1132-29-2Relevant academic research and scientific papers
Potent Synergy between Spirocyclic Pyrrolidinoindolinones and Fluconazole against Candida albicans
Premachandra, Ilandari Dewage Udara Anulal,Scott, Kevin A.,Shen, Chengtian,Wang, Fuqiang,Lane, Shelley,Liu, Haoping,Van Vranken, David L.
, p. 1672 - 1686 (2015/10/06)
A spiroindolinone, (1S,3R,3aR,6aS)-1-benzyl-6′-chloro-5-(4-fluorophenyl)-7′-methylspiro[1,2,3a,6a-tetrahydropyrrolo[3,4-c]pyrrole-3,3′-1H-indole]-2′,4,6-trione, was previously reported to enhance the antifungal effect of fluconazole against Candida albicans. A diastereomer of this compound was synthesized, along with various analogues. Many of the compounds were shown to enhance the antifungal effect of fluconazole against C. albicans, some with exquisite potency. One spirocyclic piperazine derivative, which we have named synazo-1, was found to enhance the effect of fluconazole with an EC50 value of 300 pM against a susceptible strain of C. albicans and going as low as 2 nM against some resistant strains. Synazo-1 exhibits true synergy with fluconazole, with an FIC index below 0.5 in the strains tested. Synazo-1 exhibited low toxicity in mammalian cells relative to the concentrations required for antifungal synergy. Synergy from stereochemical complexity: An attempt to synthesize analogues of a known spiroindolinone led to a series of diastereomers. One spiroindolinone, termed synazo-1, was shown to exhibit potent activity (300 pM) against C. albicans in the presence of fluconazole. Synazo-1 is a true synergizer and was also highly active against some drug-resistant C. albicans strains.
Structure-based design, synthesis, andanticonvulsant activity of isatin-1-N-phenylacetamide derivatives
Xie, Chao,Tang, Li-Ming,Li, Fu-Nan,Guan, Li-Ping,Pan, Cheng-Yan,Wang, Si-Hong
, p. 2161 - 2168 (2014/05/06)
In an effort to develop the potent anticonvulsant agents, a series of novel isatin-1-N-phenylacetamide derivatives was synthesized and screened for their in vivo anticonvulsant activity against maximal electroshock test and evaluated for their neurotoxicity by the rotarod test at the same dose levels. Ten compounds exhibited the anticonvulsant activity. 2-(5-Methyl-2,3-dioxoindolin-1- yl)-N-phenylacetamide (4b) was found to be the most potent compound of the series with an ED50 of 91.3 mg/kg, TD50 of >1,000 mg/kg, a higher protective index (PI = TD50/ED50, >11) was gained than the reference drug phenobarbital and carbamazepine. The essential structural features responsible for interaction with receptor site are established within a suggested pharmacophore. Springer Science+Business Media 2013.
Design, synthesis and antiproliferative activity evaluation of new 5-azaisoindigo derivatives
Zhao, Ping,Yan, Yun,Li, Yanzhong,Zhang, Aiying,Zhan, Xiaoping,Liu, Zenglu,Mao, Zhenmin,Chen, Shaoxiong,Wang, Liqun
, p. 1923 - 1932 (2014/08/18)
New 5-azaisoindigo derivatives were synthesized with two key intermediates 5-azaoxindole (7) and substituted indole-2,3-dione (10) in this paper. Intermediate 7 was prepared from 3-methylpyridine (1) through 6 steps containing oxidation reaction and so on. Intermediate 10 was obtained by a convenient Sandmeyer's method. The target compounds 5-azaisoindigo derivatives 11a-f were obtained by condensation of these two intermediates 7 and 10 in acidic condition. All target compounds were evaluated for their antiproliferative activity against seven cell lines by SRB assay. Compounds 11e and 11f showed significant antiproliferative activity against K562 cells (IC50: 8.9 μM and 13.6 μM, respectively).
