Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow

A highly efficient and concise bromocyclization has been successfully achieved,in which tryptamine/tryptophol derivates can be transformed to valuable HPI/TFI scaffolds with economic and green manners.Moreover,a controllable cascade transformation of bromocyclization and aromatic bromination has also been smoothly achieved to form dibrominated HPIs and TFIs.Production could be successfully scaled up under both the batch process and a continuous flow fashion.The most remarkable peculiarity of our process over all previous methods is that the generated water is the major waste.Notably,successful application of this new protocol has been demonstrated by the pharmaceutical and natural products syntheses.

First total synthesis of marine alkaloid hyrtiosulawesine

Hyrtiosulawesine was isolated from Indonesian specimens of the marine sponges Hyrtios erectus and H.reticulatu in 2002.We report here the first total synthesis of hyrtiosulawesine using an efficient and convenient synthetic strategy which could be widely used in the synthesis of otherβ-carboline compounds.All structures of new compounds were confirmed by 1H NMR,13C NMR and HRMS.

DFT-based QSAR and Action Mechanism of Phenylalkylamine and Tryptamine Hallucinogens

DFT/B3LYP/6-311G＋（d,p） basis set including solvent effect was first used to calculate a set of molecular descriptors of 55 phenylalkylamine and 20 tryptamine compounds with hallucinogenic activity. Four quantitative structure-activity relationship （QSAR） models of the hallucinogenic activity for phenylalkylamines and tryptamines were obtained by employing multiple linear regression （MLR） method. The QSAR analysis indicated that electron-related descriptors were major contributors to the hallucinogenic activities of phenylalkylamines and tryp- tamines. In addition, electron-unrelated descriptors have some impact on the hallucinogenic activities of phenylal- kylamines. Based on the results of QSAR study, a novel Conformation Complementary Judgement, Transformation and Induction （CCJTI） model had been proposed to explain different action mechanisms of phenylalkylamines and tryptamines with their target receptors. It was concluded that phenylalkylamines might combine with receptor by electronic effect, but steric factor could affect it also, whereas tryptamines could act only through the electronic effect.

Synthesis of tetrahydro-β-carbolines from phthalic anhydrides and tryptamine

Tetrahydro-b-carbolines with strictosamide skeleton have been synthesized via intermolecular condensation, selective reduction, and intramolecular cyclization starting from phthalic anhydrides and tryptamine. The reactions are carried out under mild conditions with a wide range of substrates and functional groups.