- Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases
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Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative
- Ryoo, Jae Jeong,Yu, Jeong Jae
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- Synthesis method of thioazoline-2-thioketone
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The invention discloses a synthetic method of thioazoline-2-thioketone. The synthesis method of the thioazoline-2-thioketone compound represented by a formula IV comprises the following steps: (1) ina solvent, carrying out a salt forming reaction defined in the specification on a compound represented by a formula I and chlorosulfonic acid to obtain a compound represented by a formula II; and (2)in a solvent, carrying out a cyclization reaction defined in the specification on the compound represented by the formula II and a compound represented by a formula III to obtain the thioazoline-2-thioketone compound represented by the formula IV, wherein R and R' are independently selected from hydrogen, C1-6 alkyl, C6-10 aryl substituted C1-6 alkyl and C6-10 aryl, R'' is C1-6 alkyl, and M is analkali metal. The synthesis method is simple to operate, high in yield and high in purity.
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Paragraph 0060-0063
(2020/05/29)
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- Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction
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The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.
- Sunnapu, Ranganayakulu,Banoth, Saikumar Naik,Reyno,Thomas, Aleena,Venugopal, Navyasree,Rajendar, Goreti
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p. 4103 - 4113
(2020/03/05)
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- Preparation of 1,3-Thiazolidine-2-thiones by Using Potassium Ethylxanthate as a Carbon Disulfide Surrogate
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A simple procedure is presented for preparing 1,3-thiazolidine-2-thiones by using potassium ethylxanthate and the corresponding β -amino alcohols as the starting materials in the presence of ethanol.
- Lu, Zheng,Yang, Yong-Qing,Xiong, Weixiang
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supporting information
p. 713 - 716
(2019/03/26)
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- Synthesis and Fungicidal Activity of Simple Structural 1,3-Thiazolidine-2-Thione Derivatives
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A series of simple structural 1,3-thiazolidine-2-thione derivatives with various substituents on the S-, N-, 4-, and 5-positions was synthesized with high yields from various vicinal amino alcohols via two steps and screened for their antifungal activity. Bioassay results reveal that some thiazolidine-2-thione derivatives show strong antifungal activities against P. capsici, G. zeae, S. sclerotiorum, A. alternata, B. cinerea, or R. solani. The SAR analysis indicates that N-acyl substituted and 4-alkyl substituents can enhance the antifungal activity. Notably, 4-isopropyl-N-propionylthiazoldine-2-thione shows excellent activity against B. cinerea and G. zeae with IC50 values at 3.7 g/mL and 6.5 g/mL, respectively, and 4-isobutyl-N-propionylthiazoldine-2-thione shows remarkable fungicidal activity against R. solani, S. sclerotiorum, and G. zeae with IC50 values at 1.0 g/mL, 12.1 g/mL, and 11.0 g/mL, respectively. GRAPHICAL ABSTRACT.
- Chen, Ning,Du, Hongguang,Liu, Weidong,Wang, Shanshan,Li, Xinyao,Xu, Jiaxi
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p. 112 - 122
(2015/10/29)
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- A study of the alkylation and acylation of N-acylthiazolidinethione
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Investigating the alkylation and acylation of N-acylthiazolidinethione, the desired α-alkylated products and C-acylated products are not obtained, but rather the S-alkylated products and O-acylated products are obtained. The possible mechanism proposed shows that the deprotonation agent and electrophilic species are responsible for the stability of enolates. The enolates derived from N-acylthiazolidinethiones are decomposed in the presence of base, but they are comparatively stable in the presence of Lewis acid. When electrophilic reagent is alkyl halide, the enolate decomposition is the dominating pathway, and affords the S-alkylated products; and when electrophilic reagent is acyl chloride, the formation of a highly ordered chelated transition-state is the dominating pathway, and affords the O-acylated products.
- Su,Yang,Lu,Chen,Yang
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p. 769 - 775
(2013/07/26)
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- ANTI-CANCER POLYKETIDE COMPOUNDS
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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.
