3328-73-2

Usage

Structure

A derivative of isophthalaldehyde with a hydroxyl group and a methyl group attached to the benzene ring

Applications

a. Building block in the synthesis of organic compounds and materials
b. Used in the production of polymers and pharmaceuticals
c. Employed as a fluorescent probe for detecting specific metal ions in biological and environmental samples

Properties

a. High reactivity
b. Versatility in organic synthesis
c. Valuable tool for chemical research and industrial applications

Upstream product

• 100-97-0 hexamethylenetetramine 
• 95-48-7 ortho-cresol 
• 50-00-0 formaldehyd 
• 6641-13-0 6,6'-dihydroxy-5,5'-dimethyl-3,3'-methanediyl-di-benzyl alcohol 
• 64-19-7 acetic acid 
• 76-05-1 trifluoroacetic acid 
• 15174-69-3 4-hydroxy-3-methyl-benzaldehyde 

Downstream Products

• 1290078-26-0 3-(4-methoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde 
• 1290078-27-1 3-(3,4-dimethoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde 
• 1360827-32-2 8-(3-(4-chloro-phenyl)-3-oxoprop-1-enyl),10-methyl-3,4-dihydro-2H,6H-3,6-epoxy-benzo[1,5]dioxocine 
• 1360827-45-7 C₁₇H₁₃ClO₃ 
• 1342894-89-6 8-(3-oxo-3-phenylprop-1-enyl),10-methyl-3,4-dihydro-2H,6H-3,6-epoxy-benzo[1,5]dioxocine 
• 1342894-76-1 (E)-2-hydroxy-3-methyl-5-(3-oxo-3-phenylprop-1-enyl)benzaldehyde 
• 1342894-90-9 8-(3-oxo-3-p-tolylprop-1-enyl),10-methyl-3,4-dihydro-2H,6H-3,6-epoxy-benzo[1,5]dioxocine 
• 1342894-91-0 8-(3-(4-methoxyphenyl)-3-oxoprop-1-enyl),10-methyl-3,4-dihydro-2H,6H-3,6-epoxy-benzo[1,5]dioxocine 
• 1342894-78-3 (E)-2-hydroxy-5-(3-(4-methoxyphenyl)-3-oxoprop-1-enyl)-3-methylbenzaldehyde 
• 1616108-74-7 (E)-3-(4-hydroxy-3-methyl-5-((E)-(thiazol-2-ylimino)methyl)phenyl)-1-p-tolylprop-2-en-1-one 
• 1616108-75-8 (E)-3-(4-hydroxy-3-methyl-5-((E)-(thiazol-2-ylimino)methyl)phenyl)-1-(4-methoxy phenyl)prop-2-en-1-one 
• 1616108-76-9 (E)-1-(furan-2-yl)-3-(4-hydroxy-3-methyl-5-((E)-(thiazol-2-ylimino)methyl)phenyl)prop-2-en-1-one 
• 1616108-77-0 (E)-1-(furan-2-yl)-3-(4-hydroxy-3-methyl-5-((E)-(thiazol-2-ylimino)methyl)phenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Benzofuran-chalcone hybrids as potential multifunctional agents against Alzheimer's disease: Synthesis and in vivo studies with transgenic Caenorhabditis elegans

In the search for effective multifunctional agents for the treatment of Alzheimer's disease (AD), a series of novel hybrids incorporating benzofuran and chalcone fragments were designed and synthesized. These hybrids were screened by using a transgenic Ca

Discovery of coumarin-dihydroquinazolinone analogs as niacin receptor 1 agonist with in-vivo anti-obesity efficacy

In this study, we presented rational designing and synthesis of coumarin-dihydroquinazolinone conjugates to evaluate their agonist activity at GPR109a receptor. Among the synthesized small molecule library, compound 10c displayed robust agonist action at

Synthesis and study of benzofuran-pyran analogs as BMP-2 targeted osteogenic agents

Twenty-four novel benzofuran-pyran derivatives were synthesized and evaluated for their anti-osteoporotic activity in primary cultures of rat calvarial osteoblasts in vitro. Among all the compounds screened for the alkaline phosphatase activity, three compounds 4e, 4j and 4k showed potent activity at picomolar concentrations in osteoblast differentiating stimulation. Additionally, these compounds were found effective in mineralization, assessed by alizarin red-S staining assay. Compounds were again validated through a series of other in vitro experiments. Moreover, molecular dynamics simulations demonstrated that both benzofuran and pyran moieties are requisite to fit into the active site of BMP-2 receptor, a key target of the osteogenic agents. The obtained results strongly convey that compound 4e is a potential bone anabolic agent among synthesized series, which can be further explored as a drug lead for treating osteoporosis.

