4521-45-3Relevant academic research and scientific papers
Cyclic analogue of S-benzylisothiourea that suppresses kynurenine production without inhibiting indoleamine 2,3-dioxygenase activity
Fukuda, Miwa,Sasaki, Tomomi,Hashimoto, Tomoko,Miyachi, Hiroyuki,Waki, Minoru,Asai, Akira,Takikawa, Osamu,Ohno, Osamu,Matsuno, Kenji
, p. 2846 - 2849 (2018/07/30)
Kynurenine is biosynthesised from tryptophan catalysed by indoleamine 2,3-dioxygenase (IDO). The abrogation of kynurenine production is considered a promising therapeutic target for immunological cancer treatment. In the course of our IDO inhibitor programme, formal cyclisation of the isothiourea moiety of the IDO inhibitor 1 afforded the 5-Cl-benzimidazole derivative 2b-6, which inhibited both recombinant human IDO (rhIDO) activity and cellular kynurenine production. Further derivatisation of 2b-6 provided the potent inhibitor of cellular kynurenine production 2i (IC50 = 0.34 μM), which unexpectedly exerted little effect on the enzymatic activity of rhIDO. Elucidation of the mechanism of action revealed that compound 2i suppresses IDO expression at the protein level by inhibiting STAT1 expression in IFN-γ-treated A431 cells. The kynurenine-production inhibitor 2i is expected to be a promising starting point for a novel approach to immunological cancer treatment.
A highly efficient Cu-catalyzed S-transfer reaction: From amine to sulfide
Li, Yiming,Pu, Jiahua,Jiang, Xuefeng
supporting information, p. 2692 - 2695 (2014/06/09)
A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.
Manganese-catalyzed cross-coupling of thiols with aryl iodides
Liu, Tsung-Jui,Yi, Chih-Lun,Chan, Chien-Ching,Lee, Chin-Fa
, p. 1029 - 1034 (2013/08/25)
A manganese-catalyzed cross-coupling reaction of thiols with aryl iodides, furnishing aryl thioethers in good to excellent yields has been reported; the system shows good functional group tolerance and enables the sterically demanding aryl iodides to couple with thiols. Coming up for ArI: A manganese-catalyzed cross-coupling reaction of thiols with aryl iodides that furnishes aryl thioethers in good to excellent yields has been reported. Functional groups such as unprotected alcohols and chloro substituents are tolerated under these reaction conditions. Moreover, this catalytic system enables the sterically demanding aryl iodides to couple with thiols (see scheme; R=aryl or alkyl).
A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes
Ko, Jaeyoung,Ham, Jungyeob,Yang, Inho,Chin, Jungwook,Nam, Sang-Jip,Kang, Heonjoong
, p. 7101 - 7106 (2007/10/03)
A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ pro
Synthesis of substituted dihydrobenzothiopyrans and dihydrobenzopyrans by cation-mediated cyclisation reactions
Bonfanti, Jean-Fran?ois,Craig, Donald
, p. 3719 - 3723 (2007/10/03)
Treatment with acid of thiosalicylaldehyde- and salicylaldehyde-derived phenyl 3-phenyl-2-propenyl thioethers and ethers possessing latent oxonium ion functionality triggers simple or tandem cyclisation to give substituted dihydrobenzothiopyrans and dihyd
Arylsulfanyl and heteroarylsulfanyl derivatives for treating pain
-
, (2008/06/13)
According to the invention there is provided a compound the formula I; wherein A, X, B, R1, R2, R3 and R4 are as defined in the specification.
1,3-Oxathiane ring formation through intramolecular Pummerer reaction of alkyl ortho-hydroxymethylphenyl sulfoxides
Abe, Hitoshi,Shibaike, Kentaro,Fujii, Hiroyuki,Tsuchida, Daisuke,Akiyama, Teruaki,Harayama, Takashi
, p. 291 - 298 (2007/10/03)
The intramolecular Pummerer rearrangement of 2-(2-alkyl-sulfinylphenyl)- 2-propanols (1a, 1c-1g) yielded 1,3-oxathianes (2a, 2c-2g) in the presence of p-toluenesulfonic acid and molecular sieves 3A. Alkyl halides were converted into 1,3-oxathiane derivatives in three steps via this rearrangement.
Synthesis and characterization of triosmium clusters containing the 2-(benzylthio)benzoyl ligand
Lee, Siu-Ming,Cheung, Kung-Kai,Wong, Wing-Tak
, p. 273 - 278 (2007/10/02)
Reaction of with an equimolar proportion of 2-(benzylthio)-benzaldehyde (1) gives three new compounds: two yellow isomers of (2a and 2b) and an orange crystalline compound (3).The mol
A New Reduction of Some Carboxylic Esters with Sodium Borohydride and Zinc Chloride in the Presence of a Tertiary Amine
Yamakawa, Tomio,Masaki, Mitsuo,Nohira, Hiroyuki
, p. 2730 - 2734 (2007/10/02)
In the presence of a tertiary amine, sodium borohydride (NaBH4) combined with zinc chloride (ZnCl2) showed powerful reducing properties and carboxylic esters were smoothly reduced to their corresponding alcohols which were not obtained by reduction with NaBH4 and ZnCl2 alone.Tetrahydrofuran (THF) was an efficient solvent, and the effective molar ratio of the reducing agents, NaBH4:ZnCl2:tertiary amine, was 2:1:1.In particular, aminobenzoates such as anthranilic esters, were reduced to aminobenzyl alcohols with high yields without the addition of a tertiary amine.Further, it was also found that this combination reduced nitro, cyano, and amido groups to their corresponding amino groups.
