49619-58-1

Basic information

• Product Name: 3-Formyl-6-isopropylchromone
• Synonyms: 3-FORMYL-6-ISOPROPYLCHROMONE;4H-1-BENZOPYRAN-6-ISOPROPYL-4-OXO-3-CARBOXALDEHYDE;6-ISOPROPYL-4-OXO-4H-1-BENZOPYRAN-3-CARBOXALDEHYDE;6-ISOPROPYL-4-OXO-4H-CHROMENE-3-CARBALDEHYDE;6-Isopropyl-4-oxo-4H-1-benzopuran-3-carboxaldehyde;AM-3;3-FORMYL-6-ISOPROPYLCHROMONE 99%;3-Cyano-4-methony-2-(1H)-pyridinoneC7H6N2O2
• CAS NO: 49619-58-1
• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.23
• EINECS: 1806241-263-5
• Product Categories: Miscellaneous
• Mol File: 49619-58-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 98-100 °C(lit.)
• Boiling Point: 339.8 °C at 760 mmHg
• Flash Point: 150.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.259 g/cm³
• Vapor Pressure: 8.96E-05mmHg at 25°C
• Refractive Index: 1.622
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3-Formyl-6-isopropylchromone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Formyl-6-isopropylchromone(49619-58-1)
• EPA Substance Registry System: 3-Formyl-6-isopropylchromone(49619-58-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 49619-58-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

3-Formyl-6-isopropylchromone is the suitable reagent used in a study to investigate the multidrug resistance reversal by some 3- formylchromones in human colon cancer and mouse lymphoma cells transfected with the human MDR1 gene.

General Description

3-Formyl-6-isopropylchromone (6-Isopropyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde, 6-Isopropyl-4-oxo-4H-chromene-3-carbaldehyde), a pyrazine (paradiazine) derivative, is a heterocyclic building block. It is a heterocyclic six-membered aromatic compound bearing nitrogen atoms at para positions. Combustion calorimetric experiments have been conducted to evaluate the enthalpy of combustion of 3-formyl-6-isopropylchromone. Cytotoxic activity of 3-formyl-6-isopropylchromone against normal and tumor cells in vivo has been tested.

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 
• 1203451-84-6 ethyl 3-chloro-2-hydroxy-5-(2-hydroxy-5-isopropylbenzoyl)benzoate 
• 1369903-18-3 N-((6-isopropyl-4-oxo-4H-chromen-3-yl)methylene)aniline oxide 
• 1355043-33-2 3-(2-Hydroxy-5-iso-propylbenzoyl)-7,12-dihydro-6H-indolo[2,3-a]quinolizine-1,12b-dicarboxylic acid dimethyl ester 
• 1355043-41-2 3-(2-Hydroxy-5-iso-propylbenzoyl)-9-methoxy-7,12-dihydro-6H-indolo[2,3-a]quinolizine-1,12b-dicarboxylic acid diethyl ester 

Relevant articles and documents

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.

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.

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.