A convenient synthesis of new pyrido[3,2-e][1,4]diazepine-2,5-diones and pyrido[2,3-e][1,4]diazepine-2,5-diones

A convenient synthesis of a series of pyrido[3,2-e][1,4]-diazepine-2,5-diones 8 and pyrido[2,3-e][1,4]diazepine-2,5-diones 9, is reported using the condensation of α-amino acid methyl ester derivatives with 1H-pyrido[3,2-d][1,3]oxazine-2,4-dione and 1H-pyrido[2,3-d][1,3]oxazine-2,4-dione. Compounds 8 and 9 were also synthesized by peptide coupling of α-amino acid methyl ester derivatives with β-amino acids (2 or 3) followed by the cyclisation in tetrahydrofuran with sodium hydride (NaH).     

Eco-friendly synthesis of gold nanoparticles using fruit extracts and in vitro anticancer studies

Gold nanoparticles are biocompatible and are having several applications in biomedical Sciences and Engineering. Integration of nanoscience in medicine leads to the development of biomedical products that helps the Society in a faster and safer manner. In the present research work, bioreduction and biofunctionalization of gold nanoparticles are performed with fruit extracts of Aegle marmelos, Eugenia jambolana and soursop. The nanoparticles are characterized using UV–Vis spectroscopy, Transmission Electron Microscopy, Fourier Transform Infrared Spectroscopy and Zeta potentiometer. The qualitative phytochemical analysis of the fruit extracts shows the presence of alkaloids, amino acid, flavonoids, phenol, proteins, tannin, reducing sugars and total Sugars. The in vitro anticancer activity was confirmed by MTT assay on the human breast cancer cell line MCF-7 at different concentrations. The flavonoids present in the fruit extracts are potential reducing agent which is responsible for the formation of gold nanoparticles. Stabilization of gold nanoparticles are performed by the carboxylate group present in the proteins. Also, the nanoparticles are held apart from each other by the electrostatic repulsions that exist due to the presence of like charges surrounding the gold nanoparticles. This study proves that the fruit extracts can be used for the synthesis and stabilization of gold nanoparticles. Further, the engineered nanoparticles capped with bioactive compounds are potential anticancer agents against breast cancer cell line MCF-7.     

An efficient synthesis of new thiazolidin-4-one fused s-triazines as potential antimicrobial and anticancer agents

As a part of our endeavor toward the synthesis of new heterocyclic bioactive agents, two series of thiazolidin-4-one fused s-triazines were synthesized by applying an efficient palladium catalyzed C–C Suzuki coupling using catalyst system Pd(OAC)₂, Xphos and K₃PO₄ as a base in toluene solvent. Moreover, the synthesized analogs were further screened for their in vitro antimicrobial as well as anticancer efficacy against prostate cancer PC3 cells. Some compounds displayed remarkable antimicrobial activity and noticeable anticancer activity. It was observed that, both benzonitrile and nicotinonitrile are essential to increase the different pharmacological activities. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and MS analysis.     

A domino protocol for the efficient synthesis of structurally diverse benzothiazolylquinoline-2,5-diones and their spiro analogues

Structurally diverse benzothiazolylquinoline-2,5-diones and their spiro analogues have been synthesized by an environmentally benign efficient and convenient synthetic method involving sulfamic acid catalyzed one-pot four-component reaction of Meldrum acid, 2-aminobenzothiazoles, dimedone, and isatin/carbonyl compound.     

A multi-component synthesis of 3-aryl-1-(arylmethylideneamino)pyrrolidine-2,5-diones

A multi-component synthesis of 3-aryl-1-(arylmethylideneamino)pyrrolidine-2,5-diones is described. A mixture of N-isocyaniminotriphenylphosphorane, an aldehyde, and Meldrum's acid undergo a 1:2:1 addition reaction under mild conditions to afford the title compounds in good to excellent yields.     

Highly regioselective C4-hydrazinylation of 2,4-dichloroquinolines: expedient synthesis of aminoquinoline substituted pyrrolidin-2,5-diones via hydrazinylquinolines

A new class of hydrazinylquinoline regio-isomers has been synthesized through S_NAr reaction of 2,4-dichloroquinolines with hydrazine hydrate. The reaction stops at the mono-substitution product with high regioselectivity at the C₄ rather than C₂ position of dichloroquinolines. The hydrazinylquinolines were subsequently converted into aminoquinoline substituted pyrrolidin-2,5-diones in the presence of Eaton’s reagent.     

