Sophazrine--a Novel Quinolizidine Alkaloid from Sophora griffithii

Atta-ur-Rahman, _; Pervin, Azra; Choudhary, M. Iqbal; Hasan, Nahid; Şener, Bilge

doi:10.1021/np50076a001

Cited by 18 publications

(2 citation statements)

References 11 publications

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“…For theoretical studies of anagyrine and the crystal structure of anagyrine hydrochloride monohydrate, see: Galasso et al (2006). For a related crystal structure, see: Atta-ur-Rahman et al (1991…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of anagyrine perchlorate

et al. 2015

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The title molecular salt, C15H21N2O+·ClO4 −, crystallizes with four cations (A, B, C and D) and four anions in the chiral unit cell (space group P21). The alkaloid was isolated from the aerial parts of Genista Hispanica collected in the Samarkand region of Uzbekistan. Each cation is protonated at the N atom that bridges the alkaloid rings C and D. In each cation, ring A is almost planar and ring B adops a sofa conformation with the methylene group bridging to the C ring as the flap. Rings C and D adopt chair conformations with a cis ring junction in all four cations. In the crystal, A+B and C+D dimeric pairs linked by pairs of N—H⋯O hydrogen bonds are observed, which generate R 2 2(16) loops in each case. The dimers are consolidated by weak aromatic π–π stacking interactions between the A rings [centroid–centroid distances = 3.913 (3) and 3.915 (3) Å].

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Section: Related Literaturementioning

confidence: 99%

Crystal structure of anagyrine perchlorate

et al. 2015

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“…Plants of the genus Sophora (Leguminosae) are known to contain structurally diverse and biologically active quinolizidine alkaloids. − Phytochemical investigations of these plants have led to the isolation of a number of quinolizidine alkaloids, such as matrine-type, sparteine-type, cytisine-type, and aloperine-type alkaloids, − some of which exhibit antiviral, , anti-inflammatory, and antitumor activities. Owing to the interesting structures and diverse bioactivities of these alkaloids, these compounds have attracted the attention of increasing numbers of chemists for the development of synthetic strategies.…”

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Sophalines E–I, Five Quinolizidine-Based Alkaloids with Antiviral Activities against the Hepatitis B Virus from the Seeds of Sophora alopecuroides

et al. 2018

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Five novel quinolizidine-based alkaloids (1-5) were obtained from the seeds of Sophora alopecuroides L. Compounds 1 and 2 are the first examples of sparteine-indolizine and matrine-indolizine alkaloids, respectively, whereas 3 and 4 are epimeric normatrine-julolidine alkaloids with unusual skeletons. The structures of these compounds were determined by spectroscopic methods, single-crystal X-ray diffraction, and electronic circular dichroism analyses. Hypothetical biosynthetic pathways of 1-5 were proposed. Compound 2 exhibited significant antiviral activity against the hepatitis B virus.

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A Flexible Strategy for the Synthesis of Tri‐ and Tetracyclic Lupin Alkaloids: Synthesis of (+)‐Cytisine, (±)‐Anagyrine, and (±)‐Thermopsine

Gray

Gallagher

2006

Angewandte Chemie

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Sophazrine--a Novel Quinolizidine Alkaloid from Sophora griffithii

Cited by 18 publications

References 11 publications

Crystal structure of anagyrine perchlorate

Crystal structure of anagyrine perchlorate

Sophalines E–I, Five Quinolizidine-Based Alkaloids with Antiviral Activities against the Hepatitis B Virus from the Seeds of Sophora alopecuroides

A Flexible Strategy for the Synthesis of Tri‐ and Tetracyclic Lupin Alkaloids: Synthesis of (+)‐Cytisine, (±)‐Anagyrine, and (±)‐Thermopsine

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