1020-40-2Relevant articles and documents
Zeolite-catalyzed simple synthesis of different heterocyclic rings, part 2
Hegedues, Adrienn,Vigh, Ilona,Hell, Zoltan
, p. 428 - 431 (2004)
A simple and environmentally friendly synthesis was developed for the preparation of 2-arylimidazoline derivatives and 2-arylbenzoxazole derivatives using a small pore size zeolite. The similar reaction was not applicable to the preparation of the sulfur-containing analogs cysteamine or 2-aminothiophenol, probably because of a disadvantageous reaction between the zeolite and the thio compound.
Discovery of new low-molecular-weight p53-Mdmx disruptors and their anti-cancer activities
Uesato, Shinichi,Matsuura, Yoshihiro,Matsue, Saki,Sumiyoshi, Takaaki,Hirata, Yoshiyuki,Takemoto, Suzuho,Kawaratani, Yasuyuki,Yamai, Yusuke,Ishida, Kyoji,Sasaki, Tsutomu,Enari, Masato
, p. 1919 - 1926 (2016)
Although several p53-Mdm2-binding disruptors have been identified to date, few studies have been published on p53-Mdmx-interaction inhibitors. In the present study, we demonstrated that o-aminothiophenol derivatives with molecular weights of 200-300 selectively inhibited the p53-Mdmx interaction. S-2-Isobutyramidophenyl 2-methylpropanethioate (K-178) (1c) activated p53, up-regulated the expression of its downstream genes such as p21 and Mdm2, and preferentially inhibited the growth of cancer cells with wild-type p53 over those with mutant p53. Furthermore, we found that the S-isobutyryl-deprotected forms 1b and 3b of 1c and S-2-benzamidophenyl 2-methylpropanethioate (K-181) (3c) preferentially inhibited the p53-Mdmx interaction over the p53-Mdm2 interaction, respectively, by using a Flag-p53 and glutathione S-transferase (GST)-fused protein complex (Mdm2, Mdmx, DAPK1, or PPID). In addition, the interaction of p53 with Mdmx was lost by replacing a sulfur atom with an oxygen atom in 1b and 1c. These results suggest that sulfides such as 1b, 3b, 4b, and 5b interfere with the binding of p53-Mdmx, resulting in the dissociation of the two proteins. Furthermore, the results of oral administration experiments using xenografts in nude mice indicated that 1c reduced the volume of tumor masses to 49.0% and 36.6% that of the control at 100 mg/kg and 150 mg/kg, respectively, in 40 days.
Synthesis of C- and N-Substituted 1,5,2,6-Dithiadiazocanes –Electrophilic-Nucleophilic Thioamination (ENTA) Reagents
Bagd?iūnas, Gintautas,Javorskis, Tomas,Jurys, Arminas,Orentas, Edvinas
supporting information, p. 3329 - 3335 (2021/07/02)
A synthetic method is presented for S?N bond formation starting from cheap and affordable materials. We show that (un)substituted N-protected cyclic eight-membered C2-symmetric sulfenamides have been prepared in a few steps using this procedure. The synthetic utility of these ambipolar derivatives was demonstrated in a variety of synthetic transformations affording different S,N-heterocyles of pharmaceutical relevance in one or two steps from simple starting materials. (Figure presented.).
Solid phase synthesis of benzothiazolyl compounds
Mourtas, Spyros,Gatos, Dimitrios,Barlos, Kleomenis
, p. 2201 - 2204 (2007/10/03)
2-Aminobenzenethiol, bound through its thiol function to the 2-chlorotrityl (Clt)-, trityl (Trt)-, 4-methyltrityl (Mtt)- and 4-methoxytrityl (Mmt)-resins, was acylated at the amino-function by aliphatic and aromatic acids. The obtained 2-N-acyl-aminobenzenethiols were cleaved from the resin by treatment with trifluoroacetic acid solutions in dichloromethane. The 2-N-acyl-aminobenzenethiols released from the resin were cyclised to the corresponding 2-substituted benzothiazoles, by standing in a solution of dithiothreitol in DMF or methanol for 1-3 h at room temperature.
THERMAL REARRANGEMENT OF O-THIOACYL DERIVATIVES OF N-ACYL-N-ARYLHYDROXYLAMINES
Drozd, V.N.
, p. 317 - 326 (2007/10/02)
The ability of the Ar-N-O-C=S system of atoms to undergo a thermal rearrangement of the Claisen type was investigated.On the basis of the experimental data it was concluded that the process is predominantly nonconcerted in nature.
