87700-67-2Relevant articles and documents
Palladium-catalyzed C–P bond activation of aroyl phosphine oxides without the adjacent “anchoring atom”
Chen, Xingyu,Liu, Xiaoyan,Zhu, Hong,Wang, Zhiqian
, (2021/01/14)
A novel palladium-catalyzed decarbonylation of aroyl phosphine oxides to prepare phosphine oxides from carboxylic acids is developed. Without the adjacent “anchoring atom”, the challenging C–P bond activation is achieved in high selectivity. The disclosure of this reaction provides a new example of C–P bond activation and helps to extend the understanding of the property of C–P bond.
Chiral Br?nsted acid-catalyzed dynamic kinetic resolution of atropisomeric: Ortho -formyl naphthamides
Gao, Zeng,Hang, Xiao-Chun,Jiang, Gaoxi,Qian, Jinlong,Yang, Huameng,Zhang, Jinlong
supporting information, p. 7265 - 7268 (2020/07/14)
Despite the widespread use of naphthamide atropisomers in biologically active compounds and asymmetric catalysis, few catalytic methods have succeeded in the enantioselective synthesis of these compounds. Herein, a chiral Br?nsted acid (CBA) catalysis strategy was developed for readily scalable dynamic kinetic resolution of challenging ortho-formyl naphthamides with pyrrolylanilines. The chiral axis of the atropisomeric amide and a stereogenic center were simultaneously established for a new family of potential biologically active pyrrolopyrazine compounds with high enantio- and diastereoselectivities (up to >20 : 1 d.r. and 98 : 2 e.r.). Epimerization experiments of its derivatives reveal that the N-substitution of the nearby stereogenic center could affect the configurational stability of the axially chiral aromatic amides. These results might be useful for the construction of other kinds of novel axially chiral molecules with a low rotational barrier.
Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst
Okita, Toshimasa,Muto, Kei,Yamaguchi, Junichiro
supporting information, p. 3132 - 3135 (2018/05/28)
A Ni-catalyzed decarbonylative methylation of aromatic esters was achieved using methylaluminums as methylating agents. Dimethylaluminum chlorides uniquely worked as the methyl source. Because of the Lewis acidity of aluminum reagents, less reactive alkyl esters could also undergo the present methylation. By controlling the Lewis acidity of aluminum reagents, a chemoselective decarbonylative cross-coupling between alkyl esters and phenyl esters was successful.
Synthesis, evaluation of antimicrobial activity and theoretical analyses of novel sulfathiazole derivatives
Zengin, Gulay,Mert, Adem,Zengin, Huseyin
, p. 1 - 11 (2019/01/16)
Sulfathiazole derivatives (4-alkyl-1-naphthoylamino-N-thiazol-2-yl)benzenesulfonamides were synthesized, characterized by spectroscopic methods (FTIR, UV, NMR, PL), and tested for in vitro antimicrobial activity. These sulfathiazole derivatives were found to be more effective than the parent compound. According to the photoluminescence data, the compounds synthesized were found to give an intensive fluorescent blue light. Quantitative structure-activity relationship studies of these compounds and theoretical evaluations were carried out.
Synthesis and characterization of 3-aminoquinoline derivatives and studies of photophysicochemical behaviour and antimicrobial activities
Zengin, Gulay,Nafea Al Kawaz, Ali Muayad,Zengin, Huseyin,Mert, Adem,Kucuk, Bedia
, p. 45 - 55 (2015/10/05)
A series of 3-aminoquinoline derivatives were synthesized, where their chemical structures were confirmed by various analytical techniques, such as, Elemental Analysis, Nuclear Magnetic Resonance Spectroscopy (1H and 13C NMR), Liquid Chromatography-Mass-Mass Spectroscopy (LC-MS-MS), Ultraviolet-Visible Spectroscopy (UV-Vis), Fourier Transform Infrared Spectroscopy (FTIR) and Photoluminescence (PL). The quinoline ring core, typical of aminoquinolines, and a naphthalene group was combined to devise (4-alkyl-1-naphthyl)-quinolin-3-ylamide derivatives. These derivatives were designed and synthesized in light of the chemical and biological profiles of these important subunits. All the compounds were evaluated for their in vitro antibacterial and antifungal activities by the paper disc diffusion method with Gram-positive Bacillus subtilis, Bacillus megaterium and Staphylococcus aureus, Gram-negative Enterobacter aerogenes, Eschericha coli, Klebsiella pneumoniae and Pseudomonas aeruginosa and yeasts Candida albicans, Saccharomyces cerevisiae and Yarrovia lipolytica. These compounds showed antimicrobial activities against Gram-positive and Gram-negative bacteria and several yeasts, and thus their activity was not restricted to any particular type of microorganism.
