四川轮环藤根中两种海岛轮环藤-N-氧化物的分离鉴定

从中国特有植物四川轮环藤(Cyclea sutchuenensis Gagnep.)根中分得两种海岛轮环藤碱-N-氧化物。采用波谱分析和化学方法鉴定, 证明分别为海岛轮环藤碱-2β-N-氧化物(3)和海岛轮环藤碱-2'β-N-氧化物(4)。二者均为新生物碱, 是首尾氧桥双苄基异喹啉生物碱-N-氧化物。从该植物根中还分得已知的海岛轮环藤碱(1)和海岛轮环藤酚碱(2)。本文首次详细报道并分析了2的1^H NMR和13^C NMR数据。经三种人癌细胞实验, 证明2具有显著的抗癌活性。     

四川轮环藤根中两种海岛轮环藤-N-氧化物的分离鉴定

从中国特有植物四川轮环藤(Cyclea sutchuenensis Gagnep.)根中分得两种海岛轮环藤碱-N-氧化物。采用波谱分析和化学方法鉴定, 证明分别为海岛轮环藤碱-2β-N-氧化物(3)和海岛轮环藤碱-2'β-N-氧化物(4)。二者均为新生物碱, 是首尾氧桥双苄基异喹啉生物碱-N-氧化物。从该植物根中还分得已知的海岛轮环藤碱(1)和海岛轮环藤酚碱(2)。本文首次详细报道并分析了2的1^H NMR和13^C NMR数据。经三种人癌细胞实验, 证明2具有显著的抗癌活性。     

由藜芦醛合成娃儿藤碱

以藜芦醛(1)、3,4-二甲氧基苯乙酸(2)、(S)-L-脯氨酸(6)等为原料,经8步反应,合成了一种抗肿瘤活性(s)-( )-娃儿藤碱。先由化合物1和2在乙酸酐/三乙胺催化下反应得到3,4-二甲氧基一反式-α-(3′, 4′-二甲氧基苯基)．肉桂酸(3),在0℃、三氟乙酸存在下用VOF_3对其关环成2,3,6,7-四甲氧基-9-羧基菲(4),然后用喹啉作介质,在230℃、无水CuSO_4催化下脱去羧基,得到2,3,6,7-四甲氧基菲(5),再和(S)-N- (三氟乙酰)-L-脯氨酰氯(6b)傅-克反应得到(S)-N-(三氟乙酰基)-2,3,6,7-四甲氧基-9-L-脯氨酰基菲(7),并对产物进行了柱纯化,所得产物在三氟化硼乙醚存在下用三乙基硅烷还原羰基,然后脱去三氟乙酰保护基,最后在盐酸存在下用甲醛闭环得到目标产物(10)。用NMR和MS表征了中间体和目标产物的结构。该合成反应条件温和,总收率为3．5％,产品纯度98．5％(HPLC)。     

菲并吲哚里西啶生物碱及其盐类衍生物的抗病毒活性和构效关系研究

本文研究了菲并吲哚里西啶生物碱1~17和(S)-6-O-脱甲基安托芬的盐类衍生物18~31对烟草花叶病毒的抗病毒活性和构效关系.发现其中部分化合物表现出很高的体内和体外抗病毒活性,尤其是(R)-6-O-脱甲基安托芬(14)和(S)-6-O-脱甲基安托芬氢碘酸盐(18)表现出了比商品化抗病毒剂宁南霉素更高的抗病毒活性,可以作为潜在的抗植物病毒剂.     

