N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines

Gruzdev, Dmitry А.; Vakarov, Sergey А.; Левит, Г. Л.; Краснов, В. П.

doi:10.1007/s10593-014-1432-4

Cited by 19 publications

(3 citation statements)

References 47 publications

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“…Coupling of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 2 with tosyl- S -prolinoyl chloride resulted in diastereoisomers 10a and 10b ( Scheme 2 ). 20 The diastereomeric mixture was column separable and the individual isomers were separated using an isocratic 9:1, dichloromethane and ethyl acetate mobile system. The absolute configuration of the diastereoisomers was determined by X-ray crystallography analyses ( Figure S1 ).…”

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confidence: 99%

Structure–Activity Relationship Studies with Tetrahydroquinoline Analogs as EPAC Inhibitors

Sonawane¹,

Zhu²,

Garrison³

et al. 2017

ACS Med. Chem. Lett.

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EPAC proteins are therapeutic targets for the potential treatment of cardiac hypertrophy and cancer metastasis. Several laboratories use a tetrahydroquinoline analog, CE3F4, to dissect the role of EPAC1 in various disease states. Here, we report SAR studies with tetrahydroquinoline analogs that explore various functional groups. The most potent EPAC inhibitor 12a exists as a mixture of inseparable E (major) and Z (minor) rotamers. The rotation about the N-formyl group indeed impacts the activity against EPAC.

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confidence: 99%

Structure–Activity Relationship Studies with Tetrahydroquinoline Analogs as EPAC Inhibitors

Sonawane¹,

Zhu²,

Garrison³

et al. 2017

ACS Med. Chem. Lett.

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“…Among them, compounds with high antimycobacterial were found (Krasnov et al., ). To obtain enantiomerically pure heterocyclic amines (the precursors of bases 1 and 2 ), the method of kinetic resolution of racemates was used (Gruzdev, Vakarov, Levit, & Krasnov, ; Gruzdev et al., ; Krasnov et al., ). Four bases of the series (conjugates of 2‐aminopurine with the enantiomers of 7,8‐difluoro‐3,4‐dihydro‐3‐methyl‐2 H ‐[1,4]benzoxazine [( R )‐ 1, 2 and ( S )‐ 1 , 2 ], (Figure ) were used in the enzymatic synthesis of β‐ D ‐arabinosides (Eletskaya et al., ).…”

Section: Introductionmentioning

confidence: 99%

“…Among them, compounds with high antimycobacterial were found (Krasnov et al, 2016). To obtain enantiomerically pure heterocyclic amines (the precursors of bases 1 and 2), the method of kinetic resolution of racemates was used (Gruzdev, Vakarov, Levit, & Krasnov, 2014;Gruzdev et al, 2013;Krasnov et al, 2003). (Eletskaya et al, 2016).…”

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confidence: 99%

Enzymatic synthesis of novel purine nucleosides bearing a chiral benzoxazine fragment

et al. 2019

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A series of ribo‐ and deoxyribonucleosides bearing 2‐aminopurine as a nucleobase with 7,8‐difluoro‐ 3,4‐dihydro‐3‐methyl‐2H‐[1,4]benzoxazine (conjugated directly or through an aminohexanoyl spacer) was synthesized using an enzymatic transglycosylation reaction. Nucleosides 3‐6 were resistant to deamination under action of adenosine deaminase (ADA) Escherichia coli and ADA from calf intestine. The antiviral activity of the modified nucleosides was evaluated against herpes simplex virus type 1 (HSV‐1, strain L2). It has been shown that at sub‐toxic concentrations, nucleoside (S)‐4‐[2‐amino‐9‐(β‐D‐ribofuranosyl)‐purin‐6‐yl]‐7,8‐difluoro‐3,4‐dihydro‐3‐methyl‐2H‐[1,4]benzoxazine exhibit significant antiviral activity (SI > 32) on the model of HSV‐1 in vitro, including an acyclovir‐resistant virus strain (HSV‐1, strain L2/R).

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Kinetic study of reactions of aniline and benzoyl chloride in a microstructured chemical system

Wang

Zhang

et al. 2015

AIChE Journal

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The reaction between aniline and benzoyl chloride is well known for producing high performance polymers and chemicals. But the fast main reaction and reversible consecutive side reaction make process rather complicated and no thorough kinetics study has ever been reported before. A microstructured chemical system, consisting of a micromixer, preheat exchange coiled capillaries, a delay loop, and a microhydrolyzer, was designed to carry out this reaction using N‐methyl‐2‐pyrrolidone as the solvent. A kinetic model was established, and the values of kinetic constants, pre‐exponential factors and activation energies of each reaction as well as their confidence intervals were acquired. With this model each substance concentration vs. residence time were obtained to help understand reaction process and further optimize operating conditions. Compared to earlier reports on this reaction, this microstructured chemical system provides more accurate parameters and can develop a reliable platform for kinetic study of similar chemical reactions. © 2015 American Institute of Chemical Engineers AIChE J, 61: 3804–3811, 2015

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N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines

Cited by 19 publications

References 47 publications

Structure–Activity Relationship Studies with Tetrahydroquinoline Analogs as EPAC Inhibitors

Structure–Activity Relationship Studies with Tetrahydroquinoline Analogs as EPAC Inhibitors

Enzymatic synthesis of novel purine nucleosides bearing a chiral benzoxazine fragment

Kinetic study of reactions of aniline and benzoyl chloride in a microstructured chemical system

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