2210-74-4Relevant academic research and scientific papers
Solid state properties of 1,2-epoxy-3-(2-methoxyphenyloxy)-propane - Valuable intermediate in non-racemic drug synthesis
Bredikhin, Alexander A.,Strunskaya, Elena I.,Zakharychev, Dmitry V.,Krivolapov, Dmitry B.,Litvinov, Igor A.,Bredikhina, Zemfira A.
, p. 3361 - 3366 (2005)
Racemic 1,2-epoxy-3-(2-methoxyphenyloxy)-propane 1 undergoes spontaneous resolution upon crystallization. This fact is confirmed by coincidence of the IR spectra of racemic and scalemic crystalline samples of 1, by thermal analysis (single eutectic V-shape binary melting phase diagram), and X-ray analysis (space group P212121, Z = 4). Racemic 1 could be resolved into (S)-(+)- and (R)-(-)-1 by a preferential crystallization procedure.
Efficient synthesis of 8-methoxy-3,4-dihydro-2H-1-benzopyran-3-ol
Shindikar,Viswanathan
, p. 1141 - 1145 (2011)
The article reports a practical, simple, and inexpensive procedure for the synthesis of 8-methoxy-3,4-dihydro-2H-1-benzopyran-3-ol (1). 2-Methoxy phenol on treatment offers the oxirane compound, which undergoes ring cleavage under acidic conditions to give a chlorohydrin, which on acylation and cyclization in the presence of stannic chloride followed by hydrolysis of the acetyl group, yields the desired compound (1).
Alternating and regioregular copolymers with high refractive index from COS and biomass-derived epoxides
Hu, Lan-Fang,Li, Yang,Liu, Bin,Zhang, Ying-Ying,Zhang, Xing-Hong
, p. 49490 - 49497 (2017)
This study describes the catalytic formation of alternating and regioregular copolymers from carbonyl sulfide (COS) and epoxides along with eugenol-based glycidyl ether (EGE) and guaiacol-based glycidyl ether (GGE), derived from eugenol and guaiacol, respectively. The (salen)CrCl [salen = N,N′-bis(salicylidene) cyclohexanediimine] complex, accompanied with various organic bases, was highly active towards the EGE/COS, GGE/COS copolymerization and EGE/GGE/COS terpolymerization. The turnover of frequency (TOF) of the (salen)CrCl complex for the EGE/COS copolymerization was up to 12000 h-1. The number-average molecular weight (Mn) of the resultant EGE/COS copolymer was up to 62.2 kg mol-1. In the presence of 0.5-1.5 mol% chlorohydrin, which was a by-product of the synthetic process of EGE, α-Cl, ω-OH EGE/COS copolymers were obtained. This result suggests that chlorohydrin could act as a very efficient chain transfer agent for the copolymerization. The EGE/COS, GGE/COS, and EGE/GGE/COS copolymers were soluble in most of the common solvents and exhibited a high refractive index of more than 1.58 with high Abbe numbers of up to 40.4. This study provides an unprecedented and sustainable synthetic route for making soluble sulfur-rich polymers with high optical properties.
Lariat Ethers. Synthesis and Cation Binding of Macrocyclic Polyethers Possessing Axially Disposed Secondary Donor Groups
Gokel, George W.,Dishong, Dennis M.,Diamond, Craig J.
, p. 1053 - 1054 (1980)
The synthesis and cation binding properties of a series of macrocyclic polyethers which possess ligating arms that enhance cation binding is presented.
Substituted diaryl compound and preparation method and application thereof
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Paragraph 0073-0075; 0076, (2021/09/15)
The invention relates to the field of medicinal chemistry, in particular to a substituted diaryl compound (I). The preparation method comprises the following steps: medicine preparation and medical application thereof. Test results show that the substituted diaryl compound has a good inhibition effect on human lung cancer (A549), human ovarian cancer (SKOV3), human melanoma (A375) and human colon cancer (LOVO) cells. Formula (I):
A low toxic CRM1 degrader: Synthesis and anti-proliferation on MGC803 and HGC27
Jia, Shilong,Jin, Cheng-Yun,Li, Xiaobo,Liu, Mengbo,Meng, Xia,Wang, Menglin,Wu, Xinxin,Xu, Hai-Wei,Yu, Lu
, (2020/08/19)
Chromosome region maintenance 1 (CRM1) is the sole nuclear exporter of several tumor suppressor, a growth regulatory protein as an attractive cancer drug target. In the present work, a novel CRM1 degrader was discovered from newly synthesized α, β-unsaturated-δ-lactone based on a natural product Goniothalamin. It induces apoptosis of both MGC803 and HGC27 cell lines via degrading CRM1. Selective inhibition was observed for the proliferation of gastric cancer cell lines MGC803, HGC27 comparing to Human Gastric Mucosal Epithelial Cell Line (GES1). For the first time, CRM1 inhibitor or degrader inducing apoptosis in gastric carcinoma was investigated.