利用自由基反应合成（S）-（＋）-娃儿藤碱及其类似物

通过自由基反应,成功的合成了（S）-（＋）-娃儿藤碱（1）及其类似物．以2,3,6,7．四甲氧基菲甲酸为原料通过两或三步分别制得（-）-N-（2,3,6,7,四甲氧基-9-菲苄基）．2．溴甲基四氢吡咯（7）和（-）-N-（2,3,6,7-四甲氧基-9-菲甲酰基）-2-溴甲基四氢吡咯（9）．在催化量的偶氮二异丁腈参与下,溴化物（7）与三正丁基氢化锡反应没有得到预期的产物（S）-（＋）-娃儿藤碱,却以较高的收率得到N-（2,3,6,7-四甲氧基-9-菲苄基）哌啶（2）.通过分析机理,改用溴化物（9）为底物在同样的条件下分别以33．6％和65％的收率制得（S）-（＋）-9-娃儿藤酮（10）和（-）-N-（2,3,6,7-四甲氧基-9-菲甲酰基）-2-甲基四氢吡咯（11）．通过实验发现,化合物（10）和（11）的收率与偶氮二异丁腈的加入量密切相关．我们认为偶氮二异丁腈在该反应中充当着双重角色,并提出了可能机理．化合物（10）和（11）经四氢锂铝还原顺利得到（S）-（＋）-娃儿藤碱（1）和其结构类似物（＋）-N-（2,3,6,7-四甲氧基-9-菲苄基）-2-甲基四氢吡咯．     

交让木树皮中的新虎皮楠生物碱的结构研究

本文报道从虎皮楠科植物交让木的树皮中分到4个新的和7个已知的虎皮楠生物碱的结构研究。4个新生物碱分别命名为脱氧交让木碱（dehydroxymacropodumineA）(1), 4,21-脱乙酰-23-脱甲基-脱氧交让木胺（4,21-deacetyl-23-demethyl-deoxyyuzurimine） (2),7-氧杂--脱氧交让木胺（7-oxo-deoxyyuzurimine）(3),和4-乙酰氧-虎皮楠素B （4-acetoxydaphmanidinB）(4)。新化合物1-4的结构是通过仔细解析其波谱数据和与已知结构相关的化合物波谱数据比较而确定。脱氧交让木碱（dehydroxymacropodumineA）(1) 具有罕见的11元环的大环内酯结构,是从自然界中分到的第二个具有这一新颖结构特征的生物碱。     

藤三七中一个新黄烷醇和抗HIV活性成分

利用各种色谱(硅胶和凝胶)方法, 从藤三七[Boussingaultia gracilis Miers var. pseudobaselloides Bailey]的70%(体积分数)的乙醇提取物中分离得到2个黄烷醇类化合物(1, 2)和4个黄酮类化合物(3~6). 采用UV, IR, MS 和1D, 2D NMR方法, 分别鉴定出如下化合物: 7-羟基-5-甲氧基-8-甲基-6-甲酰基-3,4-黄烷二醇, 命名为藤三七醇A(1); 4,7-二羟基-5-甲氧基-8-甲基-6-甲酰基黄烷(2); 7-O-methylunonal(3); 5,7-二羟基-6, 8-二甲基-2-苯基-4H-1-苯并吡喃-4-酮(4); Desmosflavone(5)和Demethoxymatteucinol(6). 其中化合物1是一个新的黄烷二醇化合物, 化合物2~6为首次从该植物中分离得到. 抗HIV-1活性筛选结果表明: 化合物1, 2, 5, 6对HIV-1诱导合胞体的形成具有一定的抑制作用, 其半数有效浓度(EC50)分别为45.09, 48.73, 55.47 和 82.75 μmol/L, 治疗指数(TI)分别为1.41, 1.20, 7.15 和>8.51.     

