27109-47-3Relevant articles and documents
Identification and synthesis of three cyclodidepsipeptides as potential precursors of enniatin B in Fusarium sporotrichioides
Smelcerovic, Andrija,Yancheva, Denitsa,Cherneva, Emiliya,Petronijevic, Zivomir,Lamshoeft, Marc,Herebian, Diran
, p. 397 - 402 (2011)
A pathogenic fungus, Fusarium sporotrichioides Sherb., was isolated from Hypericum barbatum Jacq. The volatile compounds of broth and mycelium were analyzed using GC-MS and three cyclodidepsipeptides (dioxomorpholines), 3,6-di(propan-2-yl)-4-methyl-morpholine-2,5-dione, 3-(2-methylpropyl)-6-(propan- 2-yl)-4-methyl-morpholine-2,5-dione and 3-(butan-2-yl)-6-(propan-2-yl)-4-methyl- morpholine-2,5-dione, were found for the first time in the natural products. The structures of the compounds were confirmed by comparison of the analytical data for the natural products with samples obtained via synthetic methods. The conformational features and vibrational spectra of the three cyclodidepsipeptides were characterized by density functional theory (DFT) calculations and IR spectroscopy. The cyclic hexadepsipeptide enniatin B was identified by a LC-MS/MS analysis of the non-volatile products of broth and mycelium. The above-mentioned three cyclodidepsipeptides are probably synthesized using similar biosynthetic ways to enniatin B involving a nonribosomal mechanism.
Benzoxazinone-containing 3,5-dimethylisoxazole derivatives as BET bromodomain inhibitors for treatment of castration-resistant prostate cancer
Xue, Xiaoqian,Zhang, Yan,Wang, Chao,Zhang, Maofeng,Xiang, Qiuping,Wang, Junjian,Wang, Anhui,Li, Chenchang,Zhang, Cheng,Zou, Lingjiao,Wang, Rui,Wu, Shuang,Lu, Yongzhi,Chen, Hongwu,Ding, Ke,Li, Guohui,Xu, Yong
, p. 542 - 559 (2018/05/24)
The bromodomain and extra-terminal proteins (BET) have emerged as promising therapeutic targets for the treatment of castration-resistant prostate cancer (CRPC). We report the design, synthesis and evaluation of a new series of benzoxazinone-containing 3,5-dimethylisoxazole derivatives as selective BET inhibitors. One of the new compounds, (R)-12 (Y02234), binds to BRD4(1) with a Kd value of 110 nM and blocks bromodomain and acetyl lysine interactions with an IC50 value of 100 nM. It also exhibits selectivity for BET over non-BET bromodomain proteins and demonstrates reasonable anti-proliferation and colony formation inhibition effect in prostate cancer cell lines such as 22Rv1 and C4-2B. The BRD4 inhibitor (R)-12 also significantly suppresses the expression of ERG, Myc and AR target gene PSA at the mRNA level in prostate cancer cells. Treatment with (R)-12 significantly suppresses the tumor growth of prostate cancer (TGI = 70%) in a 22Rv1-derived xenograft model. These data suggest that compound (R)-12 is a promising lead compound for the development of a new class of therapeutics for the treatment of CRPC.
Enantioselective synthesis of quaternary α-amino acids via l -tert-leucine-derived squaramide-catalyzed conjugate addition of α-nitrocarboxylates to enones
Bera, Kalisankar,Satam, Nishikant S.,Namboothiri, Irishi N. N.
, p. 5670 - 5680 (2016/07/14)
Enantioselective Michael addition of tertiary α-nitroesters to β-unsubstituted vinyl ketones has been carried out in the presence of an l-tert-leucine-derived squaramide as organocatalyst. The products, quaternary α-nitroesters, were formed in excellent yield and moderate to good ee's in most cases. Scale-up of the reaction and synthetic applications of the products, including transformation to representative quaternary α-amino acids, have also been demonstrated.
