Category: 6850-57-3

Das, Amrita published the artcileRh(I)-catalyzed imine-directed C-H functionalization via the oxidative [3+2] cycloaddition of benzylamine derivatives with maleimides, Application In Synthesis of 6850-57-3, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(8), 1123-1126, database is CAplus and MEDLINE.

The Rh(I)-catalyzed imine-directed oxidative [3+2] cycloaddition of benzylamines derivatives with maleimides for synthesis of pyrrolopyrroles I [R = Ph, 2-thienyl, cyclohexyl, etc.; R¹ = H, Me, Bn, etc.] was reported. A wide range of both benzylamines derivatives and maleimides was applicable to the reaction. A one-pot three component strategy using benzylamines, 2-pyridinecarboxaldehyde and maleimides was successfully achieved. Mechanistic studies including deuterium labeling experiments suggested that a zwitterionic intermediate was formed and was a key intermediate through the Rh-catalyzed activation of a benzylic C(sp³)-H bond of the imine.

Chemical Communications (Cambridge, United Kingdom) published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Application In Synthesis of 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Das, Amrita published the artcileRh(II)-Catalyzed C-H Alkylation of Benzylamines with Unactivated Alkenes: The Influence of Acid on Linear and Branch Selectivity, HPLC of Formula: 6850-57-3, the publication is Organic Letters (2021), 23(11), 4273-4278, database is CAplus and MEDLINE.

The Rh-catalyzed C-H alkylation of benzylamine derivatives 2RC₆H₄CH₂NHC(O)R¹ (R = Me, methoxy, trifluoromethyl; R¹ = pyridin-2-yl) and I (X = H) with unactivated 1-alkenes R²HC=CH² (R² = pentyl, cyclohexylmethyl, 4-(acetyloxy)butyl, etc.) that proceeds via a picolinamide directing group is reported. The crucial role of an acid additive in this transformation is confirmed. Aromatic acids showed high linear selective products e.g., N-(2-heptyl-6-methylbenzyl)picolinamide, and aliphatic acids provided branched alkylation products e.g., N-(2-(hexan-2-yl)-6-methylbenzyl)picolinamide as the major product. The reaction has a broad scope for benzylamines and alkenes. Deuterium labeling experiments suggest that a Rh-carbene intermediate is involved in the case of linear product formation. A different reaction pathway, however, appears to be involved in the case of branched alkylation products, and this pathway also appeared to be a minor pathway in linear-selective reactions.

Organic Letters published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, HPLC of Formula: 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Tremblay, Marie-Helene published the artcileHybrid Organic Lead Iodides: Role of Organic Cation Structure in Obtaining 1D Chains of Face-Sharing Octahedra vs 2D Perovskites, Formula: C8H11NO, the publication is Chemistry of Materials (2022), 34(3), 935-946, database is CAplus.

R(CH₂)_nNH₃⁺ cations (R = aryl, substituted cyclohexyl; n = 1, 2) can form hybrid lead iodides that include both 2D layered perovskites of formula [R(CH₂)_nNH₃]₂PbI₄ and 1D structures consisting of 1D wires of face-sharing PbI₆ octahedra and having the formula [R(CH₂)_nNH₃]PbI₃ (face-sharing lead-iodide chains, FSLICs). Using a series of such cations we find that 1D FSLIC formation is favored when hydrogen bonding is possible between the ammonium moiety of one cation and a hydrogen-bond acceptor substituent of the same or another cation. A total of 16 new hybrid organic lead iodide crystal structures, 11 of which are FSLICs, are reported. The FSLIC structures can be further categorized according to the arrangement of neighboring wires. The optical properties of these materials are largely insensitive to the identity of the organic cations and to the resulting structural details. However, there is a correlation between the exciton energy and the pattern in which the wires are arranged relative to one another. D. functional theory calculations indicate that the dispersion at the top of the valence band varies depending on the relative wire arrangement.

Chemistry of Materials published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C7H8BFO2, Formula: C8H11NO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Mechouche, N. published the artcileSynthesis and evaluation of the pharmacological activity of open analogues of cromakalim carrying urea and thiourea moieties, Name: (2-Methoxyphenyl)methanamine, the publication is International Journal of Research in Pharmacy and Chemistry (2022), 12(1), 6-24, database is CAplus.

Some new ring-opened analogs of cromakalim I [R¹ = Me, Et, Bn; R² = H, Me; R³ = i-Pr, t-Bu, Ph, etc.; X = H, OMe, Br; Y = O, S] bearing urea and thiourea moieties were synthesized and tested as vasodilators rat trachea and aorta of resp., and as stimulators of elastin synthesis from isolated humain vascular smooth muscle cells. Cromakalim, pinacidil, diazoxide, and verapamil were used as refrences compounds in the vasodilating experiments while diazoxide was used as a reference in the elastin experiments Furthur investigations were undertaken to determine the mechanism of action of the vasodilator activity. The pharmacol. results on rat aorta rings revealed that the most active vasodilator compound was I [R¹ = Et, R² = Me, R³ = 4-CNC₆H₅, X = Br, Y = S] and was almost 15-fold more active than diazoxide, but was 4-fold and 11 folds less active than pinacidil and cromakalim resp. FInvestigations on elastin synthesis showed that diazoxide significantly elevated elastin quantity by 34%.

