93368-76-4Relevant academic research and scientific papers
Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents
Cui, Fei-Hu,Chen, Jing,Mo, Zu-Yu,Su, Shi-Xia,Chen, Yan-Yan,Ma, Xian-Li,Tang, Hai-Tao,Wang, Heng-Shan,Pan, Ying-Ming,Xu, Yan-Li
supporting information, p. 925 - 929 (2018/02/22)
A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.
A cuprous catalytic phenmethyl nitrine with styrene synthesis of 2, 5 - disubstituted-oxazole
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Paragraph 0053, (2017/08/25)
The invention discloses a preparation method for synthesizing 2,5-disubstituted oxazoles from benzyl azide and styrene under the catalysis of sub copper. The method comprises the following steps of (1) preparing a substituent azide; (2) reacting azide with styrene to prepare a product. According to the method, the raw materials are simple, reaction conditions are moderate, and the method has high application value, and is suitable for industrial production.
A Highly Efficient Single-Chain Metal-Organic Nanoparticle Catalyst for Alkyne-Azide "click" Reactions in Water and in Cells
Bai, Yugang,Feng, Xinxin,Xing, Hang,Xu, Yanhua,Kim, Boo Kyung,Baig, Noman,Zhou, Tianhui,Gewirth, Andrew A.,Lu, Yi,Oldfield, Eric,Zimmerman, Steven C.
supporting information, p. 11077 - 11080 (2016/11/01)
We show that copper-containing metal-organic nanoparticles (MONPs) are readily synthesized via Cu(II)-mediated intramolecular cross-linking of aspartate-containing polyolefins in water. In situ reduction with sodium ascorbate yields Cu(I)-containing MONPs that serve as highly efficient supramolecular catalysts for alkyne-azide "click chemistry" reactions, yielding the desired 1,4-adducts at low parts per million catalyst levels. The nanoparticles have low toxicity and low metal loadings, making them convenient, green catalysts for alkyne-azide "click" reactions in water. The Cu-MONPs enter cells and perform efficient, biocompatible click chemistry, thus acting as intracellular nanoscale molecular synthesizers.
A combination of trimethylsilyl chloride and hydrous natural montmorillonite clay: An efficient solid acid catalyst for the azidation of benzylic and allylic alcohols with trimethylsilyl azide
Tandiary, Michael A.,Masui, Yoichi,Onaka, Makoto
, p. 15736 - 15739 (2015/02/19)
We present a new procedure to convert in situ natural montmorillonite clay into a partially acidified one using a catalytic amount of trimethylsilyl chloride and trace water. We demonstrate that the acidic montmorillonite can catalyze the direct azidation
An efficient transformation from benzyl or allyl halides to aryl and alkenyl nitriles
Zhou, Wang,Xu, Jiaojiao,Zhang, Liangren,Jiao, Ning
supporting information; experimental part, p. 2888 - 2891 (2010/08/22)
(Figure presented) A novel approach to aryl or alkenyl nitriles from benzyl and allyl halides has been developed. A tandem TBAB-catalyzed substitution and the subsequent novel oxidative rearrangement are involved in this transformation. To the best of our knowledge, this is the first transformation from allyl halides to alkenyl nitriles. The broad reaction scope and the mild conditions may make these methods of use in organic synthesis.
Endothelin antagonists: Substituted mesitylcarboxamides with high potency and selectivity for ET(A) receptors
Wu, Chengde,Decker, E. Radford,Blok, Natalie,Bui, Huong,Chen, Qi,Raju,Bourgoyne, Andree R.,Knowles, Vippra,Biediger, Ronald J.,Market, Robert V.,Lin, Shuqun,Dupré, Brian,Kogan, Timothy P.,Holland, George W.,Brock, Tommy A.,Dixon, Richard A. F.
, p. 4485 - 4499 (2007/10/03)
We have previously disclosed the discovery of 2,4-disubstituted anilinothiophenesulfonamides with potent ET(A)-selective endothelin receptor antagonism and the subsequent identification of sitaxsentan (TBC11251, 1) as a clinical development compound (Wu et al. J. Med. Chem. 1997, 40, 1682 and 1690). The orally active 1 has demonstrated efficacy in a phase II clinical trial of congestive heart failure (Givertz et al. Circulation 1998, 98, Abstr. 3044) and was active in rat models of myocardial infarction (Podesser et al. Circulation 1998, 98, Abstr. 2896) and acute hypoxia-induced pulmonary hypertension (Chen et al. FASEB J. 1996, 10 (3), A104). We now report that an additional substituent at the 6-position of the anilino ring further increases the potency of this series of compounds. It was also found that a wide range of functionalities at the 3-position of the 2,4,6-trisubstituted ring increased ETA selectivity by ~10-fold while maintaining in vitro potency, therefore rendering the compounds amenable to fine-tuning of pharmacological and toxicological profiles with enhanced selectivity. The optimal compound in this series was found to be TBC2576 (7u), which has ~10- fold higher ETA binding affinity than 1, high ET(A)/ET(B) selectivity, and a serum half-life of 7.3 h in rats, as well as in vivo activity.
