49619-58-1

Usage

InChI:InChI=1/C13H12O3/c1-8(2)9-3-4-12-11(5-9)13(15)10(6-14)7-16-12/h3-8H,1-2H3

Upstream product

• 1634-36-2 1-(2-hydroxy-5-isopropylphenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 99-89-8 4-Isopropylphenol 
• 2664-32-6 4-isopropylphenyl acetate 

Downstream Products

• 50743-32-3 6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile 
• 1026418-59-6 2-benzo[1,3]dioxol-5-yl-6-isopropyl-4-(4-methoxy-phenyl)-2H-chromene-3-carboxylic acid methyl ester 
• 1005791-80-9 [3-(4-fluorobenzoyl)-4-hydroxyphenyl]-(2-hydroxy-5-isopropylphenyl)methanone 
• 1005791-85-4 [3-(2-fluorobenzoyl)-4-hydroxyphenyl]-(2-hydroxy-5-isopropylphenyl)methanone 
• 1005791-88-7 (2-hydroxy-5-isopropylphenyl)-[4-hydroxy-3-(2-methylbenzoyl)phenyl]methanone 
• 911217-76-0 3-ethyl-7-(2-hydroxy-5-isopropylbenzoyl)-2-phenyl-4-thiophen-2-yl-4H-pyrimido[1,2-a]pyrimidine-3-carboxylate 
• 1028436-11-4 C₃₁H₃₀O₄ 
• 1162661-52-0 ethyl 3-(2-hydroxy-5-(2-hydroxy-5-isopropylbenzoyl)phenyl)-3-oxopropanoate 
• 1203451-84-6 ethyl 3-chloro-2-hydroxy-5-(2-hydroxy-5-isopropylbenzoyl)benzoate 
• 1208121-56-5 5,6-dimethoxycarbonyl-2,3-dimethyl-8-formyl-7-(2'-hydroxy-5'-isopropylbenzoyl)-5H-[1,3]thiazolo[3,2-a]pyridine 
• 1214755-64-2 dimethyl 2-(cyclohexylamino)-5-(6'-isopropyl-4'-oxo-4H-chromen-3'-yl)furan-3,4-dicarboxylate 
• 1287736-29-1 trimethyl 5-(2-hydroxy-5-isopropylbenzoyl)benzene-1,2,3-tricarboxylate 
• 1307915-89-4 C₂₁H₂₃NO₆ 
• 1307915-81-6 C₂₈H₂₉NO₈S 

Relevant academic research and scientific papers

Design, synthesis and docking studies of novel thienopyrimidine derivatives bearing chromone moiety as mTOR/PI3Kα inhibitors

Two series of thienopyrimidine derivatives (10a-k, 16a-j) bearing chromone moiety were designed and synthesized. All the compounds were evaluated for inhibitory activity against mTOR kinase at a concentration of 10uM. Four selected compounds were further evaluated for the IC50 values against mTOR kinase, PI3Kα kinase and two cancer cell lines. Some of the target compounds exhibited moderate to excellent mTOR/PI3Kα kinase inhibitory activity and cytotoxicity. The most promising compound 16i showed good inhibitory activity against mTOR/PI3Kα kinase and good antitumor potency for H460 and PC-3 cell lines with IC50 values of 0.16 ± 0.03 μM, 2.35 ± 0.19 μM, 1.20 ± 0.23 μM and 0.85 ± 0.04 μM, which were 8.6, >5, 7.9 and 19.1 times more active than compound I (1.37 ± 0.07 μM, >10 μM, 9.52 ± 0.29 μM, 16.27 ± 0.54 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the chromone moiety is necessary for the potent antitumor activity and cytotoxicity of these compounds. Substitution of the chromone moiety at the 6-position has a significant impact to the inhibitory activity, in particular a carboxylic acid group, produced the best potency.

