Cleavage of Carboxylic Esters by Aluminum and Iodine

Sang, Dayong; Yue, Huaxin; Fu, Yang; Tian, Juan

doi:10.1021/acs.joc.1c00034

Cited by 14 publications

(11 citation statements)

References 48 publications

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“…R f = 0.47 (cyclohexane/EtOAc 9:1). Mp = 199−201 °C (coherent with the literature 27 ). 1 H NMR (300 MHz, chloroform-d) δ 8.15 (d, J = 7.6 Hz, 2H), 7.32−7.10 (m, 2H), 2.47−2.15 (s, 3H).…”

Section: Synthesis Of 4-acetoxybenzoic Acid (82)mentioning

confidence: 99%

Subnanomolar Affinity and Selective Antagonism at α7 Nicotinic Receptor by Combined Modifications of 2-Triethylammonium Ethyl Ether of 4-Stilbenol (MG624)

et al. 2022

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Modifications of the cationic head and the ethylene linker of 2-(triethylammonium)ethyl ether of 4-stilbenol (MG624) have been proved to produce selective α9*-nAChR antagonism devoid of any effect on the α7subtype. Here, single structural changes at the styryl portion of MG624 lead to prevailing α7-nAChR antagonism without abolishing α9*-nAChR antagonism. Nevertheless, rigidification of the styryl into an aromatic bicycle, better if including a H-bond donor NH, such as 5-indolyl (31), resulted in higher and more selective α7-nAChR affinity. Hybridization of this modification with the constraint of the 2-triethylammoniumethyloxy portion into (R)-N,N-dimethyl-3pyrrolidiniumoxy substructure, previously reported as the best modification for the α7-nAChR affinity of MG624 (2), was a winning strategy. The resulting hybrid 33 had a subnanomolar α7-nAChR affinity and was a potent and selective α7-nAChR antagonist, producing at the α7-, but not at the α9*-nAChR, a profound loss of subsequent ACh function.

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Section: Synthesis Of 4-acetoxybenzoic Acid (82)mentioning

confidence: 99%

Subnanomolar Affinity and Selective Antagonism at α7 Nicotinic Receptor by Combined Modifications of 2-Triethylammonium Ethyl Ether of 4-Stilbenol (MG624)

et al. 2022

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“…13 C NMR (CDCl 3 , 100 MHz) δ 170. 3, 163.9, 132.3, 121.7, 113.7, 55.5; EI-MS m/z (%): 152 [M] + (65), 151 (100), 135(52), 123 (18), 84 (10), 77 (15), 49 (11) [16]. (100), 153(89), 125 (20), 79 (18), 45(42) [23].…”

Section: Extraction and Isolationmentioning

confidence: 99%

Structure related α-glucosidase inhibitory activity and molecular docking analyses of phenolic compounds from Paeonia suffruticosa

et al. 2022

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In the continuous search for α-glucosidase inhibitors, eleven phenolic compounds (1-11) were isolated from the root bark of Paeonia suffruticosa. Their α-glucosidase inhibitory activity and inhibition mechanism were investigated using an in vitro inhibition assay and molecular docking studies. Compounds 2, 5, 6, and 8-11 (IC 50 between 290 and 431 µM) inhibited α-glucosidase more effectively than the reference compound acarbose (IC 50 =1463 ± 29.5 µM). Among them, compound 10 exhibited the highest α-glucosidase inhibitory effect with an IC 50 value of 290.4 ± 9.6 µM. Compounds 2, 5, 9 10 and 11 were found to be competitive inhibitors, while compounds 6 and 8 were noncompetitive inhibitors of α-glucosidase. Computational analyses showed that the main binding forces between the compounds and the main residues were hydrogen bonds. The results indicated that these compounds had considerable α-glucosidase inhibitory activity.

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“…General methylation procedure B and workup procedure B using petroleum ether/CH 2 Cl 2 (2 mL/2 mL) mixture as the extraction solvent instead of petroleum ether (chromatography: petroleum ether/EtOAc, 15:1) afforded O -methylated product 10 27 (36 mg, 24% yield) as a colorless liquid.…”

Section: -Methoxy- N N -Dimethylanil...mentioning

confidence: 99%

A Mild Heteroatom (O-, N-, and S-) Methylation Protocol Using Trimethyl Phosphate (TMP)–Ca(OH)2Combination

Tang

2022

Synthesis

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A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2 combination has been developed, which proceeds in DMF, or water, or under neat conditions at 80 oC or at room temperature. A series of O-, N- and S-nucleophiles, including phenols, sulfonamides, N-heterocycles such as 9H-carbazole, indole derivatives, 1,8-naphthalimide, and aryl/alkyl thiols are suitable substrates of this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmental friendly nature of this protocol make it an attractive alternative to the conventional base prompted heteroatom methylation procedures.

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Cleavage of Carboxylic Esters by Aluminum and Iodine

Cited by 14 publications

References 48 publications

Subnanomolar Affinity and Selective Antagonism at α7 Nicotinic Receptor by Combined Modifications of 2-Triethylammonium Ethyl Ether of 4-Stilbenol (MG624)

Subnanomolar Affinity and Selective Antagonism at α7 Nicotinic Receptor by Combined Modifications of 2-Triethylammonium Ethyl Ether of 4-Stilbenol (MG624)

Structure related α-glucosidase inhibitory activity and molecular docking analyses of phenolic compounds from Paeonia suffruticosa

A Mild Heteroatom (O-, N-, and S-) Methylation Protocol Using Trimethyl Phosphate (TMP)–Ca(OH)2Combination

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