluoromethyl)benzene, the publication is Journal of Agricultural and Food Chemistry (2021), 69(10), 3005-3014, database is CAplus and MEDLINE.

Insecticide synergists are sought-after due to their potential in improving the pesticide control efficacy with a reduced dose of an active ingredient. We previously reported that a cis-configuration neonicotinoid (IPPA08) exhibited specific synergistic activity toward neonicotinoid insecticides. In this study, we synthesized a series of structural analogs of IPPA08 by converting the pyridyl moiety of IPPA08 into Ph groups, via facile double-Mannich condensation reactions between nitromethylene compounds and glutaraldehyde. All of the oxabridged neonicotinoid compounds were found to increase the toxicity of imidacloprid against Aphis craccivora. Notably, compound (I) at 0.75 mg/L lowered the LC₅₀ value of imidacloprid against A. craccivora by 6.54-fold, while a 3.50-fold reduction of the LC₅₀ value was observed for IPPA08. The results of bee toxicity test showed that compound I display selectivity in its effects on imidacloprid toxicity against the honey bee (Apis mellifera L.). In summary, replacing the pyridyl ring with a Ph ring was a viable approach to obtain a novel synergist with oxabridged moiety for neonicotinoid insecticides.

Journal of Agricultural and Food Chemistry published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H17Br, Safety of 1-(Chloromethyl)-4-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Li, Zhong-Rui published the artcileExperience-based discovery (EBD) of aryl hydrazines as new scaffolds for the development of LSD1/KDM1A inhibitors, Safety of 1-(Chloromethyl)-4-(trifluoromethyl)benzene, the publication is European Journal of Medicinal Chemistry (2019), 432-444, database is CAplus and MEDLINE.

Phenelzine was first employed to design new aryl hydrazine-based LSD1 inhibitors based on the experience-based discovery (EBD) strategy. Among these compounds, D8 potently inhibited LSD1 (IC₅₀ = 882.30 nM) in a reversible manner. Compound D8 was selective to LSD1 over MAO-A/B and showed H3K4me2 competitive binding to LSD1. The interaction between H3K4me2 and LSD1 was also confirmed by the Co-IP assay. In LSD1 overexpressed A549 cells, compound D8 dose-dependently induced accumulation of LSD1 substrates H3K4me1/2 and H3K9me1/2, showed cellular target engagement to LSD1 and significantly inhibited cell migration of A549 cells. Docking studies suggested that compound D8 occupied the peptide binding region and therefore blocked the access of the peptide substrate to the FAD, finally leading to the demethylase activity inhibition of LSD1. The findings indicate that aryl hydrazines are new scaffolds for the design of LSD1 inhibitors, the identification of D8 provides further evidence for our previously proposed general principle that fused heterocycles with an amine group are potentially active toward LSD1 by competitive binding to LSD1 with H3 peptide substrates.

European Journal of Medicinal Chemistry published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H6ClF3, Safety of 1-(Chloromethyl)-4-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Chen, Ming-Tsz published the artcileN-Heterocyclic carbene-palladium complexes for Suzuki-Miyaura coupling reaction with benzyl chloride and aromatic boronic acid leading to diarylmethanes, Name: 1-(Chloromethyl)-4-(trifluoromethyl)benzene, the publication is Applied Organometallic Chemistry (2019), 33(6), n/a, database is CAplus.

A family of N-heterocyclic carbene-palladium(II)-N,N-dimethylbenzylamine complexes ((NHC)LPdCl₂; L = N,N-dimethylbenzylamine) was synthesized as well as characterized using single-crystal X-ray diffraction and spectroscopic data. These complexes exhibited higher catalytic activities for Suzuki-Miyaura coupling of benzyl chlorides with arylboronic acids to afford diarylmethanes under milder conditions. Using the optimum conditions, the expected coupling products were obtained in moderate to high yields.

Applied Organometallic Chemistry published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H6ClF3, Name: 1-(Chloromethyl)-4-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wang, Shuai published the artcileStructure-Based Design, Synthesis, and Biological Evaluation of New Triazolo[1,5-a]Pyrimidine Derivatives as Highly Potent and Orally Active ABCB1 Modulators, Computed Properties of 939-99-1, the publication is Journal of Medicinal Chemistry (2020), 63(24), 15979-15996, database is CAplus and MEDLINE.

