New lamellarin alkaloids from an unidentified ascidian from the Arabian Sea

Reddy, M. Venkata Rami; Faulkner, D. John; Venkateswarlu, Y.; Rao, M. Rama

doi:10.1016/s0040-4020(97)00073-2

Cited by 112 publications

(92 citation statements)

References 5 publications

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“…In the reaction medium the C-2 of pyrimidine became relatively positive, easily accepted the hydroxide ion from water of intermediate (152) yielding the final benzothiazepine 153 (60% yield) [32][33][34][35][36] (Scheme 30). To enhance the anxiolytic activity of some azepine derivatives by the introduction of a trifluoromethyl group in the dia-, oxa-or thiazepine, trifluoroacetyl ketene acetals 167 were reacted with o-aminothiophenol derivatives in the presence of xylene, applying a multimode microwave oven (8-12 min at 980 W).…”

Section: Reaction Of Exocyclic -Unsaturated Ketones With O-aminmentioning

confidence: 99%

“…To enhance the anxiolytic activity of some azepine derivatives by the introduction of a trifluoromethyl group in the dia-, oxa-or thiazepine, trifluoroacetyl ketene acetals 167 were reacted with o-aminothiophenol derivatives in the presence of xylene, applying a multimode microwave oven (8-12 min at 980 W). Although this methodology uses microwave inert solvents (e.g., toluene or xylene), which are not serving in the energy transfer processes, it gave the 3-substituted 2-hydroxy-2-trifluoromethyl-1,5-benzothiaz-epine derivatives 168 in good yields, suggesting absorption of the microwaves by the reactants [33,35,36,39] …”

Section: Reaction Of Exocyclic -Unsaturated Ketones With O-aminmentioning

confidence: 99%

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Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

El‐Bayouki

2013

Organic Chemistry International

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Section: Reaction Of Exocyclic -Unsaturated Ketones With O-aminmentioning

confidence: 99%

Section: Reaction Of Exocyclic -Unsaturated Ketones With O-aminmentioning

confidence: 99%

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

El‐Bayouki

2013

Organic Chemistry International

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“…More than thirty lamellarins have been isolated to date, but only few show interesting bioactive properties [1][2][3][4][5][6][7][8][9].…”

Section: Isolation Of Lamellarinsmentioning

confidence: 99%

Recent Advances in Lamellarin Alkaloids: Isolation, Synthesis and Activity

Plá¹,

Alberício²,

Álvarez

2008

ACAMC

106

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Lamellarins are a large family of marine alkaloids with potential anticancer activity that have been isolated from diverse marine organisms, mainly ascidians and sponges. All lamellarins feature a 3,4-diarylpyrrole system. Pentacyclic lamellarins, whose polyheterocyclic system has a pyrrole core, are the most active compounds. Some of these alkaloids are potently cytotoxic to various tumor cell lines. To date, Lam-D and Lam-H have been identified as lead compounds for the inhibition of topoisomerase I and HIV-1 integrase, respectively-nuclear enzymes which are over-expressed in deregulation disorders. Moreover, these compounds have been reported for their efficacy in treatment of multi-drug resistant (MDR) tumors cells without mediated drug efflux, as well as their immunomodulatory activity and selectivity towards melanoma cell lines. This article is an overview of recent literature on lamellarins, encompassing their isolation, recent synthetic strategies for their total synthesis, the preparation of their analogs, studies on their mechanisms of action, and their structure-activity relationships (SAR).

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“…in 1985. [2][3][4][5][6][7][8][9][10][11][12][13][14][15] These lamellarins exhibit a number of interesting biological activities such as potent cytotoxicity against cancer cell lines, 8,9,11,12,[14][15][16][17][18][19][20][21] multi-drug resistance (MDR) reversal activity, 15,16 anti-HIV activity, 11,18,22 topoisomerase I inhibitory activity, 23,24 inhibition of mitochondrial function, [25][26][27][28] and protein kinases inhibitory activity. 29 Lamellarins possess a unique 14-phenyl-6H- [1]benzopyrano- According to X-ray crystallographic analyses of several lamellarins, the aryl group attached to C1 is This paper is dedicated to Professor Dr. Victor Snieckus on the occasion of his 77 th birthday.…”

Section: Up To Now Approximately Fifty Lamellarins Have Been Charactmentioning

confidence: 99%

Rotational Energy Barrier around the C1–C11 Single Bond in Lamellarins: A Study by Variable-Temperature NMR

Fukuda¹,

Itoyama

Minagawa³

et al. 2014

HETEROCYCLES

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-In order to estimate the free energy barrier to rotation around the C1-C11 single bond in lamellarins, new lamellarin analogues (1a), (1b), (2a), and (2b) possessing diastereotopic protons or carbons at the C1 aryl moiety were synthesized. Variable-temperature 1 H and 13 C NMR measurements of these analogues revealed that the free energy barriers to rotation around the C1-C11axis in 5,6-saturated and 5,6-unsaturated lamellarins were around 72-74 and 83-87 kJ/mol, respectively.

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New lamellarin alkaloids from an unidentified ascidian from the Arabian Sea

Cited by 112 publications

References 5 publications

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

Recent Advances in Lamellarin Alkaloids: Isolation, Synthesis and Activity

Rotational Energy Barrier around the C1–C11 Single Bond in Lamellarins: A Study by Variable-Temperature NMR

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