105589-11-5Relevant academic research and scientific papers
Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A
Stolze, Sara C.,Meltzer, Michael,Ehrmann, Michael,Kaiser, Markus
, p. 8857 - 8859 (2010)
The solid phase total synthesis of the marine cyanobacterial Ahp-cyclodepsipeptide Symplocamide A is reported as a model for a general route for the synthesis of tailor-made non-covalent serine protease inhibitors. The Royal Society of Chemistry 2010.
Efficient synthesis of benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-ω- iodoalkanoates
Koseki, Yohei,Yamada, Haruka,Usuki, Toyonobu
experimental part, p. 580 - 586 (2011/06/21)
The efficient synthesis of four benzyl 2-(S)-[(tert-butoxycarbonyl)amino]- ω-iodoalkanoates {benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-3- iodopropanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-4-iodobutanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-
Potent and fully noncompetitive peptidomimetic inhibitor of multidrug resistance P-glycoprotein
Arnaud, Ophélie,Koubeissi, Ali,Ettouati, Laurent,Terreux, Rapha?l,Alamé, Ghina,Grenot, Catherine,Dumontet, Charles,Di Pietro, Attilio,Paris, Jo?lle,Falson, Pierre
supporting information; experimental part, p. 6720 - 6729 (2010/11/16)
Nα-Boc-l-Asp(OBn)-l-Lys(Z)-OtBu (reversin 121, 1), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-l-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (IC50) of 0.6 and 0.2 μM, which are 2-and 7-fold lower than that of the parent molecule. The difference in IC50 between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC50. Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the H and R drug-transport sites.
Synthetic studies of the cyclic depsipeptides bearing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit. Total synthesis of the proposed structure of micropeptin T-20
Yokokawa, Fumiaki,Inaizumi, Akiko,Shioiri, Takayuki
, p. 1459 - 1480 (2007/10/03)
The first total synthesis of a cyclic depsipeptide possessing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit was successfully achieved in a convergent manner by the oxidative construction of the Ahp unit at the later stage of the synthesis. This synthetic work provides data indicating that the structure of the target Ahp-depsipeptide, micropeptin T-20, should be re-examined.
Synthetic studies of micropeptin T-20, a novel 3-amino-6-hydroxy-2-piperidone (Ahp)-containing cyclic depsipeptide
Yokokawa, Fumiaki,Inaizumi, Akiko,Shioiri, Takayuki
, p. 5903 - 5908 (2007/10/03)
The synthetic studies of micropeptin T-20 including the late installation of the Ahp (3-amino-6-hydroxy-2-piperidone) residue through oxidation and cyclization of a homoserine to the requisite hemiaminal are described.
Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors
Marsham, Peter R.,Wardleworth, J. Michael,Boyle, F. Thomas,Hennequin, Laurent F.,Kimbell, Rosemary,Brown, Melody,Jackman, Ann L.
, p. 3809 - 3820 (2007/10/03)
The synthesis is described of a series of analogues of the potent thymidylate synthase (TS) inhibitor, N-[4-[N-[(3,4-dihydr0-2,7-dimethyl-4- oxo-6-quinazolinyl)methyl]-N-prop-2-ynylamino]2-fluorobenzoyl]-L-glutamic acid (4, ZM214888), in which the glutami
