Total Synthesis of Kuanoniamine A, 11-Hydroxyascididemin, and Neocalliactine Acetate

Kitahara, Yoshiyasu; Nakahara, Shinsuke; Yonezawa, T.; Nagatsu, Masanori; Kubo, Akinori

doi:10.3987/com-92-6321

Cited by 20 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ascididemin 131.2 , one of the most prominent examples of pyridoacridine alkaloids, was first synthesized in 1989 by Bracher, who performed self-condensation of enamine 131.6 to close ring E in the final step (Scheme ). This approach enabled the synthesis of related alkaloids, such as 2-bromoleptoclinidone, neocalliactine acetate, and kuanoniamine A , ( 131.3 – 5 ), as well as several synthetic analogues. − A refinement of the Bracher synthesis, in which the final ring closure was achieved by reaction with paraformaldehyde, was reported by Copp and co-workers. − Mechanistically related syntheses of 131.2 were reported by the groups of Kashman and Echavarren . The Kashman route ,, is particularly efficient because it closes two rings in a single reaction step, and enables the synthesis of analogues with extended fusion, such as benzoascididemin or 131.15 .…”

Section: Phenalenoidsmentioning

confidence: 98%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

View full text Add to dashboard Cite

Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

show abstract

Section: Phenalenoidsmentioning

confidence: 98%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The organic extracts were dried on MgSO4 and concentrated over a vacuum to give the pentacyclic compound 6 as a yellow solid (1.62 g, 70%); mp 224 °C. 1 (18); 327 (100); 299 (22); 297 (9); 269 (10); 253 (24); 242 (11); 241 (33). tR is 8.51 min (97% purity), using system I, and tR is 11.99 min (100% purity), using system II.…”

Section: -(2-acetyl-4-benzylamino-phenylamino)quinoline-58dione (A18)mentioning

confidence: 99%

“…The mixture was extracted with CH2Cl2, and the organic layer was dried over MgSO4 and concentrated to dryness to give the expected amino compound as a blue solid (0.32 g, 88%); mp > 260 °C. (11); 268 (8). tR was 3.47 min (99% purity) using system I and 4.99 min (97% purity) using system II.…”

Section: -(2-acetyl-4-benzylamino-phenylamino)quinoline-58dione (A18)mentioning

confidence: 99%

“…Some substituted ascididemins such as bromoleptoclinidone 2 , 11-hydroxyascididemin 3 , and neocalliactine 4 were also isolated from marine sources, whereas 11-methoxyascididemin 5 , 1- and 3-nitroascididemins ( 6 and 7 ), and ring E-substituted ascididemins were obtained by total synthesis. Bracher and Kitahara et al , have described 3-methoxyascididemin 16 as an intermediate product in two separate total synthesis processes of neocalliactine 4 (Figure ).

1 (a) Numbered according to IUPAC nomenclature rules.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and In Vitro Antitumor Activity of Novel Ring D Analogues of the Marine Pyridoacridine Ascididemin: Structure−Activity Relationship

et al. 2002

View full text Add to dashboard Cite

Marine compounds with pyridoacridine skeletons are known to exhibit interesting antitumor activities. Ascididemin has already been reported as displaying significant antitumor activities in vitro and has also been found to have a relatively high global toxicity in vivo. We synthesized a series of 16 analogues (among which 11 compounds were different from previously described ones) with the aim of developing new anticancer agents with significantly improved efficacy/tolerability ratios. These compounds were obtained either by total synthesis from 5,8-quinolinedione and substituted 2-aminoacetophenones or by the direct substitution of ascididemin. The different compounds and ascididemin used as the control compound were tested at six different concentrations on 12 different human cancer cell lines of various histopathological types (glioblastomas and breast, colon, lung, prostate, and bladder cancers). The IC(50) value (i.e., the drug concentration inhibiting the mean growth value of the 12 cell lines by 50%) of these compounds ranged over five log concentrations, i.e., between 10 000 and 0.1 nM. For several new chemical entities, the antitumor activity (determined in vitro) and tolerability (determined in vivo) were superior to those of the parent alkaloids, i.e., ascididemin and 2-bromoleptoclinidone.

show abstract

Ascidians (Tunicates)–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

View full text Add to dashboard Cite

The article contains sections titled: Metabolites of Polyclinidae Long‐Chain Sulfated Alkanes and Terpenes of Sidnyum turbinatum Terpenes and Meroterpenes Para‐ and Metacyclophanes: Longithorones and Related Derivatives Simple Aromatic Derivatives Nitrogenous and Non‐Nitrogenous Macrolides Long‐Chain Amines and Amino Alcohols, Sphingosines Piperidine Alkaloids: Pseudodistomins Indole and β‐Carboline Alkaloids Quinoline and Pyridoacridine Alkaloids Bis‐Steroidal Alkaloids of Ritterella tokioka : Ritterazines Purines and Nucleosides Miscellaneous Nitrogenous Derivatives Metabolites of Ascidiidae Vanadium, Intracellular Acidity of Blood Cells, and Peptide Ligands Metabolites of Cionidae Metabolites of Diazonidae Metabolites of Perophoridae Metabolites Isolated from Species of the Genus Perophora Tetrahydroisoquinoline Alkaloids: Ecteinascidins Metabolites of Molgulidae and Pyuridae Lipids and Non‐Nitrogenous Derivatives Nitrogenous Derivatives, Antimicrobial Peptides, and Proteins Metabolites of Styelidae Non‐Nitrogenous Derivatives Phenylethylamine Derivatives, Various Alkaloids Antibacterial Purines and Peptides

show abstract

Total Synthesis of Kuanoniamine A, 11-Hydroxyascididemin, and Neocalliactine Acetate

Cited by 20 publications

References 0 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Synthesis and In Vitro Antitumor Activity of Novel Ring D Analogues of the Marine Pyridoacridine Ascididemin: Structure−Activity Relationship

Ascidians (Tunicates)–2

Contact Info

Product

Resources

About