- Supramolecular brush polymers prepared from 1,3,4-oxadiazole and cyanobutoxy functionalised pillar[5]arene for detecting Cu2+
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A supramolecular brush polymerPoly(P5-OXD)was constructed through the self-assembly of an A1/A2 disubstituted pillar[5]arene P5-OXD with a 1,3,4-oxadiazole unit and a cyanobutoxy group, exhibiting external stimuli responsiveness towards Cu2+ion
- Liu, Shuangyan,Wu, Qiuxia,Zhang, Tianze,Zhang, Huacheng,Han, Jie
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supporting information
p. 1287 - 1291
(2021/02/27)
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- Discovery of acylsulfonohydrazide-derived inhibitors of the lysine acetyltransferase, kat6a, as potent senescence-inducing anti-cancer agents
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A high-throughput screen designed to discover new inhibitors of histone acetyltransferase KAT6A uncovered CTX-0124143 (1), a unique aryl acylsulfonohydrazide with an IC50 of 1.0 μM. Using this acylsulfonohydrazide as a template, we herein disclose the results of our extensive structure-activity relationship investigations, which resulted in the discovery of advanced compounds such as 55 and 80. These two compounds represent significant improvements on our recently reported prototypical lead WM-8014 (3) as they are not only equivalently potent as inhibitors of KAT6A but are less lipophilic and significantly more stable to microsomal degradation. Furthermore, during this process, we discovered a distinct structural subclass that contains key 2-fluorobenzenesulfonyl and phenylpyridine motifs, culminating in the discovery of WM-1119 (4). This compound is a highly potent KAT6A inhibitor (IC50 = 6.3 nM; KD = 0.002 μM), competes with Ac-CoA by binding to the Ac-CoA binding site, and has an oral bioavailability of 56% in rats.
- Priebbenow, Daniel L.,Leaver, David J.,Nguyen, Nghi,Cleary, Benjamin,Lagiakos, H. Rachel,Sanchez, Julie,Xue, Lian,Huang, Fei,Sun, Yuxin,Mujumdar, Prashant,Mudududdla, Ramesh,Varghese, Swapna,Teguh, Silvia,Charman, Susan A.,White, Karen L.,Shackleford, David M.,Katneni, Kasiram,Cuellar, Matthew,Strasser, Jessica M.,Dahlin, Jayme L.,Walters, Michael A.,Street, Ian P.,Monahan, Brendon J.,Jarman, Kate E.,Jousset Sabroux, Helene,Falk, Hendrik,Chung, Matthew C.,Hermans, Stefan J.,Downer, Natalie L.,Parker, Michael W.,Voss, Anne K.,Thomas, Tim,Baell, Jonathan B.
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p. 4655 - 4684
(2020/06/08)
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- Redox-Neutral Borylation of Aryl Sulfonium Salts via C-S Activation Enabled by Light
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Reported here is a novel photoinduced strategy for the borylation of aryl sulfonium salts using bis(pinacolato)diboron as the boron source. This method exploits redox-neutral aryl sulfoniums to gain access to aryl radicals via C-S bond activation upon photoexcitation under transition-metal-free conditions. Therefore, it grants access to diverse arylboronate esters with good performance from easily available aryl sulfoniums accompanied by mild conditions, operational simplicity, and easy scalability.
- Huang, Chen,Feng, Jie,Ma, Rui,Fang, Shuaishuai,Lu, Tao,Tang, Weifang,Du, Ding,Gao, Jian
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p. 9688 - 9692
(2019/12/02)
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- Additive- and Photocatalyst-Free Borylation of Arylazo Sulfones under Visible Light
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We developed a photocatalyst-free and additive-free, visible light induced borylation reaction using arylazo sulfones as starting material. This protocol shows some advantages such as mild conditions, simple equipment, and wide substrate scope, which gives a complementary protocol for the preparation of arylboronates.
- Xu, Yuliang,Yang, Xinying,Fang, Hao
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p. 12831 - 12837
(2018/10/20)
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- ARYL SULFONOHYDRAZIDES
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Compound of formula (I) wherein A is selected from (i), where RF1 is H or F; (ii); (iii) a N-containing C6 heteroaryl group; and B is (B), where X1 is either CRF2 or N, where RF2 is H or F; X2 is either CR3 or N, where R3 is selected from H, Me, CI, F OMe; X3 is either CH or N; X4 is either CRF3 or N, where RF3 is H or F; where only one or two of X1, X2, X3 and X4 may be N; and R4 is selected from I, optionally substituted phenyl, optionally substituted C5-6 heteroaryl; optionally substituted C1-6 aIkyI and optionally substituted C1-6 alkoxy, which are useful in the treatment of a condition ameliorated by the inhibition of MOZ.
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Page/Page column 39; 49
(2016/12/26)
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- Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
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A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.
