Modular Assembly of Heterotrifunctional Molecules Enabled by Iodosulfonylation of Allenes and Subsequent Amination DOI
Xiaofeng Lin, Peng Cao, Shijie Liu

и другие.

Journal of Medicinal Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 20, 2024

Beyond the rapid achievements of therapeutic heterobifunctional molecules, some recent efforts have focused on constructing heterotrifunctional aiming at developing more potent and selective agents or emerging additional functions to molecules. However, synthesis these complex molecules requires a specific design lengthy steps. We developed two-step strategy for modular construction enabled by sustainable convenient iodosulfonylation allenes followed SN2′-selective amination. This successfully incorporates broad range biologically active labeling them with fluorescent group. The applications obtained compounds in protein labeling, subcellular imaging, targeted inhibition tumor cells make this highly appealing.

Язык: Английский

SNAr or Sulfonylation? Chemoselective Amination of Halo(het)arene Sulfonyl Halides for Synthetic Applications and Ultralarge Compound Library Design DOI
Vasyl Naumchyk, Vladyslav A. Andriashvili, Dmytro S. Radchenko

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3161 - 3183

Опубликована: Фев. 21, 2024

The chemoselectivity of halo(het)arene sulfonyl halide aminations is studied thoroughly under parallel synthesis conditions, and the scope limitations method are established. It shown that SNAr-reactive halides typically undergo sulfonamide during first step; second amination also possible provided SNAr-active center sufficiently reactive. On contrary, fluorides bearing an arylating moiety selective transformation at latter reactive proper control. Further sulfur–fluoride exchange (SuFEx) possible, which can be especially valuable for some classes. developed two-step double protocol provides access to a 6.67-billion compound synthetically tractable REAL-type chemical space (76% expected success rate).

Язык: Английский

Процитировано

1
SNAr or Sulfonylation? Chemoselective Amination of Halo(het)arene Sulfonyl Halides for Synthetic Applications and Ultralarge Compound Library Design DOI Creative Commons
Vasyl Naumchyk, Vladyslav A. Andriashvili, Dmytro S. Radchenko

и другие.

Опубликована: Ноя. 15, 2023

The chemoselectivity of halo(het)arene sulfonyl halide aminations is studied thoroughly under parallel synthesis conditions, and the scope limitations method are established. It shown that SNAr-reactive halides typically undergo sulfonamide at first step; second amination also possible provided SNAr-active center has sufficient reactivity. On contrary, fluorides bearing an arylating moiety selective transformation latter reactive proper temperature control. Further sulfur-fluoride exchange (SuFEx) reaction possible, which can be especially valuable for some classes. developed two-step double protocol provides access to a 7-Bln synthetically tractable REAL-type chemical space (nearly 70% expected success rate).

Язык: Английский

Процитировано

2
Chemistry in Ukraine DOI Open Access
Oleksandr O. Grygorenko, R.D. Lampeka, Валентин А. Чебанов

и другие.

The Chemical Record, Год журнала: 2024, Номер 24(2)

Опубликована: Янв. 29, 2024

Abstract In this special issue, we highlight recent advances in chemical research by scientists Ukraine, as well their compatriots and collaborators outside the country. Besides spotlighting contributions, see our task fostering global partnerships multi‐, inter‐, trans‐disciplinary collaborations, including much‐needed co‐funded projects initiatives. The three decades of renewed Ukraine independence have seen rather limited integration Ukrainian (chemical) science into communities. [1] At same time, surge collaborative initiatives between European Union (EU) echoes unfolding steps towards Ukraine's full participation to Horizon Europe Program. This recently implemented step opens enormous possibilities for researchers apply diverse EU grants. Moreover, a number journal issues collections were launched chemistry (i. e., Chemistry Heterocyclic Compounds [2] ChemistrySelect [3] ). Other scientific include ‘European School Ukrainians’ [4] ‘Kharkiv Chemical Seminar’ [5] voluntary aimed at engaging international research.

Язык: Английский

Процитировано

0
Effect of the Position of the Substituent in the Electrochemical Reduction of Nitro-Substituted Benzenesulfonyl Chlorides DOI

Michael A. Saley,

Emad M. Hamed,

Abdelaziz Houmam

и другие.

Canadian Journal of Chemistry, Год журнала: 2024, Номер 102(11), С. 761 - 771

Опубликована: Июль 11, 2024

The electrochemical reduction of a series nitro-substituted benzenesulfonyl chlorides is investigated. results the study are analysed with assistance theoretical calculations. shows that electron transfer mechanism depends on position nitro substituent phenyl ring. 3-nitrobenzenesulfonyl chloride follows stepwise where leads to an intermediate radical anion. For 4-nitrobenzenesulfonyl chloride, 2-nitrobenzenesulfonyl and 2,4-nitrobenzenesulfonyl “sticky” dissociative mechanism, S–Cl bond cleavage concerted. dissociation products (arylsulfinyl anion) show strong interactions. difference in behaviour associated overlap π * orbital σ for latter three compounds. through resonance stability arylsulfinyl radicals para ortho compounds facilitates reduced structures. Upon reduction, also produce corresponding diaryl disulfones, which easier reduce parent molecules hence induce interesting autocatalytic mechanism. Such concentration scan rate, does not take place 2,4-dinitrobenzenesulfonyl due sterical hindrance at position, as it prevents formation disulfones.

Язык: Английский

Процитировано

0
Saturated Heterocyclic Sulfamoyl Fluorides: Building Blocks for the SuFEx Chemistry DOI

Serhii Aleksandrenko,

Alexey V. Dobrydnev, Serhii Zhersh

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(42)

Опубликована: Июль 30, 2024

Abstract A scalable protocol for direct SO 2 F ‐based fluorosulfonylation of saturated (hetero)cyclic and functionalized amines is reported. The method cost‐effective applicable multigram preparation structurally diverse compounds, as illustrated by the synthesis 58 building blocks decorated with common functional groups. comparison overall yields products demonstrates advantages present over alternative approaches. obtained sp 3 ‐enriched sulfamoyl fluorides can be considered a new generation SuFEx (sulfur fluoride exchange) chemistry. synthetic utility synthesized was demonstrated late‐stage reactions tolerating functionality well transformations to provide corresponding sulfamide, sulfamate, sulfonamide derivatives.

Язык: Английский

Процитировано

0
Modular Assembly of Heterotrifunctional Molecules Enabled by Iodosulfonylation of Allenes and Subsequent Amination DOI
Xiaofeng Lin, Peng Cao, Shijie Liu

и другие.

Journal of Medicinal Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 20, 2024

Beyond the rapid achievements of therapeutic heterobifunctional molecules, some recent efforts have focused on constructing heterotrifunctional aiming at developing more potent and selective agents or emerging additional functions to molecules. However, synthesis these complex molecules requires a specific design lengthy steps. We developed two-step strategy for modular construction enabled by sustainable convenient iodosulfonylation allenes followed SN2′-selective amination. This successfully incorporates broad range biologically active labeling them with fluorescent group. The applications obtained compounds in protein labeling, subcellular imaging, targeted inhibition tumor cells make this highly appealing.

Язык: Английский

Процитировано

0