4547-68-6Relevant academic research and scientific papers
Development of prohibitin ligands against osteoporosis
Tabti, Redouane,Lamoureux, Fran?ois,Charrier, Céline,Ory, Benjamin,Heymann, Dominique,Bentouhami, Embarek,Désaubry, Laurent
supporting information, (2020/11/04)
Current therapeutic approaches to osteoporosis display some potential adverse effects and a limited efficacy on non-vertebral fracture reduction. Some sulfonylamidines targeting the scaffold proteins prohibitins-1 and 2 (PHB1/2) have been showed to inhibit the formation of osteoclasts in charge of bone resorption. Herein, we report the development of a second generation of anti-osteoclastic PHB ligands. The most potent compound, IN45, showed 88% inhibition at the low concentration of 5 μM, indicates that it might serve as a basis for the development of new antiosteoporotic drugs.
Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water
Jiang, Shuai,Cao, Wen-Bin,Li, Hai-Yan,Xu, Xiao-Ping,Ji, Shun-Jun
supporting information, p. 2619 - 2623 (2021/04/21)
A Co-catalyzed coupling of 3-(2-isocyanoethyl)indoles with organic azides in pure water for accessing spiroindolenine derivatives was developed. This strategy features mild reaction conditions, high atom-economy, excellent yields, wide substrate scopes, and broad functional group tolerance. The products were obtained simply by sequential operation involving extraction, concentration, precipitation, and filtration, without tedious column chromatography. More importantly, the aqueous catalytic system could be recycled at least ten times without reducing the catalytic activity. The strategy provides a green and efficient method for the construction of spiroindolenine derivatives.
One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity
Sreerama, Rakesh,Narasimha Swamy,Ravinder,Vasudeva Reddy,Narsimha, Sirassu
, p. 455 - 460 (2020/12/17)
A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in?vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.
Pd-catalyzed amidation of 1,3-diketones with CO and azidesviaa nitrene intermediate
Gu, Zheng-Yang,Chen, Jie,Xia, Ji-Bao
supporting information, p. 11437 - 11440 (2020/10/12)
An efficient Pd-catalyzed amidation of 1,3-diketones has been developed using carbon monoxide and organic azides. This reaction provides a step-economic approach to produce β-ketoamides from readily available compounds under mild ligand-, oxidant-, and base-free conditions. The mechanistic studies showed that the reaction occurred through anin situgenerated isocyanate intermediate.
Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage
Gui, Jiao,Xie, Haisheng,Jiang, Huanfeng,Zeng, Wei
supporting information, p. 2804 - 2807 (2019/04/30)
Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C-C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.
Intermolecular C?H Amidation of (Hetero)arenes to Produce Amides through Rhodium-Catalyzed Carbonylation of Nitrene Intermediates
Yuan, Si-Wen,Han, Hui,Li, Yan-Lin,Wu, Xueli,Bao, Xiaoguang,Gu, Zheng-Yang,Xia, Ji-Bao
supporting information, p. 8887 - 8892 (2019/05/29)
Amide bond formation is one of the most important reactions in organic chemistry because of the widespread presence of amides in pharmaceuticals and biologically active compounds. Existing methods for amides synthesis are reaching their inherent limits. Described herein is a novel rhodium-catalyzed three-component reaction to synthesize amides from organic azides, carbon monoxide, and (hetero)arenes via nitrene-intermediates and direct C?H functionalization. Notably, the reaction proceeds in an intermolecular fashion with N2 as the only by-product, and either directing groups nor additives are required. The computational and mechanistic studies show that the amides are formed via a key Rh-nitrene intermediate.
Ligand-Free, Quinoline N-Assisted Copper-Catalyzed Nitrene Transfer Reaction to Synthesize 8-Quinolylsulfimides
Xiao, Xinsheng,Huang, Sanping,Tang, Shanshan,Jia, Guokai,Ou, Guangchuan,Li, Yangyan
, p. 7618 - 7629 (2019/06/27)
An efficient copper-catalyzed, quinolyl N-directed nitrene transfer reaction to 8-quinolylsulfides was described. A variety of 8-quinolylsulfimides with different functional groups were synthesized in moderate to high yields. The obtained 8-quinolylsulfimides were proved to be promising novel type of bidentate ligands in Pd(II)-catalyzed allylic alkylation.
C-H alkenylation/cyclization and sulfamidation of 2-phenylisatogens using: N -oxide as a directing group
Guo, Lingmei,Tang, Baolan,Nie, Ruifang,Liu, Yanzhao,Lv, Shan,Wang, Huijing,Guo, Li,Hai, Li,Wu, Yong
supporting information, p. 10623 - 10626 (2019/09/06)
The first example of transition-metal-catalyzed C-H activations of 2-phenylisatogens with alkynes and sulfonyl azides has been developed using N-oxide as the directing group. Ru(ii)-Catalyzed C-H alkenylation/cyclization and Ir(iii)-catalyzed direct C-H sulfamidation proceeded with good yields and excellent functional group tolerance. Importantly, these two transformations provided straightforward routes for the synthesis of indol-3-one derivatives and sulfamidated 2-phenylisatogens respectively, which might be of considerable bioactivities.
Manganese-Catalyzed ortho-C-H Amidation of Weakly Coordinating Aromatic Ketones
Kong, Xianqiang,Xu, Bo
supporting information, p. 4495 - 4498 (2018/08/07)
An efficient manganese-catalyzed ortho-C-H amidation of weakly coordinating aromatic ketones using the readily available sulfonyl azide as the amination reagent is developed. The key step is the ketone directed aromatic metalation using the in situ generated reactive Mn intermediate, MnMe(CO)5. This method offers excellent chemical yields, high regioselectivities, and good functional group tolerance.
Manganese-Catalyzed C?H Amidation of Heteroarenes in Water
Kong, Xianqiang,Lin, Long,Xu, Bo
supporting information, p. 2801 - 2805 (2018/08/17)
We have developed an efficient manganese-catalyzed amidation of various heteroarenes via C?H bond activation using readily available sulfonyl azides. The key step is heteroarene directed electrophilic aromatic metalation using MnBr(CO)5 as catalyst. This method offers excellent chemical yields and regioselectivity with good functional group tolerance. This base metal catalyzed reaction proceeds efficiently using water as the only solvent and nitrogen is the only byproduct. (Figure presented.).
