210880-88-9Relevant academic research and scientific papers
Chichibabin/isoChichibabin pyridinium synthesis of ma'edamines C and D
Hirose, Mika,Tanaka, Nao,Usuki, Toyonobu
, (2021/06/22)
Ma'edamines C and D were isolated from an Okinawan marine sponge and exhibited a unique tetrasubstituted pyridinium skeleton. The proposed biosynthetic pathway is similar to that of desmosine and isodesmosine, which are elastin-crosslinking amino acids. In this study, first total synthesis of ma'edamines C and D was achieved via Pr(OTf)3-promoted Chichibabin/isoChichibabin pyridinium synthesis starting from the corresponding aldehydes and amine.
Synthesis and antiproliferative activity of marine bromotyrosine purpurealidin I and its derivatives
Bhat, Chinmay,Ilina, Polina,Tilli, Irene,Vorá?ová, Manuela,Bruun, Tanja,Barba, Victoria,Hribernik, Nives,Lillsunde, Katja-Emilia,M?ki-Lohiluoma, Eero,Rüffer, Tobias,Lang, Heinrich,Yli-Kauhaluoma, Jari,Kiuru, Paula,Tammela, P?ivi
, (2018/12/13)
The first total synthesis of the marine bromotyrosine purpurealidin I (1) using trifluoroacetoxy protection group and its dimethylated analog (29) is reported along with 16 simplified bromotyrosine derivatives lacking the tyramine moiety. Their cytotoxici
Synthesis of novel purpurealidin analogs and evaluation of their effect on the cancer-relevant potassium channel KV10.1
Moreels, Lien,Bhat, Chinmay,Vorá?ová, Manuela,Peigneur, Steve,Goovaerts, Hannah,M?ki-Lohiluoma, Eero,Zahed, Farrah,Pardo, Luis A.,Yli-Kauhaluoma, Jari,Kiuru, Paula,Tytgat, Jan
, (2017/12/15)
In the search for novel anticancer drugs, the potassium channel KV10.1 has emerged as an interesting cancer target. Here, we report a new group of KV10.1 inhibitors, namely the purpurealidin analogs. These alkaloids are produced by the Verongida sponges and are known for their wide variety of bioactivities. In this study, we describe the synthesis and characterization of 27 purpurealidin analogs. Structurally, bromine substituents at the central phenyl ring and a methoxy group at the distal phenyl ring seem to enhance the activity on KV10.1. The mechanism of action of the most potent analog 5 was investigated. A shift of the activation curve to more negative potentials and an apparent inactivation was observed. Since KV10.1 inhibitors can be interesting anticancer drug lead compounds, the effect of 5 was evaluated on cancerous and non-cancerous cell lines. Compound 5 showed to be cytotoxic and appeared to induce apoptosis in all the evaluated cell lines.
Synthesis of cyanoformamides from primary amines and carbon dioxide under mild conditions. Synthesis of ceratinamine
Garcia-Egido, Eduardo,Paz, Jairo,Iglesias, Beatriz,Munoz, Luis
experimental part, p. 3991 - 3999 (2009/12/06)
Treatment of primary amines with tetramethylphenylguanidine (PhTMG) and a cyanophosphonate at -10 °C under an atmosphere of carbon dioxide provides cyanoformamides in very high to excellent yields. The reaction proceeds efficiently within a short time. By
Total synthesis of dispyrin, purpurealidin E, and aplysamine-1
Yoshida, Makoto,Yamaguchi, Kentaro
scheme or table, p. 1362 - 1363 (2009/09/06)
Bromotyrosine alkaloids dispyrin (1), purpurealidin E (2), and aplysamine-1 (3) isolated from marine sponge, were synthesized from commercially available tyramine (4) as a common starting material. The overall yield was 18%, 39%, and 22% for 1 from 4 in 5
Total synthesis of antibacterial dibromotyrosine derived alkaloid purpuramine-K#
Reddy, S. Malla,Srinivasulu,Venkateswarlu
, p. 2757 - 2762 (2007/10/03)
The first total synthesis of a dibromotyrosine derived alkaloid purpuramine K 1 reported for possible anti-bacterial activity against gram-positive bacteria viz: Staphylococcus aureus, Bacillus subtilis, Bacillus sphaericus and gram-negative bacteria like Chromobacterium violaceum, Klebsiella aerogenes, and Pseudomonas aeruginosa has been achieved. The synthesis involves preparation of methyl-3-bromopropyl carbamate 6, and Boc protected 2-[3,5-dibromo, 4-hydroxy phenyl] ethyl amine 13 which is followed by coupling of these two structural fragments to give corresponding ether 14. After deprotection of Boc group in compound 14, it is reacted with 4-hydroxyphenyl pyruvic acid oxime derivative 17 using EDCI/HOBT to give compound 18, which is further transformed to purpuramine K.
A highly chemoselective Boc protection of amines using sulfonic-acid-functionalized silica as an efficient heterogeneous recyclable catalyst
Das, Biswanath,Venkateswarlu, Katta,Krishnaiah, Maddeboina,Holla, Harish
, p. 7551 - 7556 (2008/02/08)
A facile and versatile method for the chemoselective Boc protection of amines has been developed by a treatment with (Boc)2O in the presence of sulfonic-acid-functionalized silica as a catalyst. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines; aminols, amino-esters; and sulfonamides. The catalyst works under heterogeneous conditions and can be recycled.
Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge
Kotoku, Naoyuki,Tsujita, Hiroaki,Hiramatsu, Atsushi,Mori, Chinatsu,Koizumi, Noriko,Kobayashi, Motomasa
, p. 7211 - 7218 (2007/10/03)
An efficient total synthesis of bastadin 6 (1), a cyclic tetramer of brominated tyrosine derivatives from the marine sponge, Ianthella basta, with selective anti-angiogenic activity, was accomplished. We developed a novel Ce(IV)-mediated oxidative couplin
Structural activity relationship studies of zebra mussel antifouling and antimicrobial agents from verongid sponges
Diers, Jeffrey A.,Pennaka, Hari Kishore,Peng, Jiangnan,Bowling, John J.,Duke, Stephen O.,Hamann, Mark T.
, p. 2117 - 2120 (2008/04/18)
Several dibromotyramine derivatives including moloka'iamine were selected as potential zebra mussel (Dreissena polymorpha) antifoulants due to the noteworthy absence of fouling observed on sponges of the order Verongida. Sponges of the order Verongida con