- Chen, Kai,Zhang, Shuai,He, Pei,Li, Pengfei
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p. 3676 - 3680
(2016/06/09)
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- Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C-N Bond Cleavage
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By developing a mild Ni-catalyzed system, a method for direct borylation of sp2 and sp3 C-N bonds has been established. The key to this hightly efficient C-N bond borylative cleavage depends on the appropriate choice of the nickel catalyst Ni(COD)2, ICy·HCl as a ligand, and the use of 2-ethoxyethanol as the cosolvent. This transformation shows good functional group compatibility and can serve as a powerful synthetic tool for gram-scale synthesis and late-stage C-N borylation of complex compounds.
- Hu, Jiefeng,Sun, Heqing,Cai, Wangshui,Pu, Xinghui,Zhang, Yemin,Shi, Zhuangzhi
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- Sequential one-pot access to molecular diversity through aniline aqueous borylation
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On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.
- Erb, William,Albini, Mathieu,Rouden, Jacques,Blanchet, Jrme
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p. 10568 - 10580
(2015/01/08)
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- Internal Lewis acid assisted benzoic acid catalysis
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Internal Lewis acid assisted benzoic acid derivatives are introduced as new low-molecular-weight single-hydrogen-bond donor catalysts for the activation of nitroalkenes. Selected 2-borylbenzoic acid derivatives gave good yields of products in the addition of indoles to nitroalkenes. Control experiments suggest that both the internal Lewis acid coordination and the carboxylic acid functionalities are critical to the optimal performance of these catalysts. Georg Thieme Verlag Stuttgart New York.
- Auvil, Tyler J.,Mattson, Anita E.
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p. 2173 - 2180
(2012/09/22)
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- Design and synthesis of a second series of triazole-based compounds as potent dual mPGES-1 and 5-lipoxygenase inhibitors
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Microsomal prostaglandin E2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO) are pivotal enzymes in the biosynthesis of the pro-inflammatory PGE2 and leukotrienes, respectively. The design and synthesis of a second series of mPGES-1 inhibitors based on a triazole scaffold are described. Our studies allowed us to draw a tentative SAR profile and to optimize this series with the identification of compounds 10, 11 and 14-15 which displayed potent mPGES-1 inhibition in a cell-free assay. In addition, compounds 5, 10, 12 and 14-16 also blocked 5-LO activity in cell-free and cell-based test systems, emerging as very promising candidates for the development of safer and more effective anti-inflammatory drugs.
- Chini, Maria Giovanna,De Simone, Rosa,Bruno, Ines,Riccio, Raffaele,Dehm, Friederike,Weinigel, Christina,Barz, Dagmar,Werz, Oliver,Bifulco, Giuseppe
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experimental part
p. 311 - 323
(2012/09/08)
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- Identification of new γ-hydroxybutenolides that preferentially inhibit the activity of mPGES-1
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Microsomal prostaglandin E2 synthase-1 (mPGES-1) has been recognized as novel, promising drug target for anti-inflammatory and anticancer drugs. mPGES-1 catalyzes the synthesis of the inducible prostaglandin E 2 in response to pro-inflammatory stimuli, rendering this enzyme extremely interesting in drug discovery process owing to the drastic reduction of the severe side effects typical for traditional non-steroidal anti-inflammatory drugs. In the course of our investigations focused on this topic, we identified two interesting molecules bearing the γ- hydroxybutenolide scaffold which potently inhibit the activity of mPGES-1. Notably, the lead compound 2c that inhibited mPGES-1 with IC50 = 0.9 μM, did not affect other related enzymes within the arachidonic acid cascade.
- De Simone, Rosa,Bruno, Ines,Riccio, Raffaele,Stadler, Katharina,Bauer, Julia,Schaible, Anja M.,Laufer, Stefan,Werz, Oliver
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experimental part
p. 5012 - 5016
(2012/09/22)
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- Sandmeyer-type reaction to pinacol arylboronates in water phase: A green borylation process
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Copper(I)-catalyzed cross-coupling reactions of aryl diazonium salts with bis(pinacolato)diboron can proceed smoothly in the water phase at room temperature to give the corresponding arylboronate esters in good to high yields. The Sandmeyer-type borylation not only provides direct access to arylboronates bearing halo and acidic substituents, but also achieves a green borylation process. Georg Thieme Verlag Stuttgart · New York.
- Zhang, Jie,Wang, Xiaolong,Yu, Haitao,Ye, Jiahai
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experimental part
p. 1394 - 1396
(2012/06/30)
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- BICYCLIC DERIVATIVES AS P38 KINASE INHIBITORS
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New bicyclic derivatives of formula (I), wherein the meanings for the various substituents are as disclosed in the description. These compounds are useful as p38 kinase inhibitors.
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Page/Page column 46
(2008/06/13)
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- Hydroboronation process
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The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.
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Page column 20-21
(2010/02/05)
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