Isolation and X-ray crystal structure of a novel bromo-compound from two marine sponges

Cimino, Guido; Rosa, Salvatore De; Stefano, S. De; Mazzarella, L.; Puliti, R.; Sodano, G.

doi:10.1016/s0040-4039(00)86943-9

Cited by 132 publications

(73 citation statements)

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“…The unequivocal X-ray crystal structure of hymenialdisine was nicely established by Cimino et al (5) and reconfirmed in the following year by the Kitagawa group (6). In turn, these advances simplified characterization of the companion substance from Axinella sp., herein named axinohydantoin (2), as a closely related compound.…”

Section: Introductionmentioning

confidence: 83%

See 1 more Smart Citation

Antineoplastic agents. 168. Isolation and structure of axinohydantoin

Pettit¹,

Herald²,

Leet³

et al. 1990

Can. J. Chem.

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Western (Palau) and Eastern (State of Truk) Caroline Islands and Papua New Guinea sponges of the genera Axinella and Hymeniacidon were found to contain the cytostatic (PS ED50 2.5 and 2.0 (μg/mL) and antineoplastic (PS T/C 143 at 3.6 mg/kg and T/C 138 at 3.6 mg/kg) pyrrologuanidines 1a and 1b. The related hydantoin 2, designated axinohydantoin, was also isolated from an Axinella sp. and its structure was assigned by X-ray crystallographic techniques. Present experience with sponges in the Axinella and Hymeniacidon genera suggests that the previously known hymenialdisine (1b) and analogous imidazole derivatives may be widely distributed among these and related orange colored Porifera. Keywords: axinohydantoin, hymenialdisine, Axinella, Hymeniacidon, cystostatic.

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Section: Introductionmentioning

confidence: 83%

“…ref. 5. Perhaps the initial negative results were due to the sparingly soluble properties of this pyrrologuanidine.…”

Section: Introductionmentioning

confidence: 99%

Antineoplastic agents. 168. Isolation and structure of axinohydantoin

Pettit¹,

Herald²,

Leet³

et al. 1990

Can. J. Chem.

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“…The azepinoindole template has been found to be present in the marine sponge metabolite hymenialdisine [1] (1) and in paullone [2] (2), a synthetic benzazepinoindolone undergoing clinical trials [3] as an anticancer agent. Both compounds were found to be a potent kinase inhibitor of several related cyclin-dependent kinases (CDKs), [4] and hymenialdisine also exhibits potent antiproliferative, antineurodegenerative, and anti-inflammatory activities in various cell lines and animal models (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Application of 7‐endo‐trig Pictet–Spengler Cyclization to the Formation of the Benzazepine Ring: Synthesis of Benzazepinoindoles

Sharma

Agarwal

et al. 2009

Eur J Org Chem

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The preparation of benzazepinoindoles, fused heterocycles with a benzazepine moiety, was accomplished through an intramolecular 7‐endo‐trig Pictet–Spengler cyclization. The precursors comprising C‐3‐ or C‐2‐linked o‐aminobenzylindoles required for the cyclization were obtained either by treating indoles with o‐nitrobenzyl bromide followed by reduction of the nitro group or by treating 2‐nitrophenylacetic acid with DCC/DMAP followed by reduction of the aryl nitro functionality. Resulting substrates 5 and 6 were then subjected to the 7‐endo‐trig Pictet–Spengler reaction with a variety of aldehydes and ketones to furnish new polycyclic structures benzazepinoindoles. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…Chemistry/bioactivity: S. aurantium is a good source of hymenialdisine 163 and debromohymenialdisine 164, compounds that were first described from Axinella verrucosa and Acanthella auriantica by Cimino et al, 122 and also from Hymeniacidon aldis, 123 and Phakellia flabellata. 124 In addition, the 10E-geometrical isomers were reported as minor constituents of the sponge in 1996.…”

Section: Stylotella Aurantiummentioning

confidence: 99%