Month: December 2022

Liu, Wen published the artcileIron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds, Related Products of isoquinoline, the main research area is iron catalyzed enantioselective radical carboazidation diazidation alkene; azidation unsaturated carbonyl compound DFT calculation.

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N’-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcs., and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramol. five-membered transition state with the internal nitrogen of the Fe-N3 species.

Journal of the American Chemical Society published new progress about Azidation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Jatoth, Ramanna published the artcileMetal-Free TFA-Promoted Regioselective (Hetero)Arylation: Synthesis of (Hetero)Aryl Substituted and Carbazole/Oxepine Fused N-Heterocycles, COA of Formula: C8H10O2, the main research area is aryl substituted nitrogen heterocycle green preparation regioselective; nitrogen heterocycle arene arylation TFA promoted; carbazole fused nitrogen heterocycle green preparation regioselective; indole nitrogen heterocycle sequential heteroarylation hydroarylation TFA promoted; oxepine fused nitrogen heterocycle green preparation regioselective; indolyl phenol nitrogen heterocycle cascade heteroarylation arylation TFA promoted.

Metal-free TFA promoted arylation/heteroarylation was achieved under mild conditions via the reaction of chloro-derivatives of nitrogen heterocycles [e.g., =C-C(Cl)=N-] with electron rich arenes/heteroarenes for synthesis of aryl substituted nitrogen heterocycles such as I [R = H; R1 = H; RR1 = CH=CH-CH=CH; R2 = 1H-indol-3-yl, 2-hydroxy-1-naphthyl, 2,4-di-HOC6H3, etc.; R3 = Cl, CN; X = C, N]. It was also observed that apart from participating in the heteroarylation step, TFA was able to facilitate the hydroarylation/o-arylation process in the same pot affording the carbazole/oxepine fused N-heterocycles such as II [R4 = H, OMe, Br; R5 = H, Br; R6 = Ph, 4-MeC6H4; R7 = Me, Et, Bn] and III [R8 = H; R9 = H; R8R9 = CH=CH-CH=CH, CH=C(Me)-C(Me)=CH; R10 = H, Me; R11 = H, Me, Cl, Br]. The reaction proceeded with similar efficiency on gram scale.

Advanced Synthesis & Catalysis published new progress about Arylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, COA of Formula: C8H10O2.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kaur, Jaspreet published the artcilePhotocatalyst-Free, Visible-Light-Mediated C(sp3)-H Arylation of Amides via a Solvent-Caged EDA Complex, Safety of 1,3-Dimethoxybenzene, the main research area is arylation EDA complex.

A photocatalyst-free and mild visible light photochem. procedure for C(sp3)-H arylation of amides is described. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)-H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction taking place in a solvent cage holding components in a close proximity.

Organic Letters published new progress about Arylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Safety of 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kobayashi, Daishiro published the artcilePeptide cyclization mediated by metal-free S-arylation: S-protected cysteine sulfoxide as an umpolung of the cysteine nucleophile, Application In Synthesis of 151-10-0, the main research area is cyclic stapled peptide synthesis; solid phase peptide synthesis oxidative cyclization cystein sulfoxide arylation; thioether linkage formation reaction mechanism sulfoxide tryptathionine; aromatic electrophilic substitution; S-arylation; peptide cyclization; stapling; sulfoxides; tryptathionine.

Covalent linking of side chains provides a method to produce cyclic or stapled peptides that are important in developing peptide-based drugs. A variety of crosslinking formats contribute to fixing the active conformer and prolonging its biol. activity under physiol. conditions. One format uses the cysteine thiol to participate in crosslinking through nucleophilic thiolate anions or thiyl radicals to form thioether and disulfide bonds. Removal of the S-protection from an S-protected Cys derivative generates the thiol, which functions as a nucleophile. S-Oxidation of a protected Cys allows the formation of a sulfoxide that operates as an umpolung electrophile. Herein, the applicability of S-p-methoxybenzyl Cys sulfoxide (Cys(MBzl)(O)) to the formation of a thioether linkage between tryptophan and Cys has been investigated. The reaction of peptides containing Cys(MBzl)(O) and Trp with trifluoromethanesulfonic acid (TFMSA) or methanesulfonic acid (MSA) in TFA in the presence of guanidine hydrochloride (Gn · HCl) proceeded to give cyclic or stapled peptides possessing the Cys-Trp thioether linkage. In this reaction, strong acids such as TFMSA or MSA are necessary to activate the sulfoxide. Addnl., Gn · HCl plays a critical role in producing an electrophilic Cys derivative that combines with the indole by aromatic electrophilic substitution. The findings led us to conclude that the less-electrophilic Cys(MBzl)(O) serves as an acid-activated umpolung of a Cys nucleophile and is useful for S-arylation-mediated peptide cyclization.

