TY - JOUR
T1 - Developing neolignans as proangiogenic agents
T2 - Stereoselective total syntheses and preliminary biological evaluations of the four guaiacylglycerol 8-O-4'-coniferyl ethers
AU - Buckler, Joshua N.
AU - Banwell, Martin G.
AU - Kordbacheh, Farzaneh
AU - Parish, Christopher R.
AU - Santiago, Fernando S.
AU - Khachigian, Levon M.
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/10/31
Y1 - 2017/10/31
N2 - Stereoselective total syntheses of the four stereoisomeric forms of guaiacylglycerol 8-O-4'-coniferyl ether, viz., compounds 1, ent-1, 2, and ent-2, have been established. The key step involves an Evans/Seebach auxiliarycontrolled and syn-selective aldol process followed, in the reaction sequences leading to the anti-compounds, by a Mitsunobu reaction involving a benzylic alcohol residue. The proangiogenic properties of the synthetic materials were evaluated in a human microvascular endothelial cell tubule formation assay, thus revealing that they are all active, with the 8S-configured compounds 1 and 2 being the most potent.
AB - Stereoselective total syntheses of the four stereoisomeric forms of guaiacylglycerol 8-O-4'-coniferyl ether, viz., compounds 1, ent-1, 2, and ent-2, have been established. The key step involves an Evans/Seebach auxiliarycontrolled and syn-selective aldol process followed, in the reaction sequences leading to the anti-compounds, by a Mitsunobu reaction involving a benzylic alcohol residue. The proangiogenic properties of the synthetic materials were evaluated in a human microvascular endothelial cell tubule formation assay, thus revealing that they are all active, with the 8S-configured compounds 1 and 2 being the most potent.
UR - http://www.scopus.com/inward/record.url?scp=85032622239&partnerID=8YFLogxK
U2 - 10.1021/acsomega.7b01459
DO - 10.1021/acsomega.7b01459
M3 - Article
SN - 2470-1343
VL - 2
SP - 7375
EP - 7388
JO - ACS Omega
JF - ACS Omega
IS - 10
ER -