Synthesis and evaluation of novel chromone analogs for their inhibitory activity against interleukin-5.
A novel series of chromone analogs were synthesized and evaluated for their inhibitory activity against interleukin-5. Among them compounds 5-Cyclohexylmethoxy-3-(4-hydroxybenzyl)-4H-chromen-4-one (6a, 98% inhibition at 30 microM, IC50<3.0 microM) and 5-Cyclohyxylmethoxy-3-(hydroxymethyl)-4H-chromen-4-one (8a, 84% inhibition at 30 microM, IC50=7.6 microM) showed most potent activity. The structural requirement of chromone analogs possessing the inhibitory activity against IL-5 could be summarized as: (i) importance of hydrophobic group such as cyclohexylmethoxy at 5th position of ring A, (ii) requirement of ring B with small size of hydrogen bonding group with electron donating property such as phenolic hydroxyl group at 4th position and (iii) planarity of the chromen-4-one ring.
College of Pharmacy and Institute of Drug Research and Development, Chungnam, National University, Daejeon 305-764, Republic of Korea.
Pillaiyar
P
Thanigaimalai
Tuan Anh
TA
Le Hoang
Ki-Cheul
KC
Lee
Vinay K
VK
Sharma
Seong-Cheol
SC
Bang
Jun Ho
JH
Yun
Eunmiri
E
Roh
Youngsoo
Y
Kim
Sang-Hun
SH
Jung
D002460:Cell Line; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D057927:Hydrophobic and Hydrophilic Interactions; D020128:Inhibitory Concentration 50; D015848:Interleukin-5 / Q000037:antagonists & inhibitors*; D010539:Permeability; D013329:Structure-Activity Relationship
D002867:Chromones; D015848:Interleukin-5