Synthesis and bioactivity of beta-carboline derivatives

The beta-carboline alkaloids possess a wide diversity of important biochemical effects and pharmacological properties. A series of beta-carboline derivatives were synthesized from L-tryptophan through the Pictet-Spengler reaction and oxidation of K2Cr2O7 by a sequential one-pot synthesis method. In vitro anti-bacterial, insecticidal, and cytotoxic activities of all synthesized compounds were investigated by the tablet diffusion, leaf disc, and MTT methods, respectively. Some of the compounds (1-1, 1-2, 1-3 and 1-12) exhibited obvious anti-bacterial effects and some (1-3) had significant cytotoxic activities against tumor cells 3LL, MCF-7, BGC-823 and QGY-7701, with IC50 values of 7.79, 5.75, 3.53 and 4.02 microg/mL, respectively. No insecticidal activity against third stage instar larvae of Mythimna separata Walker were observed under the tested concentration.     

Synthesis and bioactivity of novel coumarin derivatives

A series of coumarin derivatives (6-8) containing (E)-methyl 2-(methoxyimino)-2-phenylacetate, (E)-2-(methoxyimino)-N-methyl-2-phenylacetamide and methyl methoxy(phenyl)carbamate were synthesized from substituted resorcinols (1) and substituted beta-keto esters (2) as starting material via cyclization and condensation reactions. The test results indicated that (E)-methyl 2-{2-[(3-hexyl-4-methyl-coumarin-7-yloxy)methyl]phenyl}-2-(methoxyimino)acetate (6f) was the optimal structure with good fungicidal activity against cucumber grey mold (CGM) giving 100% control at 100 mg L(-1) concentration, much higher than that of coumoxystrobin. Methyl 2-[(3,4-dimethyl-coumarin -7-yloxy)methyl]phenyl(methoxy)carbamate (8a) was another optimal structure with good fungicidal activity against wheat powdery mildew (WPM) showing 100% control at 50 mg L(-1) concentration, at the same level as that of the commercial kresoxim-methyl, and very significantly higher than that of coumoxystrobin (no control against WPM at 400 mg L(-1)).     

Synthesis and bioactivity of novel phthalimide derivatives

Novel phthalimide derivatives （4a, 4b and 6a-6e） were designed as hybrids of thalidomide and NO-ASA, and their chemical synthesis and in vitro biological activities were presented. The preliminary results showed that compared to thalidomide 4a and 4b exhibited enhanced activities against ECV304 and HepG2 cells, whereas 6e was more potent against HepG2 cells. 2007 Yi Hua Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.     

Synthesis and bioactivity of pyrazole acyl thiourea derivatives

Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, 1H-NMR, 13C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests.     

Synthesis and bioactivity evaluation of some novel sulfonamide derivatives

A simple and convenient method for the synthesis of biologically active sulfonamide derivatives was achieved. All the title compounds were characterized by spectral and elemental analysis. They were further screened in vitro for their abilities towards antibacterial, antifungal and antioxidant activities. The compound N,N'-(3,3′-dimethoxybiphenyl-4,4′-diyl)bis(4-fluorobenzenesulfonamide) (5b) and N-(3-(9H-carbazol-4-yloxy)-2-hydroxypropyl)-4-fluoro-N-isopropylbenzenesulfonamide (5e) exhibited good activity when compared to the standard bactericide, Chloramphenicol and fungicide, Ketoconazole respectively. The compounds (2S)-N-((2S,4S)-5-(4-Chloro-phenylsulfonamido)-4-hydroxy-1, 6-diphenylhexan-2-yl)-3-methyl-2-(2-oxotetrahydropyrim-idin-1(2H)-yl)butan-amide (4f) and (2S)-N-((2S,4S)-5-(4-fluorophenylsulfonamido)-4-hydroxy-1,6-diphenyl-hexan-2-yl)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)bu-tana-mide (5f) exhibited good antioxidant activity when compared with standard antioxidant, Ascorbic acid.     

Synthesis,characterization and bioactivity determination of ferrocenyl urea derivatives

Fourteen new ferrocene derivatives containing urea linker were synthesized from the reaction of ferrocenecarbonyl azide with aromatic amines. The structures of the synthetic compounds were confirmed by ¹H NMR, ¹³C NMR, IR, mass spectrometry and elemental analysis. These organometallic compounds were evaluated by in vitro protease assay using fluorogenic substrate peptide, and several showed potent inhibition against HIV‐1 protease. Copyright © 2012 John Wiley & Sons, Ltd.     

含三唑啉硫酮槟榔碱衍生物合成和生物活性

烟酸经酯化、肼解、与取代芳酸异硫氰酸酯缩合成1－（3－吡啶甲酰基）－4－芳基氨基硫脲（2），2经环合成生成2－（3－吡啶）－4－芳基－1，3，4－三唑啉－5－酮（3），接着用碘甲烷对吡啶环季铵化得相应的季铵盐4，4用硼氢化钠还原可得目标物2－（1－甲基－1，2，5，6－四氢吡啶－3－4）－4－芳基－1，2，4－三唑啉－5－硫酮（5），对所合成的目标化合物进行了舒张血管活性实验。     

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.     

4-芳氨基-6,7-二甲氧基喹唑啉的合成及生物活性研究

以4-氯-6,7-二甲氧基喹唑啉和4-(2-芳基)乙烯基苯胺或4-[2-(2-呋喃基)]乙烯基苯胺为原料合成了5种4-芳氨基-6,7-二甲氧基喹唑啉类化合物.利用IR、NMR和元素分析等表征手段对其进行了结构确认.这5种化合物对HT-29和MDA-MB-231两种细胞模型的体外抗癌活性测试结果表明,部分化合物具有良好的...     

