121840-97-9Relevant articles and documents
Synthesis and Structure-Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin
Kienle, Maryline,Eisenring, Patrick,Stoessel, Barbara,Horlacher, Oliver P.,Hasler, Samuel,Van Colen, Gwéna?lle,Hartkoorn, Ruben C.,Vocat, Anthony,Cole, Stewart T.,Altmann, Karl-Heinz
, p. 1105 - 1131 (2020/03/10)
A series of derivatives of the antimycobacterial natural product pyridomycin have been prepared with the C2 side chain attached to the macrocyclic core structure by a C-C single bond, in place of the synthetically more demanding enol ester double bond found in the natural product. Hydrophobic C2 substituents of sufficient size generally provide for potent anti-Mtb activity of these dihydropyridomycins (minimum inhibitory concentration (MIC) values around 2.5 μM), with several analogs thus approaching the activity of natural pyridomycin. Surprisingly, some of these compounds, in contrast to pyridomycin, are insensitive to overexpression of InhA in Mycobacterium tuberculosis (Mtb). This indicates that their anti-Mtb activity does not critically depend on the inhibition of InhA and that their overall mode of action may differ from that of the original natural product lead.
A stereoselective approach for the total synthesis of [2(S)-phenyl- propionyl]-2-piperidinone-3-(R)-yl-ester and its diastereomer
Krishna, Palakodety Radha,Arun Kumar, Pendyala Venkata,Mallula, Venkata Satyanarayana,Ramakrishna, Kallaganti V.S.
, p. 2319 - 2326 (2013/03/29)
Stereoselective total synthesis of isomers of [2-phenyl-propionyl]-2- piperidinone-3(R)-yl-ester has been achieved using commercially available starting materials like trans cinnamaldehyde and 4-pentene-1-ol. The key steps are Steglich conditions for the esterification of the two crucial intermediates; reduction of the azide to amine under Staudinger reaction conditions with concomitant intramolecular amidation reaction in one pot afforded the target compound(s). However, the total syntheses revealed that the structural revision is necessary for the reported natural product.
Cycle-specific organocascade catalysis: Application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis
Simmons, Bryon,Walji, Abbas M.,MacMillan, David W. C.
supporting information; experimental part, p. 4349 - 4353 (2009/10/23)
-