کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1393334 1501203 2009 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Regioselective synthesis and stereochemical structure of anti-tumor active dispiro[3H-indole-3,2′-pyrrolidine-3′,3″-piperidine]-2(1H),4″-diones
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Regioselective synthesis and stereochemical structure of anti-tumor active dispiro[3H-indole-3,2′-pyrrolidine-3′,3″-piperidine]-2(1H),4″-diones
چکیده انگلیسی

Reaction of 3,5-bis(arylmethylene)-1-methyl-4-piperidinones 1a–1g with azomethine ylides (generated in situ via decarboxylative condensation of isatins 2a,2b with sarcosine 3) in refluxing ethanol afforded 4′-aryl-5″-(arylmethylene)-dispiro[3H-indole-3,2′-pyrrolidine-3′,3″-piperidine]-2(1H),4″-diones 4a–4m as the sole product in a high regioselective manner. Anti-tumor activity screening of 4e,4f,4k,4m, as representative examples of the synthesized compounds, at a dose of 10 μM utilizing 59 different human tumor cell lines representing leukemia, melanoma and cancers of the lung, colon, brain, ovary, breast, prostate and kidney exhibited that, the tested compounds reflect mild activity against most of the used human tumor cells. Meanwhile, all the tested compounds reveal considerable anti-tumor properties against colon (HCT-116), breast (T-47D), leukemia [HL-60 (TB), MOLT-4, RPMI-8226] and prostate (PC-3) cancers. Anti-inflammatory properties of the prepared compounds (at a dose of 50 mg/kg body weight) using in vivo acute carrageenan-induced paw oedema in rats exhibited that all the tested compounds possess considerable anti-inflammatory activity especially 4a,4k,4l which reveal remarkable activities with potency 125.5, 139.3 and 126.4, respectively, relative to indomethacin which was used as a reference standard (at a dose of 10 mg/kg body weight).

Regioselective synthesis and stereochemical structure of anti-tumor active dispiro[3H-indole-3,2′-pyrrolidine-3′,3″-piperidine]-2(1H),4″-diones.Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 44, Issue 3, March 2009, Pages 1257–1264
نویسندگان
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