63767-58-8Relevant academic research and scientific papers
Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones
Stojanovi?, Milovan,Bugarski, Slobodan,Baranac-Stojanovi?, Marija
, p. 13495 - 13507 (2020/11/13)
2,3-Dihydro-4-pyridone skeleton is an important building block in organic synthesis because it features several reaction sites with nucleophilic or electrophilic properties. Herein, we disclose a method for its formation by intramolecular cyclization of ester-tethered enaminones, which can easily be synthesized from readily available materials, such as amines, activated alkynes, and activated alkenes. 2,3-Dihydro-4-pyridones have been isolated in 41-90% yields. We also demonstrate the transformation of these heterocycles into another important class of compounds, 4-pyridones, by utilizing 2,3,5,6-tetrachloro-p-benzoquinone (chloranil) as an oxidizing agent. The latter products were isolated in 65-94% yields.
Design, synthesis and biological activity evaluation of novel methyl substituted benzimidazole derivatives
Liu, Qianqian,Ren, Yujie,Zhang, Tianrong
, (2020/03/03)
Ten new dabigatran derivatives (7a–j) with high docking scoring were designed, synthesised and biologically evaluated. The inhibitory in vitro activity of these compounds on thrombin was evaluated on the basis of preliminary activity screening results. The IC50 values of compounds 7a, 7d and 7j were 1.92, 2.17 and 1.54 nM, respectively, and are equivalent to the dabigatran (IC50 = 1.20 nM). Therefore, the most active compound, 7j, was selected to further investigate the anticoagulant activity in rats. Compound 7j presented excellent in vivo inhibitory effects on arteriovenous thrombosis, and the inhibition rate was (84.19 ± 1.14) %. The anticoagulant activity of compound 7k synthesised in the previous work was evaluated in vivo, and its inhibition rate was (85.58 ± 2.89) %. This rate was nearly equivalent to that of dabigatran (85.07 ± 0.61) %. Results indicated that compounds 7a, 7d, 7j and 7k can be further studied as novel antithrombin drug candidates.
Preparation method of 3-(phenyl amino)ethyl propionate type compound
-
Paragraph 0026, (2018/09/29)
The invention belongs to the technical field of chemical synthesis and particularly relates to a preparation method of a 3-(phenyl amino)ethyl propionate type compound. The method is realized throughthe following steps: mixing an aromatic amine compound w
A green and convenient approach for the one-pot solvent-free synthesis of coumarins and β-amino carbonyl compounds using Lewis acid grafted sulfonated carbon@titania composite
Kour, Manmeet,Paul, Satya
, p. 327 - 337 (2017/02/10)
Abstract: This paper reports an efficient protocol for the synthesis of coumarins via Pechmann reaction, and β-amino carbonyl compounds via aza-Michael reaction using catalytic amount of solid Lewis acid catalyst, C@TiO2–SO3–SbCl2. Six different catalysts were prepared by covalent immobilization of homogeneous Lewis acids onto sulfonated carbon@titania composite derived from amorphous carbon and nano-titania. Among various catalysts tested, C@TiO2–SO3–SbCl2 showed superior catalytic activity. The catalyst could be recycled without significant loss of its catalytic activity and demonstrated versatile catalysis for a wide range of substrates. Graphical abstract: [Figure not available: see fulltext.]
Aza-Michael mono-addition using acidic alumina under solventless conditions
Bosica, Giovanna,Abdilla, Roderick
, (2016/07/07)
Aza-Michael reactions between primary aliphatic and aromatic amines and various Michael acceptors have been performed under environmentally-friendly solventless conditions using acidic alumina as a heterogeneous catalyst to selectively obtain the corresponding mono-adducts in high yields. Ethyl acrylate was the main acceptor used, although others such as acrylonitrile, methyl acrylate and acrylamide were also utilized successfully. Bi-functional amines also gave the mono-adducts in good to excellent yields. Such compounds can serve as intermediates for the synthesis of anti-cancer and antibiotic drugs.
