FUROXAN类化合物作为NO供体在心血管作用方面的研究

Ｆｕｒｏｘａｎ即１，２，５－口恶二唑－２－氧化物，具有多种生物活性，近年来对其作为ＮＯ供体的研究较多。本文总结了Ｆｕｒｏｘａｎ类化合物在心血管系统作用方面的研究情况，并结合“ＭｅｄｉｃｉｎａｌＣｈｅｍｉｃａｌＨｙｂｒｉｄｉｚａｔｉｏｎ”方法的应用，列举了已合成的哌唑嗪的Ｆｕｒｏｘａｎ类似物和硝苯地平的Ｆｕｒｏｘａｎ类似物。简介了Ｆｕｒｏｘａｎ释放ＮＯ的机制及有关化合物的构效关系及生物活性。

Synthesis and biological evaluation of nitric oxide-releasing matrine derivatives as anticancer agents

A series of furoxan-based nitric oxide-releasing matrine derivatives(10a-f) were synthesized.The biological evaluation showed that compounds 10a,10b,10e and 10f had stronger cytotoxic activities than 5-fluorouracil against human hepatoma cells(HepG2) in vitro.

Solubility and metastable zone width measurement of 3,4-bis (3-nitrofurazan-4-yl) furoxan (DNTF) in ethanol + water

The solubility and supersolubility of 3,4-bis(3-nitrofurazan-4-yl)furoxan(DNTF) in ethanol + water at different operation were determined by laser monitoring system under atmospheric pressure to study the metastable zone width(MSZW). The modified Apelblat equation was adopted to correlate the experimental solubility data, and the correlation result showed perfect consistent with the experimental data. The standard dissolution enthalpy, standard dissolution entropy and Gibbs energy were calculated according to the experimental solubility data. The effect of the cooling rate, stirring rate, temperature and the concentration of ethanol + water on the MSZW was studied. It was found that the MSZW of DNTF increased with the increasing cooling rate, decreasing temperature, decreasing stirring rate and decreasing ratio of water. And the apparent nucleation order of DNTF in ethanol + water was calculated by the relationship between the cooling rate and the MSZW.

Synthesis and biological evaluation of nitric oxide-releasing sixalkoxyl biphenyl derivatives as anticancer agents

A series of novel nitric oxide-donating sixalkoxyl biphenyl derivatives （14a-1） were synthesized by coupling furoxan with alkoxyl biphenyl skeleton using amino acids as the spacers, and their cytotoxicity against HepG2 cells in vitro were evaluated by MTT method. It was found that 14c, 14d, 14f, 14i, 14j and 14k showed more potent cytotoxic activities than control 5-fluorouracil. NO release assay of target compounds indicated that the maximum amount of NO released by most active compounds 14c and 14j was about 6 × 10^-2 μmol/L, whereas 14a and 14h with very weak activity only released NO of 1 × 10^-2 μmol/L.

Synthesis and Crystal Structure of Methyl 12-Bromo-13,14-furoxan-deisopropyldehydroabietate

Methyl 12-bromo-13,14-furoxan-deisopropyldehydroabietate, C18H22BrN2O4, has been synthesized and characterized by IR,^1H NMR, ^13C NMR and single-crystal X-ray diffraction method. It crystallizes in orthorhombic, space group P212121 with a = 6.652（2）, b = 12.832（4）, c = 20.483（6）°A, V = 1748.5（9） °A^3, Z = 4, Mr = 410.29, D, = 1.559 g/cm^3, λ= 0.71070°A, μ（MoKα） = 2.377 mm^-1, F（000） = 844, the final R = 0.0243 and wR = 0.0533 for 3780 observed reflections with I〉 2σ（I）. The C-H and bromine atom are involved in intermolecular hydrogen bonds which link the molecules into a one-dimensional chain.

