97339-24-7

Upstream product

• 504-29-0 2-aminopyridine 
• 64-17-5 ethanol 
• 18398-36-2 3,4-dichloro-[1,2]naphthoquinone 
• 5397-78-4 2-acetamido-3-chloro-1,4-naphthoquinone 
• 7248-75-1 NSC40344 
• 4105-21-9 2-phenylimidazo[1,2-a]pyridine 
• 119448-82-7 ethyl 2-phenylimidazo[1,2-a] pyridine-3-carboxylate 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 

Relevant academic research and scientific papers

Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine-5,6-diones: Synthesis, enzymatic reduction and cytotoxic activity

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.

Flavoenzyme-mediated reduction reactions and antitumor activity of nitrogen-containing tetracyclic ortho-quinone compounds and their nitrated derivatives

Nitrogen-based tetracyclic ortho-quinones (naphtho[1'2':4.5]imidazo[1,2-a]pyridine-5,6-diones, NPDOs) and their nitro-substituted derivatives (nitro-(P)NPDOs) were obtained by condensation of substituted 2,3-dichloro-1,4-naphthoquinones with 2-amino-pyridine and -pyrimidine and nitration at an elevated temperature. The structural features of the compounds as well as their global and regional electrophilic potency were characterized by means of DFT computation. The compounds were highly reactive substrates of single- and two-electron (hydride) - transferring P-450R (CPR; EC 1.6.2.4) and NQO-1 (DTD; EC 1.6.99.2), respectively, concomitantly producing reactive oxygen species. Their catalytic efficiency defined in terms of the apparent second-order rate constant (kcat/KM (Q)) values in P-450R- and NQO-1-mediated reactions varied in the range of 3-6 × 107 M-1 s-1 and 1.6-7.4 × 108 M-1 s-1, respectively. The cytotoxic activities of the compounds on tumor cell lines followed the concentration-dependent manner exhibiting relatively high cytotoxic potency against breast cancer MCF-7, with CL50 values of 0.08-2.02 μM L-1 and lower potency against lung cancer A-549 (CL50 = 0.28-7.66 μM L-1). 3-nitro-pyrimidino-NPDO quinone was the most active compound against MCF-7 with CL50 of 0.08 ± 0.01 μM L-1 (0.02 μg mL-1)) which was followed by 3-nitro-NPDO with CL50 of 0.12 ± 0.03 μM L-1 (0.035 μg mL-1)) and 0.28 ± 0.08 μM L-1 (0.08 μg mL-1) on A-549 and MCF-7 cells, respectively, while 1- and 4-nitro-quinoidals produced the least cytotoxic effects. Tumor cells quantified by AO/EB staining showed that the cell death induced by the compounds occurs primarily through apoptosis.

Synthesis method of naphtho[1', 2': 4, 5]imidazo[1, 2-a]pyridine-5, 6-diketone compound

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.

FeCl3-catalyzed C-3 functionalization of imidazo[1,2-a]pyridines with diazoacetonitrile under oxidant- and ligand-free conditions

A facile synthesis of 2-(imidazo[1,2-a]pyridin-3-yl)acetonitriles via FeCl3-catalyzed site-selective C(sp2)-H alkylation of imidazo[1,2-a]pyridines with diazoacetonitrile is presented. This new method features with an environmentally benign catalyst, easily obtainable substrates, and oxidant- and ligand-free reaction conditions. Moreover, the importance of the products thus obtained is showcased by their ready transformation into some synthetically and pharmaceutically interesting products with good efficiency.

Diazobenzo[a]fluorene derivatives as visible photosensitizers for free radical polymerization

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.

Mono-- or diketone tetracyclic derivatives and therapeutical uses thereof

Invention concerning the therapeutic use of tetracyclic derivatives and their pharmaceutically acceptable salts having the following general formula: STR1 in which, independently of the other: X is a carbon or nitrogen atom, T is a carbon or nitrogen atom, L is an oxygen atom or ketone functional protective group, R1 is an atom of hydrogen, an atom of halogen, or a C1 to C5 alkyl radical, R2 is a hydrogen atom, a halogen atom, a nitro radical, or a C1 to C5 alkyl radical, n and m are equal to 0 or to 1, but not independently of the other, so that if n is equal to 1, then m is equal to 0, and if n is equal to 0, then m is equal to 1.