167935-97-9Relevant academic research and scientific papers
Optimization of dipeptidic inhibitors of cathepsin L for improved Toxoplasma gondii selectivity and CNS permeability
Zwicker, Jeffery D.,Diaz, Nicolas A.,Guerra, Alfredo J.,Kirchhoff, Paul D.,Wen, Bo,Sun, Duxin,Carruthers, Vern B.,Larsen, Scott D.
supporting information, p. 1972 - 1980 (2018/04/14)
The neurotropic protozoan Toxoplasma gondii is the second leading cause of death due to foodborne illness in the US, and has been designated as one of five neglected parasitic infections by the Center for Disease Control and Prevention. Currently, no trea
Synthesis of the southern tripeptide (C1-N12) of sanglifehrins using asymmetric organocatalysis
Radhika, Laghuvarapu,Chandrasekhar, Srivari
, p. 3602 - 3609 (2015/08/11)
The tripeptide southern region of the novel cyclophilin binding natural product macrolides, namely sanglifehrins, is synthesized involving asymmetric organocatalysis as chirality-inducing step. List's asymmetric α-amination was used in the synthesis of th
Synthesis of (-)-quinocarcin by directed condensation of α-amino aldehydes
Kwon, Soojin,Myers, Andrew G.
, p. 16796 - 16797 (2007/10/03)
An enantioselective synthesis of the natural antiproliferative agent quinocarcin was achieved by the directed condensation of optically active α-amino aldehyde intermediates. Condensation of the N-protected α-amino aldehyde 1, prepared in eight steps (19% yield) from (R,R)-pseudoephedrine glycinamide, with the C-protected α-amino aldehyde derivative 2, prepared in seven steps (34% yield) from (R,R)-pseudoephedrine glycinamide, afforded the corresponding imine in quantitative yield. Without isolation, direct treatment of this imine intermediate with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and hydrogen cyanide led to cleavage of the fluorenylmethoxycarbonyl (Fmoc) protective group followed by addition of cyanide (Strecker reaction) to form the bis-amino nitriles 3 as a mixture of diastereomers, in 91% yield. Treatment of the diastereomers 3 with trimethylsilyl cyanide and zinc chloride in 2,2,2-trifluoroethanol at 60 °C led to stepwise cyclization to form the tetracyclic product 4 (42% yield from 1 and 2). The latter intermediate was transformed into (-)-quinocarcin (1) in five steps (45% yield). The yield of quinocarcin was 19% from 1 and 2 (7 steps), and 4% from pseudoephedrine glycinamide (15 steps). Copyright
Design and synthesis of plasmepsin I and plasmepsin II inhibitors with activity in Plasmodium falciparum-infected cultured human erythrocytes
N?teberg, Daniel,Hamelink, Elizabeth,Hultén, Johan,Wahlgren, Mats,Vrang, Lotta,Samuelsson, Bertil,Hallberg, Anders
, p. 734 - 746 (2007/10/03)
A series of protease inhibitors targeted at the malarial enzymes plasmepsin I and II, and encompassing a basic hydroxyethylamine transition state isostere scaffold, was prepared. The substituents in the P1′ position were varied and the biological activiti
Development of tripeptidyl farnesyltransferase inhibitors.
Lee, Hee-Yoon,Sohn, Jeong-Hun,Kwon, Byoung-Mog
, p. 1599 - 1602 (2007/10/03)
The first example of tripeptide inhibitors of farnesyltransferase with sub-micromolar inhibition activity was developed based on the fact that CVFM is not a substrate for farnesyltransferase.
Total synthesis of the novel immunosuppressant sanglifehrin A
Nicolaou,Murphy,Barluenga,Ohshima,Wei,Xu,Gray,Baudoin
, p. 3830 - 3838 (2007/10/03)
The total synthesis of the novel immunosuppressant sanglifehrin A (SFA, 1) is described. The approach is flexible, convergent, and stereoselective. The use of Paterson's aldol methodology was pivotal for the preparation of the novel, highly substituted sp
Synthesis of the macrocyclic core of sanglifehrin A
Nicolaou,Ohshima,Ohshima, Takashi,Murphy,Murphy, Fiona,Barluenga,Barluenga, Sofia,Xu,Xu, Jinyou,Winssinger,Winssinger, Nicolas
, p. 809 - 810 (2007/10/03)
The synthesis of the macrocyclic core of sanglifehrin A, a newly discovered natural product, is described.