Palladium-catalyzed directing group-assisted C8-triflation of naphthalenes
Yang, Zhi-Wei,Zhang, Qi,Jiang, Yuan-Ye,Li, Lei,Xiao, Bin,Fu, Yao
supporting information, p. 6709 - 6711 (2016/06/01)
The transition-metal-catalyzed direct triflation of naphthyl amides and naphthyl ketones has been accomplished for the first time. Benzophenone (BP) was found to be a suitable ligand for the cross-coupling reactions. Density functional theory (DFT) calculations revealed that excessive amounts of HOTf inhibit the reductive elimination of the C-F bond to realize the unusual reductive elimination of the C-OTf bond.
COMPOSITION AND METHODS FOR TREAT1NG GLIOBLASTOMA
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Page/Page column 44, (2012/03/11)
The disclosure provides methods of treating glioblastoma, methods of screening for compounds that treat glioblastoma, and pharmaceutical compositions useful in the treatment of glioblastoma
Synthesis and characterization of cannabimimetic aminoalkylindole based 5-(4-alkyl-1-naphthoylamino)-1,3,4-thiadiazole-2-sulfonamides
Zengin, Gulay,Nalbantbasi, Zehra,Zengin, Huseyin,Turkmen, Hasan
experimental part, p. 707 - 714 (2012/01/05)
A novel series of cannabimimetic aminoalkylindole-based sulfonamide derivatives was synthesized. These new compounds were synthesized by reacting acyl chlorides of naphthoic acids with deacetylated acetazolamide in the presence of N-ethyl-morpholine to give structures incorporating 1-naphthoyl groups of cannabimimetic aminoalkylindoles and a five-membered heteroring typical of antiglaucoma sulfa drugs. The synthesized compounds were characterized using standard techniques. Photoluminescence of these derivatives was also studied, where more electron-donating groups on the aromatic ring at the para-position caused an increase in the intensity of the main peaks and shifts to higher emission wavelengths.
ISOINDOLE DERIVATIVES USEFUL FOR TREATING PAIN, GASTROINTESTINAL DISEASES AND CANCER
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Page/Page column 52, (2008/06/13)
Compounds of formula I or pharmaceutically acceptable salts thereof: [Chemical formula should be inserted here. Please see paper copy] I wherein X, R1, R2, R3, m and n are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.
Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: Steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists
Huffman, John W.,Zengin, Gulay,Wu, Ming-Jung,Lu, Jianzhong,Hynd, George,Bushell, Kristen,Thompson, Alicia L.S.,Bushell, Simon,Tartal, Cindy,Hurst, Dow P.,Reggio, Patricia H.,Selley, Dana E.,Cassidy, Michael P.,Wiley, Jenny L.,Martin, Billy R.
, p. 89 - 112 (2007/10/03)
The synthesis and pharmacology of 47 1-alkyl-3-(1-naphthoyl)indoles (R = C3H7 and C5H11, R′ = H and CH3) is described. Naphthoyl substituents include 4- and 7-alkyl groups, plus 2, 4, 6, and 7-methoxy groups. Three of these compounds are highly selective CB2 receptor agonists. In an effort to improve indole-based CB2 cannabinoid receptor ligands and also to develop SAR for both the CB1 and CB2 receptors, 47 indole derivatives were prepared and their CB1 and CB2 receptor affinities were determined. The indole derivatives include 1-propyl- and 1-pentyl-3-(1- naphthoyl)indoles both with and without a 2-methyl substituent. Naphthoyl substituents include 4- and 7-alkyl groups as well as 2-, 4-, 6-, 7-methoxy and 4-ethoxy groups. The effects of these substituents on receptor affinities are discussed and structure-activity relationships are presented. In the course of this work three new highly selective CB2 receptor agonists were identified, 1-propyl-3-(4-methyl-1-naphthoylindole (JWH-120), 1-propyl-2-methyl-3-(6-methoxy-1-naphthoylindole (JWH-151), and 1-pentyl-3-(2-methoxy-1-naphthoylindole (JWH-267). GTPγS assays indicated that JWH-151 is a full agonist at CB2, while JWH-120 and JWH-267 are partial agonists. Molecular modeling and receptor docking studies were carried out on a set of 3-(4-propyl-1-naphthoyl)indoles, a set of 3-(6-methoxy-1- naphthoyl)indoles and the pair of N-pentyl-3-(2-methoxy-1-naphthoyl)indoles. Docking studies indicated that the CB1 receptor affinities of these compounds were consistent with their aromatic stacking interactions in the aromatic microdomain of the CB1 receptor.