International Journal of Research in Pharmacy and Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Name: (2-Methoxyphenyl)methanamine.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Luxenburger, Andreas published the artcileDiscovery of AL-GDa62 as a Potential Synthetic Lethal Lead for the Treatment of Gastric Cancer, Synthetic Route of 6850-57-3, the publication is Journal of Medicinal Chemistry (2021), 64(24), 18114-18142, database is CAplus and MEDLINE.

Diffuse gastric cancer and lobular breast cancer are aggressive malignancies that are frequently associated with inactivating mutations in the tumor suppressor gene CDH1. Synthetic lethal (SL) vulnerabilities arising from CDH1 dysfunction represent attractive targets for drug development. Recently, SLEC-11 (1) emerged as a SL lead in E-cadherin-deficient cells. Here, we describe our efforts to optimize 1. Overall, 63 analogs were synthesized and tested for their SL activity toward isogenic mammary epithelial CDH1-deficient cells (MCF10A-CDH1^-/-). Among the 26 compounds with greater cytotoxicity, AL-GDa62 (3)(I) was four-times more potent and more selective than 1 with an EC₅₀ ratio of 1.6. Furthermore, 3 preferentially induced apoptosis in CDH1^-/- cells, and Cdh1^-/- mammary and gastric organoids were significantly more sensitive to 3 at low micromolar concentrations Thermal proteome profiling of treated MCF10A-CDH1^-/- cell protein lysates revealed that 3 specifically inhibits TCOF1, ARPC5, and UBC9. In vitro, 3 inhibited SUMOylation at low micromolar concentrations

Journal of Medicinal Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Synthetic Route of 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Favalli, Nicholas published the artcileLarge screening of DNA-compatible reaction conditions for Suzuki and Sonogashira cross-coupling reactions and for reverse amide bond formation, Safety of (2-Methoxyphenyl)methanamine, the publication is Bioorganic & Medicinal Chemistry (2021), 116206, database is CAplus and MEDLINE.

Progress in DNA-encoded chem. library synthesis and screening crucially relies on the availability of DNA-compatible reactions, which proceed with high yields and excellent purity for a large number of possible building blocks. In the past, exptl. conditions have been presented for the execution of Suzuki and Sonogashira cross-coupling reactions on-DNA. In this article, our aim was to optimize Suzuki and Sonogashira reactions, comparing our results to previously published procedures. We have tested the performance of improved conditions using 606 building blocks (including boronic acids, pinacol boranes and terminal alkynes), achieving >70% conversion for 84% of the tested mols. Moreover, we describe efficient exptl. conditions for the on-DNA synthesis of amide bonds, starting from DNA derivatives carrying a carboxylic acid moiety and 300 primary, secondary and aromatic amines, as amide bonds are frequently found in DNA-encoded chem. libraries thanks to their excellent DNA compatibility.

Bioorganic & Medicinal Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Safety of (2-Methoxyphenyl)methanamine.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Penthala, Narsimha R. published the artcileAntitumor properties of novel sesquiterpene lactone analogs as NFκB inhibitors that bind to the IKKβ ubiquitin-like domain (ULD), SDS of cas: 6850-57-3, the publication is European Journal of Medicinal Chemistry (2021), 113675, database is CAplus and MEDLINE.

Melampomagnolide B (MMB) is a parthenolide (PTL) based sesquiterpene lactone that has been used as a template for the synthesis of a plethora of lead anticancer agents owing to its reactive C-10 primary hydroxyl group. Such compounds have been shown to inhibit the IKKβ subunit, preventing phosphorylation of the cytoplasmic IκB inhibitory complex. The present study focuses on the synthesis and in vitro antitumor properties of novel benzyl and phenethyl carbamates of MMB. Screening of these MMB carbamates identified analogs with potent growth inhibition properties against a panel of 60 human cancer cell lines (71% of the mols. screened had GI₅₀ values < 2μM). Two analogs, the 4-methoxybenzyl carbamate (I) and the 4-bromophenethyl carbamate, were the most active compounds Lead compound I inhibited cell proliferation in M9 ENL AML cells, and in TMD-231, OV-MD-231 and SUM149 breast cancer cell lines. Interestingly, mechanistic studies showed that I did not inhibit p65 phosphorylation in M9 ENL AML and OV-MD-231 cells, but did inhibit phosphorylation of both p65 and IκBα in SUM149 cells. 4-Methoxybenzyl carbamate also reduced NFκB binding to DNA in both OV-MD-231 and SUM149 cells. Mol. docking studies indicated that I and the 4-bromophenethyl carbamate are both predicted to interact with the ubiquitin-like domain (ULD) of the IKKβ subunit. These data suggest that in SUM149 cells, I is likely acting as an allosteric inhibitor of IKKβ, whereas in M9 ENL AML and OV-MD-231 cells. 4-Methoxybenzyl carbamate is able to inhibit an event after IκB/p65/p50 phosphorylation by IKKβ that leads to inhibition of NFκB activation and reduction in NFκB-DNA binding. The 4-methoxybenzyl carbamate analog I was by far the most potent compound in either carbamate series, and was considered an important lead compound for further optimization and development as an anticancer agent.

