Biomimetic synthesis of an antitumour indole sesquiterpene alkaloid, 12-epi-ent-pentacyclindole

Marcos, Isidro S.; Moro, Rosalina F.; Costales, Isabel; Basabe, P.; Dı́ez, David; Mollinedo, Faustino; Urones, Julio G.

doi:10.1016/j.tet.2013.06.075

Cited by 16 publications

(11 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…ent-Halimic acid methyl ester, 38, has been used as a starting material for the synthesis of several terpene-alkaloids, such as (+)-agelasine C, 39, (Scheme 1) [45,[69][70][71][72][73]. With this synthesis, the authors were able to establish the structure and absolute configuration of the natural product (−)-agelasine C, 40, correcting the structure originally proposed for epi-agelasine C, for this one was proposed the structure of 41 [45].…”

Section: Halimane-purine Synthesis (+)-Agelasine Cmentioning

confidence: 99%

Antibacterial Natural Halimanes: Potential Source of Novel Antibiofilm Agents

et al. 2020

Self Cite

View full text Add to dashboard Cite

The development of new agents against bacteria is an urgent necessity for human beings. The structured colony of bacterial cells, called the biofilm, is used to defend themselves from biocide attacks. For this reason, it is necessary to know their structures, develop new agents to eliminate them and to develop new procedures that allow an early diagnosis, by using biomarkers. Among natural products, some derivatives of diterpenes with halimane skeleton show antibacterial activity. Some halimanes have been isolated from marine organisms, structurally related with halimanes isolated from Mycobacterium tuberculosis. These halimanes are being evaluated as virulence factors and as tuberculosis biomarkers, this disease being one of the major causes of mortality and morbidity. In this work, the antibacterial halimanes will be reviewed, with their structural characteristics, activities, sources and the synthesis known until now.

show abstract

Section: Halimane-purine Synthesis (+)-Agelasine Cmentioning

confidence: 99%

Antibacterial Natural Halimanes: Potential Source of Novel Antibiofilm Agents

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…Tessmannic acid (220) and its methyl ester (221) exhibit antibacterial and antifungal activity. 82,184 Butanolides 225, 226 and 230 are biologically active as antitumour agents.…”

Section: Secohalimenes and Norhalimenes Groupmentioning

confidence: 99%

“…217 7Sesqui-and diterpene-alkaloids. 128,[218][219][220][221][222] Synthesis from ent-halimic acid methyl ester (39) of several natural halimanes, such as ent-halimanolides, chettaphanin I and II and agelasine C (a diterpene-purine derivative), will be commented on in the following points. These syntheses have made it possible to corroborate their structures.…”

Section: Ent-halimic Acid As Precursor Of Biologically Active Compounmentioning

confidence: 99%

Halimane diterpenoids: sources, structures, nomenclature and biological activities

et al. 2018

Self Cite

View full text Add to dashboard Cite

Covering: 1970 to 2017 Diterpenes with a halimane skeleton constitute a small group of natural products that can be biogenetically considered as being between labdane and clerodane diterpenoids. Some of these compounds show biological activities, such as antitumour, mosquito repellency, germination inhibition and antimicrobial, as well as being biomarkers for tuberculosis. To the best of our knowledge, there are no reviews on these compounds. In this review, halimane skeleton diterpenoids are classified according to their biogenetic origin, characterization and/or the enzymes involved in their biosynthesis. Herein, a review of their synthesis or synthetic approaches is communicated.

show abstract

“…Figure 5 shows some of the diterpene or sesquiterpene derivatives synthesized from ent -halimic acid: 1. ent -halimanolides [2,56,57,58]; 2. chettaphanin I and II [4,5]; 3. sesterterpenolides [6,59,60]. Figure 6 shows other groups of compounds prepared from 2 , among which are as follows: 4. hybrid compounds: sesterterpenolide bioconjugates and glycerophospholipids [61]; 5. rearranged derivatives: ent -labdanes [62], abeopicrasanes [63], and a propellane [64]; 6. sequiterpene-quinone/hidroquinones [65]; 7. terpene alkaloids: sesqui- and diterpene-alkaloids [7,8,66,67,68,69].…”

Section: Ent-halimic Acid As a Precursor Of Biologically Active Comentioning

confidence: 99%

The Methylene-Cycloalkylacetate (MCA) Scaffold in Terpenyl Compounds with Potential Pharmacological Activities

et al. 2019

Self Cite

View full text Add to dashboard Cite

Recently, the methylene-cycloakylacetate (MCA) scaffold has been reported as a potential pharmacophore for neurite outgrowth activity. In this work, natural diterpenes that embed MCA fragments are reviewed, as they are major components of Halimium viscosum: ent-halimic acid, the prototype for these bioactive compounds. Herein, structures, sources, and activities for the natural diterpenes, as well as their synthetic derivatives of interest, are reviewed.

show abstract

Biomimetic synthesis of an antitumour indole sesquiterpene alkaloid, 12-epi-ent-pentacyclindole

Cited by 16 publications

References 26 publications

Antibacterial Natural Halimanes: Potential Source of Novel Antibiofilm Agents

Antibacterial Natural Halimanes: Potential Source of Novel Antibiofilm Agents

Halimane diterpenoids: sources, structures, nomenclature and biological activities

The Methylene-Cycloalkylacetate (MCA) Scaffold in Terpenyl Compounds with Potential Pharmacological Activities

Contact Info

Product

Resources

About