58109-94-7Relevant academic research and scientific papers
Rongalite as a sulfone source: A novel copper-catalyzed sulfur dioxide anion incorporation process
Chen, Xiang-Long,Tang, Bo-Cheng,He, Cai,Ma, Jin-Tian,Zhuang, Shi-Yi,Wu, Yan-Dong,Wu, An-Xin
supporting information, p. 13653 - 13656 (2020/11/13)
A novel copper-catalyzed sulfur dioxide anion incorporation cascade for the synthesis of 1-thiaflavanone sulfones has been disclosed using rongalite as an economic and safe sulfone source. A series of 1-thiaflavanone sulfones were synthesized from easily prepared 2′-iodochalcone derivatives in excellent yields. This transformation proceeds through consecutive formation of two C-S bonds, which is the first example of SO22- being used to construct sulfone motifs under copper-catalyzed conditions.
Synthesis and evaluation of thiochroman-4-one derivatives as potential leishmanicidal agents
Vargas, Esteban,Echeverri, Fernando,Vélez, Iván D.,Robledo, Sara M.,Qui?ones, Wiston
, (2018/01/17)
The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity.
Copper-Catalyzed Domino Synthesis of 2-Arylthiochromanones through Concomitant C-S Bond Formations Using Xanthate as Sulfur Source
Sangeetha, Subramani,Muthupandi, Pandi,Sekar, Govindasamy
supporting information, p. 6006 - 6009 (2016/01/09)
An efficient domino process for the synthesis of thioflavanones has been described using a copper catalyst without addition of any external ligand. A variety of thioflavanones have been synthesized from easily accessible 2′-iodochalcones or 2′-bromochalco
Elimination, ring-contraction, and fragmentation reactions of 1-thioflavanone 1-oxides
Somogyi
, p. 1159 - 1165 (2007/10/03)
Epimeric thioflavanone sulfoxides (2b) were selectively transformed into thioflavone (1a), thioaurone (3a), and di(2-cinnamoylphenyl) disulfide (4). Disulfide 4 can be recyclized into thioaurones (3a-c) and thioflavanones (2a, 5) with heterolysis of the S - S bond. The 3-p-anisylidene sulfoxide analog of 2b (6) transforms, with fragmentation, into 4′-methoxythioaurone 3b.
Chemo- and diastereoselectivity in the dimethyldioxirane oxidation of 2,3-dihydro-4H-1-benzothiopyran-4-ones and 4H-1-benzothiopyran-4-ones. Unusual reactivity of 4H-1-benzothiopyran-4-one 1-oxides1
Patonay,Adam,Levai,Koever,Nemeth,Peters,Peters
, p. 2275 - 2280 (2007/10/03)
The oxidation of the 1-thiochromanones 1-3 by dimethyldioxirane (DMD) produced the corresponding sulfoxides 4-6 or sulfones 7-9; their relative amounts depended on the amount of oxidant used. A low diastereoselectivity was observed in the sulfoxidation of
Contribution to the Transformations of 1-Thioflavanoids with Hypervalent Oxidants
Somogyi, Laszlo
, p. 959 - 960 (2007/10/02)
Permanganate oxidation transforms 1-thioflavanone (1a) to the corresponding 1,1-dioxide 1c.Periodate oxidation of 1a affords in the cold mainly the corresponding sulfoxide 1b, and that of 1a or 1-thioflavone 1-oxide (2b) provides on heating 1-thioflavone
