4714-25-4Relevant academic research and scientific papers
Synthesis, characterization, structure and catalytic activity of (NNN) tridentate azo-imine nickel(II), palladium(II) and platinum(II) complexes
Mandal, Paritosh,Lin, Chia-Her,Brand?o, Paula,Mal, Dasarath,Felix, Vitor,Pratihar, Jahar Lal
, p. 171 - 177 (2016)
The newly designed tridentate ligand, 2,2′-(bisdiamino)azobenzene, H2L, 1 derived from the oxidative coupling of o-phenylenediamine in presence of NaOH base, upon reaction with Ni(II), Pd(II) and Pt(II) separately in methanol yielded [(HL)Ni(PPh3)]ClO4, 2, [(HL)Pd(PPh3)]ClO4, 3 and [(L)Pt(PPh3)], 4 which were characterized by spectral data and authenticated by single crystal X-ray diffraction of 1-4. The diffraction analysis revealed that the ligand binds the metals (Ni(II), Pd(II)) in monoanionic and Pt(II) in dianionic tridentate (N,N,N) fashion offering distorted square planar geometry where fourth position is occupied by one PPh3group. One ClO4-ion satisfies the charge of the former aggregate [(HL)Ni(PPh3)]+and [(HL)Pd(PPh3)]+. Suzuki and Heck coupling reactions were carried out, in presence of air and moisture, using [(HL)Pd(PPh3)]ClO4, 3 as catalysts for a variety of substrates.
One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols
Abaev, Vladimir T.,Chalikidi, Petrakis N.,Demidov, Oleg P.,Gutnov, Andrey V.,Magkoev, Taimuraz T.,Trushkov, Igor V.,Uchuskin, Maxim G.
, p. 9838 - 9846 (2021/07/28)
Two approaches for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs have been developed. The developed protocols are complementary: the direct mixing of alcohol, trimethylsilyl bromide, and triphenylphosphine in 1,4-dioxane followed by heating at 80 °C was found to be more efficient for acid-sensitive substrates, such as salicyl or furfuryl alcohols as well as secondary benzyl alcohols, while a one-pot procedure including sequential addition of trimethylsilyl bromide and triphenylphosphine gave higher yields for benzyl alcohols bearing electroneutral or electron-withdrawing substituents.
Visible-light-driven Cadogan reaction
Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 2582 - 2586 (2021/03/09)
Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
Synthesis, characterization, crystal structure and catalytic activity of amido azo palladium(II) complex
Pratihar, Jahar Lal,Mandal, Paritosh,Mal, Dasarath,Lin, Chia-Her
, p. 553 - 559 (2020/06/22)
Abstract: The newly designed tridentate ligand, 2-((2-aminophenyl)diazenyl)-N-benzylaniline, 1 has been synthesized by the reaction between 2,2′-diaminoazobenzene and benzyl chloride in presence of K2CO3. This ligand was reacted with Na2[PdCl4] in methanol to give the new Pd(II) complex?2. Both the ligand and complex were characterized by usual spectroscopic techniques. Furthermore, the solid-state structure of complex 2 was determined using single crystal X-ray diffraction analysis. It revealed that the ligand binds with Pd(II) in dianionic tridentate (N,N,N) fashion offering distorted square planar geometry where fourth position is occupied by one phosphine ligand. The performance of the Pd(II) phosphine complex as catalyst was evaluated in the homogenous Suzuki and Heck reactions under mild conditions in presence of air and moisture. The Pd(II) complex showed good catalytic activities for the coupling of several aryl halides (iodides and bromides) with phenyl boronic acid and styrene providing excellent yields. After catalytic reactions, the catalyst has been recovered by simple chromatographic separation and reused for next reaction and its activity checked up to three cycles without sufficient loss. Graphic abstract: The newly designed tridentate ligand, 2-((2-aminophenyl)diazenyl)-N-benzylaniline and its corresponding palladium(II) complex were synthesized and structurally characterized. The neutral palladium(II) amido complex with phosphine as ancillary ligand was formed through two amino proton elimination from ligand precursor. The newly synthesized Palladium(II) complex acts as potential catalyst toward C–C bond formation for a variety of substrate under mild conditions in presence of air and moisture.[Figure not available: see fulltext.].
Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response
Chen, Chun-Han,Chuang, Hsun-Yueh,Hung, To-Yu,Lai, Mei-Jung,Liao, Yu-Hsuan,Lin, Mei-Hsiang,Liou, Jing-Ping,Liu, Yi-Min,Wu, Wei-Cheng
, (2020/03/13)
Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI50 of 22 ± 2 and 12 ± 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 μM, and 1.47 μM, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs.
