- Renal-selective prodrugs for control of renal sympathetic nerve activity in the treatment of hypertension
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Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are de
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Page/Page column 66-67
(2010/11/30)
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- New crown-carrier Cα,α-disubstituted glycines derived from α-methyl-(L)-DOPA
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The side-chain catechol function of α-methyl-(L)-DOPA was utilized for the synthesis of a new series of crown-carrier Cα,α-disubstituted glycines. During N-protection of α-methyl-(L)-DOPA methyl ester (H-Mdp-OMe) with Boc anhydride, the formation of N,O-di-Boc derivatives was observed. Selective aminolysis of the catechol tert-butyl carbonate group was achieved using pyrrolidine as nucleophile. Treatment of the resulting Boc-Mdp-OMe by Cs2CO3 in MeOH, followed by bis-O-alkylation with cyclization using various polyethyleneglycol ditosylates or catechol-derived bis-polyethyleneglycol ditosylates in DMF at 60°C, led to the derivatives Boc-[15-C-5]-Mdp-OMe, Boc-[18-C-6]-Mdp-OMe, Boc-[benzo-18-C-6]-Mdp-OMe, Boc-[benzo-24-C-8]-Mdp-OMe and then after saponification, to the corresponding Nα-protected amino acids. The tripeptides Fmoc-Ala-[18-C-6]-Mdp-Ala-OMe and Boc-Aib-[18-C-6]-Mdp-Ala-OMe were prepared in solution by using Ala and Aib UNCAs for coupling at the N terminus of the [18-C-6]-Mdp residue and the EDC/HOAt method for coupling Ala at its C terminus.
- Wright, Karen,Melandri, Francesca,Cannizzo, Caroline,Wakselman, Michel,Mazaleyrat, Jean-Paul
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p. 5811 - 5820
(2007/10/03)
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- A facile method for the side-chain protection of α-methyl-β-3,4-dihydroxyphenyl-L-alanine (αMeDopa) for solid-phase peptide synthesis
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Two approaches have been used to prepare N(α)-tert-butoxycarbonyl-α-methyl-β-3,4-dimethoxy-, or dibenzyloxyphenyl-L-alanine, N(α)-Boc-α-MeDopa(R)2, where R is the methyl or benzyl ether. In the first approach, α-methyl-β-3,4-dihydroxyphenyl-L-a
- Hsieh,deMaine
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