Trisulfides over disulfides: highly selective synthetic strategies, anti-proliferative activities and sustained H₂S release profiles

Abstract

Highly selective synthesis of trisulfides over disulfides is demonstrated along with their potential as anti-proliferative agents and sustained donors of H2S.

Unsymmetrical Disulfides Synthesis via Cs2CO3‐Catalyzed Three‐Component Reaction in Water

“…[13] Inorganic sulfur salts such as Na 2 S, Na 2 S 2 O 3 , and KSCN are safe, odorless and inexpensive and have been successfully used in the synthesis of organosulfide compounds. [14] As a green reaction media, water attracted much interest due to its ready availability, and lack of toxicity and flammability. [12i,15] Herein, we report a facile method for the synthesis of unsymmetrical disulfides via a Cs 2 CO 3 -catalyzed three-component reaction of thioacetate, Na 2 S 2 O 3 , and benzyl halide in water (Scheme 1c).…”

Thioredoxin reductase-triggered fluorogenic donor of hydrogen sulfide: a model study with a symmetrical organopolysulfide probe with turn-on near-infrared fluorescent emission

“…The lack of H 2 S donation from disulfide compounds was also validated in our earlier reports. 22,41 As the H 2 S estimation using MB assay is not completely quantitative in nature, H 2 S release was further confirmed using the reported nucleophilic substitution-cyclization-based turn-on fluorescent probe WSP2. 42 To identify and exclude the background reaction of WSP2 with thiols (DTT and GSH), WSP2 was first incubated with the thiols for 60 min and the emission response was measured.…”

“…The maximum peak intensity was observed after around 30 min and dropped gradually over time. 41 It should be mentioned here that the H 2 S release from DCI-PS can be tuned slightly by varying the individual components of the polysulfide during the synthesis of polysulfide alcohol 6. The distribution of polysulfide alcohol 6 could be varied slightly with the preparation of Na 2 S n with the variation of the relative ratio of sulfur powder to Na 2 SÁ9H 2 O (Table S1, ESI †).…”

A Review of Heterolytic Synthesis Methodologies for Organotri- and Organotetrasulfane Synthesis

“…This they found could be suppressed using formaldehyde, and the reaction was optimised recently by Hemant Srivastava and Krishna Bhabak in 2019 (entry 6, Scheme 2). 23 Milligan and Swan also went on to use their method to prepare cyclic trisulfanes from di-Bunte salts (Scheme 2, entry 7). 24 Indeed, cyclic polysul-…”