106685-36-3

Upstream product

• 33626-98-1 methyl 6-bromo-2-naphthoate 
• 5773-80-8 6-bromo-2-naphthoic acid 
• 86471-14-9 ethyl 6-bromo-naphthalene-2-carboxylate 
• 1334137-88-0 C₂₁H₂₀O₄ 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 

Downstream Products

• 1334138-66-7 C₅₁H₅₈N₄O₁₁S₂ 
• 1334136-20-7 (11aS)-8-(3-(5-(4-(6-(3,4-dimethoxyphenyl)-2-naphthoyl)piperazine-1-carbonyl)-2-methoxyphenoxy)propoxy)-7-methoxy-2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(11aH)-one 
• 1334137-68-6 C₁₉H₁₅ClO₃ 
• 1334137-49-3 C₃₁H₃₀N₂O₆ 
• 1334136-43-4 C₃₄H₃₅BrN₂O₆ 

Relevant academic research and scientific papers

Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents

Abstract Eight 2-phenylnaphthalenoids (2PNs) (3a-h) and twenty four 2-phenylbenzofuranoids (2PBFs) (4a - 4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either TopoI or TopoIIα inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 μM against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoIIα inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoIIα inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoIIα. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoIIα inhibitors.

Synthesis of aryl-substituted naphthalene-linked pyrrolobenzodiazepine conjugates as potential anticancer agents with apoptosis-inducing ability

A library of new aryl-substituted naphthalene C8-linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates with various linker architectures were designed, synthesized, and evaluated for their anticancer activity against a panel of 11 human cancer cell lines. All 32 conjugates show anticancer potential, with some of them exhibiting particularly high activity (0.01-0.19μM). Thermal denaturation studies showed effective DNA binding capacity relative to DC-81. In assays for biological activity relating to cell-cycle distribution, these PBD conjugates induce G0/G1-phase arrest and also cause an increase in the levels of p53 and caspase-9 proteins, followed by apoptotic cell death. One conjugate in particular is the most promising candidate of the series, with the potential to be selected for further studies, either alone or in combination with existing anticancer therapies. Getting into the groove: Pyrrolobenzodiazepine (PBD) conjugates showed an effective ability to bind DNA. They induce G0/G1-phase arrest, enhance the expression levels of p53 and caspase-9, and induce apoptosis. One conjugate stands out as particularly promising; it is a suitable candidate for further study, either alone or in combination with current anticancer therapies.