6333-15-9Relevant articles and documents
An unsymmetrical covalent organic polymer for catalytic amide synthesis
Yadav, Deepika,Awasthi, Satish Kumar
, p. 179 - 186 (2019/12/28)
Herein, we present the first report on the Covalent Organic Polymer (COP) directed non-classical synthesis of an amide bond. An economical route has been chosen for the synthesis of APC-COP using p-aminophenol and cyanuric chloride. APC-COP acts as a smart, valuable and sustainable catalyst for efficient access to the amide bond under mild conditions at room temperature in 30 min. APC-COP exhibits selectivity towards carboxylic acids over esters. The key features of this protocol involve the variety of parameters, viz. wider substrate scope, no use of additive and recyclability, which makes this approach highly desirable in gramscale synthesis. Moreover, we have shown the practical utility of the present method in the catalytic synthesis of paracetamol.
Synthesis and structure-activity relationships of small-molecular di-basic esters, amides and carbamates as flaviviral protease inhibitors
Sundermann, Tom R.,Benzin, Clarissa V.,Dra?i?, Tonko,Klein, Christian D.
, p. 187 - 194 (2019/05/21)
Inhibitors of the flaviviral serine proteases, which are crucial for the replication of dengue and West-Nile virus, have attracted much attention over the last years. A dibasic 4-guanidinobenzoate was previously reported as inhibitor of the dengue protease with potency in the low-micromolar range. In the present study, this lead structure was modified with the intent to explore structure-activity relationships and obtain compounds with increased drug-likeness. Substitutions of the guanidine moieties, the aromatic rings, and the ester with other functionalities were evaluated. All changes were accompanied by a loss of inhibition, indicating that the 4-guanidinobenzoate scaffold is an essential element of this compound class. Further experiments indicate that the target recognition of the compounds involves the reversible formation of a covalent adduct.
Preparation method of electronic-grade 4,4'-diaminobenzanilide
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Paragraph 0013; 0014; 0026; 0027, (2018/08/28)
The invention discloses a preparation method of electronic-grade 4,4'-diaminobenzanilide. The preparation method comprises the following steps: 1, 4,4'-dinitrobenzanilide is prepared from 4-nitroaniline and 4-nitrobenzoyl chloride through a reaction; 2, crude 4,4'-diaminobenzanilide is obtained from 4,4'-dinitrobenzanilide through catalytic hydrogenation; 3, crude 4,4'-diaminobenzanilide obtainedin step 2, a recrystallization solvent and activated carbon are added to an autoclave simultaneously, recrystallization and activated carbon decoloration are performed simultaneously at 100-150 DEG Cunder nitrogen protection, and electronic-grade 4,4'-diaminobenzanilide is obtained. The appropriate recrystallization solvent is selected and recrystallization and activated carbon decoloration are performed simultaneously, so that electronic-grade 4,4'-diaminobenzanilide with high purity and low ion content is obtained finally, and special requirements of high-performance electronics industry are met.
Biological evaluation and molecular docking studies of nitro benzamide derivatives with respect to in vitro anti-inflammatory activity
Tumer, Tugba B.,Onder, Ferah Comert,Ipek, Hande,Gungor, Tugba,Savranoglu, Seda,Tok, Tugba Taskin,Celik, Ayhan,Ay, Mehmet
, p. 129 - 139 (2016/12/22)
A series of nitro substituted benzamide derivatives were synthesized and evaluated for their potential anti-inflammatory activities in vitro. Firstly, all compounds (1–6) were screened for their inhibitory capacity on LPS induced nitric oxide (NO) production in RAW264.7 macrophages. Compounds 5 and 6 demonstrated significantly high inhibition capacities in a dose-dependent manner with IC50 values of 3.7 and 5.3 μM, respectively. These two compounds were also accompanied by no cytotoxicity at the studied concentrations (max 50 μM) in macrophages. Molecular docking analysis on iNOS revealed that compounds 5 and 6 bind to the enzyme more efficiently compared to other compounds due to having optimum number of nitro groups, orientations and polarizabilities. In addition, 5 and 6 demonstrated distinct regulatory mechanisms for the expression of the iNOS enzyme at the mRNA and protein levels. Specifically, both suppressed expressions of COX-2, IL-1β and TNF-α significantly, at 10 and 20 μM. However, only compound 6 significantly and considerably decreased LPS-induced secretion of IL-1β and TNF-α. These results suggest that compound 6 may be a multi-potent promising lead compound for further optimization in structure and as well as for in vivo validation studies.
