β-Phenylethylamines and the isoquinoline alkaloids

Abstract

This review covers beta-phenylethylamines and isoquinoline alkaloids and compounds derived from them, including further products of oxidation, condensation with formaldehyde and rearrangement, some of which do not contain an isoquinoline system, together with naphthylisoquinoline alkaloids, which have a different biogenetic origin. The occurrence of the alkaloids, with the structures of new bases, together with their reactions, syntheses and biological activities are reported. The literature from July 2001 to June 2002 is reviewed, with 581 references cited.

Cytotoxicity of Aporphine, Protoberberine, and Protopine Alkaloids from Dicranostigma leptopodum (Maxim.) Fedde

“…Compounds 5 and 6 were reported to have weak cytotoxicity, such as nontoxic to KB cells, but showed activities in inhibiting cell proliferation of hepatocellular carcinoma [14–18]. The result was consistent with the literature that compound 7 often showed better cytotoxicity than compound 8 against cancer cell lines such as A549, HT-29, KB, and P-388 [19–21]. …”

Metal‐Free Cross‐Dehydrogenative Coupling of Heterocycles with Aldehydes

“…Isoquinoline alkaloids are widely distributed in nature and exhibit important biological and medicinal properties. [3] Moreover, acylated heterocycles are present in numerous drugs and pharmacologically significant biological probes. In this context, we envisaged that the developed method for C À H bond functionalization would provide rapid access to natural alkaloids from simple, widely available chemicals, thus representing an improvement on traditional multistep approaches.…”

“…Nitrogen-containing heterocycles are abundant in nature and have extensive applications in chemistry and biology. [3] Numerous methods for the de novo synthesis of electrondeficient heterocycles have been described, but their functionalization by cross-dehydrogenative coupling is far less studied. In contrast to the acylation of electron-rich aromatic compounds (Friedel-Crafts reaction), very few methods are available for the acylation of electron-deficient heterocycles.…”

1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae)

“…13 1 H /2 pulse, 9.0 µs; 13 C /2 pulse, 11.6 µs; proton domain (F 2 ) spectral width, 2.5 kHz; data points, 2K; acquisition time, 0.41 s; digital resolution, 2.44 Hz; relaxation delay, 1.9 s; four transients per increment; 13 C decoupling during the acquisition by GARP; 13 C domain (F 1 ) spectral width, 12.5 kHz; 128 increments; resolution, 97 Hz per data point; zero-filled to 512 data points; /2 shifted sine-bell squared (QSINE, SSB D 2) weighting function in both dimensions. Typical gradient-selected 1 …”