131744-19-9Relevant academic research and scientific papers
syn-Diastereoselective glycolate aldol addition reactions of an N(3)-(p-methoxyphenoxy)acetyloxazolidine-2-thione
Haynes, Craig S.,Goodman, Cassie A.,Bruce, Juandah,Genin, Sarah C.,Austermuehle, Brad J.,Leong, Victor L.,Leise, Austin R.,Larson, Robert,Hamaker, Christopher G.,Hitchcock, Shawn R.
, p. 98 - 104 (2017)
An N3-(p-methoxyphenoxy)acetyloxazolidine-2-thione has been synthesized and employed in glycolate asymmetric aldol addition reactions with aromatic and aliphatic aldehydes. It was determined that the titanium tetrachloride medicated aldol reaction afforded diastereoselectivities that ranged from 75:25 to 94:6 when the reaction was conducted at ?78?°C. The absolute stereochemistry of the aldol adducts was determined by1H NMR spectroscopy and X-ray crystallography. The1H NMR spectra of the aldol adducts contained a signal (the α-proton of the glycolate position of the aldol side chain) that was highly deshielded due to conformational restriction about the N(3)-(p-methoxyphenoxy)acetyl side chain and the oxazolidine-2-thione auxiliary.
Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations
Yu, Jeongjae,Armstrong, Daniel W.,Ryoo, Jae Jeong
, p. 74 - 84 (2017/12/26)
We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).
Convenient approach to chiral 4-monosubstituted 1,3-oxazolidine-2-thiones
Lu, Zheng,Yang, Yong-Qing,Li, Jiu-Hui,Wei, Jun-Nan,Wang, Yi-Zhu
supporting information, p. 2215 - 2219 (2017/10/31)
Chiral 4-monosubstituted 1,3-oxazolidine-2-thiones are regarded as one of the modified version of Evans auxiliaries in asymmetric aldol condensation, which can generate two adjacent chiral carbon centers in one time They have advantages over Evans auxiliaries in some aspects, however, their application is highly limited by their preparation approaches as toxic or flammable chemicals are involved. Here, a mild and applicable procedure for preparing the chiral oxazolidine-2-thione auxiliaries has been developed in this article. Potassium ethylxanthate and the corresponding chiral amino alcohols as the starting material in absolute ethanol are mixed and the mixture are heated under reflux for 1 h in open air to provide 1,3-oxazolidine-2-thiones chiral auxiliaries in moderate to excellent yields.
Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones
Sun, Chu-Han,Lu, Yi,Zhang, Qing,Lu, Rong,Bao, Lin-Qing,Shen, Mei-Hua,Xu, Hua-Dong
supporting information, p. 4058 - 4063 (2017/07/10)
There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.
Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction
Tan, Wei,Wei, Jianpeng,Jiang, Xuefeng
supporting information, p. 2166 - 2169 (2017/04/27)
An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.
Synthesis, X-ray analysis, and biological activities of novel oxazolidinethiones
Saygili, Nezire,?zalp, Meral,Yildirim, Leyla Tatar
, p. 1264 - 1269 (2015/04/27)
Oxazolidinethione compounds were synthesized starting from racemic and enantiopure β-amino alcohols. The molecular structure of oxazolidinethione 6a was elucidated by single-crystal x-ray crystallography. Oxazolidinethione compounds screened for antimicro
Potent and Selective Inhibitors of Histone Deacetylase-3 Containing Chiral Oxazoline Capping Groups and a N-(2-Aminophenyl)-benzamide Binding Unit
Marson, Charles M.,Matthews, Christopher J.,Atkinson, Stephen J.,Lamadema, Nermina,Thomas, N. Shaun B.
, p. 6803 - 6818 (2015/09/22)
A novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamide unit. Among several new inhibitors of this type exhibiting Class I selectivity and potent inhibition of HDAC3-NCoR2, in vitro assays for the inhibition of HDAC1, HDAC2, and HDAC3-NCoR2 by N-(2-aminophenyl)-benzamide 15k gave respective IC50 values of 80, 110, and 6 nM. Weak inhibition of all other HDAC isoforms (HDAC4, 5, 6, 7, and 9: IC50 > 100000 nM; HDAC8: IC50 = 25000 nM; HDAC10: IC50 > 4000 nM; HDAC11: IC50 > 2000 nM) confirmed the Class I selectivity of 15k. 2-Aminoimidazolinyl, 2-thioimidazolinyl, and 2-aminooxazolinyl units were shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)-benzamides previously reported, but the 2-aminooxazolinyl unit was the most potent in inhibiting HDAC3-NCoR2. Many of the new HDAC inhibitors showed higher solubilities and lower binding to human serum albumin than that of Mocetinostat. Increases in histone H3K9 acetylation in the human cell lines U937 and PC-3 was observed for all three oxazolinyl inhibitors evaluated; those HDAC inhibitors also lowered cyclin E expression in U937 cells but not in PC-3 cells, indicating underlying differences in the mechanisms of action of the inhibitors on those two cell lines.
ANTI-CANCER POLYKETIDE COMPOUNDS
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Paragraph 0157, (2013/10/21)
Provided herein, inter alia, are anticancer polyketides. The uses of the polyketides described herein include treatment of cancer, for example, through regulation of the spliceosome and detection of spliceosome inhibition.
Total synthesis of γ-trifluoromethylated analogs of goniothalamin and their derivatives
Chen, Jun-Ling,You, Zheng-Wei,Qing, Feng-Ling
, p. 143 - 150 (2013/10/01)
An efficient method for the construction of chiral γ- trifluoromethylated α,β-unsaturated δ-lactone, a widely existing pharmacophore, has been developed and successfully applied for synthesis of γ-trifluoromethylated goniothalamins. The key steps included Evans-Aldol reaction of chiral titanium enolate of α-CF3 imide, Wittig olefination and lactonization. The transformation of γ-trifluoromethylated α,β-unsaturated δ-lactone to a series of trifluoromethylated styryllactones was also investigated.
