کد مقاله کد نشریه سال انتشار مقاله انگلیسی ترجمه فارسی نسخه تمام متن
5513042 1540975 2017 10 صفحه PDF سفارش دهید دانلود رایگان
عنوان انگلیسی مقاله ISI
Multicomponent access to androstano-arylpyrimidines under microwave conditions and evaluation of their anti-cancer activity in vitro
ترجمه فارسی عنوان
دسترسی چندگانه به اندروستا آریل پرییمیدین ها در شرایط مایکروویو و ارزیابی فعالیت ضد سرطان در آزمایشگاهی
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کلمات کلیدی
استروئیدها، واکنش های چندگانه، مایکروویو، پیریمیدین ها، ساختار-عملکرد رابطه، خاصیت سرطان پروستات،
موضوعات مرتبط
علوم زیستی و بیوفناوری بیوشیمی، ژنتیک و زیست شناسی مولکولی زیست شیمی
چکیده انگلیسی


- Microwave-assisted one-pot multicomponent reactions were carried out.
- Pyrimidine heteroring was introduced into rings D and A of the sterane nucleus.
- Acetylated ring A-fused 4′-arylpyrimidin-2′-ones exhibited exceptional cytotoxicity.
- Prostate cancer cell specific 2′-arylpyrimidines have been identified.

Novel ring D- and A-fused pyrimidines in the androstane series were efficiently synthesized within 10-15 min in polar protic solvents under microwave irradiation via two kinds of multicomponent heterocyclization reactions followed by spontaneous or promoted oxidation. The rates of the one-pot catalyst-free transformations of steroidal β-ketoaldehydes, ammonium acetate and substituted benzaldehydes in EtOH were found to be affected slightly by the steric and electronic feature of the substituents on the aromatic ring of the arylaldehyde component and the different reactivities of rings D and A of the sterane core. At the same time, the acid-catalyzed Biginelli-type reaction of dihydrotestosterone acetate, urea and arylaldehydes, and subsequent Jones oxidation of the primarily formed dihydropyrimidinones led to the corresponding ring A-fused 1H-pyrimidin-2-ones in moderate yields independently of the substituents on the aromatic moiety. The synthesized compounds were tested in vitro on human cancer cell lines as well as on non-cancerous fibroblast cells by the MTT assay in order to investigate their biological effects. As a result of the pharmacological screen, a remarkable structure-function relationship has been observed as the acetylated Biginelli products exhibited higher toxicity compared to the deacetylated version of each compound. Furthermore, in case of three 2′-arylpyrimidine derivatives a strong prostate cancer cell specific activity has been identified.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: The Journal of Steroid Biochemistry and Molecular Biology - Volume 172, September 2017, Pages 79-88
نویسندگان
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