919092-53-8

Upstream product

• 699-83-2 2,6-dihydroxylacetophenone 
• 14100-97-1 cyclohexylmethyl methanesulfonate 
• 2550-36-9 Cyclohexylmethyl bromide 

Downstream Products

• 919092-35-6 (E)-1-(2-(cyclohexylmethoxy)-6-hydroxyphenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 
• 919092-47-0 (E)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxopropene-1-yl]phenylacetamide 
• 919092-38-9 (E)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzoic acid 
• 1237754-09-4 C₂₂H₂₃ClO₃ 
• 1237754-05-0 C₂₅H₃₀O₆ 

Relevant academic research and scientific papers

Discovery of novel 3-(hydroxyalkoxy)-2-alkylchromen-4-one analogs as interleukin-5 inhibitors

A series of novel chromen-4-one analogs 9a-d and 10a-u was designed, synthesized and evaluated for their IL-5 inhibitory activity. Most of the chromen-4-one analogs showed strong inhibitory activity in low micro molar potency. Among them, 5-(cyclohexylmet

Novel analogs of N-acylhydroxyethylaminomethyl-4H-chromen-4-one scaffold as IL-5 inhibitors

A number of N-acyl substituted hydroxyethylaminomethyl-4H-chromen-4-ones 6a–u were prepared and evaluated for their IL-5 inhibitory activity. Among them, the compound 6r (95.0% inhibition at 30?μM, IC50?=?10.0?μM, C?log?P?=?4.1549) showed most potent inhibitory activity. The structure activity relationship revealed that the bulkier or hydrophobic substituents at urea, carbamate or amide group resulted in good inhibitory activity against IL-5. Moreover, electron donating group at phenyl ring (6g and 6s) is much more active than electron withdrawing group (6f). Finally, replacement of cyclohexylmethoxy group at 5th position of ring A with bulky aliphatic substituents resulted in the loss of activity.

Novel hydroxyethylaminomethylchromenones derivatives which inhibit the interleukin-5 activity

The present invention relates to a novel hydroxyethylaminomethylchromenone derivative, a manufacturing method thereof, or a pharmaceutical composition including the hydroxyethylaminomethylchromenone derivative for preventing or treating allergic diseases. Since the hydroxyethylaminomethylchromenone derivative is low-molecular, non-peptide-based material, the derivative has no non-specific reaction for proteins unlike existing treating agents known for allergic diseases. In addition, the hydroxyethylaminomethylchromenone derivative of the present invention is an amine-form compound, and thereby, remarkably increasing water solubility compared to the existing hydroxyethylaminomethylchromenone derivatives manufactured, as well as having higher effects of inhibiting interleukin-5 activities due to difference in chemical structures, such that the compound of the present invention can be effectively used as an inhibitor for allergic diseases. Furthermore, since the existing hydroxyethylaminomethylchromenone derivatives have a chiral center, it produces inconvenience as it requires to check whether the an isomer exists or not. However, the present invention solves the inconvenience so as to have an advantage of being capable of easily manufacturing a compound. [Reference numerals] (AA,CC) Compound 3d; (BB,DD) Compound 4i

Anti-proliferative effect of chalcone derivatives through inactivation of NF-κB in human cancer cells

To investigate the anti-proliferative effect of NF-κB inhibitor, a series of analogs of (E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4- hydroxyphenyl)prop-2-en-1-one (5a) were prepared and evaluated for their NF-κB inhibition and anti-proliferative activity against various human cancer cell lines. Compounds (E)-1-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3- (4-hydroxyphenyl)prop-2-en-1-one (5e) and (E)-4-(3-(2-(3,3-dimethylbutoxy)-6- hydroxyphenyl)-3-oxoprop-1-enyl)benzenesulfonamide (5p) showed good NF-κB inhibition as well as potent anti-proliferative activity. SAR studies showed that all the compounds with potent or moderate NF-κB inhibition displayed good anti-proliferative activity. All the analogs (5b-r) maintained a good correlation between their NF-κB inhibition and anti-proliferative activity though the extent is not directly proportional to each other.

Identification of novel chromenone derivatives as interleukin-5 inhibitors

A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety.

Design and synthesis of novel chromenone derivatives as interleukin-5 inhibitors

A novel series of chromenone analogs were synthesized and evaluated for their inhibitory activity against interleukin-5. Among them 5- (cyclohexylmethoxy)-3-[3-hydroxy-3-(4-hydroxyphenyl)propyl]-4H-chromen-4-one (9b, 94% inhibition at 30 μM, IC50 = 4.0 μM) and 5-(cyclohexylmethoxy)-3-[3-hydroxy-3-(4-methoxyphenyl)propyl]-4H-chromen-4-one (9c, 94% inhibition at 30 μM, IC50 = 6.5 μM) showed the most potent activity. According to the SAR studies introduction of propanone unit in between chromenone and ring B as in 5-(cyclohexylmethoxy)-3-[3-(4-phenyl)-3- oxopropyl]-4H-chromen-4-ones (8) moderately increased the activity. However, the reduction of these propanones 8 to propanols 9 remarkably enhanced the activity. A small substituent at position 4 of ring B in 9, especially with hydrogen bonding capability, provides favorable contribution. Disappearance of IL-5 inhibitory activity upon saturation of chroman-4-one of 9 to chroman-4-ones 10 proves the critical importance of planar chromen-4-one unit of this scaffold in the IL-5 inhibition.

A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB

To define the structural features responsible for the activity of 2,4-dihydroxy-6-isopentyloxychalcone, a newly established inhibitor of LPS induced NF-κB activation (IC50 = 10 μM), a series of its analogues was prepared and studied for their i

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?μM, IC50?50?=?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.

Structural requirement of chalcones for the inhibitory activity of interleukin-5

Novel chalcones were found as potent inhibitors of interleukin (IL)-5. 1-(2-Benzyloxy-6-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one (2b, 78.8% inhibition at 50 μM, IC50 = 25.3 μM) was initially identified as a potent inhibitor of IL-5. Th

Synthesis and structure-activity relationships of novel IKK-β inhibitors. Part 3: Orally active anti-inflammatory agents

A series of 2-amino-3-cyano-4-alkyl-6-(2-hydroxyphenyl)pyridine derivatives was synthesized and evaluated as IκB kinase β (IKK-β) inhibitors. Modification of a novel IKK-β inhibitor 1 (IKK-β IC 50=1500nM, Cell IC50=8000nM) at the 4-p