57544-34-0

Usage

Uses

Used in Organic Synthesis:
6-CHLORO-2H-CHROMENE-3-CARBALDEHYDE is used as a key intermediate in organic synthesis for the development of new drugs and bioactive molecules. Its unique chemical structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-CHLORO-2H-CHROMENE-3-CARBALDEHYDE is utilized as a building block for the design and synthesis of novel pharmaceutical agents. Its reactivity and structural features enable the development of molecules with improved pharmacological properties.
Used in Antifungal Applications:
6-CHLORO-2H-CHROMENE-3-CARBALDEHYDE is studied for its potential as an antifungal agent. Its unique chemical structure and reactivity contribute to its ability to target and inhibit the growth of various fungi, making it a promising candidate for the development of new antifungal drugs.
Used in Antimicrobial Applications:
6-CHLORO-2H-CHROMENE-3-CARBALDEHYDE is also being investigated for its antimicrobial properties. Its ability to target and inhibit the growth of bacteria makes it a potential candidate for the development of new antimicrobial agents, addressing the growing concern of antibiotic resistance.
Used in Agrochemical Development:
6-CHLORO-2H-CHROMENE-3-CARBALDEHYDE may have applications in the development of agrochemicals, such as pesticides and fungicides. Its potential as an antifungal and antimicrobial agent could be harnessed to protect crops from various pathogens, thereby increasing agricultural productivity.
Used in Materials Science:
In the field of materials science, 6-CHLORO-2H-CHROMENE-3-CARBALDEHYDE may find applications in the development of new materials with specific properties. Its unique chemical structure and reactivity could be utilized to create materials with enhanced performance characteristics.
Further research is needed to fully understand and exploit the potential of 6-CHLORO-2H-CHROMENE-3-CARBALDEHYDE in various fields, including its applications in organic synthesis, medicinal chemistry, antifungal and antimicrobial agents, agrochemical development, and materials science.

InChI:InChI=1/C10H7ClO2/c11-9-1-2-10-8(4-9)3-7(5-12)6-13-10/h1-5H,6H2

Upstream product

• 635-93-8 5-chlorosalicyclaldehyde 
• 107-02-8 acrolein 
• 107-18-6 allyl alcohol 

Downstream Products

• 83823-06-7 6-chloro-2H-1-benzopyran-3-carboxylic acid 
• 1224510-37-5 (E)-3-(6-chloro-2H-chromen-3-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 1224510-35-3 (E)-3-(6-chloro-2H-chromen-3-yl)-1-(2-chlorophenyl)prop-2-en-1-one 
• 1224510-34-2 (E)-3-(6-chloro-2H-chromen-3-yl)-1-(2-fluorophenyl)prop-2-en-1-one 
• 1224510-36-4 (E)-3-(6-chloro-2H-chromen-3-yl)-1-(2,4-dichlorophenyl)prop-2-en-1-one 
• 1251862-38-0 (E)-6-chloro-3-(4-chlorostyryl)-2H-chromene 
• 1251862-43-7 6-chloro-3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-2H-chromene 
• 1251862-39-1 (E)-6-chloro-3-styryl-2H-chromene 
• 1351524-24-7 (E)-6-chloro-3-[3-(4-chlorophenyl)prop-1-en-1-yl]-2H-chromene 
• 1351524-23-6 (E)-6-chloro-3-(3-phenylprop-1-en-1-yl)-2H-chromene 
• 164265-01-4 (+/-)-6-chloro-2,3-dihydro-4H-1-benzopyran-3-carboxylic acid 

Relevant academic research and scientific papers

Design, one-pot synthesis, molecular docking study, and antibacterial evaluation of novel 2H-chromene based imidazo[1,2-a]pyridine derivatives as potent peptide deformylase inhibitors

An efficient, environmentally friendly, one-pot three-component synthesis of a series of 2H-chromene-based imidazo[1,2-a]pyridines had been designed and were synthesized. This protocol was developed by the reaction of substituted 2H-chromene aldehydes and

Diastereoselective synthesis of novel spiro indanone fused pyrano[3,2-: c] chromene derivatives following hetero-Diels-Alder reaction and in vitro anticancer studies

The development of concise methods for the synthesis of small functionalised spirocyclic molecules is important in the search of new bioactive molecules. To contribute this, here we represent a diastereoselective oxa-hetero-Diels-Alder reaction for the synthesis of novel spiro indanone fused pyrano[3,2-c]chromene derivatives and studied their in vitro anticancer activities. Using previously less explored cyclic ketone i.e. indane-1,3-dione and 3-vinyl-2H-chromene derivatives, we obtained novel spiro-heterocyclic frameworks at the interphase between "drug-like" molecules and natural products. Various spiro indanone fused pyrano[3,2-c]chromene derivatives were synthesized regiospecifically bearing a quaternary stereocenter in high yields (up to 85%) with excellent diastereoselectivity in toluene using 4 ? MS as additive under reflux condition at 120 °C. In vitro cytotoxic studies of these compounds against MCF-7 (breast cancer), HCT-116 (colon cancer), H-357 (oral cancer), MD-MB-231(Breast cancer) cell lines were evaluated by MTT {3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide} assay in vitro. The screening results revealed that many of the compounds are showing moderate to high levels of anticancer activities against the tested cancer cell lines and some displayed potent inhibitory activities in comparison to the commercial anticancer drug 5-fluorouracil (5-FU). Among the series, compound 3′c showed most potent cytotoxicity (15.0-27.5 μM) in three cancer cell lines (MCF-7, HCT-116 and MD-MB-231).