European Journal of Medicinal Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, SDS of cas: 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Lim, Su-Jin published the artcileTraceless Solid-Phase Synthesis of 7-Aminothiazolo[4,5-d]pyrimidine-Based Library via Dimroth Rearrangement, Synthetic Route of 6850-57-3, the publication is Journal of Organic Chemistry (2021), 86(18), 12517-12527, database is CAplus and MEDLINE.

In this work, a novel protocol for the synthesis of 7-aminothiazolo[4,5,-d]pyrimidine scaffold libraries on solid support was developed using a traceless linker. Dimroth rearrangement afforded the desired intermediate with a fused heterocyclic thiazolo[4,5,-d]pyrimidine core skeleton. To diversify the synthesized library, three types of building blocks were introduced to the resin-bound thiazolo[4,5,-d]pyrimidine through N-acylation, N-alkylation, and nucleophilic substitution with amines, during cleavage from the resin. The synthesized compounds were produced in seven steps, with overall yields of 11-48%. Addnl., physicochem. properties, as well as drug-likeness of the library were calculated

Journal of Organic Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Synthetic Route of 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Sun, Jufeng published the artcileTargeting the S100A2-p53 Interaction with a Series of 3,5-Bis(trifluoromethyl)benzenesulfonamides: Synthesis and Cytotoxicity, COA of Formula: C8H11NO, the publication is ChemMedChem (2021), 16(18), 2851-2863, database is CAplus and MEDLINE.

In silico approaches identified N-(6-((4-bromobenzyl)amino)hexyl)-3,5-bis(trifluoromethyl)benzenesulfonamide I [X = (CH₂)₄; R¹ = 4-BrC₆H₄; R² = H] as a potential inhibitor of the S100A2-p53 protein-protein interaction, a validated pancreatic cancer drug target. Subsequent cytotoxicity screening revealed it to be a 2.97μM cell growth inhibitor of the MiaPaCa-2 pancreatic cell line. This is in keeping with the hypothesis that inhibiting this interaction would have an anti-pancreatic cancer effect with S100A2, the validated PC drug target. A combination of focused library synthesis [24 compounds I (X = nothing, CH₂, CH₂CH₂; R¹ = 4-BrC₆H₄, 3,4-Cl₂C₆H₃, 1-naphthyl, etc.; R² = H, Me)] and cytotoxicity screening identified a Pr alkyl diamine spacer as optimal; the nature of the terminal Ph substituent had limited impact on observed cytotoxicity, whereas N-methylation was detrimental to activity. In total 15 human cancer cell lines were examined, with most analogs showing broad-spectrum activity. Near uniform activity was observed against a panel of six pancreatic cancer cell lines: MiaPaCa-2, BxPC-3, AsPC-1, Capan-2, HPAC and PANC-1. In all cases there was good to excellent correlation between the predicted docking pose in the S100A2-p53 binding groove and the observed cytotoxicity, especially in the pancreatic cancer cell line with high endogenous S100A2 expression. This supports S100A2 as a pancreatic cancer drug target.

ChemMedChem published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C9H20Cl2Si, COA of Formula: C8H11NO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Ebrahimi, Seyyed Mohammad published the artcileSynthesis of 2,5-dihydro-3-furans using nano-CoAl₂O₄, Computed Properties of 6850-57-3, the publication is Research on Chemical Intermediates (2021), 47(8), 3189-3199, database is CAplus.

Nano-CoAl₂O₄ has been used as an efficient catalyst for the preparation of 5-oxo-2,5-dihydro-3 furancarboxylates by multi-component reaction of phenylglyoxal, di-Me acetylenedicarboxylate and primary amines. The best results were obtained in the presence of 4 mg of nano-CoAl₂O₄ in CH₂Cl₂ at room temperature Exptl. simplicity, wide range of products, great yields in concise times, the retrievable of the nanocatalyst and low catalyst loading are some of the substantial features of this method.

Research on Chemical Intermediates published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Computed Properties of 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem