122439-11-6Relevant articles and documents
Development of oxathiino[6,5-b]pyridine 2,2-dioxide derivatives as selective inhibitors of tumor-related carbonic anhydrases IX and XII
Nocentini, Alessio,Supuran, Claudiu T.,?alubovskis, Raivis,Domra?eva, Ilona,Grandāne, Aiga
, (2020)
Oxathiino[6,5-b]pyridine 2,2-dioxides are identified as a new class of isoform-selective nanomolar inhibitors of tumor associated human carbonic anhydrases (hCA) IX and XII. At the same time they do not inhibit or poorly inhibit cytosolic isoforms hCA I and II. Oxathiino[6,5-b]pyridine 2,2-dioxides exhibited good antiproliferative properties on tumor cell lines MCF-7 (Human breast adenocarcinoma), A549 (human lung (alveolar) adenocarcinoma) and HeLa (epithelioid cervix carcinoma).
Base-free catalytic wittig-/cross-coupling reaction sequence as short synthetic strategy for the preparation of highly functionalized arylbenzoxepinones
Pudnika, Linda,Domraceva, Ilona,Werner, Thomas,Zalubovskis, Raivis,Grandane, Aiga
, p. 3545 - 3554 (2021/07/02)
The facile synthesis of highly functionalized building blocks with potential biological activity is of great interest to medicinal chemistry. The benzoxepinone core structures commonly exhibit biological activity. Thus, a short and efficient synthetic route towards benzoxepine containing scaffold, which enables late stage modification was developed. Namely, base-free catalytic Wittig reactions enabled the synthesis of bromobenzoxepinones from readily available starting materials. Subsequent, Suzuki-Miyaura and Stille reactions proved to be suitable methods to access a variety of benzoxepinone diaryl derivatives by late stage modification in only three steps. This three-step reaction sequence is suitable for high throughput applications and gives facile access to highly complex molecular structures, which are suitable for further functionalization. The antiproliferative properties of selected arylbenzoxepinones were tested in vitro on monolayer tumor cell line A549. Notably, in this initial screening, these compounds were found to be active in the micromolar range.
Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
Akram, Manjur O.,Shinde, Popat S.,Chintawar, Chetan C.,Patil, Nitin T.
supporting information, p. 2865 - 2869 (2018/05/03)
Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.
Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes
Lian, Chang,Yue, Guanglu,Zhang, Haonan,Wei, Liyan,Liu, Danyang,Liu, Sichen,Fang, Huayi,Qiu, Di
, p. 4019 - 4023 (2018/10/04)
A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distannanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demonstrates the potential applications of this method in organic synthesis.
Ni-Catalyzed Stannylation of Aryl Esters via C?O Bond Cleavage
Gu, Yiting,Martín, Rúben
, p. 3187 - 3190 (2017/03/17)
A Ni-catalyzed stannylation of aryl esters with air- and moisture-insensitive silylstannyl reagents via Csp2 ?O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C?heteroatom bond formations.
Efficient one-pot cross-coupling of two aryl halides by stannylation/stille reaction in water under microwave irradiation
Tan, Xin,Zhou, Zi Jie,Zhang, Jia Xin,Duan, Xin Hong
supporting information, p. 5153 - 5157 (2014/09/29)
A simple and highly efficient one-pot approach has been developed for the Pd(PPh3)4-catalyzed cross-coupling of two different aryl or heteroaryl bromides/iodides. This method involves the combined use of microwave irradiation and water as a single solvent to achieve sequential stannylation and Stille cross-coupling reactions, which allows rapid access to a wide variety of biaryls in good to high yields. Furthermore, utilizing this step-economical protocol, 2,5-dibromopyridine was iteratively diarylated and the Boscalid intermediate was also synthesized in a one-pot manner. Copyright
Sonochemical synthesis of bis(tri-n-butylstannyl) aromatic compounds via Barbier-like reactions
Gerbino, Darío C.,Fidelibus, Pablo M.,Mandolesi, Sandra D.,Ocampo, Romina A.,Scoccia, Jimena,Podestá, Julio C.
, p. 24 - 32 (2013/10/01)
This paper reports a study of the synthesis of aryltri-n-butylstannanes via a sonochemical Barbier reaction of aryl- and heteroaryl bromides with bis(tri-n-butyltin) oxide (2) in THF. Our results demonstrate that, despite previous reports on contrary, the aryltributylstannanes can also be obtained under the same reaction conditions via sonicated reactions between aryl monobromides and tri-nbutyltin chloride (2). A comparative study of the reactions of electrophiles 2 and 3 with bromobenzene, 2-bromopyridin, o- and m-bromoanisole, m-bromotoluene, 9-bromophenthrene, and 9-bromoanthracene, indicates that the corresponding aryl- and heteroaryl-tri-n-butylstannyl derivatives are obtained in about the sameyields. Best reaction conditions and the results obtained in the investigation of the sonicated reactions between several aromatic and heteroaromatic dibromides are also reported. It was found that the reactions using 1,2-, 1,3-, and 1,4-dibromobenzenes, 4,40-dibromobiphenyl, 1,4-dibromonaphthalene, 2,5-and 3,5-dibromopyridines, and 2,5-dibromothiophene lead to the corresponding bis(tri-n-butylstannylated) derivatives in many cases in very high yields. Also the excellent results obtained in the sonicated reactions of 1,3,5-tribromobenzene with 2 and 3 are reported.
New and simple one-step cobalt-catalyzed preparation of functionalized arylstannanes from the corresponding aryl bromides or iodides
Gosmini, Corinne,Perichon, Jacques
, p. 216 - 217 (2007/10/03)
The process for the preparation of functionalized arylstannanes from the corresponding aryl bromides or iodides was described. The corresponding arylstannane was detected by gas chromatography using an internal standard alkane. The two-step coupling react