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- Discovery of potent, isoform-selective inhibitors of histone deacetylase containing chiral heterocyclic capping groups and a N-(2-aminophenyl)benzamide binding unit
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The synthesis of a novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contain a heterocyclic capping group and a N-(2-aminophenyl)benzamide unit that binds in the active site. In vitro assays for the inhibition of HDAC1, HDAC2, HDAC3-NCoR1, and HDAC8 by the N-(2-aminophenyl)benzamide 24a gave respective IC50 values of 930, 85, 12, and 4100 nM, exhibiting class I selectivity and potent inhibition of HDAC3-NCoR1. Both imidazolinone and thiazoline rings are shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl) benzamides previously reported, an example of each ring system at 1 μM causing an increase in histone H3K9 acetylation in the human cell lines Jurkat and HeLa and an increase in cell death consistent with induction of apoptosis. Inhibition of the growth of MCF-7, A549, DU145, and HCT116 cell lines by 24a was observed, with respective IC50 values of 5.4, 5.8, 6.4, and 2.2 mM.
- Marson, Charles M.,Matthews, Christopher J.,Yiannaki, Elena,Atkinson, Stephen J.,Soden, Peter E.,Shukla, Lena,Lamadema, Nermina,Thomas, N. Shaun B.
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p. 6156 - 6174
(2013/09/02)
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- Kinetic resolution of N-acyl-thiolactams via catalytic enantioselective deacylation
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Methanolysis of N-acyl-thiazolidin-2-thiones and -oxazolidin-2-thiones in the presence of acyl transfer catalyst benzotetramisole (BTM) proceeds in a highly enantioselective fashion thus enabling kinetic resolution of these substrates.
- Bumbu, Valentina D.,Yang, Xing,Birman, Vladimir B.
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supporting information
p. 2790 - 2793
(2013/07/19)
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- Enantioselective synthesis of the C5-C23 segment of biselyngbyaside
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Stereo and enantioselective synthesis of C5-C23 fragment of cytotoxic marine natural product biselyngbyaside is achieved using E-selective methyl lithium addition onto enyne, Crimmin's acetate aldol reaction, Sharpless asymmetric epoxidation, and Julia-Kocienski olefination as the key steps.
- Chandrasekhar, Srivari,Rajesh, Gontla,Naresh, Tumma
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supporting information
p. 252 - 255
(2013/02/23)
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- Structure of FD-895 revealed through total synthesis
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The total synthesis of FD-895 was completed through a strategy that featured the use of a tandem esterification ring-closing metathesis (RCM) process to construct the 12-membered macrolide and a modified Stille coupling to append the side chain. These stu
- Villa, Reymundo,Mandel, Alexander L.,Jones, Brian D.,La Clair, James J.,Burkart, Michael D.
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p. 5396 - 5399
(2013/01/15)
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- Double molecular recognition with aminoorganoboron complexes: Selective alcoholysis of β-dicarbonyl derivatives
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Double duty: Aminoorganoboron (AOB) complexes recognize alcohol and β-dicarbonyl units, and thereby facilitate chemo- and site-selective alcoholysis of the latter (see scheme). The complex activates both reaction partners. This strategy enables C-C, C-N, and C-O bond cleavage in addition/elimination reactions under near neutral pH conditions and provides a new method for functional group conversions. Copyright
- Oishi, Shunsuke,Saito, Susumu
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supporting information; experimental part
p. 5395 - 5399
(2012/06/18)
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- Formal asymmetric synthesis of echinopine A and B
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(Chemical Equation Presented) Enticing structures: The formal syntheses of 1 and 2 were accomplished by using a cascade strategy involving an enyne cycloisomerization reaction and an intramolecular Diels-Alder reaction starting from 3. The resulting 4 underwent a late-stage ring contraction to enable the preparation of a reported advanced intermediate, thereby constituting a formal synthesis of the structurally intriguing title compounds.
- Peixoto, Philippe A.,Severin, Rene,Tseng, Chih-Chung,Chen, David Y.-K.
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supporting information; experimental part
p. 3013 - 3016
(2011/05/12)
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- A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines
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Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid, oxidation of the thiazolidine-2-thione intermediates generated from, vicinal amino alcohols or aziridines and carbon disulfide. The stereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize optically active substituted taurines.
- Chen, Ning,Jia, Weiyi,Xu, Jiaxi
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supporting information; experimental part
p. 5841 - 5846
(2010/03/03)
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- On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals
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Titanium enolates from chiral N-propanoyl-1,3-thiazolidine-2-thiones containing bulky substituents at C4 turned out to be excellent platforms to get highly stereocontrolled cross-coupling reactions with acetals. Related oxazolidinethiones also afforded go
- Baiget, Jessica,Cosp, Annabel,Gálvez, Erik,Gómez-Pinal, Loreto,Romea, Pedro,Urpí, Fèlix
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p. 5637 - 5644
(2008/09/21)
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- Synthesis of the macrocyclic core of (-)-pladienolide B
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(Chemical Equation Presented) An efficient synthesis of the macrocyclic core of (-)-pladienolide B is disclosed. The concise route relies on a chiral auxiliary-mediated asymmetric aldol addition and an osmium-catalyzed asymmetric dihydroxylation to install the three oxygenated stereocenters of the macrocycle. This purely reagent-controlled and flexible strategy sets the stage for future analogue syntheses and structure-activity relationship plotting of the appealing anticancer lead structure pladienolide B.