Improving the activity and enantioselectivity of PvEH1, a Phaseolus vulgaris epoxide hydrolase, for o-methylphenyl glycidyl ether by multiple site-directed mutagenesis on the basis of rational design
Li, Chuang,Kan, Ting-Ting,Hu, Die,Wang, Ting-Ting,Su, Yong-Jun,Zhang, Chen,Cheng, Jian-Qing,Wu, Min-Chen
, (2019/08/01)
Substrate spectrum assay exhibited that PvEH1, which is an epoxide hydrolase from P. vulgaris, had the highest specific activity and enantiomeric ratio (E) for racemic o-methylphenyl glycidyl ether (rac-1) among tested aryl glycidyl ethers (1–5). To produce (R)-1 via kinetic resolution of rac-1 efficiently, the catalytic properties of PvEH1 were further improved on the basis of rational design. Firstly, the seven single-site variants of PvEH1-encoding gene (pveh1) were PCR-amplified as designed, and expressed in E. coli BL21(DE3). Among all expressed single-site mutants, PvEH1L105I and PvEH1V106I had the highest specific activities of 17.6 and 16.4 U/mg protein, respectively, while PvEH1L196D had an enhanced E value of 9.2. Secondly, to combine their respective merits, one triple-site variant, pveh1L105I/V106I/L196D, was also amplified, and expressed. The specific activity, E value, and catalytic efficiency of PvEH1L105I/V106I/L196D were 23.1 U/mg, 10.9, and 6.65 mM?1 s?1, respectively, which were 2.0-, 1.8- and 2.4-fold higher than those of wild-type PvEH1. The source of PvEH1L105I/V106I/L196D with enhanced E value for rac-1 was preliminarily analyzed by molecular docking simulation. Finally, the scale-up kinetic resolution of 100 mM rac-1 was conducted using 5 mg wet cells/mL E. coli/pveh1L105I/V106I/L196D at 25 °C for 1.5 h, producing (R)-1 with 95.0% ees, 32.1% yield and 3.52 g/L/h space-time yield.
Design, Synthesis, and Biological Evaluation of a New Series of Carvedilol Derivatives That Protect Sensory Hair Cells from Aminoglycoside-Induced Damage by Blocking the Mechanoelectrical Transducer Channel
O'Reilly, Molly,Kirkwood, Nerissa K.,Kenyon, Emma J.,Huckvale, Rosemary,Cantillon, Daire M.,Waddell, Simon J.,Ward, Simon E.,Richardson, Guy P.,Kros, Corné J.,Derudas, Marco
, p. 5312 - 5329 (2019/06/07)
Aminoglycosides (AGs) are broad-spectrum antibiotics used for the treatment of serious bacterial infections but have use-limiting side effects including irreversible hearing loss. Here, we assessed the otoprotective profile of carvedilol in mouse cochlear cultures and in vivo zebrafish assays and investigated its mechanism of protection which, we found, may be mediated by a block of the hair cell's mechanoelectrical transducer (MET) channel, the major entry route for the AGs. To understand the full otoprotective potential of carvedilol, a series of 18 analogues were prepared and evaluated for their effect against AG-induced damage as well as their affinity for the MET channel. One derivative was found to confer greater protection than carvedilol itself in cochlear cultures and also to bind more tightly to the MET channel. At higher concentrations, both carvedilol and this derivative were toxic in cochlear cultures but not in zebrafish, suggesting a good therapeutic window under in vivo conditions.
Design, synthesis and biological evaluation of novel desloratadine derivatives with anti-inflammatory and H1 antagonize activities
Li, Feng,Xu, Qinlong,Zhu, Qihua,Chu, Zhaoxing,Lin, Gaofeng,Mo, Jiajia,Zhao, Yan,Li, Jiaming,He, Guangwei,Xu, Yungen
, (2019/11/03)
To improve the anti-inflammatory activity of desloratadine, we designed and synthesized a series of novel desloratadine derivatives. All compounds were evaluated for their anti-inflammatory and H1 antagonistic activities. Among them, compound 2c showed the strongest H1 antagonistic and anti-inflammatory activity. It also exhibited promising pharmacokinetic profiles and low toxicity. All these results suggest that compound 2c as a novel anti-allergic agent is worthy of further investigation.
Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide
Maeda, Chihiro,Mitsuzane, Mayato,Ema, Tadashi
supporting information, p. 1853 - 1856 (2019/03/11)
Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO2. Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.
