Cytotoxic 1,3-Thiazole and 1,2,4-Thiadiazole Alkaloids from Penicillium oxalicum: Structural Elucidation and Total Synthesis.

نویسندگان

  • Zheng Yang
  • Nianyu Huang
  • Bang Xu
  • Wenfeng Huang
  • Tianpeng Xie
  • Fan Cheng
  • Kun Zou
چکیده

Two new thiazole and thiadiazole alkaloids, penicilliumthiamine A and B (2 and 3), were isolated from the culture broth of Penicillium oxalicum, a fungus found in Acrida cinerea. Their structures were elucidated mainly by spectroscopic analysis, total synthesis and X-ray crystallographic analysis. Biological evaluations indicated that compound 1, 3a and 3 exhibit potent cytotoxicity against different cancer cell lines through inhibiting the phosphorylation of AKT/PKB (Ser 473), one of important cancer drugs target.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Synthesis and Antimicrobial Activity of Some 2-[(4-Substituted-Phenyl-3-Chloro-Azetidin-2-One)-5-(2'-Methylamino-4-Phenyl-1', 3'-Thiazolyl-]-1, 3,4-Thiadiazoles

A new 2-[(4-substituted-phenyl-3-chloroazetidin-2-one)-5-(2'-methylamino 4-phenyl-1', 3'-thiazolyl-]-1, 3, 4-thiadiazoles, 5(a-n) were synthesized from 2-substituted-benzylideneamino-5-[2'-methylamino-4'-phenyl-1',3'-thiazolyl]-1,3, 4-thiadiazole, 4(a-n) using 2-amino-4phenyl-1, 3-thiazole as a starting material. The synthesised compounds have been screened in vitro for their antimicrobial acti...

متن کامل

Synthesis, Characterization and Molecular Docking of Novel Bioactive Thiazolyl-Thiazole Derivatives as Promising Cytotoxic Antitumor Drug.

Reactions of ethylidenethiocarbohydrazide with hydrazonoyl halides gave 1,3-thiazole or 1,3,4-thiadiazole derivatives according to the type of hydrazonoyl halides. Treatment of ethylidenethiosemicarbazide with hydrazonoyl halides and dimethylacetylene dicarboxylate (DMAD) afforded the corresponding arylazothiazoles and 1,3-thiazolidin-4-one derivatives, respectively. The structures of the synth...

متن کامل

Synthesis and docking study on thiadiazolo[3,2-a][1,3]diazepin-8(5H)-one derivatives as selective GABA(A) agonists

HIE-124 is a new member of ultra-short acting hypnotics’ drug family. In this research, the synthesis ofanalogues of HIE-124 drug in the heterocyclic thiazole ring replaced to thiadiazole, will be presented.Thiadiazolodiazepines during a two-step reaction starting from the amino thiadiazole resultedfrom-various derivatives of benzoic acid and thiosemicarbazide were synthesized. In the first ste...

متن کامل

Synthesis of the 1 , 2 , 4 - thiadiazole alkaloids polycarpathiamines A and B †

In the presence of 1 mol% of a copper(II) catalyst and air, a readily available N-acetyl-N-thioacylguanidine undergoes a one-pot benzylic oxidation–oxidative heterocyclization sequence to give the 3-amino5-acyl-1,2,4-thiadiazole core of polycarpathiamines A (2) and B (3) and thus facilitating the first synthesis of both natural products. This methodology offers a straightforward alternative to ...

متن کامل

Synthesis and Docking Study on Thiadiazolo[3,2-a][1,3]diazepin-8(5H)-one Derivatives as Selective GABAA agonists

HIE-124 is the new member of ultra-short acting hypnotics drug family. In this research, thiadiazole can act as the bio-isosteric replacement of thiazole in synthesized compounds as HIE-124 derivatives. HIE-124 drug, in which the heterocyclic thiazole ring replaced to thiadiazole, will be presented. Thiadiazolodiazepines were synthesized by a two-step reaction starting from the amino thiadiazol...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Molecules

دوره 21 3  شماره 

صفحات  -

تاریخ انتشار 2016