644-33-7Relevant academic research and scientific papers
Ethylene-Bridged Tetradentate Bis(amidines): Supramolecular Assemblies through Hydrogen Bonding and Photoluminescence upon Deprotonation
Calderón-Díaz, Alvaro,Arras, Janet,Miller, Ethan T.,Bhuvanesh, Nattamai,McMillen, Colin D.,Stollenz, Michael
, p. 3243 - 3250 (2020)
Sterically crowded tetradentate bis(amidines) encapsulate their N–H functionalities or unveil them to undergo inter- and intramolecular hydrogen bonding both in solid state and solution, depending on a subtle interplay between the amidine backbone substituents. X-ray crystallography reveals for four distinct ZZ(syn/syn) and EE(syn/syn) bis(amidines) that bulky terminal N-Mes groups in combination with N2C-tBu or N2C-Ph substituents result in steric protection of the N–H moieties, whereas less crowded terminal p-tBu(C6H4) groups either show encapsulation (N2C-tBu) or hydrogen bonding (N2C-Ph), the latter resulting in a bis(amidine) dimer formed by inter- and intramolecular hydrogen bonds. Moreover, a supramolecular solvent adduct consisting of one bis(amidine) and four ethanol molecules is presented. DFT calculations show that both the dimerization and formation of the solvent adduct is associated with a significant energy gain (dimerization: ΔE = –27.7 kcal/mol; formation of ethanol adduct: ΔE = –64.3 kcal/mol). The corresponding four Li bis(amidinates) are weakly blue to green-emissive in THF solution. Overall, a new series of highly flexible bis(amidines) has been examined.
Synthesis, characterization, in vitro biological and molecular docking evaluation of N,N'-(ethane-1,2-diyl)bis(benzamides)
Aziz, Hamid,Saeed, Aamer,Jabeen, Farukh,Ullah, Nazif,Rehman, Ashfaq Ur
, p. 2425 - 2436 (2021/03/03)
The present research describes the synthesis, characterization, in vitro biological and docking evaluation of N,N'-(ethane-1,2-diyl)bis(benzamides) (3a-3j). Consequently, in in vitro hRBCs hemolysis assay, only the bis-amide (3d) induced 52.4% hemolysis at higher concentration (1000?μg/mL) that decreased drastically with concentration (250?μg/mL) to 27.9% (CC50 = 400.41). Similarly, the tested bis-amide (3j) was found to be the least toxic with 7.8% hemolysis at higher concentration (1000?μg/mL) that gradually decreases to 6.1% (CC50 = 19,347.83) at lower concentration (250?μg/mL). Accordingly, the tested bis-amides were found to be highly biocompatible against hRBCs at higher concentrations with much higher CC50 values (> 1000?μg/mL). The biocompatible bis-amides (3a-3j) were subjected to in vitro DNA ladder assay to analyze their apoptotic potential. The results obtained suggest the tested bis-amides (3a-3j) are highly degradative toward DNA causing the appearance of more than one bands or complete degradation of DNA except (3a), (3c), (3i) and (3?g). Moreover, the synthesized bis-amides (3a-3j) were tested in in vitro antileishmanial assay to unveil their leishmaniacidal potential. The results obtained clearly indicated that some of the tested bis-amides displayed good dose dependent response. The tested bis-amides were highly active at higher concentration (1000?μg/mL) against the leishmanial promastigotes and their % inhibitory potential decreased drastically with concentration (250?μg/mL). Consequently, at higher concentration (1000?μg/mL), the bis-amide (3f) caused 85% inhibition and was ranked as the most effective leishmaniacidal bis-amides followed by the bis-amide (3?g) with 73.54% inhibition of leishmanial promastigotes. However, in terms of their IC50 values, the best leishmaniacidal potential was displayed by the bis-amide (3f) followed by (3b), (3j) and (3?g) with IC50 values increasing in the order of 633.16, 680.22, 680.22 and 712.93?μg/mL, respectively. Molecular docking studies revealed that bis-amides having electron-donating groups showed good binding potential against antileishmanial target. Graphic abstract: [Figure not available: see fulltext.].
One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine
Golub, Tatiana,Dou, Gui-Yuan,Zeng, Cheng-Chu,Becker, James Y.
supporting information, p. 7961 - 7964 (2019/10/11)
Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).
Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis
Golub, Tatiana,Becker, James Y.
, p. 861 - 868 (2018/04/30)
In general, bisamides derived from diamines and involving 3 and 4 methylene groups as spacers between the two amide functionalities behave similar to monoamides upon anodic oxidation in methanol/LiClO4 because both types undergo majorly mono- and dimethoxylations at the α-position to the N atom. However, in cases where the spacer contains two methylene groups only the anodic process leads mostly to CH2-CH2 bond cleavage to afford products of type RCONHCH2OCH3. Moreover, upon replacing LiClO4 with Et4NBF4 an additional fragmentation type of product was generated from the latter amides, namely RCONHCHO. Also, the anodic process was found to be more efficient with C felt as the anode, and in a mixture of 1:1 methanol/acetonitrile co-solvents.
ANTIMICROBIAL COMPOUNDS
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Page/Page column 41; 42, (2015/05/19)
The invention provides compounds for use in treating microbial infection in an animal. Example compounds include Pyridin-3-ylmethyl (4-((2-aminophenyl)- carbamoyl)benzyl)carbamate ("Entinostat"). The compounds can act via induction of the innate antimicrobial peptide defense system, and stimulation of autophagy.
Structure-property relationships of aromatic polyamides and polythioamides: comparative consideration with those of analogous polyesters, polythioesters and polydithioesters
Nagasawa, Masayuki,Ishii, Tatsuya,Abe, Daisuke,Sasanuma, Yuji
, p. 96611 - 96622 (2015/11/24)
Conformational characteristics and configurational properties of aromatic polyamides and polythioamides, analogues of common aromatic polyesters such as poly(ethylene terephthalate) and poly(trimethylene terephthalate), have been investigated via NMR experiments and molecular orbital calculations on model compounds, and the refined rotational isomeric state calculations for the polymers. The polyamides and polythioamides were actually synthesized and characterized in terms of solubility, molecular weight, crystallinity, thermal transition, and thermal stability. Herein, the experimental results are discussed mainly from the viewpoint of the conformational characteristics and compared with those obtained from analogous aromatic polyesters, polythioesters, and polydithioesters to reveal the effects of the heteroatoms O, S, and NH included in the backbone on the polymer structures and properties.
One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles
Carrilho, Rui M.B.,Almeida, Ana R.,Kiss, Mercédesz,Kollár, László,Skoda-F?ldes, Rita,D?browski, Janusz M.,Moreno, Maria José S.M.,Pereira, Mariette M.
supporting information, p. 1840 - 1847 (2015/05/27)
An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70%) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100°C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest yield of the target dibenzamides (ca. 65%) was obtained with 1,4-diaminobenzene as coupling amine, at 100°C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N′(butane-1,4-diyl)dibenzamide and androst-16-ene-based dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM.
An efficient, green and scale-up synthesis of amides from esters and amines catalyzed by Ru-MACHO catalyst under mild conditions
Han, Qian,Xiong, Xingquan,Li, Sizhong
, p. 85 - 88 (2014/12/11)
An efficient, green and scale-up synthesis of amides from esters and amines has been developed using Ru-MACHO as a readily available catalyst. A diverse range of amides were obtained in moderate to excellent yields (55-98%). Furthermore, when the scale of the amidation reaction was increased to 240.0 mmol, the desired amide still could be obtained in high yield (48.2 g of N-benzylbenzamide, 95%).
Bisamides as ligands in Suzuki coupling reactions catalyzed by palladium
Da Costa, Daniel P.,Nobre, Sabrina M.
, p. 4582 - 4584 (2013/08/23)
This protocol uses palladium chloride and bisamides as ligands for Suzuki cross-coupling reactions, in mild (25 for 2 h) aerobic conditions. This study was efficient for arylboronic acids and/or aryl bromides with activating or deactivating substituents in the ring with high yields (81-95%).
Efficient and continuous monoacylation with superior selectivity of symmetrical diamines in microreactors
Maurya, Ram Awatar,Hoang, Phan Huy,Kim, Dong-Pyo
scheme or table, p. 65 - 68 (2012/03/26)
Efficient and continuous monoacylation of symmetrical diamines performed in microreactors yielded superior selectivity to that predicted by statistical considerations. It is highly valuable that the kinetically controlled product in high yields was achieved without any special catalyst at ambient temperature.