An efficient synthesis of cyclic urethanes from Boc-protected amino acids through a metal triflate-catalyzed intramolecular diazocarbonyl insertion reaction

A simple and efficient synthesis of cyclic urethanes and related oxazinanones 1a-l from diazoketones 3a-l is described. The transformation involves generation of carbenes by activation of diazo groups using metal triflates in intramolecular diazocarbonyl insertion reactions in high overall yields.     

Synthesis and in vitro antitumor activity of substituted anthracene-1,4-diones

Based on a rational approach, 6-substituted 1,4-anthracenediones were synthesized and found to exhibit potent cytotoxic activity against murine and human leukemic cells. The synthetic sequence includes a double Friedel-Crafts reaction, reductive quinone formation, and selective bromination of the alkyl side chain. A key intermediate, 6-bromomethyl-1,4-anthracenedione (10), was synthesized and converted to various active antitumor agents, including a water-soluble phosphate ester pro-drug. The interconversion reactions include displacement of the bromide with various nucleophiles and basic hydrolysis to the alcohol and subsequent oxidation to provide the aldehyde. Based on their ability to decrease L1210 and HL-60 tumor cell viability, 1,4-dihydroxyanthraquinones are inactive but 1,4-anthracenediones have interesting antitumor activity, which may be abolished by modification of the A-ring and improved by substitution of the C-ring. The cytostatic and cytotoxic activity of the representative compound 10 was verified at the National Cancer Institute in studies on the 60-human tumor cell line panel in the in vitro antitumor screening. A wide spectrum of tumor cells are sensitive to 10 inhibition, and concentrations required to inhibit tumor cell growth by 50% (GI₅₀) at 48 h are <10 nM in HL-60 and MOLT-4 and 37.1 nM in SR leukemia. Preliminary studies suggest that the molecular targets and mechanisms of action of 10 may be different from those of daunomycin.     

Metal-free multicomponent synthesis and in vitro antioxidant activity of indolylpyrazolopyrimidines

Multisubstituted indolylpyrazolopyrimidines were synthesized in good yields with base promoted one-pot multicomponent system from aldehyde, ketone, and indolylpyrazolamine. Milder and cost-effective conditions are the highlights of the present protocol. Among the synthesized compounds ( 4a-j ) 4b , 4c , 4e , and 4f have shown significant better in vitro antioxidant activity compared to standard ascorbic acid.     

Eco-friendly synthesis of 1,4-benzodiazepine-2,5-diones in the ionic liquid [<Emphasis Type="Italic">bmim</Emphasis>]Br

The green reaction of isatoic anhydrides with α-amino acids in presence of the ionic liquid 1-butyl-3-methylimidazolium bromide afforded 1,4-benzodiazepine-2,5-diones in excellent yields in absence of a catalyst. The reaction workup is simple and the ionic liquid was easily recovered from the reaction and reused. The methodology was quite general and a range of cyclic and acyclic α-amino acids were examined to produce 1,4-benzodiazepine-2,5-diones. Correspondence: Khosrow Jadidi, Department of Chemistry, Shahid Beheshti University, PO Box 1983963113, Tehran, Iran.     

A Simple Approach to the Synthesis of 1,4-Bis(arylsulfonyl)tetrahydropyrazine-2,5-diones

Summary.  The addition of triphenylphosphine to dimethyl acetylenedicarboxylate in the presence of arylsulfonylglycyl chlorides leads to 1,4-bis-arylsulfonyl-tetrahydropyrazine-2,5-diones and dimethyl (E)-2-chloro-2-butenedioate. Corresponding author. E-mail: isayavar@yahoo.com Received June 3, 2002; accepted June 10, 2002     

Novel efficient anticancer agents and DNA-intercalators of 1,2,3-triazol-1,8-naphthalimides: design, synthesis, and biological activity

Two novel series of 3-1,2,3-triazol-1,8-naphthalimides 5a-e, 7a-e were synthesized easily by employing ‘click reaction’. Their bioactivities were evaluated. Compounds 5a-e were found to be more toxic against MCF-7 cells while 7a-e were more potent against 7721 cells, in particular 7a, the IC₅₀ value of which against cell lines of MCF-7 and 7721 was 0.348 μM and 0.258 μM, respectively. Due to the phenyl group linked to 1,2,3-triazole, compound 5a not only showed higher DNA affinity but also more efficient DNA damaging ability than compound 7a.     

