- Design, synthesis and evaluation of the antibacterial activity of new Linezolid dipeptide-type analogues
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Worldwide studies towards development of new drugs with a lower rate in emergence of bacterial resistance have been conducted. The molecular docking analysis gives a possibility to predict the activity of new compounds before to perform their synthesis. In this work, the molecular docking analysis of 64 Linezolid dipeptide-type analogues was performed to predict their activity. The most negative scores correspond to six Fmoc-protected analogues (9as, 9bs, 9bu, 10as, 10ax and 10ay) where Fmoc group interacts in PTC for Linezolid. Twenty-six different Fmoc-protected Linezolid dipeptide-type analogues 9(as-bz) and 10(as-bz) were synthesized and tested in antimicrobial experiments. Compounds 9as, 9ay, 9ax, 10as, 10ay and 9bu show significant activity against group A Streptococcus clinical isolated. Analogue 10ay also display high activity against ATCC 25923 Staphylococcus aureus strain and MRSA-3, MRSA-4 and MRSA-5 clinical isolates, with MIC values lower than Linezolid. The highest activity against multidrug-resistant clinical isolates of Mycobacterium tuberculosis was exhibited by 9bu. Finally, a cytotoxicity assay with ARPE-19 human cells revealed a non-cytotoxic effect of 9bu and 10ay at 50 and 25 μM, respectively.
- García-Olaiz,Alcántar-Zavala, Eleazar,Ochoa-Terán, Adrián,Cabrera, Alberto,Mu?iz-Salazar, Raquel,Montes-ávila, Julio,Salazar-Medina, Alex J.,Alday, Efrain,Velazquez, Carlos,Medina-Franco, José L.,Laniado-Laborín, Rafael
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supporting information
(2019/12/23)
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- Total synthesis and stereochemical reassignment of tasiamide B
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The first total synthesis of tasiamide B, an octapeptide bearing 4-amino-3-hydroxy-5-phenylpentanoic acid unit isolated from the marine cyanobacteria Symploca sp. is described. A simple and efficient way was found to avoid the pyroglutamylation of Nα-Me-Gln and led to a reassignment of the Nα-Me-L-Phe of tasiamide B to be N α-Me-D-Phe, which was also supported by 1D and 2D NMR. Copyright
- Sun, Tiantian,Zhang, Wei,Zong, Chengli,Wang, Peng,Li, Yingxi
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experimental part
p. 364 - 374
(2011/03/22)
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- N-benzyl-protection of amino acid derivatives by reductive alkylation with α-picoline-borane
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A convenient method for N-protection of amino acid derivatives with a benzyl group by reductive alkylation of amino acid derivatives with α-picoline-borane is described. Amino acid esters or amino alcohols were treated with aryl aldehydes in methanol/acetic acid in the presence of -picoline-borane to give N-benzyl-protected amino acid derivatives in good yields. Georg Thieme Verlag Stuttgart - New York.
- Kawase, Yasushi,Yamagishi, Takehiro,Kutsuma, Teruo,Kataoka, Tadashi,Ueda, Kimio,Iwakuma, Takeo,Nakata, Tadashi,Yokomatsu, Tsutomu
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experimental part
p. 1673 - 1677
(2010/06/22)
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- Vanadium-catalyzed asymmetric oxidation of sulfides using Schiff base ligands derived from ss-amino alcohols with two stereogenic centers
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Novel Schiff base ligands derived from ss-amino alcohols with two stereogenic centers were prepared and. used in the preparation of optically pure sulfoxides by using aqueous hydrogen peroxide as the oxidant. A variety of sulfides were smoothly converted into the corresponding sulfoxides cata-lyzed by the chiral vanadium-Schiff base complex. Good yields (>80%) with excellent: enantioselectivities (>99%ee) were obtained in most cases.
- Wu, Yinuo,Liu, Juntao,Li, Xingshu,Chan, Albert S. C.
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supporting information; scheme or table
p. 2607 - 2610
(2009/07/25)
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- Boron-mediated aldol reactions of ethyl α-(N,N)-dibenzylamino ketones: Control of enolisation geometry and aldehyde π-facial selectivity
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The boron-mediated aldol reactions of a range of chiral α-(N,N)-dibenzylamino ketones with aldehydes can be controlled to provide stereodefined adducts. Complementary induction can be achieved with cHex2BCl/Me2NEt leading to preferential formation of the 1,2-anti-2,4-syn adducts, while Bu2BOTfiPr2NEt provides 1,2-syn-2,4-anti adducts.
- Paterson, Ian,Mackay, Angela C.
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p. 9269 - 9272
(2007/10/03)
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