- Design, Synthesis, Radiosynthesis and Biological Evaluation of Fenretinide Analogues as Anticancer and Metabolic Syndrome-Preventive Agents
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Fenretinide (4-HPR) is a synthetic derivative of all-trans-retinoic acid (ATRA) characterised by improved therapeutic properties and toxicological profile relative to ATRA. 4-HPR has been mostly investigated as an anti-cancer agent, but recent studies sho
- Patruno, Ilaria,Thompson, Dawn,Dall'Angelo, Sergio,Windhorst, Albert D.,Vugts, Danielle J.,Poot, Alex J.,Mody, Nimesh,Zanda, Matteo
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p. 1579 - 1590
(2020/07/13)
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- Fe(III)-Catalyzed Aerobic Intramolecular N-N Coupling of Aliphatic Azides with Amines
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An Fe(III)-catalyzed intramolecular N-N coupling of aliphatic azidoamines that forms diverse five- and six-membered semisaturated diazoheterocycles using air as an oxidant is reported, providing an alternative to hydrazine-based methods. Mechanistic studies suggest that a N-radical induced intramolecular homolytic substitution (SH2) is involved in ring closure. The power of this N-N bond-forming method is also demonstrated by using it as the final step in a total synthesis of (-)-newbouldine.
- Zhang, Yue,Duan, Dongyu,Zhong, Ying,Guo, Xin-Ai,Guo, Jiawei,Gou, Jing,Gao, Ziwei,Yu, Binxun
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supporting information
p. 4960 - 4965
(2019/09/03)
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- One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides
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A simple and versatile method for the preparation of linear, trisubstituted triazenes is reported. The procedure is based on the reaction of Grignard reagents with 1-azido-4-iodobutane or 4-azidobutyl-4-methylbenzenesulfonate. These organic azides enable the regioselective formation of triazenes via an intramolecular cyclization step. The new method can be used for the preparation of aryl, heteroaryl, vinyl, and alkyl triazenes. The synthetic utility of vinyl triazenes is demonstrated by acid-induced C-N, C-O, C-F, C-P, and C-S bond-forming reactions.
- Suleymanov, Abdusalom A.,Scopelliti, Rosario,Fadaei Tirani, Farzaneh,Severin, Kay
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supporting information
p. 3323 - 3326
(2018/06/11)
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- Discovery of the First Environment-Sensitive Near-Infrared (NIR) Fluorogenic Ligand for α1-Adrenergic Receptors Imaging in Vivo
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Fluorescent ligands are gaining popularity as tools to aid GPCR research. Nonetheless, in vivo application of such tools is hampered due to their short excitation wavelengths in the visible range and lack of fluorogenic switch. Here we report the discovery of fluorescent ligands (3a-f) for α1-adrenergic receptors (α1-ARs) by conjugating the environment-sensitive fluorophore cyane 5 (Cy5) with the quinazoline pharmacophore. Among them, the conjugated compound 3a, with acylated piperazine and the shortest carbon chain spacer, exhibited potent binding and remarkable changes in fluorescence (10-fold) upon binding to α1-AR. Furthermore, it could be employed to selectively and specifically label α1-ARs with no washing procedures in single cells, prostate tissue slices, intact tumor xenografts and organs in living mice. Especially, the slice imaging results gave direct and visual evidence that there is a close relationship between α1-ARs and pathological prostate. It is anticipated that our fluorescent tools will find broad applications in the study of α1-AR pharmacology and physiology to aid development of novel therapeutics.
- Ma, Zhao,Lin, Yuxing,Cheng, Yanna,Wu, Wenxiao,Cai, Rong,Chen, Shouzhen,Shi, Benkang,Han, Bo,Shi, Xiaodong,Zhou, Yubin,Du, Lupei,Li, Minyong
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p. 2151 - 2162
(2016/03/25)
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- Sulforaphane and erucin, natural isothiocyanates from broccoli, inhibit bacterial quorum sensing
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Sulforaphane and erucin, two natural isothiocyanates that are highly abundant in broccoli and other cruciferous vegetables, were found to strongly inhibit quorum sensing and virulence in Pseudomonas aeruginosa. Mechanistic evaluations of these effects suggest that these isothiocyanates are antagonists of the transcriptional activator LasR. The Royal Society of Chemistry 2013.
- Ganin, Hadas,Rayo, Josep,Amara, Neri,Levy, Niva,Krief, Pnina,Meijler, Michael M.
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p. 175 - 179
(2013/03/13)
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- Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain
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A series of neoglycoconjugates derived from deoxynojirimycin has been prepared by click connection with functionalised adamantanes. They have been assayed as glycosidase inhibitors, as inhibitors of the glycoenzymes relevant to the treatment of Gaucher disease, as well as correctors of the defective ion-transport protein involved in cystic fibrosis. We have demonstrated that it is possible to selectively either strongly inhibit ER-α-glucosidases and ceramide glucosyltransferase or restore the activity of CFTR in CF-KM4 cells by varying the length of the alkyl chain linking DNJ and adamantane.
- Ardes-Guisot, Nicolas,Alonzi, Dominic S.,Reinkensmeier, Gabriele,Butters, Terry D.,Norez, Caroline,Becq, Frederic,Shimada, Yousuke,Nakagawa, Shinpei,Kato, Atsushi,Bleriot, Yves,Sollogoub, Matthieu,Vauzeilles, Boris
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supporting information; experimental part
p. 5373 - 5388
(2011/08/22)
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- An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles
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(matrix presented) Fused 5-heterotetrazole ring systems are synthesized in high yield via intramolecular [2 + 3] cycloadditions of organic azides and heteroatom-substituted nitriles. Cyanates, thiocyanates, and cyanamides are all competent dipolarophiles for this reaction. A variety of scaffolds are tolerated when the new enclosed ring is five- or six-membered.
- Demko, Zachary P.,Sharpless, K. Barry
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p. 4091 - 4094
(2007/10/03)
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