Alkaloids of Stephania hernandifolia VIII. Methylhernandine

Summary A new hasubanan alkaloid with the composition C₂₀H₂₇O₆N, mp 152–153°C (ether-methanol) has been isolated from the herbStephania hernandifolia and has been called methylhernandine. The alkaloid has been shown to be identical with the methylamino alcohol obtained in the hydrolysis of hernandifoline.All-Union Scientific Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 455–457, July–August.     

Vinervine — A new alkaloid from the aboveground part of Vinca erecta RGL. ET schmalh

Summary From the aboveground part ofV. erecta gathered in the Shargun' settlement in the Surkhan-Darya region 1% of total alkaloids was isolated, and in the separation of these the bases vincanidine and a new phenolic base vinervine (C₂₀H₂₂O₃N₂) were obtained. Vinervine is an alkaloid of the 2-methyleneindoline group.Translated from Izvestiya Akademii Nauk SSSR, Khimicheskaya, No. 12, pp. 2152–2155, December, 1965     

The structure of korsine

Conclusions A new alkaloid korsine, C₂₇H₄₃O₃N, has been isolated from the bulbs ofKorolkowia sewerzowii. Its structure and configuration have been established on the basis of a study of its chemical properties and IR, UV, NMR, and mass spectra.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 3, pp. 161–168, 1968     

Structure of petiline

Conclusions 1. Imperialine, edpetilidine, and the new alkaloid petiline C₂₇H₄₃O₂N have been isolated from the epigeal part ofP. raddeana.2. On the basis of a study of the chemical properties and the IR, UV, NMR, and mass spectra a most probable structure and a partial configuration have been proposed for petiline.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 3, pp. 168–174, 1968     

Alkaloids of Sophora alopecuroides

Summary On the basis of spectral characteristics and chemical transformations, a new alkaloid with the composition C₁₅H₂₂O₂N₂ isolated fromSophora alopecuroides has been assigned the most probable structure of 13,14-dehydrosophoridine N-oxide.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 541–544, July–August, 1977.     

Investigation of Aconite alkaloids

Summary The composition of the alkaloids in plants of the genus Aconitum —A. kirinense,A. altaicum, A. coreanum, andA. nemorosum — has been studied. Four new alkaloids of composition C₂₆H₄₁O₈N·HNO₃, C₃₅H₄₁O₁₀N·HBr, C₂₀H₂₅O₃N, and C₂₃H₂₉O₆N have been isolated.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 2, pp. 113–116, 1965.     

Ethyl 2‐methoxy‐6‐[(triphenylphosphoranylidene)amino]nicotinate and ethyl 2‐methylsulfanyl‐6‐[(triphenylphosphoranylidene)amino]nicotinate

The molecules of ethyl 2‐methoxy‐6‐[(triphenylphosphoranylidene)amino]nicotinate, C₂₇H₂₅N₂O₃P, (I), and ethyl 2‐methylsulfanyl‐6‐[(triphenylphosphoranylidene)amino]nicotinate, C₂₇H₂₅N₂O₂PS, (II), have almost identical bond lengths and molecular conformations, and both show evidence for polarized electronic structures. However, the crystal structures, as illustrated by the weak hydrogen bonds linking the molecules, are significantly different. The significance of this study lies in the observation that two compounds which are almost identical in constitution, configuration and conformation nonetheless adopt different crystal structures.     

Alkaloids of Stephania delovayi III. Stephodeline

Summary From the epigeal part ofStephania delovayi Diels (Menispermaceae) have been isolated cycleanine and a new amorphous alkaloid, stephodeline, with the composition C₂₁H₂₇O₅N, a structure for which is proposed.All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 650–653, September–October, 1973.     

Synthesis of formamidines from 2-amino-3-methylquinazolin-4-one and its 6-nitro derivative

The condensation of 2-amino-3-methylquinazolin-4-one and its 6-nitro derivative with dialkyl-, arylalkyl-, and heterylformamides has given the corresponding formamidines of the quinazolinone series. The details of the compounds synthesized are as follows X, R, R′, yield (%), mp (°C, ethanol), R_f (chloroform-methanol (20:1) Al₂O₃): empirical formula: H, CH₃, CH₃, 77, 238–240, 0.49, C₁₂H₁₄ON₄; H, C₂H₅, C₂H₅, 65, 208–210, 0.96, C₁₄H₁₈ON₄; H, CH₃, C₆H₅, 84, 162–164, 0.54, C₁₇H₁₆ON₄; H, (CH₂)₂O(CH₂)₂, 60, 196–197, 0.43, C₁₄H₁₆O₂N₄; H, (CH₂)₅, 6.6, 196–198, 0.4, C₁₅H₁₈·ON₄; NO₂, CH₃, CH₃, 64. 194–196, 0.83, C₁₂H₁₃O₃N₅; NO₂, C₂H₅, C₂H₅, 37, 142–144, 0.8, C₁₄H₁₇O₃N₅; NO₂; CH₃, C₆H₅, 38, 298, 0.88, C₁₇H₁₅O₃N₅; NO₂, (CH₂)₂O(CH₂)₂, 60, 148–150, 0.7, C₁₄H₁₅O₄N₅. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 680–684, September–October, 1980.     

