In continuation of research on alkaloids of Peganum harmala L. [1][2][3][4] and the search for new biologically active quinazoline, quinazolone, and indole compounds, we studied N-alkylation of (±)-peganine (1), (±)-vasicinone (2), and harmine (3), respectively, with methyliodide, boric acid chelated to ethyleneglycol, and protonation by dilute H 2 SO 4 . These alkaloids were isolated from common P. harmala collected in Kurdaisk Region, Dzhambul Oblast′ (Republic of Kazakhstan) and were identified by the published physicochemical constants [5,6].It was found that 1 reacted with methyliodide and boric acid chelated to ethyleneglycol in DMF or EtOH to form iminium salts 4 and 5, respectively.Reaction of 2 with methyliodide under the above conditions also occurred at the azomethine N atom and gave iminium salt 6. The results were interesting in view of a previous report [7] that salts of 1-acyldeoxyvasicinone form readily and can be used for further syntheses.Harmine (3) reacted with methyliodide to give β-carbolinium salt 7. Treatment of 3 with dilute H 2 SO 4 in MeOH gave the bis-hydrate of bis-[N(2)-harminium]sulfate (8), the structure of which was elucidated by an x-ray structure analysis (XSA).The asymmetric unit of the unit cell contained two molecules of 8, one SO 4 −2 , and two waters of solvation. The closest structural analog of 8 was harmine hydrochloride (9) [5], the structure of which was studied by XSA [8]. The geometry of all three molecules of 8 (in our instance two independent ones) agreed within 3σ and had similar corresponding meansquare values [9]. Intermolecular interactions were analyzed using the program PLATON [10]. Molecules of 8 were bonded through H-bonds to SO 4 −2 and waters of solvation (Fig. 1). Table 1 lists the H-bond parameters. Molecules of 8 were placed in stacks with a face-to-face shift through π...π-interaction with an interplanar distance 3.36 °A and a distance between centers of five-membered rings of neighboring molecules in the stack 3.424(2) and 3.440(2) °A . Harmine (3) is known to exhibit psychotomimetic activity [11]. We obtained some new data on the biological activity of 3 and its derivatives.Harmine (3) and the bis-hydrate of bis-[N(2)-harminium]sulfate (8) exhibited pronounced anticholinesterase activity greater (0.182 μA and 0.125 μA) than the model inhibitor proserine (0.115 μA).
Plant metabolites containing the 11H-indolizino [8,7-b]indole unit such as the alkaloids harmicidine [1] and trichotomine [2] have valuable pharmacological properties. The tetrahydro- 11H-indolizino[8,7-b]indole fragment is a structural element of plant cytotoxic indole-containing subincanadine alkaloids [3,4]. We attempted to construct this heterocyclic unit by synthetic transformations of the available plant alkaloid, harmine (1). Some reactions of this compound have been described in our previous work [5,6].We have shown that the reaction of harmine 1 with phenacyl bromides 2a-c in ethanol leads to the formation of harminium salts 3a-c. Similarly, the action of ethyl bromoacetate on harmine 1 leads to quaternized salt 4 (Scheme 1). We should point out that the preparation of 9H--carbolinium salts holds interest in light of the high antimicrobial (including antimalarial) activity of various quaternized -carboline derivatives [7-9].Phenacylharminium salts 3a-c undergo facile cyclization upon treatment with KOH to give 11H-indolizino [8,7-b]indole derivatives 5a-c in 77-85% yield. Thus, this method reproduces a reported approach to the synthesis of indolizines [10].The methods described for constructing the indolizino [8,7-b]indole unit are based on the Pictet-Spengler [11,12] and Bischler-Napieralski reactions [13,14] of tryptamine or tryptophan derivatives, the reaction of 3,4-dihydro--carboline with 2-acetoxyacrylates [15,16], and the 1,3-dipolar cycloaddition of derivatives of -carboline azomethine ylids [17]. Our method for obtaining this heterocyclic unit features a high yield of
The N-oxides of harmine and glaucine were obtained. The influence of the produced compounds on the phagocytosis-stimulating activity of human blood monocytes in vitro was studied. It was established that harmine and glaucine N-oxides have pronounced phagocytosis-stimulating properties.Derivatives of b-carboline and aporphine exhibit anticholinesterase, sedative, muscle-relaxant, hypotensive, bronchodilating, and antibacterial properties [1][2][3].Considering the aforementioned, further studies on the search and expansion of the raw-material alkaloid base and the isolation and elucidation of their structures seemed advisable. This would enable new effective drugs to be created.The available natural alkaloids harmine (I) and glaucine (II) were selected as the subjects of the investigations. I is indicated to treat insults of the peripheral nervous system and Parkinson's disease and consequences of the disruption of brain blood circulation [3]. II is used as an anti-cough agent [4]. In continuation of research in this area, we synthesized new derivatives of I and II containing the NO group. It was found that gentle heating of I and II with selenium dioxide in MeOH formed harmine N-oxide (III) and glaucine N-oxide (IV) in 90 and 75% yields, respectively.The formation of the N ® O group in III was confirmed by 13 C NMR spectra in which resonances for C-1 and C-3 shifted to strong field by Dd 6 and 9 ppm compared with the corresponding resonances of I. The PMR spectrum of III showed a shift of the methyl resonance to weak field by 0.3 ppm. 458 0091-150X/11/4508-0458
News of the Academy of sciences of the Republic of Kazakhstan 2 NAS RK is pleased to announce that News of NAS RK. Series of chemistry and technologies scientific journal has been accepted for indexing in the Emerging Sources Citation Index, a new edition of Web of Science. Content in this index is under consideration by Clarivate Analytics to be accepted in the Science Citation Index Expanded, the Social Sciences Citation Index, and the Arts & Humanities Citation Index. The quality and depth of content Web of Science offers to researchers, authors, publishers, and institutions sets it apart from other research databases. The inclusion of News of NAS RK. Series of chemistry and technologies in the Emerging Sources Citation Index demonstrates our dedication to providing the most relevant and influential content of chemical sciences to our community. Қазақстан Республикасы Ұлттық ғылым академиясы "ҚР ҰҒА Хабарлары. Химия және технология сериясы" ғылыми журналының Web of Science-тің жаңаланған нұсқасы Emerging Sources Citation Index-те индекстелуге қабылданғанын хабарлайды. Бұл индекстелу барысында Clarivate Analytics компаниясы журналды одан әрі the Science Citation Index Expanded, the Social Sciences Citation Index және the Arts & Humanities Citation Index-ке қабылдау мәселесін қарастыруда. Webof Science зерттеушілер, авторлар, баспашылар мен мекемелерге контент тереңдігі мен сапасын ұсынады. ҚР ҰҒА Хабарлары. Химия және технология сериясы Emerging Sources Citation Index-ке енуі біздің қоғамдастық үшін ең өзекті және беделді химиялық ғылымдар бойынша контентке адалдығымызды білдіреді. НАН РК сообщает, что научный журнал «Известия НАН РК. Серия химии и технологий» был принят для индексирования в Emerging Sources Citation Index, обновленной версии Web of Science. Содержание в этом индексировании находится в стадии рассмотрения компанией Clarivate Analytics для дальнейшего принятия журнала в the Science Citation Index Expanded, the Social Sciences Citation Index и the Arts & Humanities Citation Index. Web of Science предлагает качество и глубину контента для исследователей, авторов, издателей и учреждений. Включение Известия НАН РК в Emerging Sources Citation Index демонстрирует нашу приверженность к наиболее актуальному и влиятельному контенту по химическим наукам для нашего сообщества.
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