Counter-current chromatography separation of isatin derivatives using the sandmeyer methodology
Almeida, Ma?rcia R.,Leita?o, Gilda G.,Silva, Ba?rbara V.,Barbosa, Jussara P.,Pintoa, Angelo C.
scheme or table, p. 764 - 769 (2010/08/13)
A rapid and efficient method, using high-speed counter-current chromatography (HSCCC) technique, was developed for the separation of isomeric isatin derivatives, prepared following the Sandmeyer route. The biphasic solvent system composed of hexane:ethyl acetate:ethanol:water 1:0.5:0.5:1 (v/v/v/v) was used for all separations.
Heterocyclic systems containing bridgehead nitrogen atom: Synthesis and bioactivity of 2,3-dihydro-4H-thiazino-as-triazinoindole and quinoxalinothiazoloindolo-as-triazine and their isomeric systems
Mohan, Jag,Kumar, Vineet
, p. 95 - 97 (2007/10/03)
2,3-Dihydro-7-methyl-5H-as-triazinoindole-3-thione 2 on condensation with 1,3-dibromopropane and 2,3-dichloroquinoxaline gives the cyclized products, 2,3-dihydro-9-methyl-4H-thiazino-as-triazinoindole 4 and 10-methylquinoxalinothiazoloindolo-as-triazine 6 respectively and not the angular isomers, 2,3-dihydro-9-methyl-1H-thiazino-as-triazinoindole 3 and 2-methylquinoxalinothiazoloindolo-as-triazine 5.The uniquivocal synthesis of the latter 3 and 5 have been accomplished by reaction of 6-methylisatin-3-thiosemicarbazone 1 with 1,3-dibromopropane and 2,3-dichloroquinoxalines, respectively.The antibacterial and antifungal activity of the synthesized compounds have also been evaluated.
Condensed bridgehead nitrogen heterocyclic systems: Synthesis and antimicrobial activity of thiazolo[3′,2′:2,3]-as-triazino[5,6-b]indoles and isomeric thiazolo[2′,3′:3,4]-as-triazino[5,6-b]indoles
Mohan, Jag,Kumar, Vineet
, p. 1030 - 1033 (2007/10/03)
2,3-Dihydro-7-methyl-5H-as-triazino[5,6-6]indole-3-thione 4 on condensation with α-haloketones gives 3-aroylmethylthio-7-methyl-5H-as-triazino[5,6-6]indole hydrobromides 5 which on PPA catalysed cyclisation furnishes 3-aryl-8-methylthiazolo[3′,2′:2,3]-as-
Biological activities and quantitative structure-activity relationships of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones as aldose reductase inhibitors
Yamagishi,Yamada,Ozaki,Asao,Shimizu,Suzuki,Matsumoto,Matsuoka,Matsumoto
, p. 2085 - 2094 (2007/10/02)
A series of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones were prepared and tested for aldose reductase inhibitory activity. The 6'- halogenated derivatives were found to be highly potent in vitro inhibitors of male rabbit lens aldose reductase and in vivo inhibitors of polyol accumulation in the sciatic nerves of galactosemic rats. Of these, (4R)-6'- chloro-3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione (67) showed the most potent in vitro and in vivo activities. An oral dose of 3 g/kg of compound 67 caused neither death nor behavioral abnormality in the preliminary acute toxicity study using mice and rats. Compound 67 was selected as a candidate for further evaluation. The quantitative structure- activity relationships in this series are also discussed.
The melosatins-a novel class of alkaloids from melochia tomentosa1 1 Part 13 in the series, Potential Carcinogens. For Part 12 see Ref. 2.
Kapadia,Shukla,Basak,Sokoloski,Fales
, p. 2441 - 2447 (2007/10/02)
Details of the isolation of malosatin A, B, and C and the synthesis of melosatin A are presented. Melosatin C has been characterized as 7-methoxy-4-(5-phenylpentyl)isatin. Several Me and OMe substituted isatins are synthesized as models and UV and mass sp
