147363-23-3Relevant academic research and scientific papers
General Strategy for Integrated Bioorthogonal Prodrugs: Pt(II)-Triggered Depropargylation Enables Controllable Drug Activation in Vivo
Sun, Tao,Lv, Tian,Wu, Jianbing,Zhu, Mingchao,Fei, Yue,Zhu, Jie,Zhang, Yihua,Huang, Zhangjian
, p. 13899 - 13912 (2020/12/02)
Bioorthogonal decaging reactions for controllable drug activation within complex biological systems are highly desirable yet extremely challenging. Herein, we find a new class of Pt(II)-triggered bioorthogonal cleavage reactions in which Pt(II) but not Pt(IV) complexes effectively trigger the cleavage of O/N-propargyl in a variety of ranges of caged molecules under biocompatible conditions. Based on these findings, we propose a general strategy for integrated bioorthogonal prodrugs and accordingly design a prodrug 16, in which a Pt(IV) moiety is covalently connected with an O2-propargyl diazeniumdiolate moiety. It is found that 16 can be specifically reduced by cytoplasmic reductants in human ovarian cancer cells to liberate cisplatin, which subsequently stimulates the cleavage of O2-propargyl to release large amounts of NO in situ, thus generating synergistic and potent tumor suppression activity in vivo. Therefore, Pt(II)-triggered depropargylation and the integration concept might provide a general strategy for broad applicability of bioorthogonal cleavage chemistry in vivo.
A mild copper catalyzed method for the selective deprotection of aryl allyl ethers
Hemming, David S.,Talbot, Eric P.,Steel, Patrick G.
supporting information, p. 17 - 20 (2016/12/23)
Copper boryl reagents enable the selective cleavage of aryl allyl ethers to the corresponding phenols in good to moderate yields.
Macrocyclic analogues of the diuretic insect neuropeptide helicokinin I show strong receptor-binding
Tran Van, Chien,Nennstiel, Dirk,Scherkenbeck, Jürgen
, p. 3278 - 3286 (2015/08/03)
Abstract Helicokinin I, a diuretic neuropeptide of the relevant cotton pest Helicoverpa zea represents a promising target for the design of insect neuropeptide mimetics. Using a ring-closing metathesis reaction, N-terminal bridged macrocyclic helicokinin
One-pot isomerization-cross metathesis-reduction (ICMR) synthesis of lipophilic tetrapeptides
Jida, Mouhamad,Betti, Cecilia,Schiller, Peter W.,Tourwe, Dirk,Ballet, Steven
supporting information, p. 342 - 351 (2014/08/05)
An efficient, versatile and rapid method toward homologue series of lipophilic tetrapeptide derivatives (herein, the opioid peptides H-TIPP-OH and H-DIPP-OH) is reported. High atom economy and a minimal number of synthetic steps resulted from a one-pot ta
New cyclic peptides via ring-closing metathesis reactions and their anti-bacterial activities
Boyle, Timothy P.,Bremner, John B.,Coates, Jonathan,Deadman, John,Keller, Paul A.,Pyne, Stephen G.,Rhodes, David I.
experimental part, p. 11270 - 11290 (2009/04/06)
As part of a program investigating cyclic peptides with an internal aromatic hydrophobic scaffold as potential novel anti-bacterial agents, we explored the synthesis of simple tyrosine-based systems. These were prepared via key intermediates containing internal allylglycine and allyltyrosine residues for subsequent ring-closing metathesis reactions. Although the resulting anti-bacterial activity against Staphylococcus aureus was modest, this represents a novel and simple route to this class of compounds. One intermediate acyclic dipeptide precursor showed good activity against S. aureus with an MIC of 7.8 μg/mL. Crown Copyright
Synthesis of two new chiral fluorous bis(oxazolines) and their applications as ligands in catalytic asymmetric reactions
Bayardon, Jerome,Sinou, Denis
, p. 2965 - 2972 (2007/10/03)
Two new chiral fluorous bis(oxazolines) with a fluorous content of 56.9% and 59.3%, respectively, have been prepared starting from (S)-serine and (S)-tyrosine. Applications of these compounds as fluorous box ligands in asymmetric alkylations gave ees up to 92%, and in allylic oxidations ees up to 50%. Recycling and reuse of the ligands in asymmetric alkylation and of the catalytic system in allylic oxidation gave the same enantioselectivities.
Practical Synthesis of a Highly Enantioselective Receptor for Peptides
Erickson, Shawn D.,Simon, Julian A.,Still, W. Clark
, p. 1305 - 1308 (2007/10/02)
A practical synthesis of a highly enantioselective, C3-symmetric host molecule (2) has been developed.The basic strategy is a significant improvement over the relatively lenghty previous synthesis and involves direct addition of a Boc-tyrosine amide anion derivative 4 to methyl 3,5-bis(bromomethyl)benzoate to give an advanced intermediate (5).The final step, a triple macrolactamization, closes three 19-membered rings simultaneously to produce the bridged macrotricyclic receptor in 70-80percent yield.