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.     

Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring

A series of novel pyrazole oxime derivatives containing oxazole ring were designed and synthesized. The title compounds were structurally confirmed by 1H NMR, 13C NMR spectra and elemental analyses. Preliminary bioassay results showed that some of the title compounds displayed promising fungicidal activity besides insecticidal and acaricidal activity. Particularly, compound 8c exhibited potent fungicidal activity against cucumber Pseudoperonospora cubensis beyond good insecticidal activity against Aphis craccivora and Nilaparvata lugens.     

Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives

New polysubstituted N-arylpyrazole derivatives were synthesized from N1-arylsydnone with acetylene and boronic acid, including 2-thiophenyl, 3-thiophenyl, 2-benzo[b]thiophenyl, or dibenzothiophenyl-4-boronic acid, via 1,3-dipolar cycloaddition and Suzuki coupling reaction. Based on the growth inhibitory activity results against lung carcinoma (NCI-H226), nasopharyngeal (NPC-TW01), and T-cell leukemia (Jurkat) cancer cells, compounds 5d and 7d with dibenzothiophenyl bioisostere possessed the significant inhibitory activity for NPC-TW01 (32 μM and 16 μM) and NCI-H226 (16 μM and 8.9 μM), respectively.     

6-氨基-3-取代吲哚的合成和生物活性研究

6-氨基-3-取代吲哚及其衍生物是一种重要的医药和有机化工中间体,不仅能合成一些具有生理活性和药理活性的化合物,如:合成一些具有药物活性的色胺类化合物及其衍生物[1,2];合成一些植物生长调节剂,如吲哚-3-乙腈和吲哚-3-乙酸类化合物[3];合成一些具有生物活性的天然化合物Drag     

Synthesis and bioactivity of new phosphorylated R,R'-substituted sulfoximines

R,R'-disubstituted sulfoximines were phosphorylated with O,O-diethylchloro phosphate and phosphorothionate to obtain new organophosphorus compounds. After purification they were characterized by GC-MS and (1)H-NMR. The toxicity of the synthesized O,O-diethyl N-(R,R'-disubstituted sulfoximine) phosphoro-amidothionates was assayed on Musca domestica. It was found that the methyl phenyl derivative was the most toxic compound, followed by the dipropyl and dibutyl derivatives. The dihexyl compound was the less toxic of all the assayed compounds, being one hundred times less toxic than a paraoxon standard The anticholinesterasic activity of the corresponding phosphoramidates was assayed on homogenates of house flies' heads, giving values similar to paraoxon for the methyl phenyl derivative.     

Synthesis,bioactivity and preliminary mechanism of action of novel trifluoromethyl pyrimidine derivatives

In this study, a series of trifluoromethyl pyrimidine derivatives 5a-5v were designed and synthesized. All synthetic compounds were original. Bioassay results showed that some of the target compounds were proved to have higher antiviral and antifungal activities than those of commercial agents. Especially, EC₅₀ values of the curative activity of compound 5j and the protection activity of compound 5m were 126.4 and 103.4 µg/mL, respectively, which were lower than that of ningnanmycin. Microscale thermophoresis experiment proved that there was a good interaction between compound 5m and TMV-CP. Meanwhile, the antifungal activity results showed that compound 5u had a significant on in vitro against Rhizoctonia solani (RS) activity, with the EC₅₀ value of 26.0 µg/mL, which was equal to that of azoxystrobin. As well, in vivo experiments on rice leaves showed that compound 5u could effectively control RS, and the effect of 5u on the cell morphology of RS was observed by scanning electron microscopy.     

Synthesis and bioactivity of novel strobilurin derivatives containing the pyrrolidine-2,4-dione moiety简

（E）-Methyl-2-（2-（bromomethyl）phenyl）-3-methoxyacrylate was reacted with substituted 1-acetylpyr-rolidine-2,4-diones and 3-（1-（hydroxylamino）ethylidene）pyrrolidine-2,4-diones respectively to synthesize two series of/%methoxyacrylate derivatives containing the pyrrolidine-2,4-dione moiety. The structures of the targeted compounds were confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. The fungicidal activity against Rhizoctonia solani, Botrytis cinerea and Fusarium graminearum was evaluated. The bioassay results demonstrated that these compounds showed visible fungicidal activity.     

Synthesis, antiviral and antifungal bioactivity of 2-cyano-acrylate derivatives containing phosphonyl moieties

Alkyl 2-cyano-3-methylthio-3-phosphonylacrylates were synthesized by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylates with dialkyl phosphites. The structures of the new compounds were characterized by elemental analyses, IR, 1H-, 13C- and 31P-NMR spectral data. These compounds were tested in vitro against pathogenic fungi, namely, Fusarium graminearum, Cytospora mandshurica and Fusarium oxysporum. Amongst all compounds, 2d and 2t were found to be effective against the tested fungi at 50 microg/mL. A half-leaf method was used to determine the in vivo protective, inactivation and curative efficacies of the title products against tobacco mosaic virus (TMV). Title compounds 2a and 2b were found to possess good in vivo curative, protection and inactivation effects against TMV with inhibitory rates at 500 mg/L of 60.0, 89.4 and 56.5 and 64.2, 84.2 and 61.2 %, respectively. To the best of our knowledge, this is the first report on the antiviral and antifungal activity of alkyl 2-cyano-3-methylthio-3-phosphonylacrylates.     

Synthesis of new o-isobornylphenol derivatives

The hydroxymethyl, pyridinium methyl, or dialkylaminomethyl groups were introduced into the aromatic ring of the o-isobornylphenol molecule. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1754–1757, October, 2006.