- Skaanderup, Philip R.,Jensen, Thomas
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supporting information; experimental part
p. 2821 - 2824
(2009/05/27)
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- MATRIX METALLOPROTEINASE INHIBITORS
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The present invention relates to β-hydroxy and amino substituted carboxylic acids, which act as matrix metalloprotease inhibitors, particularly diastereomerically pure β-hydroxy carboxylic acids, corresponding processes for the synthesis of and pharmaceutical compositions containing the compounds of the present invention. Compounds of the present invention are useful in the treatment of various inflammatory, autoimmune and allergic diseases, such as methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis, wound healing disorders, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by the over-expression and over- activation of a matrix metalloproteinase using the compounds.
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Page/Page column 55
(2008/06/13)
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- Asymmetric aldol additions: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones
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Asymmetric aldol additions using chlorotitanium enolates of N-acyloxazolidinone, oxazolidinethione, and thiazolidinethione propionates proceed with high diastereoselectivity for the Evans or non-Evans syn product depending on the nature and amount of the base used. With 1 equiv of titanium tetrachloride and 2 equiv of (-)-sparteine as the base or 1 equiv of (-)-sparteine and 1 equiv of N-methyl-2-pyrrolidinone, selectivities of 97:3 to >99:1 were obtained for the Evans syn aldol products using N-propionyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones. The non-Evans syn aldol adducts are available with the oxazolidinethione and thiazolidinethiones by altering the Lewis acid/amine base ratios. The change in facial selectivity in the aldol additions is proposed to be a result of switching of mechanistic pathways between chelated and nonchelated transition states. The auxiliaries can be reductively removed or cleaved by nucleophilic acyl substitution. Iterative aldol sequences with high diastereoselectivity can also be accomplished.
- Crimmins,King,Tabet,Chaudhary
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p. 894 - 902
(2007/10/03)
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- Titanium Enolates of Thiazolidinethione Chiral Auxiliaries: Versatile Tools for Asymmetric Aldol Additions
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formula presented Asymmetric aldol additions using chlorotitanium enolates of thiazolidinethione propionates proceed with high diastereoselectivity for the "Evans" or "non-Evans" syn product depending on the nature and amount of the base used. With (-)-sparteine as the base, selectivities of 97:3 to > 99:1 were obtained for the Evans syn products with 2 equivalents of base and for the non-Evans syn when 1 equiv of base was employed. The thiazolidinethione auxiliaries are easily removed, and the aldol adducts can be readily transformed to various functional groups. Even direct reduction to the aldehyde with diisobutylaluminum hydride is possible.
- Crimmins, Michael T.,Chaudhary, Kleem
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p. 775 - 777
(2007/10/03)
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- Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides
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Four examples of the chiral thiazolidin-2-one 1,1-dioxides 5 have been prepared by reaction of the appropriate amino alcohols 11 with CS2 in aqueous sodium hydroxide to give the thiazolidine-2-thiones 12, followed by oxidation with KMnO4 under phase-transfer conditions in the presence of benzoic acid, either directly or via the thiazolidin-2-ones 13. Upon flash vacuum pyrolysis (FVP) at 650°C, 5a-c decompose mainly by loss of SO2 to give an alkene and benzyl isocyanate together with other products from fragmentation of the N-benzyl group. A significant minor pathway involves net loss of CO2 and water to give the 2-phenyl-4,5-dihydrothiazoles 21 together with their aromatisation products 22 and 23. A mechanism for this new heterocyclic transformation is proposed involving initial expansion to a cyclic carbamic-sulnnic anhydride (2,1,4-oxathiazin-3-one 1-oxide). The fully assigned 13C NMR spectra are presented for 5, 12 and 13 and the 33S NMR spectrum has been obtained for 5c.
- Aitken, R. Alan,Armstrong, David P.,Galt, Ronald H. B.,Mesher, Shaun T. E.
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p. 2139 - 2145
(2007/10/03)
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