Benzofuran-pyran hybrids: A new class of potential bone anabolic agents

Benzofuran moiety is an important pharmacophore showing positive effects on bone health. In the present study, sixteen benzofuran-pyran hybrids were synthesized and were evaluated for their osteogenic effects on primary osteoblast cells isolated from calv

Synthesis and bio-evaluation of indole-chalcone based benzopyrans as promising antiligase and antiproliferative agents

DNA replication and repair are complex processes accomplished by the concerted action of a network of enzymes and proteins. DNA ligases play a crucial role in these processes by catalyzing the nick joining between DNA strands. As compared to normal cells,

Benzthiazole-derived chromogenic, fluorogenic and ratiometric probes for detection of hydrazine in environmental samples and living cells

Benzothiazole-based chromogenic and ratiometric fluorescent chemodosimetric probes CD1 and CD2, were synthesized and characterized. The probes are designed in such a way that the excited state intramolecular proton transfer (ESIPT) of the benzothiazole moiety gets blocked. Upon treatment with hydrazine in organo-aqueous medium[DMSO: H2O; 2:1 (v/v)] at physiological pH, the aectyl protective group of probes CD1 and CD2 were removed readily in presence hydrazine and ESIPT of the probes were switched on, which resulted remarkable photo-physical changes. These two ESIPT–based ratiometric fluorescent probes were shown to be selective and sensitive for hydrazine among different cations, anions and amines studied in organo-aqueous medium[DMSO: H2O; 2:1 (v/v)] at physiological pH, by fluorescence, absorption, and visual emission color change. These key features allows the two probes to be employed for hydrazine detection by simple visual inspection. DFT and TDDFT calculations were performed in order to demonstrate the sensing mechanism and the electronic properties of probe and hydrazinolysis product. An easy-to-prepare test strips, obtained by dipping the TLC plates into the solution of CD1 and CD2, were able to detect hydrazine in practical samples. Moreover, the utility of the probes CD1 in showing the hydrazine recognition in live cells has also been demonstrated using Vero cells as monitored by fluorescence imaging.

Design, synthesis and anticancer activity of dihydropyrimidinone-semicarbazone hybrids as potential human DNA ligase 1 inhibitors

A series of new dihydropyrimidinone-semicarbazone hybrids were successfully synthesised by integrating regioselective multicomponent reaction with the pharmacophore hybridization approach. All the synthesised compounds were evaluated for their hLig1 inhibition potency and most of them were found to be good to moderately active. Out of the tested derivatives, compound 6f showed selective anti-proliferative activity against HepG2 cells in a dose-dependent manner with an IC50 value of 10.07 ± 1.2. It also reduced cell survival at ≤20 μM concentration. Further, analysis of treated HepG2 cell lysates by western blot assay showed increased γ-H2AX levels and upregulation of p53, leading to apoptosis. In silico docking results explain the binding modes of compound 6f to the DNA-binding domain of hLig1 enzyme thereby preventing its nick sealing activity. In addition, the favourable pharmacokinetic properties suggest that this new class of hLig1 inhibitors could be promising leads for further drug development.

Design, synthesis and in vitro evaluation of coumarin-imidazo[1,2-a]pyridine derivatives against cancer induced osteoporosis

A series of biologically important 6-(imidazo[1,2-a]pyridin-2-yl)-2H-chromen-2-one derivatives were synthesized by employing the silver(I) catalysed Groebke-Blackburn-Bienayme multicomponent reaction. The synthesized compounds were tested in a primary calvarial osteoblast cells by alkaline phosphatase assay and an alizarin red-S staining assay for their possible osteoprotective properties. Further, the effects of active compounds 6h, 6l, and 6o on the expression of osteogenic genes BMP2, RUNX2, COL1, and OCN were measured by qPCR. Out of three promising compounds, 6l and 6o significantly induced apoptosis in MDA-MB-231 cancer cells via mitochondrial depolarisation without affecting normal cells. In an in vitro co-culture model of bone metastasis, we investigated the ability of coumarin-imidazo[1,2-a]pyridine hybrids to reverse the negative impact of MDA-MB-231 cancer cells on osteoblast differentiation. The results illustrate the potential of designed hybrids to re-establish the bone homeostasis. These findings demonstrate the significance of newly synthesized hybrids as lead molecules, possessing both anti-osteoporotic and anticancer properties that can be developed into new therapeutic agents to alleviate osteoporosis and bone metastasis.

Hybrids of coumarin-indole: Design, synthesis and biological evaluation in Triton WR-1339 and high-fat diet induced hyperlipidemic rat models

In this study, a series of coumarin-indole hybrids have been synthesized and evaluated for their lipid lowering activity. Preliminary biological screening of the synthesized compounds was undertaken in an in vitro model of the HMG-CoA reductase enzyme, an

Highly efficient synthesis of chalcones from poly carbonyl aromatic compounds using bf3-et2o via a regioselective condensation reaction

A new, simple, highly efficient method for the synthesis of different types of carbonyl chalcones through a regioselective condensation reaction of appropriate 5-acetyl-2-hydroxybenzaldehyde with various substituted acetophenones and 4-hydroxyisothalaldehyde with various substituted aldehydes using BF3-Et2O as a reagent is described.