A mild and efficient method for the synthesis of 2,5-dihydro-5-imino-2-methylfuran-3,4-dicarboxylates via an isocyanide-based multicomponent reaction

The zwitterion formed from an alkyl or aryl isocyanide and dialkyl acetylenedicarboxylate reacts with acetic anhydride or phthalic anhydride to form 2,5-dihydro-5-imino-2-methylfuran-3,4-dicarboxylates or benzo-fused spirolactones in relatively good yields at room temperature without using a catalyst.     

Synthesis of 1-alkyl-3-arylamino-pyrrole-2,5-diones

Reaction of 1-alkyl-3-alkylaminopyrrole-2,5-diones with primary arylamine hydrochlorides in methanol or DMSO gives 1-alkyl-3-arylaminopyrrole-2,5-diones which could also be obtained from the reaction of arylaminofumarates with primary aliphatic amines. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1001–1007, July, 2007.     

Simple,rapid, and clean condensation of sulfonamide and maleic anhydride derivatives: Synthesis of novel 1H- Pyrrole-2,5-diones under heterogeneous conditions

H₆P₂W₁₈O₆₂ is used as an efficient catalyst for the synthesis of novel N-substituted sulfonyl maleimides (1H-Pyrrole-2,5-diones) via the condensation of sulfonamide and maleic anhydride derivatives. The Dawson heteropolyacid was used with a catalytic amount of 2 mmol% in acetonitrile at reflux. The reuse of H₆P₂W₁₈O₆₂ as heterogeneous catalyst several times without decrease in their activity, short reaction times, easy isolation of desired products with good to excellent yields shows the advantages of this novel methodology.     

Total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine

<正>All stereoisomers of asperphenamate 1a and patriscabratine 2a were achieved with a high yield,and total synthesis of 2a is firstly described here.The absolute configuration of patriscabratine was determined as(S,S).The compounds 1a-d and 2a-d have been tested by MTT assay in T47D,MDA-MB231,HL60,Hela and SGC-7901 cell lines in vitro.Among them,the(R,S) stereoisomer shows the strongest anticancer effects,while the(S,R) shows the weakest one.     

2-Aminopyrrole-2,5-diones 2. Vinyl nucleophilic substitution of the alkylamino group in 1-alkyl-3-alkylaminopyrrole-2,5-diones by arylamines

In vinyl nucleophilic substitution (S_N vin) with the hydrochlorides or 4-toluenesulfonates of primary arylamines 1-alkyl-3-alkylaminopyrrole-2,5-diones form the corresponding 1-alkyl-3-arylaminopyrrole-2,5-diones, which are also produced in situ from the corresponding arylaminofumarates and primary alkylamines. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 668–675, May, 2008.     

An efficient one-pot solvent-free synthesis and photophysical properties of 9-aryl/alkyl-octahydroxanthene-1,8-diones

A facile and efficient protocol for the synthesis of 9-aryl/alkyl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydroxanthene-1,8-diones has been developed by one-pot reaction of dimedone with aldehydes in the presence of InCl₃ or P₂O₅ under solvent-free conditions. The optical behaviors of the xanthenediones have been investigated by UV-vis and fluorescence spectroscopy. The present approach offers the advantages of simple methodology, clean and mild reaction, high atom-economy, short reaction time, low environmental impact, wide substrate scope, high yield, and excellent purity.     

One-pot synthesis, antibacterial and antifungal activities of novel 2,5-disubstituted-1,3,4-oxadiazoles

A series of novel 2,5-disubstituted-1,3,4-oxadiazoles have been synthesized from long-chain alkanoic and alkenoic acids. The structures of these compounds have been elucidated by elemental and spectral （IR, ^1H NMR, ^13C NMR, MS） analysis. Furthermore, compounds were screened for in vitro antibacterial activity against the representative panel of two Gram-positive and two Gram- negative bacteria. All the synthesized compounds were also tested for their inhibitory action against five strains of fungus. The various compounds show potent inhibitory action against test organisms. 2007 Abdul Rauf. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.     

Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives

<正>Solasodine 11 is a steroidal alkaloid with various biological activities.Herein,8 novel solasodine derivatives were synthesized and their effect on prostate cancer cell proliferation was assessed in vitro.Significant improvement in antiproliferative activity was achieved among some of the synthetic analogs.In particular,19 exhibited the most potent inhibitory effect against the proliferation of PC-3 cell line(IC_(50) = 3.91μmol/L).