A total synthesis of isoliensinine

Kametani, Tetsuji; Takano, Seiichi; Iida, Hideo; Shinbo, Masafu

doi:10.1039/j39690000298

Cited by 8 publications

(3 citation statements)

References 3 publications

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“…In 1969, Karnetani et al reported the chemical synthesis route of isoliensinine (Kametani et al, 1969; Supplementary Figure S2A). Cyclization of amide 3) obtained by condensation of 4benzyloxy-3-methoxyphenethylamine 1) and 4methoxyphenylacetic acid 2) at 180-190°C underwent a Bischler-Napieralski reaction to yield 3,4-dihydroisoquinoline (4), which further gave rise to 4′-O-methyl-N-methylcoclaurine 7) through multiple reactions (5,6).…”

Section: Chemosynthesis and Biosynthesismentioning

confidence: 99%

Isoliensinine: A Natural Compound with “Drug-Like” Potential

Cheng

Zhou

et al. 2021

Front. Pharmacol.

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Isoliensinine, a bisbenzylisoquinoline alkaloid isolated from Nelumbo nucifera Gaertn, exerts a variety of beneficial effects, such as antitumor, cardioprotective, antioxidant, antidepressant, and anti-HIV effects, and ameliorates T2DM with hyperlipidemia and Alzheimer’s disease. In this article, the recent literature on isoliensinine, including its pharmacology, pharmacokinetics, and synthesis and extraction, is summarized. Moreover, possible future prospects and research directions are also discussed. Studies on isoliensinine were found by searching a combination of keywords including “pharmacology,” “pharmacokinetics,” and “synthesis and extraction” in the main databases, including PubMed, Google Scholar, Web of Science, NCBI, and Wan Fang. Many studies have pointed out that a major limitation of isoliensinine is its poor solubility in aqueous media. Considering its advantages and limitations, isoliensinine can be used as a lead compound to develop novel efficient and low-toxicity derivatives. The available literature indicates that isoliensinine displays “drug-like” potential. Additionally, there are many related issues and novel mechanisms that need to be explored.

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Section: Chemosynthesis and Biosynthesismentioning

confidence: 99%

Isoliensinine: A Natural Compound with “Drug-Like” Potential

Cheng

Zhou

et al. 2021

Front. Pharmacol.

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“…Coclaurine ( 1a ) and its O- benzylated and/or O- methylated derivatives were prepared by the classical Bischler−Napieralski 3,4-dihydroisoquinoline synthesis and subsequent reduction of the intermediates with NaBH 4 , − followed in most cases by N- alkylation. N- Methylation was best carried out with aqueous formaldehyde and NaBH 4 , ,, and N- ethylation and N- propylation were performed by treating the secondary amines with ethyl iodide or propyl bromide in acetonitrile containing NaHCO 3 , respectively. 12- O- Benzylcoclaurine ( 9a ) was prepared conveniently by selective debenzylation of 7,12- O,O ‘ -dibenzylcoclaurine ( 6a ) with SnCl 4 …”

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confidence: 99%

Simplified Tetrandrine Congeners as Possible Antihypertensive Agents with a Dual Mechanism of Action

et al. 2003

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A series of O- and/or N-substituted derivatives of (+/-)-coclaurine (1a) were synthesized as simplified structural mimics of the antihypertensive alkaloid tetrandrine (2) and assayed for binding to brain cortical sites labeled with the alpha(1)-adrenergic radioligand [(3)H]prazosin or the calcium channel radioligand [(3)H]diltiazem. The introduction of O-benzyl groups on the coclaurine molecule, which exhibits only adrenergic antagonist activity, led to the appearance of calcium channel blocking activity comparable to that of tetrandrine while retaining adrenolytic activity in the same concentration range. Contraction of aortal rings with noradrenaline or KCl was relaxed more potently by some of these coclaurine derivatives than by tetrandrine, suggesting leads for the development of novel antihypertensive drugs with a dual mechanism of action.

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“…From the viewpoint of the structure-activity relationship, we synthesized three stereoisomers of neferine and O-methylneferine, 5,13,14) and examined these pharmacological activities.…”

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confidence: 99%