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Ceratamine A

Names

[ CAS No. ]:
634151-15-8

[ Name ]:
Ceratamine A

[Synonym ]:
CERATAMINE A
4-[(3,5-Dibromo-4-methoxyphenyl)methyl]-6-methyl-2-(methylamino)imidazo[4,5-d]azepin-5(6H)-one
4-(3,5-dibromo-4-methoxybenzyl)-6-methyl-2-(methylamino)imidazo[4,5-d]azepin-5(6H)-one

Biological Activity

[Description]:

Ceratamine A is an antimitotic heterocyclic alkaloid isolated from the marine sponge Pseudoceratina sp., acts as a microtubule-stabilizing agent. Ceratamine A exhibits cytotoxicity against human cancer cell lines[1][2][3].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin
Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[References]

[1]. Manzo E, et al. Ceratamines A and B, antimitotic heterocyclic alkaloids isolated from the marine sponge Pseudoceratina sp. collected in Papua New Guinea. Org Lett. 2003 Nov 27;5(24):4591-4.

[2]. Nodwell M, et al. Synthetic approaches to the microtubule-stabilizing sponge alkaloid ceratamine A and desbromo analogues. J Org Chem. 2009 Feb 6;74(3):995-1006.

[3]. Pan X, et al. Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A. Bioorg Med Chem Lett. 2018 Mar 1;28(5):866-868.

Chemical & Physical Properties

[ Density]:
1.722g/cm3

[ Boiling Point ]:
543.271ºC at 760 mmHg

[ Molecular Formula ]:
C17H16Br2N4O2

[ Molecular Weight ]:
468.14300

[ Flash Point ]:
282.36ºC

[ Exact Mass ]:
465.96400

[ PSA ]:
69.04000

[ LogP ]:
3.56760

[ Index of Refraction ]:
1.683

Related Compounds