5411-13-2Relevant articles and documents
Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
Zhao, Rong,Dong, Wenwen,Teng, Jiangge,Wang, Zhiwei,Wang, Yunzhong,Yang, Jianguo,Jia, Qiang,Chu, Changhu
supporting information, (2020/12/21)
A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.
Synthesis of new hydrazone derivatives and evaluation of their monoamine oxidase inhibitory activity
Tok, Fatih,Sa?l?k, Begüm Nurpelin,?zkay, Yusuf,Ilg?n, Sinem,Kaplanc?kl?, Zafer As?m,Ko?yi?it-Kaymak??o?lu, Bedia
, (2021/06/15)
A novel series of hydrazone derivatives were designed and synthesized. Their structures were characterized by IR, 1H NMR, 13C NMR and HR-MS spectroscopic methods. The newly synthesized compounds were evaluated for their inhibitory ac
Synthesis and biological evaluation of novel ligustrazine-chalcone derivatives as potential anti-triple negative breast cancer agents
Chen, Shaobin,Huang, Jianan,Huang, Qinghui,Li, Yuanzhi,Luo, Yingqi,Wang, Chengxu,Wu, Wenhao,Yu, Lihong,Zha, Dailong,Zhang, Chao,Zhang, Jianye,Zhou, Wenmin
, (2021/07/21)
A series of novel ligustrazine-chalcone hybrids were synthesized and evaluated for their in vitro and in vivo antitumor activities. The results showed that most of these compounds exhibited significant in vitro cytotoxicity against MDA-MB-231, MCF-7, A549
A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions
Chen, Cheng,Cheng, Hua,Du, Min-Chen,Qian, Liang,Qin, Xin,Sang, Wei,Yao, Wei-Zhong,Yuan, Ye,Zhang, Rui
supporting information, p. 3972 - 3982 (2021/06/17)
In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.
Switching from biaryl formation to amidation with convoluted polymeric nickel catalysis
Sen, Abhijit,Dhital, Raghu N.,Sato, Takuma,Ohno, Aya,Yamada, Yoichi M.A.
, p. 14410 - 14418 (2020/12/21)
A stable, reusable, and insoluble poly(4-vinyl-pyridine) nickel catalyst (P4VP-NiCl2) was prepared through the molecular convolution of poly(4-vinylpyridine) (P4VP) and nickel chloride. We proposed a coordination structure of the Ni center in the precatalyst based on elemental analysis and Ni K-edge XANES, and we confirmed that it is consistent with Ni K-edge EXAFS. The Suzuki?Miyaura-type coupling of aryl halides and arylboronic esters proceeded using P4VP-NiCl2 (0.1 mol % Ni) to give the corresponding biaryl compounds in up to 94% yield. Surprisingly, when the same reaction of aryl halides and arylboronic acid/ester was carried out in the presence of amides, the amidation proceeded predominantly to give the corresponding arylamides in up to 99% yield. In contrast, the reaction of aryl halides and amides in the absence of arylboronic acid/ester did not proceed. P4VP-NiCl2 successfully catalyzed the lactamization for preparing phenanthridinone. P4VP-NiCl2 was reused five times without significant loss of catalytic activity. Pharmaceuticals, natural products, and biologically active compounds were synthesized efficiently using P4VPNiCl2 catalysis. Nickel contamination in the prepared pharmaceutical compounds was not detected by ICP-MS analysis. The reaction was scaled to multigrams without any loss of chemical yield. Mechanistic studies for both Suzuki?Miyaura and amidation were performed.
New cyanopyridine-based scaffold as PIM-1 inhibitors and apoptotic inducers: Synthesis and SARs study
Farrag, Amel M.,Ibrahim, Mona H.,Mehany, Ahmed B.M.,Ismail, Magda M.F.
, (2020/10/27)
Two novel series of 6-(4-benzamido-/4-phthalimido)-3-cyanopyridine derivatives were designed and synthesized as inhibitors of PIM-1 kinase. Based on cytotoxicity results via MTT assay against prostate carcinoma PC3, human hepatocellular carcinoma HepG2 and breast adenocarcinoma MCF-7 cell lines, the most potent cytotoxic cyanopyridine hits, 6, 7, 8, 12 and 13 were 1.5–3.3 times more inhibitor of cell proliferation than the reference standard, 5-FU. Selectivity profile of the latter compounds on normal human cells (WI-38), was executed, indicating that they are highly selective (IC50 > 145 μM) in their cytotoxic effect. The promising compounds were further evaluated as PIM-1 kinase inhibitors. These compounds elicited remarkable inhibition of PIM-1 kinase (76.43–53.33%). Extensive studies on apoptosis were conducted for these compounds; they enhanced caspase-3 and boosted the Bax/Bcl-2 ratio 27-folds in comparison to the control. Molecular docking study of the most potent compound, 13 in PIM-1 kinase active site was consistent with the in vitro activity. Finally, prediction of chemo-informatic properties released compound 13 as the most promising ligand.