Chemistry – A European Journal published new progress about Arylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Application In Synthesis of 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zhang, Bowen published the artcileC-H Functionalization Approach for the Synthesis of Chiral C2-Symmetric 1,5-Cyclooctadiene Ligands, Safety of 4-Methoxyphenylacetic acid, the main research area is chiral cyclooctadiene stereoselective preparation; diazo cyclooctadiene rhodium catalyst ligand diastereoselective enantioselective allylic insertion.

Chiral cyclooctadiene (COD) derivatives are readily prepared by rhodium-catalyzed allylic C-H functionalization of COD.Either mono or difunctionalization of COD is possible generating the products in high yield, diastereoselectivity and enantioselectivity. The double C-H functionalization generates C2 sym. COD derivatives with four new stereogenic centers in >99% ee, which can be readily converted to a series of chiral COD ligands. Preliminary evaluations revealed that the COD ligands can be used in rhodium-catalyzed asym. arylation of cyclohex-2-enone, leading to the conjugate addition products in up to 76% ee.

Organic Letters published new progress about Arylation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Safety of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Lee, Jae Bin published the artcileAnnulative π-Extension of Unactivated Benzene Derivatives through Nondirected C-H Arylation, COA of Formula: C8H10O2, the main research area is arylation annulation benzene palladium catalyst triphenylene preparation.

Annulative π-extension chem. provides a concise synthetic route to polycyclic arenes. Herein, we disclose a nondirected annulation approach of unactivated simple arenes. The palladium-catalyzed 2-fold C-H arylation event facilitates tandem C-C linkage relays to furnish fully benzenoid triphenylene frameworks using cyclic diaryliodonium salts. The inseparable regioisomeric mixture of 1- and 2-methyltriphenylenes is identified by the combined anal. of ion mobility-mass spectrometry, gas-phase IR spectroscopy, and mol. simulation studies.

Organic Letters published new progress about Arylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, COA of Formula: C8H10O2.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Sun, Denan published the artcileTransient directing ligand- and solvent-controlled C-H/C-H cross-coupling/quaternization cyclization/dequaternization of benzaldehydes with thiophenes, Related Products of isoquinoline, the main research area is benzaldehyde thiophene rhodium catalyst regioselective cross coupling reaction; thiophenyl benzaldehyde preparation; benzothiophene benzaldehyde alanine tandem arylation quaternization cyclization dequaternization; fused heterocyclic compound preparation.

Rh(III)-catalyzed oxidative C-H/C-H cross-coupling between benzaldehydes and thiophenes was accomplished for the first time. In such reactions, transient directing ligands (TDLs) not only promote ortho-C-H activation, but also control chemoselectivity through a suitable combination with different solvents.

Chemical Communications (Cambridge, United Kingdom) published new progress about Arylation. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Yang, Dingwei published the artcileNa+/Ca2+ exchange inhibitor, KB-R7943, attenuates contrast-induced acute kidney injury, Application In Synthesis of 117-96-4, the main research area is KBR7943 renoprotectant sodium calcium exchanger inhibitor acute kidney injury.

Background: Intracellular Ca2+ overload is considered to be a key factor in contrast-induced acute kidney injury (CI-AKI). The Na+/Ca2+ exchanger (NCX) system is one of the main pathways of intracellular Ca2+ overload. We investigated the effects of KB-R7943, an inhibitor of the reverse mode of NCX, on CI-AKI in a rat model. Method: Rats were divided into control group, CI-AKI group and pretreatment groups (with KB-R7943 dose of 5 or 10 mg/kg). CI-AKI was induced by diatrizoate administration in rats with cholesterol-supplemented diet for 8 wk. Renal function and renal hemodynamics were determined 1 day following contrast medium administration. Renal histopathol. was observed by light microscope. Renal tubular apoptosis was examined by TUNEL. Renal endothelin-1 (ET-1) was measured by RIA. Renal malondialdehyde (MDA) and catalase (CAT) were measured as oxidative markers. Results: Levels of serum creatinine (Scr), renal ET-1, MDA and CAT, and resistance index (RI) of renal blood vessels increased significantly in CI-AKI rats. The increases in Scr and RI of renal blood vessels induced by diatrizoate were suppressed significantly and dose-dependently by pretreatment with KB-R7943. Histopathol. and TUNEL results showed that the contrast medium-induced severe renal tubular necrosis and apoptosis were significantly and dose-dependently attenuated by KB-R7943. KB-R7943 significantly suppressed the increment of renal ET-1 content and MDA and CAT level induced by contrast medium administration. Conclusion: Activation of the reverse mode of NCX, followed by ET-1 overproduction and increased oxidative stress, seems to play an important role in the pathogenesis of CI-AKI. The inhibitor of the reverse mode of NCX, KB-R7943, has renoprotective effects on CI-AKI.