Palladium-melamine complex anchored on magnetic nanoparticles: A novel promoter for C-C cross coupling reaction
Bodaghifard, Mohammad Ali
, p. 57 - 64 (2019/03/06)
A palladium-melamine complex deposited on Fe3O4@SiO2 nanoparticles (MNPs-Mel-Pd) was considered as an effective catalyst for C-C cross-coupling (Mirozoki-Heck) reaction. Surface and magnetic properties of the prepared core-shell hybrid nanocatalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis, energy-dispersive X-ray, vibrating sample magnetometry, transmission and scanning electron microscopy techniques and ICP/OES analysis. It was found that the heterogeneous nanocatalyst could be recovered simply and reused numerous times without loss of its catalytic activity. The advantages of this new methodology are: isolation of highly pure products without chromatography techniques, reusability of the catalyst using a magnet, easy workup procedure and negligible leaching of palladium.
Structural development of tetrachlorophthalimides as liver X receptor β (LXRβ)-selective agonists with improved aqueous solubility
Nomura, Sayaka,Endo-Umeda, Kaori,Fujii, Shinya,Makishima, Makoto,Hashimoto, Yuichi,Ishikawa, Minoru
, p. 796 - 801 (2018/02/09)
LXRβ-selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. We have reported a series of tetrachlorophthalimide analogs as an LXRβ-selective agonist. However, they exhibited poor aqueous solubility probably due to its high hydrophobicity and highly rigid and plane structure. In this report, we present further structural development of tetrachloro(styrylphenyl)phthalimides as the LXRβ-selective agonists with improved aqueous solubility.
Pure space steric hindrance effect on intramolecular proton transfer in excited state and photophysics of conjugated new dyes under near-IR laser irradiation
Su, Jihong,Lu, Yao,Ding, Ge,Wang, Zhenqiang,Huang, Fanrui,Gao, Fang,Luo, Ziping,Li, Hongru
, p. 92 - 102 (2017/07/22)
This study presented a variety of new extended conjugated dyes bearing internal proton transfer segments, which were characterized with different extent of space steric hindrance. Besides, the dyes lack of proton transfer moieties were synthesized as the
Synthesis method of ferrocenyl pyrimidine polydentate ligand and application thereof in Heck reaction
-
Paragraph 0050-0051; 0058-0059; 0061-0064, (2018/03/13)
The invention discloses a synthesis method of a ferrocenyl pyrimidine polydentate ligand and application thereof in Heck reaction. Ferrocene, pyridine-2-formaldehyde and amidine salt are adopted as the raw materials, and by means of the three-step reaction of acetylation, aldol condensation and condensation cyclization, the ferrocenyl pyrimidine polydentate ligand can be synthesized, the synthesis method has the advantages of simple operation, mild conditions and no use of expensive reagents, and is easy for mass preparation. The invention also relates to application of the ligand in palladium catalyzed Heck coupling reaction. The result shows that the ferrocenyl pyrimidine tridentate ligand 6h has good thermal stability and efficient catalytic activity. The coupling reaction can be carried out under the condition adopting water as the solvent, and the substrate has a wide applicable range, and tedious anhydrous and anaerobic operation is unnecessary.
Azo-amide palladium(II) complexes: Synthesis, characterization and application in C–C cross-coupling reactions
Pratihar, Jahar Lal,Mandal, Paritosh,Lin, Chia-Her,Lai,Mal, Dasarath
, p. 224 - 230 (2017/08/08)
The newly designed tridentate ligands bis-2,2′-(N-alkylamino)azobenzene, 1a-1d, have been prepared by the reaction between 2,2′-diaminoazobenzene and alkyl halides in the presence of K2CO3. These ligands were reacted with Na2[PdCl4] in a 1:1 ratio in methanol to give the new Pd(II) complexes 2a–2d. All the compounds were characterized by 1H NMR, IR spectroscopy and elemental analysis. Furthermore, the solid-state structures of the ligand 1a and two complexes (2a and 2c) were determined using single crystal X-ray diffraction analysis. The diffraction analysis revealed that the ligands bind with the Pd(II) ion in a monoanionic tridentate (N,N,N) fashion, offering a distorted square planar geometry where the fourth position is occupied by one chloride ligand. The air/moisture stable complex 2a was employed as an efficient catalyst for the Suzuki and Heck reactions under mild conditions. The catalyst exhibits high catalytic activities for the coupling of several aryl halides with phenyl boronic acid and styrene, providing excellent yields. Further, the catalyst can be easily recovered by simple chromatographic separation and reused up to three times without significant loss of its catalytic activity.
