The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.

Abstract

Chemical investigation of a Fijian ascidian, Polyandrocarpa sp., has resulted in the isolation of two new 2-aminoimidazolone-derived compounds, polyandrocarpamines A (1) and B (2). The structures of these unique metabolites were determined by the interpretation of spectroscopic data and confirmed by total synthesis. The stereospecific synthesis of 1 was accomplished using aldol condensation chemistry to generate an arylidene thiohydantoin that was subsequently transaminated to yield polyandrocarpamine A. Demethylation of synthetic 1 afforded polyandrocarpamine B. Both the natural product and synthetic polyandrocarpamines were assigned Z geometries about the exocyclic double bond (C-5/C-7) on the basis of 13 C/ 1 H long-range coupling constants, which were measured using a gHSQMBC experiment.

Marine natural products

“…The ascidian Didemnum molle, collected at Ibo Island north of Mozambique, was the source of the cycloheptapeptide cyclodidemnamide B 669. 522 Coproverdine 678 is a cytotoxic alkaloid isolated by bioassaydirected fractionation of an unidentified ascidian collected at the Three Kings Islands, New Zealand. Localisation studies of the related cyclic peptides patellamides A-C suggested that the natural products are distributed throughout the tunic of the ascidian Lissoclinum patella and not located in the Prochloron sp.…”

Synthesis, characterization and cytotoxicity of palladium(II) complex of 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one

“…10 Thiohydantoins and their derivatives exist in many natural products. [11][12][13] In the past decades, great efforts have been devoted to introducing thiohydantoins and their derivatives into desirable substrates, such as pharmacophores and synthetic intermediates. [14][15][16][17] Compounds containing the thiohydantoin structural motif have been identified to display a wide range of biological activities.…”

Benzylidene 2-Aminoimidazolones Derivatives: Synthesis and <i>in Vitro</i> Evaluation of Anti-tumor Carcinoma Activity

“…The intermediate 4 was reacted with other commercially available material 4-hydroxybenzaldehyde 5a or vanillin 5b to form 6a or 6b by condensation according to the literature. 6,8) Compounds 6a, b was oxidized by tert-butylhydroperoxide (TBHP) to obtain the important intermediate 7a, b. Then corresponding amine, alkane amines or alcohol amines were introduced onto the sulfonic group of compounds 7a, b to obtain the targeted compounds 1a-k, 2a-k.…”

“…3) Polyandrocarpamines A, extracted from a Fijian ascidian, 8) has been shown to have diverse pharmacological activities. 6,9,10) Many recent reports and reviews have also highlighted that Polyandrocarpamines A exhibit potent antitumor activity.…”