Exploring Pd/Al2O3 Catalysed Redox Isomerisation of Allyl Alcohol as a Platform to Create Structural Diversity

Abstract: We report our results on exploiting the different reactivities present in the catalytic cycle of the Pd/Al2O3 catalyzed redox isomerization of allyl alcohol. We show that the reactivity of allyl alcohol derived acrolein and enol can be involved in further cascade reactions leading to a diverse set of products. While the oxidation product acrolein can react via Michael and oxa-Michael reactions, the isomerization product enol can be readily involved in aldol condensation processes. Salicylaldehydes, that are able to react on their electrophilic carbonyl and nucleophilic OH-groups with allyl alcohol derived enol and acrolein, respectively, are used to explore conditions where the structure of the product heterocycles can be controlled. Graphical Abstract: [Figure not available: see fulltext.].

Copper-catalyzed enantioselective henry reaction of enals and subsequent iodocyclization: Stereoselective construction of chiral azatricyclic frameworks

In the frame: A cascade sequence combining an asymmetric Henry reaction and a stereoselective intramolecular iodocyclization provides direct access to an enantioenriched tricyclic hexahydrochromeno[4,3-b]pyrrole framework (see scheme). The Henry reaction is catalyzed by copper in the presence of L1. Copyright

Cytotoxic activity evaluation and QSAR study of chromene-based chalcones

Chalcone and chromene motifs are synthetic or naturally occurring scaffolds with significant cytotoxic profile. Two types of novel regioisomeric chromene-chalcone hybrids, namely 1-(6-chloro or 6-methoxy-2H-chromen-3-yl)-3- phenylprop-2-en-1-one (Type A) and 3-(6-chloro or 6-methoxy-2H-chromen-3-yl)-1- phenylprop-2-en-1-one (Type B), both with different substituents on the phenyl ring attached to propenone linkage, have been evaluated for their cytotoxic activity against breast cancer cell lines (MCF-7 and MDA-MB-231). The results indicate that type A of chromene-chalcones demonstrated better cytotoxic profile than type B especially in MDA-MB-231 cell line. In addition, the growth inhibitory activity of most of the target compounds is higher than Etoposide as a reference drug. QSAR analysis of these novel compounds demonstrated that topological and geometrical parameters are among the important descriptors that influence the cytotoxic activity profile of compounds.

New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders

Substituted (E)-3-styryl-4H-chromen-4-ones 1a-d, 3-[(1E,3E)-4-phenylbuta-1, 3-dienyl]-4H-chromen-4-ones 2a-d, (E)-3-styryl-2H-chromenes 3a-d and 3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-2H-chromenes 4a-d were designed and synthesized to improve the anti-picornavirus activity of previously tested analogues. The new compounds were evaluated in vitro against human rhinovirus (HRV) serotypes 1B and 14 and enterovirus (EV) 71. All the compounds interfered with the replication of picornaviruses, although considerable differences were observed in the sensitivity of viruses to each compound. Generally, both HRVs were more susceptible than EV71 and their sensitivity was dependent upon the linker chain length as well as upon the oxidation state of the heterocyclic ring. (E)-3-Styryl-2H-chromene (3a) emerged as the most effective inhibitor of both HRVs showing IC50 values of 0.20 μM and 1.38 μM towards serotype 1B and 14, respectively. The potent activity was also coupled with low cytotoxicity resulting in high therapeutic indexes (250 and 36, respectively). Mechanism of action studies indicated that 3a, like structurally related compounds, behaves as a capsid binder interfering with the early stages of rhinovirus infection, probably at the adsorption and/or uncoating level.

Novel antileishmanial chalconoids: Synthesis and biological activity of 1- or 3-(6-chloro-2H-chromen-3-yl)propen-1-ones

A series of novel chalconoids containing a 6-chloro-2H-chromen-3-yl group were prepared through a convenient and efficient synthetic method by using 5-chloro-2-hydroxybenzaldehyde as starting material. The target compounds were evaluated against the promastigote form of Leishmania major using MTT assay. All of the evaluated compounds have shown high in vitro antileishmanial activity at concentrations less than 3.0 μM. The results of cytotoxicity assessment against mouse peritoneal macrophage cells showed that these compounds display antileishmanial activity at non-cytotoxic concentrations.

Efficient one-pot synthesis of ethyl [2-(2H-Chromene-3yl)-4-oxo-L,3- thiazolidin-3-yl]acetates

Ethyl [2-(2H-chromene-3yl)-4-oxo-1,3-thiazolidin-3yl]acetates (6a-e) were synthesized in a single pot by the reaction of 2H-3-chromenecarbaldehydes (3a-e), glycine ethyl ester hydrochloride (4), and mercaptoacetic acid (5) in diisopropylethylamine/benzene under refluxing conditions in a Dean-Stark trap.

Chromene dyes

A yellow dye having the formula: STR1 wherein: R1, R2, R3 and R4 each independently represents hydrogen, halogen, or an alkoxy group of from 1 to about 6 carbon atoms; and Z1 and Z2 each independently represents cyano, esterified carboxy, amide, a substituted or unsubstituted benzoxazole, or alkylsulfonyl; or may be taken together to form a pyrazolone, barbituric acid or Meldrum's acid residue.

6-Chloro-2,3-Dihydro-4H-1-Benzopyran Carboxylic Acids: Synthesis, Optical Resolution and Absolute Configuration

6-Chloro-2,3-dihydro-4H-1-benzopyran-2-carboxylic acid, a rigid analogue of clofibric acid, the active metabolite of the antilipidemic drug clofibrate, has been prepared together with two isomers, 6-chloro-2,3-dihydro-4H-1-benzopyran-3- and 4-carboxylic a