6311-60-0Relevant academic research and scientific papers
Non-photoisomerizable butterfly shaped tetrasubstituted azobenzenes: Synthesis and photophysical studies
Raman, Arunachalam,Neelambra, Afeefah U.,Karunakaran, Venugopal,Easwaramoorthi, Shanmugam
, p. 8818 - 8822 (2020)
Thetrans-azobenzene (AB) substituted derivatives with bulky carbazole (1), phenothiazine (2), and phenyl (3) have been synthesized to understand the effect of steric crowding around the -NN- linkage on the photoisomerization process. The substituents maintain orthogonality to the azobenzene plane and the electronic properties exhibit a combination of individual chromophores. Irradiation of1and2with various light sources including a 365 nm pen-ray lamp, and a 150 W Xe-Hg lamp, and even exposure to sunlight for a week does not yield thecisisomer revealing the exceptional photostability of the synthesized azobenzene derivatives. These studies suggest that possessing steric crowding around the azo linkage would be a potential strategy to develop photostable azobenzene-based functional materials.
Structure-based design of highly selective 2,4,5-trisubstituted pyrimidine CDK9 inhibitors as anti-cancer agents
Shao, Hao,Foley, David W.,Huang, Shiliang,Abbas, Abdullahi Y.,Lam, Frankie,Gershkovich, Pavel,Bradshaw, Tracey D.,Pepper, Chris,Fischer, Peter M.,Wang, Shudong
supporting information, (2021/02/16)
Cyclin-dependent kinases (CDKs) are a family of Ser/Thr kinases involved in cell cycle and transcriptional regulation. CDK9 regulates transcriptional elongation and this unique property has made it a potential target for several diseases. Due to the conserved ATP binding site, designing selective CDK9 inhibitors has been challenging. Here we report our continued efforts in the optimization of 2,4,5-tri-substituted pyrimidine compounds as potent and selective CDK9 inhibitors. The most selective compound 30m was >100-fold selective for CDK9 over CDK1 and CDK2. These compounds showed broad anti-proliferative activities in various solid tumour cell lines and patient-derived chronic lymphocytic leukaemia (CLL) cells. Decreased phosphorylation of the carboxyl terminal domain (CTD) of RNAPII at Ser-2 and down-regulation of anti-apoptotic protein Mcl-1 were confirmed in both the ovarian cancer model A2780 and patient-derived CLL cells.
Azo bond formation on metal surfaces
Meng, Xiangzhi,Klaasen, Henning,Viergutz, Lena,Schulze Lammers, Bertram,Witteler, Melanie C.,M?nig, Harry,Amirjalayer, Saeed,Liu, Lacheng,Neugebauer, Johannes,Gao, Hong-Ying,Studer, Armido,Fuchs, Harald
supporting information, p. 1458 - 1464 (2020/12/14)
The formation of azo compounds via redox cross-coupling of nitroarenes and arylamines, challenging in solution phase chemistry, is achieved by on-surface chemistry. Reaction products are analyzed with a cryogenic scanning tunneling microscope (STM) and X-ray photoelectron spectroscopy (XPS). By using well-designed precursors containing both an amino and a nitro functionality, azo polymers are prepared on surface via highly efficient nitro-amino cross-coupling. Experiments conducted on other substrates and surface orientations reveal that the metal surface has a significant effect on the reaction efficiency. The reaction was further found to proceed from partially oxidized/reduced precursors in dimerization reactions, shedding light on the mechanism that was studied by DFT calculations.
meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation
Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel
supporting information, p. 8018 - 8023 (2019/05/29)
Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.
A bifunctional metal–organic framework platform for catalytic applications
Müller, Philipp,Bon, Volodymyr,Senkovska, Irena,Nguyen, Khoa D.,Kaskel, Stefan
supporting information, p. 382 - 386 (2019/01/03)
DUT-71 (DUT – Dresden University of Technology), a copper paddle wheel based framework, was used as a platform for postsynthetic modification to introduce specific catalytically active sites and to enhance the catalytic activity for fine chemicals product
Targeted covalent inhibitors of MDM2 using electrophile-bearing stapled peptides
Charoenpattarapreeda, Jiraborrirak,Tan, Yaw Sing,Iegre, Jessica,Walsh, Stephen J.,Fowler, Elaine,Eapen, Rohan S.,Wu, Yuteng,Sore, Hannah F.,Verma, Chandra S.,Itzhaki, Laura,Spring, David R.
supporting information, p. 7914 - 7917 (2019/07/12)
Herein, we describe the development of a novel staple with an electrophilic warhead to enable the generation of stapled peptide covalent inhibitors of the p53-MDM2 protein-protein interaction (PPI). The peptide developed showed complete and selective covalent binding resulting in potent inhibition of p53-MDM2 PPI.
Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group
Fu, Zhengjiang,Jiang, Yongqing,Wang, Shuiliang,Song, Yuanyuan,Guo, Shengmei,Cai, Hu
supporting information, p. 3003 - 3007 (2019/05/10)
A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.
FHBC, a Hexa-peri-hexabenzocoronene–Fluorene Hybrid: A Platform for Highly Soluble, Easily Functionalizable HBCs with an Expanded Graphitic Core
Navale, Tushar S.,Ivanov, Maxim V.,Hossain, Mohammad M.,Rathore, Rajendra
supporting information, p. 790 - 794 (2017/12/26)
Materials based upon hexa-peri-hexabenzocoronenes (HBCs) show significant promise in a variety of photovoltaic applications. There remains the need, however, for a soluble, versatile, HBC-based platform, which can be tailored by incorporation of electroactive groups or groups that can prompt self-assembly. The synthesis of a HBC–fluorene hybrid is presented that contains an expanded graphitic core that is highly soluble, resists aggregation, and can be readily functionalized at its vertices. This new HBC platform can be tailored to incorporate six electroactive groups at its vertices, as exemplified by a facile synthesis of a representative hexaaryl derivative of FHBC. Synthesis of new FHBC derivatives, containing electroactive functional groups that can allow controlled self-assembly, may serve as potential long-range charge-transfer materials for photovoltaic applications.
PROCESS FOR THE PREPARATION OF ORGANIC HALIDES
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Paragraph 00139, (2017/08/01)
The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.
PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES
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Paragraph 00164, (2017/07/28)
The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.