Alkaloids of Vinca major

Summary 1. From the epigeal part ofVinca major have been isolated the known bases akuammicine, vincamajine, vincamajoridine, and ervine, and the new alkaloid majorinine with the composition C₂₂H₂₄N₂O₄, mp 195–196°C.2. On the basis of chemical transformations and IR, UV, mass, and PMR spectra using the methods of double resonance collapse and INDOR the structure of 21-hydroxy-10-methoxyvinorine and the stereochemistry (I) have been established for majorinine.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 382–387, May–June, 1977.     

Bipodal 1,1′‐acyl‐3,3,3′,3′‐tetraalkylbis(thiourea) ligands with flexible C3, C4 and C6 spacer groups

In the structures of 3,3,3′,3′‐tetraethyl‐1,1′‐(propane‐1,3‐diyldicarbonyl)bis(thiourea), C₁₅H₂₈N₄O₂S₂, (I), 3,3,3′,3′‐tetraethyl‐1,1′‐(butane‐1,4‐diyldicarbonyl)bis(thiourea), C₁₆H₃₀N₄O₂S₂, (II), and 3,3,3′,3′‐tetrabutyl‐1,1′‐(hexane‐1,6‐diyldicarbonyl)bis(thiourea), C₂₆H₅₀N₄O₂S₂, (III), compound (I) displays resonance‐assisted hydrogen bonding, (II) exhibits an inversion centre, and both (II) and (III) are characterized by intermolecular hydrogen bonds between the carbonyl O atoms and thioamide H atoms, leading to chains of hydrogen‐bonded molecules throughout the structures. The accurate structural data for these molecules is expected to assist in molecular modelling and other studies currently in progress.     

Co-crystallization of a benzimidazole derivative with carboxylic acids

The co-crystallization of a benzimidazole derivative (1, C₂₇H₂₆N₆O₃, 3-[[[2-[[(4-Cyanophenyl) amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester), with fumaric acid (FA) and maleic acid (MA), has been performed. The FA and MA molecules, both are connected with two molecules of C₂₇H₂₆N₆O₃, giving birth to a three-components compound (1·0.5FA, C₂₉H₂₈N₆O₅) and a four-components compound (1·MA, C₃₁H₃₀N₆O₇). Single-crystal X-ray diffractions show that the three different planar moieties (4-cyanophenyl, benzimidazol, and pyridin-2-yl) in compound C₂₇H₂₆N₆O₃ display “cis-form” conformation (a) in the crystal of 1, while exhibiting “intermediate-state” conformation (b) and “trans-form” conformation (c) in compounds 1·0.5FA and 1·MA, respectively. Hirshfeld surfaces analysis, DFT calculations, DSC measurements, IR and Raman spectroscopy were performed, which revealed that the thermal stability of the three conformations follows the order c > b > a.     

Alkaloids ofPetilium raddeana. V. Structure of petisidinone

From the epigeal part ofPetilium raddeana have been isolated the known alkaloids edpetiline and edpetine and the new base petisidinone with mp 217–219°C, []_D 0° (c 0.169; chloroform), C₂₇H₃₉NO₃ (I). When the known alkaloid petisidine was oxidized, a product identical with petisidinone (I) was obtained. Thus, the structure of (I) has been established as 26,23-nitrilocholestane-3,6,22-trione. Details of the IR, PMR, and mass spectra of (I) are given.Institute of the Chemistry of Plant Substances of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh soedinenii, NO. 5, pp. 620–622, September–October, 1986.     

Alkaloids ofNuphar luteum

Summary 1. The dry rhizomes ofNuphar luteum L. have yielded three sulfur-containing alkaloids: two — thiobinupharidine and neothiobinupharidine — were known substances, the third with composition C₃₀H₄₂O₄N₂S being new and having been given the name of nuphleine.2. A possible structure has been proposed for nuphleine.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 178–182, 1967     

Alkaloids ofStephania hernandifolia. III

Summary 1. A new alkaloid hernandoline with the composition C₂₀H₂₅O₅N has been isolated from the herbStephania herandifolia Walp.2. The Hofmann degradation of the methiodide of the O-methyl ether of hernandoline has given a des base acetolysis of which led to the formation of a dimethoxydiacetoxyphenanthrene.3. It has been suggested that hernandoline is similar to alkaloids related to sinomenine and hasubanonine.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 106–108, 1967     

Haplophyllum alkaloids. IV. Structure of foliosidine

An alkaloid foliosidine isolated from the plantHaplophyllum foliosum Vved. (Rutaceae family) has the formula C₁₆H₂₁O₅N. Its expanded formula is C₁₃H₁₃ (N-CH₃) (OH)₂ (OCH₃) (CO) (-O-), and it is 4-methoxy-8-(2,3-dihydroxy-3-methyl-butoxy)-N-methylcarbostyryl (I).Khimiya prirodnykh soedinenii, No. 1, pp. 27–33, 1965     

Brucine and two solvates

The crystal structures of brucine (2,3‐di­methoxy­strychnidin‐10‐one), C₂₃H₂₆N₂O₄, brucine acetone solvate, C₂₃H₂₆N₂O₄·C₃H₆O, and brucine 2‐propanol solvate dihydrate, C₂₃H₂₆N₂O₄·C₃H₇O·2H₂O, have been determined. Crystals of brucine and its 2‐propanol solvate dihydrate exhibit similar monolayer sheet packing, whereas crystals of the acetone solvate adopt a different mode of packing, as brucine pillars. The solvent appears to control the brucine self‐assembly on the basis of common donor–acceptor properties of the surfaces.     

Brucinium 3,5‐dinitro­benzoate methanol solvate,methanol disolvate and trihydrate

Crystals of brucinium 3,5‐dinitro­benzoate methanol solvate, C₂₃H₂₇N₂O₄⁺·C₇H₃N₂O₆⁻·CH₃OH, (I), brucinium 3,5‐dinitro­benzoate methanol disolvate, C₂₃H₂₇N₂O₄⁺·C₇H₃N₂O₆⁻·2CH₃OH, (II), and brucinium 3,5‐dinitro­benzoate trihydrate, C₂₃H₂₇N₂O₄⁺·C₇H₃N₂O₆⁻·3H₂O, (III), were obtained from methanol [for (I) and (II)] or ethanol solutions [for (III)]. The brucinium cations and 3,5‐dinitro­benzoate anions are linked by ionic N—H⁺⋯O⁻ hydrogen bonds. In the crystals of (I), (II) and (III), the brucinium cations exhibit different modes of packing, viz. corrugated ribbons, pillars and corrugated monolayer sheets, respectively. While in (III), the amide O atom of the brucinium cation participates in O—H⋯O hydrogen bonds, in which water mol­ecules are the donors, in (I) and (II), the amide O atom of the brucinium cation is involved in weak C—H⋯O hydrogen bonds and other brucinium cations are the donors.     

Alkaloide aus Evonymus europaea L.

From the seeds of Evonymus europaea L. (Celastraceae) the three previously described alkaloids A, B and C were isolated and their empirical formulae determined by mass spectrometry. Alkaloid B, now named evozine, C₃₂H₃₉NO₁₅ ( 14 ), alkaloid A, now named evorine, C₃₄H₄₁NO₁₆ ( 15 ), and alkaloid C, shown to be identical with Parter's & Libiseller's evonine, C₃₆H₄₃NO₁₇ ( 17 ), are respectively tri-, tetra-, and penta-O-acetyl derivatives of deacetylevonine ( 13 ), C₂₆H₃₃NO₁₂. Vigorous alkaline hydrolysis of the latter yields the previously known evonic acid ( 3 ). Deacetylevonine ( 13 ) is an ester of evonic acid ( 3 ) and a hypothetical polyhydroxy compound C₁₅H₂₄O₁₀ ( 2 ), which is unstable on alkaline hydrolysis. By partial saponification and partial acetylation, these three alkaloids can be converted into each other, at the same time giving rise to a fourth alkaloid D ( 16 ), C₃₄H₄₁NO₁₆, which we name iso-evorine. This had been obtained already by M. Osowiecki (unpublished).     

A study of the alkaloids ofSaussurea salsa andS. elegans

Conclusions 1. In the extraction ofS. salsa andS. elegans, the condensation of the neutral substances with ammonia takes place with the formation of products of a basic nature.2. FromS. elegans a new alkaloid elegantine C₂₃H₂₉O₅N has been obtained the saponification of which has given tyramine and a sesquiterpene lactone.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 6, pp. 367–370, 1968