Bisbenzylisoquinoline alkaloids

Толкачев, О. Н.; Nakova, E. P.; Evstigneeva, R. P.

doi:10.1007/bf00565820

Cited by 6 publications

(14 citation statements)

References 124 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The combined organic phases are washed with water (150 mL) and dried over Na 2 SO 4 . After filtration, the solvent is removed in vacuo and furnishes the product (44.7 28 2-[4-(Benzyloxy)-3-methoxyphenyl]ethylamine (8). Synthesized according to a modified procedure of Bermejo et al 29 To a suspension of lithium aluminum hydride (7.97 g, 210 mmol, 4.0 equiv) in anhydrous THF (200 mL) at 0 °C, 1-(benzyloxy)-2-methoxy-4-[(E)-2-nitroethenyl]benzene (15.0 g, 52.6 mmol, 1.0 equiv) dissolved in THF (200 mL) is added dropwise.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…While the bisbenzylisoquinoline alkaloids in general exhibit a wide variety of biological activities, only little is known about the biological activity of the other curare alkaloids. Nevertheless, this subgroup has been a target for total synthesis for decades, and first attempts were made by Kataoka, by Hellmann and Elser, as well as by Tolkachev and co-workers . In 1979, Naghaway and Soine reported the total synthesis of semisynthetic (+)-tubocurarine ((+)- 1 ) by using natural tubocurarine which was N-demethylated to (+)-tubocurine ((+)- 2 ) by sodium thiophenolate and subsequently remethylated to result in (+)-tubocurarine ((+)- 1 ) again …”

Section: Introductionmentioning

confidence: 99%

“…Nevertheless, this subgroup has been a target for total synthesis for decades, and first attempts were made by Kataoka, 6 by Hellmann and Elser, 7 as well as by Tolkachev and co-workers. 8 In 1979, Naghaway and Soine reported the total synthesis of semisynthetic (+)-tubocurarine ((+)-1) by using natural tubocurarine which was N-demethylated to (+)-tubocurine ((+)-2) by sodium thiophenolate and subsequently remethylated to result in (+)-tubocurarine ((+)-1) again. 9 We aimed to develop a modular synthetic strategy toward the group of curare alkaloids to establish structure−activity relationships to these alkaloids.…”

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine

2017

View full text Add to dashboard Cite

Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.

show abstract

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine

2017

View full text Add to dashboard Cite

show abstract

“…The bisbenzylisoquinoline alkaloids (BBA) constitute a large group of natural products widely distributed in plants of several families, including: Menispermaceae, Berberidaceae, Lauraceae, Annonaceae, Ranunculaceae, Hernandiaceae, Magnoliaceae and Nymphaeaceae [3]. These substances are characterized by presenting two benzylisoquinoline subunits, each one with three rings, joined by one or more ether bridges [4].…”

Section: Curine a Bisbenzylisoquinoline Alkaloidmentioning

confidence: 99%

Anti-Allergic Properties of Curine, a Bisbenzylisoquinoline Alkaloid

2015

View full text Add to dashboard Cite

Curine is a bisbenzylisoquinoline alkaloid isolated from Chondrodendron platyphyllum (Menispermaceae). Recent findings have shed light on the actions of curine in different models of allergy and inflammation. Here we review the properties and mechanisms of action of curine focusing on its anti-allergic effects. Curine pre-treatment significantly inhibited the scratching behavior, paw edema and systemic anaphylaxis induced by either ovalbumin (OVA) in sensitized animals or compound 48/80, through mechanisms of mast cell stabilization and inhibition of mast cell activation to generate lipid mediators. In addition, oral administration of curine significantly inhibited eosinophil recruitment and activation, as well as, OVA-induced airway hyper-responsiveness in a mouse model of asthma, through inhibition of the production of IL-13 and eotaxin, and of Ca 2+ influx. In conclusion, curine exhibit anti-allergic effects in models of lung, skin and systemic allergy in the absence of significant toxicity, and as such has the potential for anti-allergic drug development.

show abstract

“…Although the literature is abundant with numerous chemical and phytochemical studies of various Thalictrum species (3)(4)(5), the only references to previous work on T. foliolosum reported the isolation of the quaternary protoberberine alkaloids berberine, jatrorrhizine and palmatine (6) and the quaternary aporphine alkaloid magnoflorine (7,8) from extracts of the rhizomes. The genus Thalictrum has been a particularly rich source of benzylisoquinoline-derived alkaloids with over 100 different alkaloids having been isolated and characterized by the end of the last decade (9).…”

mentioning

confidence: 99%