Synthesis and evaluation of novel chromone analogs for their inhibitory activity against interleukin-5

Pillaiyar Thanigaimalai; Tuan Anh Le Hoang; Ki Cheul Lee; Vinay K. Sharma; Seong Cheol Bang; Jun Ho Yun; Eunmiri Roh; Youngsoo Kim; Sang Hun Jung

doi:10.1016/j.ejmech.2010.02.041

Synthesis and evaluation of novel chromone analogs for their inhibitory activity against interleukin-5

Pillaiyar Thanigaimalai, Tuan Anh Le Hoang, Ki Cheul Lee, Vinay K. Sharma, Seong Cheol Bang, Jun Ho Yun, Eunmiri Roh, Youngsoo Kim, Sang Hun Jung

Hormel Institute

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

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 μM, IC₅₀ < 3.0 μM) and 5-Cyclohyxylmethoxy-3-(hydroxymethyl)-4H-chromen-4-one (8a, 84% inhibition at 30 μM, IC₅₀ = 7.6 μM) 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.

Original language	English (US)
Pages (from-to)	2531-2536
Number of pages	6
Journal	European Journal of Medicinal Chemistry
Volume	45
Issue number	6
DOIs	https://doi.org/10.1016/j.ejmech.2010.02.041
State	Published - Jun 2010

Bibliographical note

Funding Information:
This work was supported by the Korea Research Foundation funded by Korean Government (MOEHRD) (KRF- 2007-313-E00651 ).

Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.

Keywords

Chromone analogs
Eosinophils
Inhibitor
Interleukin-5

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title = "Synthesis and evaluation of novel chromone analogs for their inhibitory activity against interleukin-5",

abstract = "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 μM, IC50 < 3.0 μM) and 5-Cyclohyxylmethoxy-3-(hydroxymethyl)-4H-chromen-4-one (8a, 84% inhibition at 30 μM, IC50 = 7.6 μM) 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.",

keywords = "Chromone analogs, Eosinophils, Inhibitor, Interleukin-5",

author = "Pillaiyar Thanigaimalai and {Le Hoang}, {Tuan Anh} and Lee, {Ki Cheul} and Sharma, {Vinay K.} and Bang, {Seong Cheol} and Yun, {Jun Ho} and Eunmiri Roh and Youngsoo Kim and Jung, {Sang Hun}",

note = "Funding Information: This work was supported by the Korea Research Foundation funded by Korean Government (MOEHRD) (KRF- 2007-313-E00651 ). Copyright: Copyright 2010 Elsevier B.V., All rights reserved.",

year = "2010",

month = jun,

doi = "10.1016/j.ejmech.2010.02.041",

language = "English (US)",

volume = "45",

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AU - Thanigaimalai, Pillaiyar

AU - Le Hoang, Tuan Anh

AU - Lee, Ki Cheul

AU - Sharma, Vinay K.

AU - Bang, Seong Cheol

AU - Yun, Jun Ho

AU - Roh, Eunmiri

AU - Kim, Youngsoo

AU - Jung, Sang Hun

N1 - Funding Information: This work was supported by the Korea Research Foundation funded by Korean Government (MOEHRD) (KRF- 2007-313-E00651 ). Copyright: Copyright 2010 Elsevier B.V., All rights reserved.

PY - 2010/6

Y1 - 2010/6

N2 - 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 μM, IC50 < 3.0 μM) and 5-Cyclohyxylmethoxy-3-(hydroxymethyl)-4H-chromen-4-one (8a, 84% inhibition at 30 μM, IC50 = 7.6 μM) 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.

AB - 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 μM, IC50 < 3.0 μM) and 5-Cyclohyxylmethoxy-3-(hydroxymethyl)-4H-chromen-4-one (8a, 84% inhibition at 30 μM, IC50 = 7.6 μM) 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.

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KW - Inhibitor

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Synthesis and evaluation of novel chromone analogs for their inhibitory activity against interleukin-5

Abstract

Bibliographical note

Keywords

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