97339-24-7Relevant articles and documents
Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine-5,6-diones: Synthesis, enzymatic reduction and cytotoxic activity
?arlauskas, Jonas,Pe?iukaityte-Alksne, Milda,Misevi?iene, Lina,Maroziene, Audrone,Polmickaite, Evelina,Staniulyte, Zita,?enas, Narimantas,Anusevi?ius, ?ilvinas
, p. 512 - 517 (2016)
Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine-5,6-diones (NPDOs), a new type of N-heterocycle-fused o-quinones, have been synthesized. They have been found to be efficient electron-accepting substrates of NADPH-dependent single-electron-transferring P-450R and two-electron transferring NQO1, generating reactive oxygen species (ROS) with a concomitant decrease in NADPH, which is consistent with redox-cycling. The reactivity of NPDOs toward P-450R (in terms of kcat/Km) varied in the range of 106-107 M-1 s-1, while their reduction by NQO1 proceeded much faster, approaching the diffusion control limit (kcat/Km ～ 108-109 M-1 s-1). NPDOs exhibited relatively high cytotoxic activity against human lung carcinoma (A-549) and breast tumor (MCF-7) cell lines (LC50 = 0.1-8.3 μM), while promyelocytic leukemia cells (HL-60) were less sensitive to NPDOs (LC50 ≥ 10 μM). 3-Nitro-substituted NPDO (11) revealed the highest potency against both A-549 and MCF-7 cell lines, with LC50 of 0.12 ± 0.03 μM and 0.28 ± 0.08 μM, respectively. Dicoumarol partly suppressed the activity of the compounds against A-594 and MCF-7 cell lines, suggesting that their cytotoxic action might be partially influenced by NQO1-mediated bioreductive activation.
Synthesis method of naphtho[1', 2': 4, 5]imidazo[1, 2-a]pyridine-5, 6-diketone compound
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Paragraph 0115-0119, (2020/07/02)
The invention discloses a synthetic method of a naphtho[1', 2': 4, 5]imidazo[1, 2-a]pyridine-5, 6-diketone compound, which belongs to the technical field of organic chemistry. The synthesis method comprises the following steps: taking 2-aryl imidazo[1, 2-a] pyridine compound and diazonium acetonitrile as raw materials; synthesizing a 3-cyanomethylated imidazo[1, 2-a]pyridine compound 3 in the presence of a catalyst, reacting the compound 3 with an alcohol under the action of an acid to obtain an imidazo [1, 2-a] pyridine-3-acetate compound 4, and finally heating PPA to condense into a ring andsimutanously forms naphtho[1', 2': 4, 5]imidazo[1, 2-a]pyridine-5,6-dione 5. The whole process of the method is carried out in the air, the used catalysts are common catalysts, the method is low in cost and environmentally friendly, the raw materials are easy to obtain, and a new synthesis path is provided for the compounds.
Diazobenzo[a]fluorene derivatives as visible photosensitizers for free radical polymerization
Podemska, Karolina,Podsiad?y, Rados?aw,Szymczak, Agnieszka Marzena,Soko?owska, Jolanta
experimental part, p. 113 - 119 (2012/04/04)
Several benzophenazine dyes containing a diazobenzo[a]fluorene moiety have been synthesized and characterized by 1H NMR spectroscopy and mass spectrometry (CI MS). The spectroscopic and electrochemical properties of these dyes were examined. These compounds were evaluated as potential light absorbing chromophores for free radical polymerization. The results are discussed on the basis of the free energy change for electron transfer from the diazobenzo[a]fluorene dyes to the electron donors/acceptors. The kinetic studies of the photoinitiated polymerization of trimethylolpropane triacrylate (TMPTA) using electron donors, such as phenylthioacetic acid, phenoxyacetic acid, N-phenylglycine and ethyl 4-N,N-dimethylaminobenzoate, and electron acceptors, such as 1-methoxy-4-phenylpyridinium tetrafluoroborate and 1-ethoxy-2- methylpyridinium hexafluorophosphate, have shown that these dyes are efficient photoinitiators for free radical polymerization in visible light. The heavy atoms present in the chemical structure may lead to excited triplet states within the dye facilitating electron transfer from these states.
