157485-07-9Relevant academic research and scientific papers
Application of 1,4-Oxazinone Precursors to the Construction of Pyridine Derivatives by Tandem Intermolecular Cycloaddition/Cycloreversion
Carrillo Vallejo, Nicole A.,Scheerer, Jonathan R.
, p. 5863 - 5869 (2021/05/04)
This study reveals a new method for the preparation of 1,4-oxazinone derivatives by Staudinger reductive cyclization of functionalized vinyl azide precursors. The resulting oxazinone derivatives prepared in this manner were intercepted with terminal alkyne substrates through an intermolecular cycloaddition/cycloreversion sequence to afford polysubstituted pyridine products. Alkyne substrates bearing propargyl oxygen substitution showed good regioselectivity in the cycloaddition operation selectively affording 2,4,6-substituted pyridines. Application of this chemistry to the synthesis of an ErbB4 receptor inhibitor is also described.
Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer
Wang, Lei,Fang, Kun,Cheng, Junfei,Li, Yu,Huang, Yahui,Chen, Shuqiang,Dong, Guoqiang,Wu, Shanchao,Sheng, Chunquan
, p. 696 - 713 (2020/02/04)
Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.
Cyclic diamine compound with condensed-ring groups
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, (2008/06/13)
A cyclic diamine compound of formula (1): wherein R1 and R2 are individually a hydrogen atom or a methoxy group, provided R1 is a methoxy group when R2 is a hydrogen atom, or a hydrogen atom when R2 is a methoxy group; A is an oxygen atom, a sulfur atom, CH═CH, CH═N or NR3, in which R3 is a hydrogen atom, or a lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, aryl or aryl lower alkyl group; B is a nitrogen atom, CH or CR4, in which R4 is a hydrogen atom, or a lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, aryl or aryl lower alkyl group; m is 1 or 2; and n is a number of 1 to 5, an acid-addition salt thereof, or a hydrate thereof. The compound has inhibitory effects on cell adhesion and is useful for treatment of allergy, asthma, rheumatism, arteriosclerosis, and inflammation.
Synthetic Studies on Duocarmycin. 1. Total Synthesis of dl-Duocarmycin A and Its 2-Epimer
Fukuda, Yasumichi,Itoh, Yoshio,Nakatani, Kazuhiko,Terashima, Shiro
, p. 2793 - 2808 (2007/10/02)
The title synthesis was first achieved by employing novel methoxycarbonylation of the C4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2-carboxylate as key steps.In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A. - Key Words: dl-duocarmycin A, dl-2-epi-duocarmycin A, total synthesis, antitumor antibiotic, cytotoxicity