自苦木中分离得到两个新的β-咔巴啉生物碱——-苦木碱辛和苦木碱壬

自苦木科植物苦木的木质部分离得到四个生物碱,经UV,IR,NMR和MS分析和物理化学常数测定,确定其中两个为新的β-咔巴啉生物碱,分别命名为苦木碱辛和苦木碱壬.苦木碱辛的结构为1-甲酰基-4-甲氧基-β-咔巴啉(1),苦木碱壬的结构为1-甲氧丙酰基-β-咔巴啉(2).另外两个为已知生物碱1-乙烯基-4-甲氧基-β-咔巴啉(3)和3-甲基铁屎米-2,6-二酮(4)     

大理紫乌头的二萜生物碱成分研究

为了研究大理紫乌头的二萜生物碱成分,采用硅胶柱层析进行化合物的分离纯化,通过NMR方法对其化合物结构进行鉴定。结果表明大理紫乌头含6个二萜生物碱成分,包括5个C_(19)-乌头碱型:塔拉萨敏(1)、14-乙酰塔拉萨敏(2)、黄草乌碱丙(3)、8-去乙酰滇乌碱(4)、印乌碱(5)和1个C_(20)-海替定型宽乌宁(6)。其中化合物3～6为首次从该物种分离得到。     

4-肟醚基喹唑啉类化合物的合成及其抗植物病毒TMV活性

4-氯喹唑啉与取代芳香肟在碱存在下进行亲核取代反应,合成了17种新型肟醚基喹唑啉衍生物,并对其结构进行了表征。生物活性测试表明,部分化合物抗植物烟草花叶病毒活性超过抗植物病毒商品药剂2,4-二氧六氢-1,3,5-三嗪。     

Antiviral activity of aconite alkaloids from Aconitum carmichaelii Debx

Four diterpenoid alkaloids, namely, (a) hypaconitine, (b) songorine, (c) mesaconitine and (d) aconitine, were isolated from the ethanol root extract of Aconitum carmichaelii Debx. The antiviral activities of these alkaloids against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) were evaluated. Antiviral activity test in vivo showed that compounds a and c, which were C19-diterpenoid alkaloids, showed inactivation efficacy values of 82.4 and 85.6% against TMV at 500 μg/mL, respectively. By contrast, compound c presented inactivation activity of 52.1% against CMV at 500 μg/mL, which was almost equal to that of the commercial Ningnanmycin (87.1% inactivation activity against TMV and 53.8% inactivation activity against CMV). C19-Diterpenoid alkaloids displayed moderate to high antiviral activity against TMV and CMV at 500 μg/mL, dosage plays an important role in antiviral activities. This paper is the first report on the evolution of aconite diterpenoid alkaloids for antiviral activity against CMV.     

Synthesis and Biological Activity of New Pyrethroid Acid Oxime－esters Containing Pyrazole Ring

A series of compounds containing oxime-ester linkage and pyrazole ring(in place of the ester linkage and the alcohol moiety in pyrethroid ester) was designed and synthesized. The structures of all the compounds prepared were confirmed by IH NMR and MS spectroscopy as well as elemental analyses. The binassay data of those compounds against tobacco mosaic virus (TMV), cucumber mosaic virus(CMV), potato virus X (PVX) and potato virus Y(PVY) were presented. Among them compound 6i was found to possess significant plant antiviral activities. But all the compounds showed low insecticidal and acaricidal activities.     

Synthesis and antiviral activities of novel 1,4-pentadien-3-one derivatives bearing an emodin moiety

A series of 1,5-diaryl-1,4-pentadien-3-one derivatives bearing an emodin group were designed and synthesized by the combination of natural products. The antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) in vivo were evaluated. Some of the derivatives displayed promising curative effect and protective activity against TMV. Compound D5 showed appreciable curative bioactivity on TMV approximately of 50% at 306.2 mg/mL, which was superior to ningnanmycin (409.3 mg/mL).     

Synthesis and Antiviral Bioactivity of Novel 2‐Substituted Methlthio‐5‐(4‐Amino‐2‐Methylpyrimidin‐5‐yl)‐1,3,4‐Thiadiazole Derivatives

A series of novel 2‐substituted methlthio‐5‐(4‐amino‐2‐methylpyrimidin‐5‐yl‐)‐1,3,4‐thiadiazole derivatives were synthesized, characterized and evaluated for antiviral activities against tobacco mosaic virus (TMV). The preliminary biological results indicated that most compounds exhibit excellent antiviral activity against TMV in vivo. Among these compounds, compounds 9c , 9i , and 9p displayed the similar curative effect against TMV (EC₅₀ = 287.05–322.47 µg/mL) to that of the commercial agent Ningnanmycin (EC₅₀ = 301.83 µg/mL). In particular, compound 9d demonstrated the best curative effect against TMV (EC₅₀ = 266.21 µg/mL), which was better than that of commercial Ningnanmycin.     

