Ultrasound mediated efficient ring opening of epoxides by in situ generated dithiocarbamates in green reaction media

Azizi, Najmedin; Gholibeglo, Elham; Maryami, Mahboobe; Nayeri, Sanaz Dehghan; Bolourtchian, Seyed Mohammad

doi:10.1016/j.crci.2012.11.020

Cited by 15 publications

(6 citation statements)

References 28 publications

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“…During the past few years, several advancements for the synthesis of β‐hydroxy dithiocarbamates have been reported. Azizi, [19a–b] Saidi, [19c–d] and Ranu [19e] reported, respectively, the one‐pot three‐component reactions of amines, carbon disulfide, and epoxides (Scheme 1a). Dilman and co‐workers described their elegant works on the synthesis of such structures with a difluorinated silicon reagent bearing pyrrolidine dithiocarbamate substituent as the nucleophile (Scheme 1b) [20] .…”

Section: Figurementioning

confidence: 99%

Synthesis of 2‐Aryl‐2‐hydroxyethyl Dithiocarbamates via Regioselective Addition of Tetraalkylthiuram Disulfides to Styrenes under Transition‐Metal‐Free Conditions

et al. 2020

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This paper describes a method for the synthesis of 2-aryl-2-hydroxyethyl dithiocarbamates via difunctionalization of alkenes involving CÀ S and CÀ O bonds formation with tetraalkylthiuram disulfides as the functional reagents. The reaction proceeded well under transition-metal-free conditions and afforded up to 88% yield of the desired products. Numerous useful functional groups were tolerated under the reaction conditions. This methodology provides a direct approach to β-hydroxy dithiocarbamates, featuring readily available starting materials and broad substrate scope, which shows its practical synthetic value in organic synthesis.

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Section: Figurementioning

confidence: 99%

Synthesis of 2‐Aryl‐2‐hydroxyethyl Dithiocarbamates via Regioselective Addition of Tetraalkylthiuram Disulfides to Styrenes under Transition‐Metal‐Free Conditions

et al. 2020

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“…They can undergo regioselective ring opening from the less hindered terminal carbon side of the epoxide ring with a wide variety of nucleophiles by SN 2 reaction. The dithiocarbamate nucleophiles generated in situ from CS 2 and amines open the epoxide ring from the terminal carbon side [39,40,41] to afford 2-hydroxy dithiocarbamates, which are found to have a wide variety of applications in organic synthesis [42,43,44,45], pharmaceuticals [46,47,48,49], and agriculture [50,51,52].…”

Section: Introductionmentioning

confidence: 99%

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

et al. 2019

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A series of 2-hydroxy-3-chrysino dithiocarbamate derivatives (3a–k) were designed, synthesized, and characterized for their structure determination by 1H NMR, 13C NMR, and HRMS (ESI) spectral data. They were screened for their in vitro biological activities against a panel of selected bacterial and fungal strains. These antimicrobial studies indicate that some of the analogues manifested significant activity compared to standard drugs. Among the synthetic analogues (3a–k), compounds 3d, 3f, and 3j exhibited very good antibacterial activity and compounds 3d, 3f, and 3h showed very good antifungal activity compared to the standard drugs penicillin and itrazole, respectively. The compounds 3e, 3g, and 3h showed moderate antibacterial activity and the compounds 3j and 3k showed moderate antifungal activity. Molecular docking studies were performed and the experimental antimicrobial screening results were also correlated with the binding energy values obtained by molecular docking. The synthesized chrysin analogues (3a–k) have obeyed Lipinski’s “rule of five” and have drug-likeness.

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“…In this work, ethyleneimine generated in situ from β-chloroethylamine was used as a nucleophile to open the epoxides in an aqueous environment. Another study demonstrated that primary amines undergo efficient ring opening reaction with epoxides [36]. The uniqueness of our results lies in the ability of triggering the ring-opening reaction of epoxide in a protein crystal.…”

Section: Discussionmentioning

confidence: 69%

Developing HIV-1 Protease Inhibitors through Stereospecific Reactions in Protein Crystals

et al. 2016

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Abstract:Protease inhibitors are key components in the chemotherapy of HIV infection. However, the appearance of viral mutants routinely compromises their clinical efficacy, creating a constant need for new and more potent inhibitors. Recently, a new class of epoxide-based inhibitors of HIV-1 protease was investigated and the configuration of the epoxide carbons was demonstrated to play a crucial role in determining the binding affinity. Here we report the comparison between three crystal structures at near-atomic resolution of HIV-1 protease in complex with the epoxide-based inhibitor, revealing an in-situ epoxide ring opening triggered by a pH change in the mother solution of the crystal. Increased pH in the crystal allows a stereospecific nucleophile attack of an ammonia molecule onto an epoxide carbon, with formation of a new inhibitor containing amino-alcohol functions.The described experiments open a pathway for the development of new stereospecific protease inhibitors from a reactive lead compound.

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Ultrasound mediated efficient ring opening of epoxides by in situ generated dithiocarbamates in green reaction media

Cited by 15 publications

References 28 publications

Synthesis of 2‐Aryl‐2‐hydroxyethyl Dithiocarbamates via Regioselective Addition of Tetraalkylthiuram Disulfides to Styrenes under Transition‐Metal‐Free Conditions

Synthesis of 2‐Aryl‐2‐hydroxyethyl Dithiocarbamates via Regioselective Addition of Tetraalkylthiuram Disulfides to Styrenes under Transition‐Metal‐Free Conditions

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

Developing HIV-1 Protease Inhibitors through Stereospecific Reactions in Protein Crystals

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