Design and syntheses of novel N′-((4-oxo-4H-chromen-3-yl)methylene) benzohydrazide as inhibitors of cyanobacterial fructose-1,6-/sedoheptulose-1,7- bisphosphatase

Cyanobacterial fructose-1,6-/sedoheptulose-1,7-bisphoshatase (Cy-FBP/SBPase) is an important target enzyme for finding inhibitors to solve harmful algal bloom (HAB). In this study, as potential inhibitors of Cy-FBP/SBPase, a series of novel chromone-connecting benzohydrazone compounds (Novel N′-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide) were designed and synthesized. Their inhibitory activities against Cy-FBP/SBPase were further examined in vitro. Some of these compounds, such as f6-f8, f11, f12 and f16, exhibit higher inhibitory activities (IC50 = 11.2-16.1 μM), especially, the compound f7 was identified as the most potent inhibitor with IC50 value of 11.2 μM. The probable binding-mode of compound f7 was further analyzed carefully by molecular docking methods. These results indicate that compound f7 could be used as a lead compound for further optimization and might have potential to be developed as a new algicide.

Formylchromone derivatives as a novel class of protein tyrosine phosphatase 1B inhibitors

Formylchromone inhibits a human protein tyrosine phosphatase PTP1B with a IC50 value of 73 μM. The chemical reactivity of formylchromone was adjusted by substitution at various positions of the formylchromone skeleton. In an initial assessment of the structure-activity relationship, the most potent inhibitor showed an IC50 of 4.3 μM against PTP1B and strong or medium selectivity against other human PTPases, LAR and TC-PTP. This compound, however, was not selective against microbial PTPases, YPTP1 and YOP. The potency and selectivity of the formylchromone derivatives expecting further improvements provides a novel pharmacophore for the design of drugs for the treatmenrt of type 2 diabetes and obesity.

Structure-activity relationships of a novel class of endothelin-A receptor antagonists and discovery of potent and selective receptor antagonist, 2-(benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4- (4-methoxyphenyl)-2H-chromene-3-carboxylic acid (S-1255). 1. Study on structure-activity relationships and basic structure crucial for ETA antagonism

A novel series of endothelin-A (ETA) selective receptor antagonists having a 2H-chromene skeleton are described. A lead compound, 2-(benzo[1,3] dioxol-5-yl)-2H-chromene-3-carboxylic acid (3), was found by modifications of our own angiotensin II antagonist. A structure-activity relationship (SAR) study of 3 reveals that the structural requirements essential for potent and selective ETA receptor binding affinity are the m,p-methylenedioxyphenyl, carboxyl, and isopropoxy groups at the 2-, 3-,and 6-positions, respectively, on the (R)-2H-chromene skeleton. The substituent at the 4-position is also important for improving the activity, and various hydrophobic functional groups of 6-9 ? such as liner, branched, and cyclic aliphatic groups, unsubstituted and substituted aryl groups, and even halogen atoms were acceptable. These results suggest that (R)-2-(benzo[1,3]dioxol-5-yl)-6-isopropoxy-2H-chromene-3-carboxylic acid, formula 108, is the crucial basic structure to be recognized by the ETA receptor. The most potent compound is (R)-48 (S-1255), which binds to the ETA receptor with an IC50 value of 0.19 nM and is 630-fold selective for the ETA receptor than for the ETB receptor. This compound has 55% oral bioavailability in rats. On the basis of the SAR, the roles of each substituent in the receptor binding are discussed.

Chromonealdehyde compounds and process for the production thereof

There are provided compounds of the general formula SPC1 Wherein R is a hydroxy, alkyl, acyloxy, halogen, nitro, substituted or unsubstituted amino, alkoxy, carboxy or a group derived from a carboxy group and m is 0, 1 or 2 except where m is 2, the two R groups are both hydroxy groups. The present invention is also concerned with a process for preparing the chromonealdehyde compounds. The chromonealdehyde compounds are characterized by antiallergic properties and are therefore useful as prophylactic and therapeutic agents for allergic asthma, allergic dermatitis and other allergic diseases and also are valuable as intermediates for the synthesis of other pharmaceutical compounds having the chromone nucleus.