Study of the synthesis,antiviral bioactivity and interaction mechanisms of novel chalcone derivatives that contain the 1,1-dichloropropene moiety

A series of novel chalcone derivatives that contain the 1,1-dichloropropene moiety was designed and synthesized. Bioactivity assays showed that most of the target compounds exhibited moderate to good antiviral activity against tobacco mosaic virus (TMV) at 500 μg/mL. Among the target compounds, compound 7h showed the highest in vivo inactivation activity against TMV with the EC₅₀ and EC₉₀ value of 45.6 and 327.5 μg/mL, respectively, which was similar to that of Ningnanmycin (46.9 and 329.4 μg/mL) and superior to that of Ribavirin (145.1 and 793.1 μg/mL). Meanwhile, the microscale thermophoresis and fluorescence spectroscopy experiments showed that the compound 7h had a strong interaction with the tobacco mosaic virus coat protein.     

Synthesis and antiviral bioactivity of novel chalcone derivatives containing purine moiety

A series of novel chalcone derivatives containing purine group was synthesized and evaluated for their antiviral activities against cucumber mosaic virus and tobacco mosaic virus. Compound 3o exhibited remarkable antiviral activities and strong combining capacity to tobacco mosaic virus coat protein.     

1-取代苯基-1,4-二氢-6-甲基-4-哒嗪酮-3-酰肼的合成及其抗烟草花叶病毒活性

植物病毒;抑制活性;1-取代苯基-1;4-二氢-6-甲基-4-哒嗪酮-3-酰肼的合成及其抗烟草花叶病毒活性     

Antiviral and Antibacterial Activities of N‐(4‐Substituted phenyl) Acetamide Derivatives Bearing 1,3,4‐Oxadiazole Moiety

In this paper, a series of N‐(4‐substituted phenyl) acetamide derivatives bearing 1,3,4‐oxadiazole moiety were synthesised. Preliminary bioassays revealed that these compounds not only exhibited favourable antiviral activities toward tobacco mosaic virus (TMV) but also demonstrated sustained inhibition activities against plant pathogenic bacteria, including Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri. Among the derivatives, TC ₈ and TC ₂₀ exerted the strongest curative activities against TMV, with half‐maximal effective concentration (EC₅₀) values of 239.5 and 236.2 µg/mL, respectively, which were comparable to that of ningnanmycin (EC₅₀=273.2 µg/mL). Given their simple synthesis, the target compounds can serve as alternative antiviral candidates.     

Design,synthesis, and anti-TMV bioactivities of nucleobase phosphonate analogs

A series of novel nucleobase derivatives and their analogues possessing diethoxyphosphoryl scaffolds were synthesized through four-step reactions and screened for their antiviral activity toward tobacco mosaic virus (TMV). Preliminary bioassays suggested that some of these simple structures displayed appreciable anti-TMV activity in vivo. Among them, compound (diethoxyphosphoryl)methyl 4-[2-(1H-benzo[d][1,2,3]triazol-1-yl)acetamido]-benzoate (a-3) exerted the strongest chemotherapeutic and protective effects against TMV with the rates of 52.8 and 72.2% at the dosage of 500 µg/mL, respectively, which were comparable with those of the commercial agricultural antiviral agent ningnanmycin (54.2 and 70.2%). Molecular docking with TMV helicases revealed that compound a-3 had strong interactions with receptor amino acid residues. Given the facile synthetic route and significant chemotherapeutic and protective potentials, compound a-3 could be further studied and exploited as a promising antiviral candidate.