A. Nabiev, and V. U. KhuzhaevA series of new convolvine derivatives based on the alkaloid from Convolvulus subhirsutus and C. pseudocanthabrica were synthesized using alkylhalides and aliphatic and aromatic acid chlorides. Results of biological tests showed that convolvine and its derivatives exhibited pronounced antihypoxic, immunomodulating, and anti-inflammatory activity.The aerial parts of Convolvulus subhirsutus and C. pseudocanthabrica growing in Uzbekistan [1] have previously yielded 10 alkaloids [2-7] that were tropane derivatives, the principal ones being convolvine and convolamine with a content of 45-50% of the total alkaloids. A quantitative determination found that the content of the alkaloid mixture in the aerial part was 0.6%; in the roots, 1.6% of the dry plant weight.The convolvine content in C. subhirsutus and C. pseudocanthabrica reaches 0.3% in the aerial part; 0.7%, in roots. As a result of the availability of convolvine, a series of its derivatives were prepared. Their pharmacological properties were studied in a search for compounds with valuable pharmacological activity. For this, convolvine (1) was reacted with alkyl halides (methyliodide, hexylbromide, amylbromide, nonylbromide, benzylchloride) to produce the corresponding derivatives N-methylconvolvine hydroiodide (2), N-amylconvolvine hydrobromide (3), N-hexylconvolvine hydrobromide (4), N-nonylconvolvine hydrobromide (5), and N-benzylconvolvine (6) according to the scheme:Convolvine was also reacted with aliphatic and aromatic acid chlorides to produce N-benzoylconvolvine (7), N-chloroacetylconvolvine (8), and N-4c-nitrobenzoylconvolvine (9), reduction of 9 produced N-4c-aminobenzoylconvolvine (10), and N-naphthoylconvolvine (11):

547.944/945Convolvine, convolamine, convolidine, phyllalbine, and the new alkaloid phyllalbine N-oxide and the aminoalcohol nortropine were isolated from the total alkaloids of Convolvulus subhirsutus and for the first time from this plant.

957.944/945 M. G. Levkovich, and O. AripovSeveral alkaloids of known structure and the new base convolinine were isolated from total alkaloids from the aerial part of Convolvulis subhirsutus growing in Uzbekistan. It has been established that convolinine is an N-hydroxyethyl derivative of convolvine and has the structure (±)-3D-(3,4-dimethoxybenzoyl)-Nhydroxyethylnortropane based on spectral data and an x-ray crystal structure. ) were isolated from the aerial part of Convolvulus subhirsutus growing in Uzbekistan [1,2]. In continuation of the study of C. subhirsutus roots collected in Tashkent Oblast, a new alkaloid (mp 128-129°C, [D] D 0°) was isolated from total alkaloids of the non-phenolic part after isolation of convolvine and convolamine by column chromatography over Al 2 O 3 of the mother liquor of the non-phenolic part of total bases from the benzene:CHCl 3 fractions. The physicochemical properties and chromatographic mobility differed from those described in the literature for tropane bases. We called it convolinine (1).The alkaloid had the formula C 18 H 25 NO 5 . The IR spectrum of the base contained absorption bands for active H at 3290 cm -1 ; ester carbonyl, at 1749; 3,4-disubstituted benzene, at 1601, 1516, 878, and 821; stretching and bending vibrations of CH 3 -, CH 2 -, and CH-, at 29222 -, and CH-, at , 28542 -, and CH-, at , 14632 -, and CH-, at , 14192 -, and CH-, at , 12842 -, and CH-, at , and 1274; and ether -C-O-C-, at 1074 and 1021.The PMR spectrum exhibited resonances for protons of two aromatic methoxyls as two 3H singlets at 3.87 and 3.89 ppm. An 8H multiplet was found in the range 1.85-2.85 that is characteristic of tropane bases for four CH 2 groups of a tropane ring in the C-2, C-4, C-6, and C-7 positions. A 2H multiplet probably for CH 2 protons bound to a N atom was observed at 3.77. A 2H multiplet for two methine protons of C-1 and C-5 in a tropane ring that is characteristic of tropane alkaloids occurred at 3.59. A 1 H triplet for H 3E that is diagnostic for tropane bases esterified on the C-3 hydroxyl was located at 5.23. Resonances for three aromatic protons with characteristic structure of meta-and para-substitution were seen at 7.60-6.80. The isolated D-proton appeared as a doublet with J = 2.0 Hz at 7.50. The other aromatic -proton gave a doublet of doublets (meta-constant J = 2.0 Hz and ortho-constant J = 8.5 Hz) at 7.58. Finally, the E-proton resonated at 6.84 as a doublet (J = 8.5 Hz). A 2H multiplet for protons of CH 2 bonded to oxygen was noted at 2.75.Based on these spectral characteristics, IR spectra (absorption bands for active H), PMR spectra, and taking into account the molecular weight of the alkaloid (M + 335) with an unsubstituted N-containing tropane core, it can be hypothesized that convolinine has a substituted N atom and that the substituent is -C 2 H 4 OH. The PMR spectra suggest that this could be a -CH 2 -CH 2 -OH group on the N atom.

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Total bases (0.03%) were obtained previously from the aerial part of Convolvulus lineatus growing in Katta-Shir gorge of Turkestan Ridge. Convolvine and convolamine were isolated from them. Based on our preliminary research on this plant [2], the isolation of the aforementioned alkaloids required confirmation.C. lineatus growing in Uzbekistan has not been investigated. We studied the plant collected from three sites of Fergana and Tashkent districts including near the villages Erdon and Nanai and along the banks of the Ertosh River. Chloroform extracts of dried and ground aerial parts gave 0.054%, 0.04, and 0.05 of alkaloid mixtures, respectively. TLC (KSK silica gel) using system 1 (CHCl 3 :CH 3 OH, 3.5:1.5) of the total bases detected six compounds with R f values 0.10, 0.21, 0.41, 0.48, 0.58, and 0.70. TLC of all three mixtures showed identical spots that differed only in intensity.A pure base as the nitrate salt with mp 204-206°C (acetone) with R f 0.10 using system 1 was isolated from the total alkaloids in acetone. The nitrate base was a light-yellow fragrant oily liquid.The UV spectrum of the alkaloidal base had one maximum with l max 307 nm (log e 2.36). Its IR spectrum contained absorption bands for stretching (2950-2802 cm -1 ) and deformation (1465-1405) vibrations of CH 2 groups and a C-N single bond (1131, 1097, 1420); an isolated carbonyl (saturated aliphatic ketone) at 1714; and a N-CH 3 group at 2643. The PMR spectrum of the base exhibited two 3H singlets for protons of two N-CH 3 at 2.88 and 2.92 ppm; a multiplet (8H) for four CH 2 groups of two pyrrolidine cycles at 1.68-2.50; a multiplet (4H) for two CH 2 groups bonded to a carbonyl at 3.50-3.65; and resonances for protons of two methylenes bonded to N at 2.98-3.12 ppm. The mass spectrum contained a peak for the molecular ion with m/z 224 [M] + and fragment ions with m/z 140, 126, 98, and 84 that were characteristic for N-methylpyrrolidine derivatives.The spectral data for the alkaloid agreed with those of the known alkaloid cuskhygrine, which was isolated earlier from C. erinaceus [3]. A mixed sample of the nitrate salt and an authentic sample of cuskhygrine did not show melting-point depression. Cuskhygrine was isolated from C. lineatus for the first time. Convolvine (R f 0.30 using system 1) and convolamine (R f 0.55 using system 1) are tropane-like alkaloids and have not been previously observed in C. lineatus.C. Olgae Rgl. et Smalth is a branching low thorny bush that is widely distributed over all Central Asia and in Uzbekistan, in Surkhandar¢ya district (Kashka-Dar¢ya River basin) [4]. Alkaloids from this Convolvulus species have not been previously investigated. We studied alkaloids from the aerial part and roots of C. Olgae collected near Guzar of Kashkadar¢ya district. According to quantitative analysis, a mixture of bases was present in the roots (0.045%) and aerial part (0.03%). Total alkaloids were obtained by CHCl 3 extraction with preliminary wetting of raw material with ammonia solution (5%). Comparative TLC using system 1 of al...