52711-92-9Relevant articles and documents
Construction of the Tetracyclic Core Structure of Dysiherbols A-C
Fu, Shaomin,Ling, Cichang,Liu, Bo,Liu, Rong,Xia, Mengwei
supporting information, p. 1642 - 1646 (2022/03/14)
A synthetic study on the construction of the tetracyclic core structure of dysiherbols A-C is presented herein. In this synthesis, intramolecular [2 + 2] cycloaddition introduces a fused 6/4 ring system, followed by a Pd-catalyzed semipinacol rearrangement/Csp2-H arylation cascade to construct the ring C, and visible-light-mediated ring-opening of cyclopropyl silyl ether installs the tetracyclic core of dysiherbols.
Design, synthesis and evaluation of 2-amino-4-m-bromoanilino-6-arylmethyl- 7H-pyrrolo[2,3-d]pyrimidines as tyrosine kinase inhibitors and antiangiogenic agents
Gangjee, Aleem,Zhao, Ying,Raghavan, Sudhir,Ihnat, Michael A.,Disch, Bryan C.
experimental part, p. 5261 - 5273 (2010/09/11)
A series of 2-amino-4-m-bromoanilino-6-benzyl pyrrolo[2,3-d]pyrimidines analogues 4-12 were synthesized and evaluated as inhibitors of receptor tyrosine kinases (RTKs). These analogues were synthesized from the appropriate α-bromomethylbenzylketones via cyclocondensation with 2,6-diamino-4- pyrimidone to afford the 2-amino-4-oxo-6-substituted benzyl pyrrolo[2,3-d] pyrimidines. Chlorination at the 4-position followed by displacement with 3-bromoaniline or 3-bromo-N-methylaniline and methylation of the 7-NH afforded the target compounds. Remarkably, dimethylation of both the 4-N and N7 afford whole cell EGFR inhibitors that are more cytotoxic than clinically used erlotinib and mono-methylation at the 4-N or N7 affords more cytotoxic whole cell PDGFR-β inhibitors than clinically used sunitinib. Methylation at either the 4-N or N7 position was detrimental to whole cell VEGFR-2 inhibition. The inhibitory data against the RTKs in this study demonstrates that methylation of the 4-NH and/or the 7-NH influences both the specificity and potency of RTK inhibition.
Modulation of luminescence intensity of lanthanide complexes by photoinduced electron transfer and its application to a long-lived protease probe
Terai, Takuya,Kikuchi, Kazuya,Iwasawa, Shin-Ya,Kawabe, Takao,Hirata, Yasunobu,Urano, Yasuteru,Nagano, Tetsuo
, p. 6938 - 6946 (2007/10/03)
Luminescent lanthanide complexes (Tb3+, Eu3+, etc.) have excellent properties for biological applications, including extraordinarily long lifetimes and large Stokes shifts. However, there have been few reports of lanthanide-based functional probes, because of the difficulty in designing suitable complexes with a luminescent on/off switch. Here, we have synthesized a series of complexes which consist of three moieties: a lanthanide chelate, an antenna, and a luminescence off/on switch. The antenna is an aromatic ring which absorbs light and transmits its energy to the metal, and the switch is a benzene derivative with a different HOMO level. If the HOMO level is higher than a certain threshold, the complex emits no luminescence at all, which indicates that the lanthanide luminescence can be modulated by photoinduced electron transfer (PeT) from the switch to the sensitizer. This approach to control lanthanide luminescence makes possible the rational design of functional lanthanide complexes, in which the luminescence property is altered by a biological reaction. To exemplify the utility of our approach to the design of lanthanide complexes with a switch, we have developed a novel protease probe, which undergoes a significant change in luminescence intensity upon enzymatic cleavage of the substrate peptide. This probe, combined with time-resolved measurements, was confirmed in model experiments to be useful for the screening of inhibitors, as well as for clinical diagnosis.
