26473-47-2Relevant articles and documents
Reactivity of isothiazolones and isothiazolone-1-oxides in the inhibition of the PCAF histone acetyltransferase
Ghizzoni, Massimo,Haisma, Hidde J.,Dekker, Frank J.
, p. 4855 - 4861 (2009)
Development of small molecule inhibitors of the histone acetyltransferase p300/CBP associated factor (PCAF) is relevant for oncology. The inhibition of the enzyme PCAF and proliferation of the cancer cell line HEP G2 by a series of 5-chloroisothiazolones was compared to a series of 5-chloroisothiazolone-1-oxides. The PCAF inhibitory potency of 5-chloroisothiazolones and 5-chloroisothiazolone-1-oxides is influenced by substitution in the 4-position. A study on the reactivity of the HAT inhibitors towards thiols and thiolates indicates that 5-chloroisothiazolones reacted quickly with propane-1-thiolate to provide many products, whereas 5-chloroisothiazolone-1-oxides provide only one defined product. Growth inhibition studies indicate that 5-chloroisothiazolones inhibit proliferation of HEP G2 cells at concentrations between 8.6 and 24 μM, whereas 5-chloroisothiazolone-1-oxides required higher concentrations or showed no inhibition.
Synthesis of macrocyclic and medium-sized ring thiolactonesviathe ring expansion of lactams
Palate, Kleopas Y.,Epton, Ryan G.,Whitwood, Adrian C.,Lynam, Jason M.,Unsworth, William P.
supporting information, p. 1404 - 1411 (2021/02/27)
A side chain insertion method for the ring expansion of lactams into macrocyclic thiolactones is reported, that can also be incorporated into Successive Ring Expansion (SuRE) sequences. The reactions are less thermodynamically favourable than the analogous lactam- and lactone-forming ring expansion processes (with this notion supported by DFT data), but nonetheless, three complementary protecting group strategies have been developed to enable this challenging transformation to be achieved.
Method for preparing 2,4-dimethyltetrahydrothiophene-3-one
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Paragraph 0030; 0032; 0033, (2017/07/21)
The invention relates to a method for preparing 2,4-dimethyltetrahydrothiophene-3-one. The method comprises the following steps: preparing an intermediate 3-mercaptoisobutyric acid from an initial raw material methacrylic acid by adopting thiourea as a mercapto group donor; preparing an intermediate 2,5-dimethyl-3-thiaadipic acid from the intermediate 3-mercaptoisobutyric acid and 2-halogenopropionic acid under the action of an alkali; and preparing 2,4-dimethyltetrahydrothiophene-3-one from the intermediate 2,5-dimethyl-3-thiaadipic acid under the action of a diluent and a metal catalyst. The method for preparing the intermediate 2,5-dimethyl-3-thiaadipic acid from the initial raw material methacrylic acid with low price has the advantages of simple steps, high yield, high product purity, small amount of three wastes in the production process, and industrial production facilitation.