ABCB1 is a promising therapeutic target for overcoming multidrug resistance (MDR). In this work, we reported the structure-based design of triazolo[1,5-a]pyrimidines as new ABCB1 modulators, of which WS-691 significantly increased sensitization of ABCB1-overexpressed SW620/Ad300 cells to paclitaxel (PTX) (IC₅₀ = 22.02 nM). Mechanistic studies indicated that WS-691 significantly increased the intracellular concentration of PTX and [³H]-PTX while decreasing the efflux of [³H]-PTX in SW620/Ad300 cells by inhibiting the efflux function of ABCB1. The cellular thermal shift assay suggested that WS-691 could stabilize ABCB1 by directly binding to ABCB1. WS-691 could stimulate the activity of ABCB1 ATPase but had almost no inhibitory activity against CYP3A4. Importantly, WS-691 increased the sensitivity of SW620/Ad300 cells to PTX in vivo without observed toxicity. Collectively, WS-691(I) is a highly potent and orally active ABCB1 modulator capable of overcoming MDR. The triazolo[1,5-a]pyrimidine may be a promising scaffold for developing more potent ABCB1 modulators.

Journal of Medicinal Chemistry published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C13H10O3, Computed Properties of 939-99-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Xu, Sheng published the artcileNi-Catalyzed Reductive Arylacylation of Alkenes toward Carbonyl-Containing Oxindoles, Computed Properties of 939-99-1, the publication is Organic Letters (2019), 21(18), 7498-7503, database is CAplus and MEDLINE.

Using iso-Bu chloroformate as a carbon monoxide equivalent, N-(bromoaryl) α-substituted acrylamides such as I underwent reductive arylacylation reactions with alkyl iodides such as iodocyclohexane or benzylic chlorides in the presence of NiBr₂(DME), and 4,4′-dimethyl-2,2′-bipyridine using manganese or zinc as reductant in 1:1 DMA:THF to yield oxoalkyl oxindoles such as II. The mechanism was studied using an alkyl iodide susceptible to radical cyclization and stoichiometric reaction of a oxindolylmethyl nickel complex; a mechanism involving reaction of alkyl radicals with nickel complexes is proposed. Reaction using a nonracemic octahydrobinaphthyl phosphoramidate ligand yielded product in 8% yield and 50% ee.

Organic Letters published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C22H32O2, Computed Properties of 939-99-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Ma, Xufeng published the artcileMixed Alkyl/Aryl Diphos Ligands for Iron-Catalyzed Negishi and Kumada Cross Coupling Towards the Synthesis of Diarylmethane, SDS of cas: 939-99-1, the publication is ChemCatChem (2021), 13(24), 5134-5140, database is CAplus.

Mixed alkyl/aryl diphos ligands have been prepared and their application in iron-catalyzed cross coupling of benzylic chlorides with diaryl zinc (Negishi) or aryl Grignard reagents (Kumada) towards the synthesis of diarylmethane has been evaluated. The iron-diphos catalytic system exhibited the enhanced activity and selectivity in the two coupling reactions. The electron-rich mixed PPh₂/PCy₂ ligands outperformed their sym. PPh₂ congeners, and led to decreased homocoupling byproduct formation. It indicates that the electronic effect of the ligands plays an important role in the catalytic performance. The Fe catalyst bearing an electron-rich PCy₂ substituent and a sterically demanding tert-Bu on ethene backbone exhibited the best catalytic performance and good functional group tolerance in the two cross coupling reactions.

ChemCatChem published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H6ClF3, SDS of cas: 939-99-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wang, Shuai published the artcileDiscovery of [1,2,4]triazolo[1,5-a]pyrimidine derivatives as new bromodomain-containing protein 4 (BRD4) inhibitors, COA of Formula: C8H6ClF3, the publication is Chinese Chemical Letters (2020), 31(2), 418-422, database is CAplus.

Targeting bromodomain-containing protein 4 (BRD4) has been proved to be an effective strategy for cancer therapy. To date, numerous BRD4 inhibitors and degraders have been identified, some of which have advanced into clin. trials. In this work, a focused library of new [1,2,4]triazolo[1,5-a]pyrimidine derivatives were discovered to be able to inhibit BRD4. WS-722 inactivated BRD4 (BD1/BD2), BRD2 (BD1/BD2) and BRD3 (BD1/BD2) broadly with the IC₅₀ values less than 5μmol/L. Besides, WS-722 inhibited growth of THP-1 cells with an IC₅₀ value of 3.86μmol/L. Like (+)-JQ1, WS-722 inhibited BRD4 in a reversible manner and enhanced protein stability. Docking studies showed that WS-722 occupied the central acetyl-lysine (Kac) binding cavity and formed a hydrogen bond with Asn140. In THP-1 cells, WS-722 showed target engagement to BRD4. Cellular effects of WS-722 on THP-1 cells were also examined, showing that WS-722 could block c-MYC expression, induce G0/G1 phase arrest and p21 up-regulation, and promote differentiation of THP-1 cells. BRD4 inhibition by WS-722 resulted in cell apoptosis and up-regulated expression of cleaved caspased-3/7 and PARP in THP-1 cell lines. The [1,2,4]triazolo[1,5-a]pyrimidine is a new template for the development of new BRD4 inhibitors.

Chinese Chemical Letters published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H15ClN2, COA of Formula: C8H6ClF3.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics