Synthesis of N-(2-aminoethyl)- and N-(3-aminopropyl)cytisine

Quinolizidine Alkaloids with Antitomato Spotted Wilt Virus and Insecticidal Activities from the Seeds of Thermopsis lanceolata R. Br

“…29 Thermseedline E (5) was given a molecular formula of C 17 H 19 N 3 O 2 by HRESIMS (m/z 320.1370 [M + Na] + , calcd for 320.1366). The 1 H and 13 C NMR spectra of 5 resembled those of cytisine (18). 13 The notable difference was the existence of an additional pyridin-2-ylmethanol component in 5, which was determined by the 1 Moreover, the correlations of H-19/H 2 -13a (H 2 -13b) indicated that both protons were cofacial (Figure 4).…”

“…Further separation of the crude alkaloids yielded 17 new QAs ( 1 – 17 ), including three new naturally occurring compounds ( 15 – 17 ), along with 15 known compounds ( 18 – 32 ) (Figure ). In addition, known analogues were identified as N -(β- d -glucopyranosyl) cytisine ( 17 ), cytisine ( 18 ), N -methylcytisine ( 19 ), (−)-12-hydroxycytisine ( 20 ), N -formylcytisine ( 21 ), N -acylcytisine ( 22 ), methyl ester of N -cytisinylacetic acid ( 23 ), cytisine-12-carbamide ( 24 ), thermopsine ( 25 ), 13β - hydroxythermopsine ( 26 ), anagyrine ( 27 ), epibaptifoline ( 28 ), baptifoline ( 29 ), (+)-5,6-dehydrolupanine ( 30 ), (−)­lupanine ( 31 ), and sparteine N1-oxide ( 32 ) …”

Quinolizidine Alkaloids and Isoflavones from the Herb of Thermopsis lupinoides and Their Antiviral, Antifungal, and Insecticidal Activities

“…Identification of known compounds done on the basis of the spectroscopic data as well as a comparison with those found in the literature as argentine ( 15 ), [(3-hydroxy-6-pyridinyl)-methyl]-cytisine ( 16 ), N -acetonylcytisine ( 17 ), N -(3-oxobutyl)­cytisine ( 18 ), (−)-rhombifoline ( 19 ), methyl ester of 3-( N -cytisinyl)­propanoic acid ( 20 ), thermseedline P ( 21 ), methyl ester of N -cytisinylacetic acid ( 22 ), thermseedline P ( 23 ), cytisine ( 24 ), N -methylcytisine ( 25 ), N -formylcytisine ( 26 ), N -acylcytisine ( 27 ), (−)-12-hydroxycytisine ( 28 ), cytisine-12-carbamide ( 29 ), thermseedline K ( 30 ), thermopsine ( 31 ) (Figure ), 13β-hydroxylthermopsine ( 32 ), thermseedline O ( 33 ), anagyrine ( 34 ), epibaptifoline ( 35 ), baptifoline ( 36 ), 13β-acetoxyanagyrine ( 37 ), (−)-lupanine ( 38 ), (+)-5,6-dehydrolupanine ( 39 ), daidzein ( 40 ), isoformononetin ( 41 ), 3 ′ ,4 ′ ,7-trihydroxyisoflavone ( 42 ), 4 ′ ,7-dihydroxy-3 ′ -methoxyisoflavone ( 43 ), cabreuvin ( 44 ), orobol ( 45 ), genistein ( 46 ), formononetin ( 47 ), 4 ′ ,7-dimethoxy-5-hydroxyisoflavone ( 48 ), 3 ′ -hydroxyglycitein ( 49 ), glycitein ( 50 ), 7-hydroxy-3-(4-hydroxy-phenyl)-5-methoxy-chromen-4-one ( 51 ), erythrinin B ( 52 ), and ononin ( 53 ) …”

“…Thermlupine J (10) was assigned the molecular formula C 15 H 18 N 2 O, which was established based on the HRESIMS spectrum (m/z 243.1484 [M + H] + , calcd for 243.1492). The NMR data indicated that 10 was homologue of thermopsine (31). The 1 H− 1 H COSY correlations of H 2 -12/H-13/H-14/ H 2 -15 (Figure 2) demonstrated that an extra double bond was fused between C-13 (δ C 123.9) and C-14 (δ C 123.8) in 10.…”