Journal of Nephrology published new progress about Apoptosis. 117-96-4 belongs to class isoquinoline, name is Diatrizoic Acid, and the molecular formula is C11H9I3N2O4, Application In Synthesis of 117-96-4.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zhang, Qiuyan published the artcileCocktail of Astragalus Membranaceus and Radix Trichosanthis suppresses melanoma tumor growth and cell migration through regulation of Akt-related signaling pathway, Related Products of isoquinoline, the main research area is Astragalus Radix Trichosanthis Akt signaling cell migration growth melanoma; Akt-related singnaling pathway; Astragalus Membranaceus; Radix Trichosanthis; herbal “cocktailâ€? migration; proliferation.

Malignant melanoma has high morbidity and mortality and limited treatment options. Traditional Chinese medicine has great potential in the clin. therapy of cancer, and the theory of compatibility is one core content of Chinese medical theory. Astragalus Membranaceus and Radix Trichosanthis are clin. effective for the treatment of various cancers. We verified the effects of AMD, RTD, and their “”cocktail”” on melanoma model in vitro and in vivo and the mechanism of its effect on the Akt-related signaling pathway by network pharmacol., MTT, flow cytometry, LDH, SOD, MDA assay, and Western blot. The network pharmacol. anal. indicated that the PI3K-Akt pathway plays a crucial role in the treatment of malignant melanoma with these two herbs. In addition, AMD, RTD, and their “”cocktail”” could inhibit the proliferation of A375 cells by reducing the survival rate in a concentration-dependent manner and by regulating the cell cycle, and the compatibility of two herbs also could inhibit melanoma growth. They could, resp., induce apoptosis and inhibit migration by affecting the expression of Bcl-2, Bax, p53, snail, E-cadherin, and N-cadherin. Furthermore, LDH activity was decreased, while SOD increased and MDA reduced. The factors of the Akt-related signaling pathway, Akt and p-Akt, were decreased. This study showed that AMD, RTD, and their “”cocktail”” could regulate cell proliferation, apoptosis, and metastasis in A375 cells through the suppression of the Akt-related signaling pathway, and the “”cocktail”” groups had detoxification and additive effects. The best compatibility of the two herbs also can inhibit tumor growth and metastasis in vivo.

Frontiers in Pharmacology published new progress about Apoptosis. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Ween, M. P. published the artcileE-cigarettes and health risks: more to the flavor than just the name, HPLC of Formula: 21834-92-4, the main research area is human electronic cigarette health risk flavor; cytokine; e-cigarette; flavor; macrophage.

The growing interest in regulating flavored E-liquids must incorporate understanding of the “”flavoring profile”” of each E-liquid-which flavorings (flavoring chems.) are present and at what concentrations not just focusing on the flavor on the label. We investigated the flavoring profile of 10 different flavored E-liquids We assessed bronchial epithelial cell viability and apoptosis, phagocytosis of bacteria and apoptotic cells by macrophages after exposure to E-cigarette vapor extract (EVE). We validated our data in normal human bronchial epithelial cells (NHBE) and alveolar macrophages (AM) from healthy donors. We also assessed cytokine release and validated in the saliva from E-cigarette users. Increased necrosis/apoptosis (16.1-64.5% apoptosis) in 16HBE cells was flavor dependent, and NHBEs showed an increased susceptibility to flavors. In THP-1 differentiated macrophages phagocytosis was also flavor dependent, with AM also showing increased susceptibility to flavors. Further, Banana and Chocolate were shown to reduce surface expression of phagocytic target recognition receptors on alveolar macrophages. Banana and Chocolate increased IL-8 secretion by NHBE, whereas all 4 flavors reduced AM IL-1β secretion, which was also reduced in the saliva of E-cigarette users compared with healthy controls. Flavorant profiles of E-liquids varied from simple 2 compound mixtures to complex mixtures containing over a dozen flavorants. E-liquids with high benzene content, complex flavoring profiles, high chem. concentration had the greatest impacts. The Flavorant profile of E-liquids is key to disruption of the airway status quo by increasing bronchial epithelial cell apoptosis, causing alveolar macrophage phagocytic dysfunction, and altering airway cytokines.

American Journal of Physiology published new progress about Apoptosis. 21834-92-4 belongs to class isoquinoline, name is 5-Methyl-2-phenylhex-2-enal, and the molecular formula is C13H16O, HPLC of Formula: 21834-92-4.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem