768-35-4Relevant academic research and scientific papers
Chirality-Driven Mode of Binding of α-Aminophosphonic Acid-Based Allosteric Inhibitors of the Human Farnesyl Pyrophosphate Synthase (hFPPS)
Feng, Yuting,Park, Jaeok,Li, Shi-Guang,Boutin, Rebecca,Viereck, Peter,Schilling, Matthew A.,Berghuis, Albert M.,Tsantrizos, Youla S.
, p. 9691 - 9702 (2019/11/03)
Thienopyrimidine-based allosteric inhibitors of the human farnesyl pyrophosphate synthase (hFPPS), characterized by a chiral α-aminophosphonic acid moiety, were synthesized as enantiomerically enriched pairs, and their binding mode was investigated by X-ray crystallography. A general consensus in the binding orientation of all (R)- and (S)-enantiomers was revealed. This finding is a prerequisite for establishing a reliable structure-activity relationship (SAR) model.
Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates
Fu, Ying,Gou, Bei-Lei,Shi, Chun-Zhao,Du, Zhengyin,Shen, Tong
, p. 4253 - 4257 (2018/09/18)
Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.
Synthesis and evaluation of sulfonamide derivatives as potent Human Uric Acid Transporter 1 (hURAT1) inhibitors
Yang, Xintuo,Pang, Xuehai,Fan, Lei,Li, Xinghai,Chen, Yuanwei
supporting information, p. 1919 - 1922 (2017/04/10)
This letter presents synthesis and structure-activity relationship study of sulfonamide derivatives as inhibitors of Human Uric Acid Transporter 1 (hURAT1). Among all tested sulfonamide derivatives, compounds 9b, 16i and 19b exhibited excellent inhibition activity with IC50 value of 10, 2, and 83?nM, respectively. In addition, compounds 9b and 19b demonstrated moderate PK profile in rats.
Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure
Smith, Michael J.,Lawler, Michael J.,Kopp, Nathaniel,McLeod, Douglas D.,Davulcu, Akin H.,Lin, Dong,Katipally, Kishta,Sfouggatakis, Chris
, p. 1859 - 1863 (2017/11/24)
The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.
Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts
Mfuh, Adelphe M.,Doyle, John D.,Chhetri, Bhuwan,Arman, Hadi D.,Larionov, Oleg V.
supporting information, p. 2985 - 2988 (2016/03/19)
We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.
Cationic platinum(II) complexes bearing aryl-BIAN ligands: Synthesis and structural and optoelectronic characterization
Obrien, Cameron,Wong, Michael Yin,Cordes, David B.,Slawin, Alexandra M. Z.,Zysman-Colman, Eli
, p. 13 - 22 (2015/01/30)
Five cationic platinum(II) complexes bearing a 2-(3′-substituted aryl)pyridine cyclometalating ligand (C^N) and a neutral Ar-BIAN ligand have been synthesized: [Pt(ppy)(PhBIAN)]PF6 (1), [Pt(3Fppy)(PhBIAN)]PF6 (2), [Pt(3MeOppy)(PhBIAN)]PF6 (3), [Pt(3MeOppy)(4-FPhBIAN)]PF6 (4), [Pt(ppy)(4-MeOPhBIAN)]PF6 (5). All complexes have been characterized by NMR spectroscopy and mass spectrometry. Complexes 2 and 3 have been characterized by X-ray crystallography. Structure-property relationships were established from UV-visible spectroscopy and cyclic voltammetry studies. Interestingly, we found that when both the C^N and the Aryl-BIAN ligands contained electron-donating MeO groups the absorption spectrum for the platinum complex extended out to 650 nm. The electrochemical studies of these complexes established that they are electronically compatible dye molecules for dye-sensitized solar cells.
One-pot cascade approach to phenanthridine-fused quinazoliniminiums from heteroenyne-allenes
Alawode, Olajide E.,Naganaboina, Vijaya Kumar,Liyanage, Thakshila,Desper, John,Rayat, Sundeep
supporting information, p. 1494 - 1497 (2014/04/03)
A one-pot cascade method to obtain functionalized phenanthridine-fused quinazoliniminiums from a variety of heteroenyne-allenes is described. This protocol involves formation of C-N and C-C bonds in a single step in the presence of a Lewis acid and trace water to afford pentacyclic title compounds in moderate to good yields.
An easy route to (hetero)arylboronic acids
Erb, William,Hellal, Akila,Albini, Mathieu,Rouden, Jacques,Blanchet, Jerome
, p. 6608 - 6612 (2014/06/09)
An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.
Mn-catalyzed aromatic C-H alkenylation with terminal alkynes
Zhou, Bingwei,Chen, Hui,Wang, Congyang
supporting information, p. 1264 - 1267 (2013/03/14)
The first manganese-catalyzed aromatic C-H alkenylation with terminal alkynes is described. The procedure features an operationally simple catalyst system containing commercially available MnBr(CO)5 and dicyclohexylamine (Cy2NH). The reaction occurs readily in a highly chemo-, regio-, and stereoselective manner delivering anti-Markovnikov E-configured olefins in high yields. Experimental study and DFT calculations reveal that (1) the reaction is initiated by a C-H activation step via the cooperation of manganese and base; (2) manganacycle and alkynylmanganese species are the key reaction intermediates; and (3) the ligand-to-ligand H-transfer and alkynyl-assisted C-H activation are the key steps rendering the reaction catalytic in manganese.
Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges
Leermann, Timo,Leroux, Frederic R.,Colobert, Francoise
supporting information; experimental part, p. 4479 - 4481 (2011/10/09)
A general and convenient protocol for the electrophilic borylation of aryl Grignard reagents prepared from arylbromides by direct insertion of magnesium in the presence of LiCl or by Mg/Br exchange with iPrMgCl?LiCl has been developed. Various aryl boronic acids were synthesized in a straightforward manner in excellent yields at 0 °C.