2 - [6-methoxy-3 - (2,3-dichlorophenyl) methyl-4-oxo -1,4-dihydro -1 (4H)-quinolyl] method for the preparation of acetic acid
-
Paragraph 0049-0052, (2016/10/08)
The invention provides a preparation method of 2-(6-methoxy-3-(2, 3-dichlorophenyl) methyl-4-oxo-1, 4-dihydro-1(4H)-quinolyl) acetic acid. The preparation method comprises the following steps: by taking 3-(4-methoxyanilino) sodium propionate as a raw material, performing amino protection treatment to prepare 3-(N-protecting group-4-methoxyanilino) propionic acid, performing Friedel-Crafts acylation reaction to prepare N-protecting group-6-methoxy-2, 3-dihydroquinolinone, and further performing deprotection treatment to prepare an intermediate, namely 6-methoxy-2, 3-dihydro-4 (1H)-quinolinone; by taking the intermediate, namely 6-methoxy-2, 3-dihydro-4 (1H)-quinolinone as a raw material, performing N-alkylation, hydrolysis and condensation reaction to prepare a target product. By adopting the preparation method, the use of a large amount of polyphosphoric acid (PPA) can be avoided, the process is environment-friendly, and the preparation method is more conductive to industrial production.
Tin-Catalyzed Selective Reductive Hydroamination of Alkynes for the Synthesis of Tertiary Amines
Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Manoranjan,Sharma, Sushila,Kumar, Neeraj
, p. 1103 - 1109 (2016/04/19)
A unique preference of tin(II) for aniline activation is disclosed. In the present work tin(II) triflate-catalyzed highly selective Markovnikov reductive hydroamination of internal as well as terminal alkynes is reported. The mechanistic study revealed the involvement of two steps in one pot wherein alkyne reduces to corresponding alkene in presence of PMHS as reducing agent followed by hydroamination of alkene. A broad range of alkynes transformed into tertiary amines with good to excellent yield. This method is equally applicable in synthesis of secondary amines.
The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solventfree conditions
Douraki, Saba Mohammadi,Massah, Ahmad Reza
, p. 1346 - 1349 (2015/11/10)
Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.
The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solvent-free conditions
Douraki, Saba Mohammadi,Massah, Ahmad Reza
, p. 1346 - 1349 (2016/02/26)
Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.
Synthesis and biological evaluation of some new 2,5-Substituted 1-Ethyl-1H-benzoimidazole fluorinated derivatives as direct thrombin Inhibitors
Li, Meilin,Ren, Yujie
, p. 353 - 365 (2015/05/13)
A new series of fluorinated 2,5-substituted 1-ethyl-1H-benzimidazole derivatives were synthesized from starting compounds 3a-i, which were prepared from acrylic acid ethyl ester and the appropriate amines using trifluoromethanesulfonic acid as a catalyst. A total of 9 novel derivatives were synthesized through 9 steps. All of them were evaluated for thrombin inhibition activity in vitro for the first time. We have altered their structures using different substituents on the amines to assess their structure-activity relationships as direct thrombin inhibitors. All the compounds were effective thrombin inhibitors, with IC50 values ranging from 3.39 to 23.30nM. Among the compounds synthesized, compounds 14a, 14b, 14d, 14e, and 14h exhibited greater anticoagulant activity than argatroban (IC50=9.36nM). Furthermore, compound 14h synthesized starting with 2-amino-pyridine was the most potent thrombin inhibitor with an IC50 value of 3.39nM. Molecular modeling studies were performed to determine the probable interactions of the most potent compounds 14a, 14e, and 14h with their protein receptor (PDB ID: 1KTS). Docking data show that the active compounds inhibit thrombin in a similar mode to that of the potent anticoagulant dabigatran. A new series of fluorinated derivatives were evaluated for their in vitro thrombin inhibition activities. 3-({2-[(4-Carbamimidoyl-2-fluoro-phenylamino)-methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}-pyridin-2-yl-amino)-propionic acid 14h shows the most potent antithrombin activity (IC50=3.39nM). Molecular docking revealed that its inhibition mode was similar to that of dabigatran.
