109482-86-2Relevant academic research and scientific papers
Metal-free synthesis of gem-difluorinated heterocycles from enaminones and difluorocarbene precursors
Chen, Jie,Fu, Rui,Jiang, Yaojia,Rong, Jiaxin,Wang, Enfu,Wang, Fei,Zhang, Jian,Zhang, Zhengyu
supporting information, p. 3477 - 3480 (2022/03/31)
A cascade strategy to synthesise gem-difluorinated 2H-furans from reactions of BrCF2CO2Et with enaminones has been described. The reactions tolerate a wide variety of functional groups under metal-free conditions. An active aminocyclopropane is proposed to be a key intermediate through the cyclopropanation of difluorocarbene with enaminones, which further triggers a regioselective C-C bond cleavage in situ to afford the corresponding gem-difluorinated 2H-furans.
Discovery of highly potent tubulin polymerization inhibitors: Design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines
Huo, Xian-Sen,Jian, Xie-Er,Ou-Yang, Jie,Chen, Lin,Yang, Fang,Lv, Dong-Xin,You, Wen-Wei,Rao, Jin-Jun,Zhao, Pei-Liang
, (2021/05/10)
By removing 5-methyl and 6-acetyl groups in our previously reported compound 3, we designed a series of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine derivatives as potential tubulin polymerization inhibitors. Among them, compound 5e displayed low nanomolar antiproliferative efficacy on HeLa cells which was 166-fold higher than the lead analogue 3. Interestingly, 5e displayed significant selectivity in inhibiting cancer cells over HEK-293 (normal human embryonic kidney cells). In addition, 5e dose-dependently arrested HeLa in G2/M phase through the alterations of the expression levels of p-cdc2 and cyclin B1, and caused HeLa cells apoptosis by regulation of expressions of cleaved PARP. Further evidence demonstrated that 5e effectively inhibited tubulin polymerization and was 3-fold more powerful than positive control CA-4. Moreover, molecular docking analysis indicated that 5e overlapped well with CA-4 in the colchicine-binding site. These studies demonstrated that 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine skeleton might be used as the leading unit to develop novel tubulin polymerization inhibitors as potential anticancer agents.
Synthesis, characterization, and antimicrobial activity investigations of ruthenium (II)–bipyridine complexes of ciprofloxacin derivatives
Al-Wahaib, Dhuha,El-Dissouky, Ali,Abrar, Nada M.,Khalil, Tarek E.
, (2021/08/07)
A series of ruthenium (II) complexes derived from the reaction between cis-bis (2,2′-bipyridine) dichloro ruthenium (II) dihydrate and enaminone derivatives of ciprofloxacin were synthesized and fully characterized using elemental analysis, cyclic voltammetry and different spectroscopic techniques (Uv–vis, FTIR, NMR, mass spectroscopy, and X-ray photoelectron spectrometry (XPS)). The isolated compounds were tested for their antibacterial and antifungal activities against gram-negative and gram-positive bacteria. The FTIR data revealed that ciprofloxacin derivatives act as bidentate ligands through the pyridone carbonyl and the carboxylate oxygen atom. The UV–visible data showed that the charge transfer CT band is blue shifted upon the coordination of the ciprofloxacin derivatives compared to the CT band of the parent complex. The XPS results revealed the characteristic peaks of Ru3p3/2 and Ru3p1/2 as well as Ru3d5/2 and Ru3d3/2, which confirmed the assembly of the ruthenium (II) ciprofloxacin derivative complexes. Cyclic voltammetry data showed that the ciprofloxacin enaminone derivatives have a similar reduction potential for the Ru (II)/Ru (III) redox couple, and it revealed that the coordination of the ruthenium (II) ion altered the redox property of the ligands and enhanced their electron transfer rate. The electrochemical and the UV–visible results suggest that the ciprofloxacin derivative ligands are (Formula presented.) -acceptor ligands. Further, the complexes showed higher antibacterial activities than the parent ciprofloxacin antibiotic and did not show antifungal activities among the tested fungi strains.
Stereoselective synthesis of trifluoromethyl-substituted 2: H -furan-amines from enaminones
Liang, Xiaoyu,Guo, Pan,Yang, Wenjie,Li, Meng,Jiang, Chengzhou,Sun, Wangbin,Loh, Teck-Peng,Jiang, Yaojia
supporting information, p. 2043 - 2046 (2020/02/22)
A straightforward strategy for synthesis of highly functionalized trifluoromethyl 2H-furans is described. The copper catalyzed method relies on a cascade cyclic reaction between enaminones and N-tosylhydrazones. This method allows the synthesis of 2-amino
Design, synthesis, and biological evaluation of triazolyl- and triazinyl-quinazolinediones as potential antitumor agents
Al-Romaizan, Abeer N.,Ahmed, Nesreen S.,Elfeky, Sherin M.
, (2019/03/07)
Novel 6(3-1H-1,2,4-triazol-1-yl)-3-phenylquinazoline-2,4(1H,3H)-diones (7a-e) were synthesized from different enaminones (6a-e) with 6-hydrazinyl-3-phenylquinazoline-2,4(1H,3H)-dione. 2,6(4-2-Substituted-1,3,5-triazin-1(2H)-yl)-3-phenylquinazoline-2,4(1H,3H)-diones (8a-k) were synthesized from the reaction of 1-(2,4-dioxo-3-phenyl-1,2,3,4-tetrahydroquinazolin-6-yl)thiourea, urea, or guanidine (3a-c) with enaminones (6a-e), and a series from 3-substituted-2-imino-1,3,5-triazin-1(2H)-yl-sulfonyl-phenyl-1-methylquinazoline-2,4(1H,3H)-dione (12a-j) were obtained from the reaction of N-(diaminomethylene)-4-(1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)benzenesulfonamide (11) with the enaminone (6a-j). The antitumor activity of the synthesized compounds was evaluated against two human cell lines: human colon carcinoma HCT116 and human hepatocellular carcinoma HEP-G2. Some of the tested compounds showed significant potency compared to the reference drug staurosporin.
Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines
Wang, Fei,Sun, Wangbing,Wang, Yixin,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 1256 - 1260 (2018/02/23)
A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.
Metal-free TBAI-catalyzed oxidative Csp3–S bond formation through Csp2–Csp2 bond and S–N bond cleavage: A new route to β-keto-Sulfones
Tang, Yucai,Chen, Ying,Liu, Hui,Guo, Min
supporting information, p. 3703 - 3705 (2018/09/14)
A novel TBAI-catalyzed radical sulfonylation of readily available N,N-dimethylenaminones with sulfonylhydrazides to afford functionalized β-keto-sulfones has been developed. Various functional groups were tolerated well under the present oxidative conditions and the corresponding β-keto-sulfone compounds were obtained in moderate to good yields. Importantly, this transformation offered the first protocol for Csp3–S bond formation by oxidative Csp2–Csp2 bond cleavage in one step.
Directed C-C bond cleavage of a cyclopropane intermediate generated from: N -tosylhydrazones and stable enaminones: Expedient synthesis of functionalized 1,4-ketoaldehydes
Ni, Meiyan,Zhang, Jianguo,Liang, Xiaoyu,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 12286 - 12289 (2017/11/20)
An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from
Palladium-Catalyzed C–S Bond Formation of Stable Enamines with Arene/Alkanethiols: Highly Regioselective Synthesis of β-Amino Sulfides
Jiang, Yaojia,Liang, Gaohui,Zhang, Cong,Loh, Teck-Peng
supporting information, p. 3326 - 3330 (2016/07/23)
A direct and regiocontrolled thiolation method to access β-amino sulfides through the palladium-catalyzed C(sp2)–H functionalization of stable enamines was described. The reaction was realized under mild conditions by adding an external phosphi
First examples of 2,6-diarylnicotinaldehydes prepared under conventional and microwave conditions
Shankaraiah,Chandrasekhar,Siva Nagi Reddy,Sabitha, Gowravaram
, p. 842 - 846 (2015/03/04)
Enaminoketones undergo unexpected self condensation in acetic acid to produce a wide range of 2,3,6-trisubstituted pyridine derivatives in excellent yields in the presence of NH4OAc. This is the first Letter on the synthesis of 2,6-diarylnicoti
