Literature DB >> 33540725

The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly.

Nan Hu1, Lorenzo V White1, Ping Lan1, Martin G Banwell1.   

Abstract

The title alkaloids, often referred to collectively as crinines, are a prominent group of structurally distinct natural products with additional members being reported on a regular basis. As such, and because of their often notable biological properties, they have attracted attention as synthetic targets since the mid-1950s. Such efforts continue unabated and more recent studies on these alkaloids have focused on using them as vehicles for showcasing the utility of new synthetic methods. This review provides a comprehensive survey of the nearly seventy-year history of these synthetic endeavors.

Entities:  

Keywords:  alkaloid; crinine; haemanthamine

Mesh:

Substances:

Year:  2021        PMID: 33540725      PMCID: PMC7867252          DOI: 10.3390/molecules26030765

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  47 in total

1.  Total Synthesis of (±)-Crinane from 6,6-Dibromobicyclo[3.1.0]hexane Using a 5- exo- trig Radical Cyclization Reaction to Assemble the C3a-Arylated Perhydroindole Substructure.

Authors:  Ping Lan; Martin G Banwell; Anthony C Willis
Journal:  J Org Chem       Date:  2018-06-07       Impact factor: 4.354

2.  In Vitro Inhibitory Effects of 8-O-Demethylmaritidine and Undulatine on Acetylcholinesterase and Their Predicted Penetration across the Blood-Brain Barrier.

Authors:  Lucie Cahlíková; Daniel I Pérez; Šárka Štěpánková; Jakub Chlebek; Marcela Šafratová; Anna Hošt'álková; Lubomír Opletal
Journal:  J Nat Prod       Date:  2015-06-01       Impact factor: 4.050

3.  Synthesis and antimalarial activity of new haemanthamine-type derivatives.

Authors:  Juan C Cedrón; David Gutiérrez; Ninoska Flores; Ángel G Ravelo; Ana Estévez-Braun
Journal:  Bioorg Med Chem       Date:  2012-07-31       Impact factor: 3.641

4.  Construction of a chiral quaternary carbon center by catalytic asymmetric alkylation of 2-arylcyclohexanones under phase-transfer conditions.

Authors:  Taichi Kano; Yumi Hayashi; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2013-05-02       Impact factor: 15.419

5.  Bulbispermine: a crinine-type Amaryllidaceae alkaloid exhibiting cytostatic activity toward apoptosis-resistant glioma cells.

Authors:  Giovanni Luchetti; Robert Johnston; Véronique Mathieu; Florence Lefranc; Kathryn Hayden; Anna Andolfi; Delphine Lamoral-Theys; Mary R Reisenauer; Cody Champion; Stephen C Pelly; Willem A L van Otterlo; Igor V Magedov; Robert Kiss; Antonio Evidente; Snezna Rogelj; Alexander Kornienko
Journal:  ChemMedChem       Date:  2012-03-02       Impact factor: 3.466

6.  A general and efficient strategy for 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids: total syntheses of (+/-)-gamma-lycorane and (+/-)-crinane.

Authors:  Shuanhu Gao; Yong Qiang Tu; Zhenlei Song; Aixia Wang; Xiaohui Fan; Yijun Jiang
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

7.  Total syntheses of (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a-epi-crinamine via the regioselective synthesis and Diels-Alder reaction of 3-aryl-5-bromo-2-pyrone.

Authors:  Thanh Tam Nguyen; Jayhyok Chang; Eun-Ju Jung; Cheon-Gyu Cho
Journal:  J Org Chem       Date:  2008-07-16       Impact factor: 4.354

Review 8.  Mesembrine alkaloids: Review of their occurrence, chemistry, and pharmacology.

Authors:  John L Krstenansky
Journal:  J Ethnopharmacol       Date:  2016-12-07       Impact factor: 4.360

9.  Gigantelline, gigantellinine and gigancrinine, cherylline- and crinine-type alkaloids isolated from Crinum jagus with anti-acetylcholinesterase activity.

Authors:  Seydou Ka; Marco Masi; Natacha Merindol; Roberta Di Lecce; Mélodie B Plourde; Matar Seck; Marcin Górecki; Gennaro Pescitelli; Isabel Desgagne-Penix; Antonio Evidente
Journal:  Phytochemistry       Date:  2020-04-23       Impact factor: 4.072

10.  The effect of Amaryllidaceae alkaloids haemanthamine and haemanthidine on cell cycle progression and apoptosis in p53-negative human leukemic Jurkat cells.

Authors:  Radim Havelek; Martina Seifrtova; Karel Kralovec; Lenka Bruckova; Lucie Cahlikova; Marketa Dalecka; Jirina Vavrova; Martina Rezacova; Lubomir Opletal; Zuzana Bilkova
Journal:  Phytomedicine       Date:  2013-10-29       Impact factor: 5.340

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