Synthesis and biological evaluation of anti-tubercular activity of Schiff bases of 2-Amino thiazoles
Cordeiro, Rachel,Kachroo, Monica
supporting information, (2020/11/09)
Tuberculosis, an infectious disease, has been reported to cause the death of 1.5 million in 2018. Due to the emergence of Multi-Drug Resistant-TB, Extensively Drug Resistant-TB, and Totally Drug Resistant-TB, many first-line and second-line drugs have been found in-effective. New drugs introduced in TB regimens such as pretomanid, bedaquiline and linezolid have been associated with toxicities. Hence, there is an urgent need for introducing safe and cost-effective antitubercular drugs. In this study, a series of Schiff bases of 2-amino thiazoles were synthesized and evaluated for their anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain by Microplate Alamar Blue assay (MABA) method. N-[4-(2-Amino-thiazol-4-yl)-phenyl]-benzamide derivative with 2-nitro (5c2), 4-hydroxy (5c4) substitution, 2-[4-(2-Amino-thiazol-4-yl)-phenyl]-isoindole-1,3-dione derivatives with 3,4,5-trimethoxy substitution (5b1) and the compound 1-[4-(2-Amino-thiazol-4-yl)-phenyl]-pyrrole-2,5-dione (4a) which is a maleic derivative bearing thiazole ring, exhibited good anti-tubercular activity (MIC 6.25 μg/ml). Drug likeness was also evaluated for all the synthesised compounds using Molinspiration software. All synthesized compounds fulfilled the parameters of the Lipinski rule of five and showed drug-like properties. Through this study, it was proved that thiazole analogues have good anti-tubercular potentials.
Double carbonylation of iodoarenes in the presence of a pyridinium SILP-Pd catalyst
Nagy, Enik?,Nagy, Petra,Papp, Máté,Skoda-F?ldes, Rita,Urbán, Béla
, (2020/04/28)
The efficiency of a palladium catalyst, immobilised on a supported ionic liquid phase (SILP) with adsorbed 1-butyl-4-methylpyridinium chloride, was investigated in aminocarbonylation reactions. Double carbonylation was found to be the main reaction using different iodoarenes and aliphatic amines as substrates. Application of aniline derivatives as nucleophiles led to the exclusive formation of substituted benzamides. The stabilisation effect of the adsorbed pyridinium ionic liquid was compared to that of imidazolium and phosphonium derivatives. It was proved that the pyridinium SILP-palladium catalyst could be reused in at least 10 cycles. Recyclability was tested in five successive runs for all of the substrates.
Decarboxylative/Oxidative Amidation of Aryl α-Ketocarboxylic Acids with Nitroarenes and Nitroso Compounds in Aqueous Medium
Barak, Dinesh S.,Dahatonde, Dipak J.,Dighe, Shashikant U.,Kant, Ruchir,Batra, Sanjay
supporting information, p. 9381 - 9385 (2020/11/30)
The decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with 5-aryl-3-nitroisoxazole-4-carboxylates and substituted dinitrobenzenes under oxidative aqueous conditions to afford N-aryl amides is described. The reaction is suggested to proceed via a radical pathway in which a benzoyl nitroxyl radical, the key intermediate formed from reaction between nitroarene and benzoyl radical from glyoxalic acid, couples with hydroxyl radical from water to produce amide. Mechanistic insight allowed the scope of the strategy to be expanded to the synthesis of amides via reaction between aryl α-ketocarboxylic acids and nitroso compounds.
Palladium-Catalyzed Amidation and Amination of (Hetero)aryl Chlorides under Homogeneous Conditions Enabled by a Soluble DBU/NaTFA Dual-Base System
Beutner, Gregory L.,Coombs, John R.,Green, Rebecca A.,Inankur, Bahar,Lin, Dong,Qiu, Jun,Roberts, Frederick,Simmons, Eric M.,Wisniewski, Steven R.
supporting information, p. 1529 - 1537 (2019/09/04)
The palladium-catalyzed coupling of aryl and heteroaryl chlorides with primary amides under mild homogeneous reaction conditions is reported. Successful C-N coupling is enabled by the use of a unique "dual-base" system consisting of DBU and NaTFA, which serve as proton acceptor and halide scavenger, respectively, using low catalyst loadings (0.5 mol %) with readily available, air-stable palladium precatalysts. The DBU/NaTFA system also enables the room-temperature coupling of primary aryl amines with aryl chlorides and is tolerant of a variety of base-sensitive functional groups.