Recent advances on the nitrogen-rich 1,2,4-oxadiazole-azoles-based energetic materials

This review covers recent advances in the synthesis and energetic performance of nitrogen-rich 1,2,4-oxadiazole-azoles-based energetic materials.These materials comprise of 1,2,4-oxadiazole subunit as a key structural motif linked to different nitrogen-rich or nitrogen-oxygen azoles:tetrazole,furazan,furoxan,1,3,4-oxadiazole,pyrazole,and triazole.Particular attention is devoted to the introduction of various energetic groups including nitro,nitramino,azo,azoxy,dinitromethyl,trinitroethyl moieties,and their combination.The physicochemical and available performance parameters including density,decomposition temperature,heat of formation,detonation pressure,detonation velocity,impact sensitivity,and friction sensitivity of typical energetic compounds are also provided and analyzed.Eventually,it was obtained that several screened compounds exhibit superior detonation properties and outstanding insensitivities,which can be classified as a new family of high-performance energetic materials.Additionally,1,2,4-oxadiazole-azoles-based energetic materials still have many thorough works to further exploited and studied,expecting to get very promising insensitive high explosives for practical application and industrialization.

Synthesis and in vitro biological evaluation of nitric oxide-releasing derivatives of hydroxylcinnamic acids as anti-tumor agents

Novel furoxan-based nitric oxide-releasing derivatives 6a-p of hydroxylcinnamic acids were synthesized by coupling the carboxyl group of hydroxylcinnamic acids with furoxan through various alkylol amines.Compounds 6a,e-i and m-p displayed more potent anti-tumor activities superior to control 5-fluorouracil（5-FU） in most cancer cells tested.Furthermore,6f could selectively inhibit tumor cells,but not non-tumor cell proliferation.This inhibition was attributed to high levels of NO released in cancer cells and potentially synergistic effect of NO donor moieties and the bioactivity of hydroxylcinnamic acids.

Synthesis of new pyrimidine nucleoside derivatives with nitric oxide donors for antiviral activity

New pyrimidine nucleoside derivatives with nitric oxide（NO） donor were systematically synthesized.The antivirus activities of these nucleoside analogues against vesicular stomatitis virus（VSV） in Wish cell were evaluated.It was demonstrated that most of compounds had stronger antiviral acitivity than acyclovir,while their toxicities were similar or lower to acyclovir.

Study of Furoxan Derivatives for Energetic Applications

Two novel energetic compounds, 3,4-bis（1＇,2＇,4＇-triazole-3＇-yl）furoxan （BTAF） and 3,4-bis（1＇-nitro-l＇,2＇,4＇-tri- azole-3＇-yl）furoxan （BNTAF）, were prepared and their structures were characterized by IR, ^1H NMR, ^13C NMR, MS techniques and elemental analysis. The properties of BTAF and BNTAF were estimated. The predicted per- formance data of BTAF are as follows： density （measured） is 1.75 g/cm3, nitrogen content 50.9%, detonation veloc- ity 7277 m/s, detonation pressure 20.1 GPa and enthalpy of formation ＋419.7 kJ/mol. The predicted performance data of BNTAF are as follows： density is 1.84 g/cm3, nitrogen content 45.2%, enthalpy of formation ＋841.5 kJ/mol, detonation velocity 8490 rn/s and detonation pressure 32.4 GPa. The main themal properties of BTAF and BNTAF were analyzed by DSC and TG techniques, the results show that BTAF melts with concomitant decompo- sition at 188.8℃, the melting point of BNTAF is at 99.2 ℃ and its first decomposition temperature is 139.2 ℃.

Energetic materials based on poly furazan and furoxan structures

Furazan and furoxan represent fascinating explosophoric units with intriguing structures and unique properties.Compared with other nitrogen-rich heterocycles,most poly furazan and furoxan-based heterocycles demonstrate superior energetic performances due to the higher enthalpy of formation and density levels.A large variety of advanced energetic materials have been achieved based on the combination of furazan and furoxan moieties with different kinds of linkers and this review provides an overview of the development of energetic poly furazan and furoxan structures during the past decades,with their physical properties and detonation characteristics summarized and compa red with traditional energetic materials.Various synthetic strategies towards these compact energetic structures are highlighted by covering the most important cyclization methods for construction of the hetercyclic scaffolds and the following modifications such as nitrations and oxidations.Given the synthetic availabilities and outstanding properties,energetic materials based on poly furazan and furoxan structures are undoubtedly listed as a promising candidate for the development of new-generation explosives,propellants and pyrotechnics.

Synthesis and bioactivity of novel nitric oxide-releasing ursolic acid derivatives

A series of furoxan-based novel nitric oxide-donating ursolic acid（UA） derivatives（7a-f） were synthesized,and their cytotoxic activities against HepG2 cells in vitro were evaluated by MTT method.It was found that 7a-d and 7f showed more potent cytotoxic activities than control 5-fluorouracil and UA.