Design, synthesis and biological evaluation of 4-Amino-N-(4-aminophenyl) benzamide analogues of quinoline-based SGI-1027 as inhibitors of DNA methylation
Rilova, Elodie,Erdmann, Alexandre,Gros, Christina,Masson, Veronique,Aussagues, Yannick,Poughon-Cassabois, Valerie,Rajavelu, Arumugam,Jeltsch, Albert,Menon, Yoann,Novosad, Natacha,Gregoire, Jean-Marc,Vispe, Stephane,Schambel, Philippe,Ausseil, Frederic,Sautel, Francois,Arimondo, Paola B.,Cantagrel, Frederic
, p. 590 - 601 (2014/03/21)
Quinoline derivative SGI-1027 (N-(4-(2-amino-6-methylpyrimidin-4-ylamino) phenyl)-4-(quinolin-4-ylamino)benzamide) was first described in 2009 as a potent inhibitor of DNA methyltransferase (DNMT) 1, 3A and 3B. Based on molecular modeling studies, performed using the crystal structure of Haemophilus haemolyticus cytosine-5 DNA methyltransferase (MHhaI C5 DNMT), which suggested that the quinoline and the aminopyridimine moieties of SGI-1027 are important for interaction with the substrates and protein, we designed and synthesized 25 derivatives. Among them, four compounds - namely the derivatives 12, 16, 31 and 32 - exhibited activities comparable to that of the parent compound. Further evaluation revealed that these compounds were more potent against human DNMT3A than against human DNMT1 and induced the re-expression of a reporter gene, controlled by a methylated cytomegalovirus (CMV) promoter, in leukemia KG-1 cells. These compounds possessed cytotoxicity against leukemia KG-1 cells in the micromolar range, comparable with the cytotoxicity of the reference compound, SGI-1027. Structure-activity relationships were elucidated from the results. First, the presence of a methylene or carbonyl group to conjugate the quinoline moiety decreased the activity. Second, the size and nature of the aromatic or heterocycle subsitutents effects inhibition activity: tricyclic moieties, such as acridine, were found to decrease activity, while bicyclic substituents, such as quinoline, were well tolerated. The best combination was found to be a bicyclic substituent on one side of the compound, and a one-ring moiety on the other side. Finally, the orientation of the central amide bond was found to have little effect on the biological activity. This study provides new insights in to the structure-activity relationships of SGI-1027 and its derivative. Ep-(igenet)-ic! Guided by modeling studies, derivatives of the known DNA methyltransferase (DNMT) inhibitor SGI-1027 were designed, synthesized and evaluated. Structure-activity relationships were derived from the results, leading to the identification of derivatives with improved potency and potential for further development.
Design, synthesis and structure-activity relationship of new HSL inhibitors guided by pharmacophore models
Al-Shawabkeh, Jumana D.,Al-Nadaf, Afaf H.,Dahabiyeh, Lina A.,Taha, Mutasem O.
, p. 127 - 145 (2014/03/21)
Hormone-sensitive lipase (HSL) is a critical enzyme involved in the hormonally regulated release of fatty acids and glycerol from adipocyte lipid stores. Its inhibition may improve insulin sensitivity and blood glucose handling in type 2 diabetes. Accordingly, many small-molecule HSL inhibitors have recently been identified. In continuation of our efforts for discovery of new HSL inhibitors, we prepared a variety of esters, amides, sulfonamides and sulfonate esters capable of fitting two pharmacophore models that we developed and published earlier. The tested compounds were synthesized via coupling reactions of aroyl chlorides or sulfonyl chlorides with phenols, amines and related derivatives. Our efforts led to the identification of interesting compounds of low micromolar anti-HSL bioactivities, which have potential to be developed into effective antidiabetic agents.
A catalytic and tert-butoxide ion-mediated amidation of aldehydes with para-nitro azides
Carbone, Giorgio,Burnley, James,Moses, John E.
, p. 2759 - 2761 (2013/04/10)
We report here a new catalytic reaction in which, para-nitro azides are acylated by aldehydes to produce amides and molecular nitrogen in a single step. The transformation is believed to proceed via an electron transfer process mediated by the tert-butoxide ion, and catalysed by a thiazolium salt derived species. The Royal Society of Chemistry 2013.
Green and efficient method for the acylation of amines and phenols in the presence of hydrotalcite in water
Massah, Ahmad Reza,Toghyani, Mitra,Najafabadi, Batool Hojati
, p. 603 - 605,3 (2020/09/16)
In this study a mild, efficient and environmentally friendly method has been developed for the synthesis of amides and esters in the presence of hydrotalcite in water at room temperature. Different types of amines and phenols have been used and in all cases the products were obtained in moderate to high yields after an easy work-up. This method follows the principles of green chemistry.
HEPATITIS C VIRUS INHIBITORS
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Page/Page column 257-258, (2011/07/30)
The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS5A protein
Novel 2-phenyl-3-{4'-[N-(4"-aminophenyl)carbamoyl]-phenyl}- quinazoline-4(3H)one-6-sulphonic acid based mono azo reactive dyes
Patel, Divyesh R.,Patel, Keshav C.
scheme or table, p. 177 - 188 (2012/01/02)
A series of new heterocyclic mono azo reactive dyes 7a-m were prepared by diazotization of 2-phenyl-3-{4'-[N-(4"-aminophenyl)carbamoyl]-phenyl}- quinazoline-4(3H)-one-6-sulphonic acid (3) and coupling with various cyanurated coupling components 6a-m and their dyeing performance on silk, wool and cotton fibres was assessed. These dyes were found to give a variety of colour shades with very good depth and levelness on the fibres. All the compounds were identified by conventional method (IR and 1H-NMR) and elemental analyses. The percentage dye bath exhaustion on different fibres was reasonably good and acceptable. The dyed fibre showed moderate to very good fastness to light, washing and rubbing.
