29366-41-4Relevant academic research and scientific papers
Chemistry of naphthazarin derivatives 13. Conformational analysis of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones by quantum chemistry methods
Glazunov,Berdyshev,Yakubovskaya,Pokhilo
, p. 1729 - 1736 (2006)
The molecular structures of various conformers of 2-hydroxy-1,4- naphthoquinone; 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones; 2,5,8-trihydroxy-1,4-naphthoquinone; and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4- naphthoquinones were studied by density functional theory (B3LYP/6-31(d), B3LYP/6-31(d, p)) and ab initio (MP2/6-31G, MP2/6-31(d)) methods. The strengths of the intramolecular hydrogen bonds formed by the β-hydroxy group with the O atom at C(1) and with the double bond π-electrons of the alkenyl substituents in the quinonoid rings were estimated. The compounds studied mainly exist as rotamers with the former-type hydrogen bonds. The splitting of the quinonoid bands of the stretching vibrations of the β-hydroxy group in the IR spectra of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4-naphthoquinones in hexane solutions is due to the existence of rotamers formed upon internal rotation of the alkenyl substituent.
Discovery of a Napabucasin PROTAC as an Effective Degrader of the E3 Ligase ZFP91
Hanafi, Maha,Chen, Xinde,Neamati, Nouri
supporting information, p. 1626 - 1648 (2021/02/27)
Napabucasin, undergoing multiple clinical trials, was reported to inhibit the signal transducer and transcription factor 3 (STAT3). To better elucidate its mechanism of action, we designed a napabucasin-based proteolysis targeting chimera (PROTAC), XD2-149 that resulted in inhibition of STAT3 signaling in pancreatic cancer cell lines without inducing proteasome-dependent degradation of STAT3. Proteomics analysis of XD2-149 revealed the downregulation of the E3 ubiquitin-protein ligase ZFP91. XD2-149 degrades ZFP91 with DC50 values in the nanomolar range. The cytotoxicity of XD2-149 was significantly, but not fully, reduced with ZFP91 knockdown providing evidence for its multi-targeted mechanism of action. The NQO1 inhibitor, dicoumarol, rescued the cytotoxicity of XD2-149 but not ZFP91 degradation, suggesting that the NQO1-induced cell death is independent of ZFP91. ZFP91 plays a role in tumorigenesis and is involved in multiple oncogenic pathways including NF-κB and HIF-1α.
Synthesis and cytotoxicity evaluation of a series of 3-alkenyl-2-hydroxy-1,4-naphthoquinones obtained by an efficient knoevenagel condensation
David, Cibelle C.,Lins, Antonio C.S.,Silva, Tania M.S.,Campos, Júlia F.,Silva, Teresinha G.,Milit?o, Gardenia C.G.,Camara, Celso A.
, p. 8 - 18 (2018/12/13)
A modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobuty
A Complete and Unambiguous 1H and 13C NMR Signals Assignment of para?Naphthoquinones, ortho- And para-Furanonaphthoquinones
Borgati, Tatiane F.,de Souza Filho, José D.,de Oliveira, Alaíde B.
, p. 1138 - 1149 (2019/08/26)
A complete and unambiguous assignment of 1H and 13C nuclear magnetic resonance (NMR) signals of 29 naphthoquinones is reported on the basis of one- and two-dimensional NMR techniques (1H, 13C, 1H-sup
