87281-16-1Relevant articles and documents
Design, synthesis and evaluation of the antibacterial activity of new Linezolid dipeptide-type analogues
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
supporting information, (2019/12/23)
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.
Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: An easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine
Manna, Sudipta Kumar,Panda, Gautam
, p. 8318 - 8324 (2015/01/09)
Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized within 5 min to 2 h in high yields from easily accessible (S)-amino acid derived chiral carbocations. The diastereoselective Friedel-Crafts reaction is promoted by a Lewis acid (AlCl3) offering trans-diastereoselectivity. The rate of the reaction and diastereoselectivity of the product are significantly influenced by steric hindrance of the amino acids substituents and aryl groups. The methodology can be applied for the synthesis of the enantiomerically enriched bioactive scaffold (3S,4R)-demethoxy-3-isopropyl diclofensine. This journal is
The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity
Hanessian, Stephen,Parthasarathy, Saravanan,Mauduit, Marc,Payza, Kemal
, p. 34 - 48 (2007/10/03)
The importance of visual imagery and relational thinking manifests itself in a heuristic approach to the design and synthesis of potential morphinomimetics as agonists of the human-receptor. The well-known class of alkaloids represented by the isopavine n
