Alkali metals dissolved in optically active solvents

Cooper, Keith D.; Walborsky, H. M.

doi:10.1021/jo00323a026

Cited by 23 publications

(7 citation statements)

References 6 publications

(6 reference statements)

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“…Chiral pentaethylene glycol ditosylate ( S,S )‐ 29 was prepared from diol ( S,S )‐ 33 using tosyl chloride (TsCl) in pyridine as a base and a solvent (see Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

et al. 2017

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New enantiopure dimethyl-substituted acridino-18-crown-6 and acridino-21-crown-7 ethers containing a carboxyl group at position 9 of the acridine ring [(S,S)-8, (S,S)-9, (R,R)-10] were synthesized. The pK values of the new crown ethers [(S,S)-8, (S,S)-9, (R,R)-10] and of an earlier reported macrocycle [(R,R)-2] were determined by UV-pH titrations. Crown ether (S,S)-8 was attached to silica gel by covalent bonds and the enantiomeric separation ability of the newly prepared chiral stationary phase [(S,S)-CSP-12] was studied by high-performance liquid chromatography (HPLC). Homochiral preference was observed and the best separation was achieved for the enantiomers of 1-NEA. Ligands (S,S)-9 and (R,R)-10 are precursors of enantioselective sensor and selector molecules for the enantiomers of protonated primary amines, amino acids, and their derivatives.

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“…Chiral pentaethylene glycol ditosylate ( S,S )‐ 29 was prepared from diol ( S,S )‐ 33 using tosyl chloride (TsCl) in pyridine as a base and a solvent (see Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Tetraethylene glycol ditosylate (S,S)-27 and pentaethylene glycol ditosylate (S,S)-28 were obtained as described in the literature. 19,40 Chiral pentaethylene glycol ditosylate (S,S)-29 was prepared from diol (S,S)-33 41 using tosyl chloride (TsCl) in pyridine as a base and a solvent (see Scheme 5).…”

Section: Synthesismentioning

confidence: 99%

Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

et al. 2017

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“…Tetraethylene glycols (S,S)-6 and (S,S)-10 (see Scheme1) were obtained as described in the literature. 8,15 Upon reduction of diesters 14, 15 and 16 with NaBH4, 4-substituted pyridine-2,6-dimethanols 17, 18 and 19 were obtained (see Scheme3) in a similar manner as described in the literature for analogous compounds. 18 In the latter literature, this type of diols were not isolated.…”

Section: Scheme 1 Synthesis Of Pyridino-crown-ether Derivatives (Ssmentioning

confidence: 92%

Synthesis of new enantiopure dimethyl- and diisobutyl -substituted pyridino-18-crown-6 ethers containing a halogen atom or a methoxy group at position 4 of the pyridine ring for enantiomeric recognition studies

Kupai¹,

Huszthy²,

Székely³

et al. 2011

Arkivoc

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New enantiomerically pure dimethyl-and diisobutyl-substituted pyridino-18-crown-6 ethers containing a halogen atom or a methoxy group at position 4 of the pyridine ring [(S,S)-1, (S,S)-2, (S,S)-3, (S,S)-4] have been synthesized. A new synthetic route and the solid state structure of the reported enantiopure dimethyl-substituted pyridino-18-crown-6 ether [(S,S)-5] containing a chlorine atom at position 4 of the pyridine ring are also described. These ligands are good candidates for enantiomeric recognition studies of protonated primary amines, amino acids and their derivatives.

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“…The optical rotations ([ α ] D ) of commercially available ( S )-(+)-tetrahydrofurfurylamine and ( R )-(–)-tetrahydrofurfurylamine were measured as +11.85 and –11.33, respectively, and are in agreement with the reported optical rotation of the ( S )- and ( R )-stereoisomers, +12 and –12, respectively. 34 We were able to resolve the enantiomers of (±)- 9b using chiral HPLC (see the Experimental Section) and to determine the enantiomeric purity of ( R )- 9b and ( S )- 9b using chiral HPLC as >98%.…”

Section: Chemistrymentioning

confidence: 99%

Development of Novel ACK1/TNK2 Inhibitors Using a Fragment-Based Approach

Lawrence

Mahajan

Luo³

et al. 2015

J. Med. Chem.

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The tyrosine kinase ACK1, a critical signal transducer regulating survival of hormone-refractory cancers, is an important therapeutic target, for which there are no selective inhibitors in clinical trials to date. This work reports the discovery of novel and potent inhibitors for ACK1 tyrosine kinase (also known as TNK2) using an innovative fragment-based approach. Focused libraries were designed and synthesized by selecting fragments from reported ACK inhibitors to create hybrid structures in a mix and match process. The hybrid library was screened by enzyme-linked immunosorbent assay-based kinase inhibition and 33P HotSpot assays. Systematic structure–activity relationship studies led to the identification of compound (R)-9b, which shows potent in vitro (IC50 = 56 nM, n = 3, 33P HotSpot assay) and in vivo (IC50 < 2 μM, human cancer cell lines) ACK1 inhibition. Both (R)-9b and (S)-9b were stable in human plasma and displayed a long half-life (t1/2 > 6 h).

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Alkali metals dissolved in optically active solvents

Cited by 23 publications

References 6 publications

Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

Synthesis of new enantiopure dimethyl- and diisobutyl -substituted pyridino-18-crown-6 ethers containing a halogen atom or a methoxy group at position 4 of the pyridine ring for enantiomeric recognition studies

Development of Novel ACK1/TNK2 Inhibitors Using a Fragment-Based Approach

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Alkali metals dissolved in optically active solvents

Cited by 23 publications

References 6 publications

Synthesis and pKa determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

Synthesis and pKa determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

Synthesis of new enantiopure dimethyl- and diisobutyl -substituted pyridino-18-crown-6 ethers containing a halogen atom or a methoxy group at position 4 of the pyridine ring for enantiomeric recognition studies

Development of Novel ACK1/TNK2 Inhibitors Using a Fragment-Based Approach

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Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies