1131-80-2Relevant articles and documents
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)
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.
3-Formylpyrazolo[1,5- a]pyrimidines as Key Intermediates for the Preparation of Functional Fluorophores
Castillo, Juan-Carlos,Tigreros, Alexis,Portilla, Jaime
, p. 10887 - 10897 (2018)
A one-pot route for the regioselective synthesis of 3-formylpyrazolo[1,5-a]pyrimidines 4a-k in good yields through a microwave-assisted process is provided. The synthesis proceeds via a cyclocondensation reaction between β-enaminones 1 with NH-3-aminopyrazoles 2, followed by formylation with an iminium salt moiety (Vilsmeyer-Haack reagent). These N-heteroaryl aldehydes 4 were successfully used as strategic intermediates for the preparation of novel functional fluorophores with yields up to 98%. The structures of the products obtained and regioselectivity of the reactions were determined on the basis of NMR measurements and X-ray diffraction analysis. Since pyrazolo[1,5-a]pyrimidines (PPs) 3 have shown an important fluorescence, photophysical properties of four 2-methylderivatives substituted at position 7 with different acceptor (A) or donor (D) groups were investigated. The compounds evaluated exhibited large Stokes shift in different solvents, but only the substituted p-methoxyphenyl (4-An) showed a strong fluorescence intensity with quantum yields up to 44% due to its greater ICT. Therefore, hybrid systems based on pyrazolo[1,5-a]pyrimidines could be used as fluorescent probes to detect biologically or environmentally relevant species.
Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones
Festa, Alexey A.,Rybakov, Victor B.,Sokolova, Ekaterina A.,Subramani, Karthikeyan,Varlamov, Alexey V.,Voskressensky, Leonid G.,van der Eycken, Erik V.
, (2020)
Pyridinium ylides are well recognized as dipoles for cycloaddition reactions. In its turn, the microwave-assisted interaction of N-(cyanomethyl)-2-alkylpyridinium salts with enaminones unexpectedly proceeds as a domino sequence of cycloisomerization and cyclocondensation reactions, instead of a 1,3-dipolar cycloaddition. The reaction takes place in the presence of sodium acetate as base and employs benign solvents. The optical properties of the resulting pyrido[2,3-b]indolizines were studied, showing green light emission with high fluorescence quantum yields.
Simple approach to access tricyclic spiro dihydrofurans in a one-pot reaction
Bingi, Chiranjeevi,Kale, Ashok,Nanubolu, Jagadeesh Babu,Atmakur, Krishnaiah
, p. 1332 - 1339 (2017)
A simple and efficient one-pot protocol is accomplished to access tricyclic spiro dihydrofurans (4) by the reaction of β-enamino ketones (1) and dimedone (2) in ethanol followed by sequential addition of N-chlorosuccinimide at ambient temperature for the
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)
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.
Synthesis of Polyaromatic Rings: Rh(III)-Catalyzed [5 + 1] Annulation of Enaminones with Vinyl Esters through C-H Bond Functionalization
Liang, Gaohui,Rong, Jiaxin,Sun, Wangbin,Chen, Gengjia,Jiang, Yaojia,Loh, Teck-Peng
, (2018)
An expedient [5 + 1] annulation method via Rh(III)-catalyzed C-H bond functionalization of enaminones to synthesize polyaromatic rings is described. The reaction tolerates a broad range of functional groups and offers a new entry to construct polycyclic a
(Pd/C-mediated)coupling-iodocyclization-coupling strategy in discovery of novel PDE4 inhibitors: A new synthesis of pyrazolopyrimidines
Kumar, P. Mahesh,Kumar, K. Siva,Meda, Chandana L.T.,Reddy, G. Rajeshwar,Mohakhud, Pradeep K.,Mukkanti,Krishna, G. Rama,Reddy, C. Malla,Rambabu,Kumar, K. Shiva,Priya, K. Krishna,Chennubhotla, Keerthana Sarma,Banote, Rakesh Kumar,Kulkarni, Pushkar,Parsa, Kishore V.L.,Pal, Manojit
, p. 667 - 672 (2012)
Pyranones fused with a pyrazolopyrimidine moiety were prepared via regioselective construction of pyranone ring using (Pd/C-mediated)coupling- iodocyclization followed by Sonogashira/Heck/Suzuki reactions. The pyrazolopyrimidine based reactant required was obtained via a new H 3PO3 mediated condensation reaction. This strategy has led to the discovery of a novel and potentially safe PDE4 inhibitor.
A new approach for the synthesis of novel naphthoquinone chalcone hybrid compounds
Nguyen, Ha-Thanh,Dang Thi, Tuyet Anh,Hoang Thi, Phuong,Le-Nhat-Thuy, Giang,Nguyen Thi, Quynh Giang,Nguyen Tuan, Anh,Le Thi, Tu Anh,Van Nguyen, Tuyen
, (2021)
A facile and efficient synthesis of novel naphthoquinone-based chalcone hybrids (7 and 24) via the microwave-assisted one-pot three-component reactions of 2-substituted-1,4-naphthoquinones, N,N-dimethylformamide dimethyl acetal (DMF-DMA), and acetophenone derivatives has been reported. Whereas the synthesis of hybrids 7 proceeded via a condensation, 1,4-addition, rotation, elimination, and [1,3]-H shift sequence of steps, the synthesis of hybrids 24 were formed through a three-step sequence including condensation, 1,4-addition, and elimination reactions.
Sulfonamide/sulfamate switch with a series of piperazinylureido derivatives: Synthesis, kinetic and in silico evaluation as carbonic anhydrase isoforms I, II, IV, and IX inhibitors
Nocentini, Alessio,Moi, Davide,Deplano, Alessandro,Osman, Sameh M.,AlOthman, Zeid A.,Balboni, Gianfranco,Supuran, Claudiu T.,Onnis, Valentina
, (2020)
We report here a thorough structure-activity relationship (SAR) with piperazinylureido sulfamates as inhibitors of human (h) carbonic anhydrase (CA, EC 4.2.1.1). A SAR investigation over the structure of reported anti-cancer zinc-binder CAIs such as SLC-0
Rhodium-catalyzed C–H activation/cyclization of enaminones with sulfoxonium ylides toward polysubstituted naphthalenes
Wang, Zhenlian,Xu, Huang
, p. 664 - 667 (2019)
A rhodium-catalyzed ortho-C–H functionalization and annulation between enaminones and sulfoxonium ylides was developed, affording a series of multi-substituted naphthalenes in good to moderate yields with excellent functional group compatibility. The proc
