A new route to allyl thiols and allyl thiocarbamates from Baylis‐Hillman adducts

Kim, Young‐Gi; Lim, Hee Nam; Lee, Kee‐Jung

doi:10.1002/jhet.3

Cited by 14 publications

(3 citation statements)

References 45 publications

(25 reference statements)

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“…Amide coupling with chloroacetyl chloride led to intermediates 55 – 62 . Replacement of the α-chlorine by a thiocyanate group was followed by hydrolysis to the respective thiocarbamates 63 – 70 using a mixture of concentrated sulfuric acid and acetic acid …”

Section: Resultsmentioning

confidence: 98%

“…Replacement of the α-chlorine by a thiocyanate group was followed by hydrolysis to the respective thiocarbamates 63−70 using a mixture of concentrated sulfuric acid and acetic acid. 47 Introduction of a benzylic group at the position of the amide nitrogen of 27 led to an active compound with an IC 50 of 20.4 ± 0.9 μM (63, Table 2). The activity was approximately 3-fold lower compared to the nonbenzylated compound (Table 1).…”

Section: Acs Infectious Diseasesmentioning

confidence: 87%

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Binding Mode Characterization and Early in Vivo Evaluation of Fragment-Like Thiols as Inhibitors of the Virulence Factor LasB from Pseudomonas aeruginosa

et al. 2018

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The increasing emergence of antibiotic resistance necessitates the development of anti-infectives with novel modes of action. Targeting bacterial virulence is considered a promising approach to develop novel antibiotics with reduced selection pressure. The extracellular collagenase elastase (LasB) plays a pivotal role in the infection process of Pseudomonas aeruginosa and therefore represents an attractive antivirulence target. Mercaptoacetamide-based thiols have been reported to inhibit LasB as well as collagenases from clostridia and bacillus species. The present work provides an insight into the structure-activity relationship (SAR) of these fragment-like LasB inhibitors, demonstrating an inverse activity profile compared to similar inhibitors of clostridial collagenase H (ColH). An X-ray cocrystal structure is presented, revealing distinct binding of two compounds to the active site of LasB, which unexpectedly maintains an open conformation. We further demonstrate in vivo efficacy in a Galleria mellonella infection model and high selectivity of the LasB inhibitors toward human matrix metalloproteinases (MMPs).

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Section: Resultsmentioning

confidence: 98%

Section: Acs Infectious Diseasesmentioning

confidence: 87%

Binding Mode Characterization and Early in Vivo Evaluation of Fragment-Like Thiols as Inhibitors of the Virulence Factor LasB from Pseudomonas aeruginosa

et al. 2018

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“…[7] And Moore found an indole alkaloid containing thiocyanate group from the blue-green algae hapalosiphon welwitschia (welwitindolinone). [11] These compounds holding CÀ SCN bond are used as versatile synthetic precursors for accessing organosulfur compounds and other products, [12][13][14] such as thiols, [15] thioethers, [16,17] thioesters, [18] hetero-cycles, [19] and bi-/tri-fluoromethyl sulfides. [20,21] As significant one of them, allylic thiocyanates have gained the most widespread popularity among chemists.…”

Section: Introductionmentioning

confidence: 99%

Thiocyanation of Allylic Alcohols Promoted by Trifluoroacetic Acid

Wen

et al. 2023

Eur J Org Chem

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A rapid and efficient acid-promoted strategy to access allylic thiocyanates using allylic alcohols as substrates and easilyavailable NH 4 SCN as the thiocyanate source is presented under metal-and oxidant-free conditions. Through screening of various kinds of acids, organic and strong trifluoroacetic acid (TFA) was found most effective. Testing of substrates showed that the strategy has remarkable functional group tolerance. A possible mechanism is provided, and the gram-scale experiment demonstrate that this novel protocol has potential industrial application value.

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Formal [3+2] Annulation Involving Allylic Bromides and Thioureas. Synthesis of 2‐Iminothiazolidines through a Base‐Catalyzed Intramolecular anti‐Michael Addition

Ferreira

Sá

2015

Adv Synth Catal

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A simple and efficient protocol was developed for the synthesis of 2-iminothiazolidines through a base-mediated [3+2] annulation involving substituted thioureas and allylic bromides bearing electron-withdrawing groups. This domino process consists of nucleophilic displacement, followed by intramolecular anti-Michael addition of the preformed allylic isothiourea under mild conditions to give the thiazolidine core.

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A new route to allyl thiols and allyl thiocarbamates from Baylis‐Hillman adducts

Abstract: A facile synthesis of trisubstituted allyl thiols and allyl thiocarbamates has been accomplished from Baylis‐Hillman adducts through bromination, thiocyanation, and acid‐assisted hydrolysis reaction. J. Heterocyclic Chem., (2009)

Cited by 14 publications

References 45 publications

Binding Mode Characterization and Early in Vivo Evaluation of Fragment-Like Thiols as Inhibitors of the Virulence Factor LasB from Pseudomonas aeruginosa

Binding Mode Characterization and Early in Vivo Evaluation of Fragment-Like Thiols as Inhibitors of the Virulence Factor LasB from Pseudomonas aeruginosa

Thiocyanation of Allylic Alcohols Promoted by Trifluoroacetic Acid

Formal [3+2] Annulation Involving Allylic Bromides and Thioureas. Synthesis of 2‐Iminothiazolidines through a Base‐Catalyzed Intramolecular anti‐Michael Addition

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