Synthesis of N-Acetonitrile Derivatives of Cytisine Alkaloid

Russian Journal of General Chemistry -     

Synthesis of New Cytisine Derivatives with Benzocrown-Ether Fragments

Acylation of cytisine with benzocrown-ethercarboxylic acid chlorides produced a series of new cytisine derivatives containing B12C4, B15C5, DB18C6, and DB24C8 fragments.     

Synthesis and Stereochemistry of New N-Substituted Cytisine Derivatives

A series of new N-substituted cytisine derivatives was synthesized. The ¹ H and ¹³ C NMR spectra of certain compounds exhibit a doubled set of signals. This is explained by formation of diastereomeric pairs in compounds containing an asymmetric center in the substituents. The signal splitting in -COHC=CHCO ₂ H and HC=O (formyl) derivatives is explained by the existence of Z and E invertomers. Their stereochemical features are discussed. Amide conjugation is confirmed by temperature experiments.     

Alternative Synthesis of the Alkaloid Guvacine and Its Derivatives

Russian Journal of Organic Chemistry - The reaction of nicotinic acid ethyl ester with phenacyl bromides containing electron-donating substituents in the benzene ring afforded the corresponding...     

Synthesis and Antimicrobial Evaluation of Calycanthaceous Alkaloid Derivatives

Chemistry of Natural Compounds - To find pesticidal lead compounds with high activity, a series of new chimonanthine derivatives was synthesized via the introduction of the functional group at the...     

合成金鸡纳生物碱衍生物的简便方法

以CaH2为缚酸剂,DMF为溶剂,金鸡纳生物碱通过3,6-二氯哒嗪或1,4-二氯-2,3-二氮杂萘桥连,高产率地合成了用作手性配体的13个金鸡纳生物碱衍生物,其结构经NMR确证.     

Cyclolization of D-Lysergic Acid Alkaloid Peptides

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单萜吲哚生物碱Uleine及其衍生物的合成进展

生物碱uleine及其衍生物从结构上看属于单萜吲哚生物碱,它们共同的结构特征是吲哚核与碱性氮原子之间只有一个碳相隔,而不像其它单萜吲哚生物碱有两个碳原子.由于其结构特异,天然含量少,因而其合成工作一直吸引着化学工作者.总结uleine生物碱及其衍生物的合成方法,根据构建环的种类不同,把合成方法分为五类.大部分方法都是以吲哚和吡啶衍生物为起始原料进行四环的合成,有几条合成路线简短易行.     

Synthesis,Structure, and Biological Activity of Cinnamoyl-Containing Cytisine and Anabasine Alkaloids Derivatives

Russian Journal of General Chemistry - The reactions of the cytisine and anabasine alkaloids with cinnamic acid chloride have been studied, and hydrazinolysis of the resulting N-cinnamoylcytisine...     

Synthesis and Antileukemia Activity Evaluation of Benzophenanthridine Alkaloid Derivatives

Thirty-three benzophenanthridine alkaloid derivatives (1a–1u and 2a–2l) were synthesized, and their cytotoxic activities against two leukemia cell lines (Jurkat Clone E6-1 and THP-1) were evaluated in vitro using a Cell Counting Kit-8 (CCK-8) assay. Nine of these derivatives (1i–l, 2a, and 2i–l) with IC₅₀ values in the range of 0.18–7.94 μM showed significant inhibitory effects on the proliferation of both cancer cell lines. Analysis of the primary structure–activity relationships revealed that different substituent groups at the C-6 position might have an effect on the antileukemia activity of the corresponding compounds. In addition, the groups at the C-7 and C-8 positions could influence the antileukemia activity. Among these compounds, 2j showed the strongest in vitro antiproliferative activity against Jurkat Clone E6-1 and THP-1 cells with good IC₅₀ values (0.52 ± 0.03 μM and 0.48 ± 0.03 μM, respectively), slightly induced apoptosis, and arrested the cell-cycle, all of which suggests that compound 2j may represent a potentially useful start point to undergo further optimization toward a lead compound.     

Derivatives of Some 2-Chloroethylphosphonic Acid Esters,with Plant Growth Regulating Activity

Abstract

A method for the synthesis of esters of 2-(dimethylsulfonium)ethylphos-phonic acid and the results of some trials showing the plant growth regulating activity of these compounds are presented. For the synthesis of the mentioned compounds, dimethyl sulphide is reacted with 2-chloroethylphosphonic acid esters; these esters are obtained through the complex[1] of AlCl₃, PCl₃ and 1,2-dichloroethan (1). Using the optimum reaction conditions, very good yields were obtained (96–99%). This complex is reacted with different alcohols to give 2-chloroethylphosphonic acid esters (2) (R?Me, Et, Pr, i-Pr, Bu, i-Bu, Pe). Using the optimum reaction conditions, in the case of methanol the maximum obtained yield was 50%. In the case of the other alcohols, the obtained yields were between 76 and 83%. An exception is i-propanol. whose ester was obtained with low yields and the reaction parameters modification have little influence on the yield. The reaction of the esters with dimethyl sulphide gives, in good yields (between 69 and 79%). esters of 2-(dimethylsulfonium)ethylphosphonic acid (3). substances with plant growth regulating activity.     

New Structural Modifications of Cotarnine Alkaloid Derivatives: Cotarnone and Dihydrocotarnine

Simplest derivatives of the cotarnine alkaloid, like cotarnone and 1,2-dihydrocotarnine, undergo electrophilic Einhorn acylamidomethylation (with 60–95% yield) and sulfochlorination with chlorosulfonic acid at position 5. At the same time cotarnone and its derivatives undergo additional O-protodemethylation. Using these and some other reactions, we synthesized a number of previously unknown derivatives of two substrates with 5-chloroacetamidomethyl, 5-arylaminomethyl, 5-aminomethyl and 5-sulfamide groups.     

Perfirine,a New Alkaloid from the Plant Haplophyllum perforatum

Chemistry of Natural Compounds - Alkaloids from the aerial part, seeds, and roots of the plant Haplophyllum perforatum collected in Kashkadarya Region, Republic of Uzbekistan, were studied. The new...     

Unusual Reaction of Alkaloid Cotarnine with 1,3-Dimethylbarbituric Acid

Russian Journal of Organic Chemistry -