23145-19-9

Basic information

• Product Name: 5-Methoxybenzofuran-2-carbaldehyde
• Synonyms: 5-Methoxy-2-benzofurancarbaldehyde;5-Methoxybenzofuran-2-carbaldehyde;5-methoxy-1-benzofuran-2-carbaldehyde
• CAS NO: 23145-19-9
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.17
• Mol File: 23145-19-9.mol

Chemical Properties

• Boiling Point: 296 °C at 760 mmHg
• Flash Point: 132.8 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 0.00147mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Methoxybenzofuran-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxybenzofuran-2-carbaldehyde(23145-19-9)
• EPA Substance Registry System: 5-Methoxybenzofuran-2-carbaldehyde(23145-19-9)

Safety Data

• Hazardous Substances Data: 23145-19-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
5-Methoxybenzofuran-2-carbaldehyde is utilized as a key intermediate in the synthesis of pharmaceutical compounds due to its potential pharmacological properties. Its unique structure allows for the creation of diverse chemical entities that can be explored for their therapeutic effects.
Used in Organic Synthesis:
In the field of organic chemistry, 5-Methoxybenzofuran-2-carbaldehyde serves as a versatile building block for the synthesis of a wide range of organic compounds. Its reactivity and functional groups enable chemists to construct complex molecules with specific properties and applications.
Used in Medicinal Chemistry:
5-Methoxybenzofuran-2-carbaldehyde is employed as a starting material in medicinal chemistry for the development of new drugs. Its presence in various synthesized compounds can contribute to their biological activity, making it an important component in the discovery of novel therapeutic agents.
Used in Chemical Research:
5-Methoxybenzofuran-2-carbaldehyde is also used in chemical research to study the properties and reactions of benzofuran derivatives and aldehydes. Understanding its reactivity and interactions with other molecules can lead to the development of new synthetic methods and applications in various chemical fields.

InChI:InChI=1/C10H8O3/c1-12-8-2-3-10-7(4-8)5-9(6-11)13-10/h2-6H,1H3

Upstream product

• 150-76-5 4-methoxy-phenol 
• 50551-56-9 ethyl 5-methoxybenzofuran-2-carboxylate 
• 1254062-17-3 (2-formyl-4-methoxyphenoxy)acetaldehyde diethyl acetal 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 10242-08-7 5-methoxybenzofuran-2-carboxylic acid 
• 7252-83-7 1-bromo-2,2-dimethoxyethane 
• 37603-26-2 2-(hydroxymethyl)-5-methoxy-benzo[b]furan 
• 23145-29-1 2-(2,2-Dimethoxy-ethoxy)-5-methoxy-benzaldehyde 

Downstream Products

• 139201-62-0 2-<2-(4-chlorophenyl)ethenyl>-5-methoxybenzofuran 
• 107092-74-0 5-Methoxy-2-[(Z)-2-nitro-3-(3,4,5-trimethoxy-phenyl)-propenyl]-benzofuran 
• 1429509-57-8 (E)-5-methoxy-2-(4-methylstyryl)benzofuran 
• 1429509-14-7 (Z)-5-methoxy-2-(4-methylstyryl)benzofuran 
• 138853-90-4 2-<2-(4-chlorophenyl)ethyl>-2,3-dihydro-6-(3-phenoxypropyl)-5-benzofuranol 
• 138853-86-8 2-<2-(4-chlorophenyl)ethyl>-2,3-dihydro-5-benzofuranol 
• 139201-63-1 2-<2-(4-chlorophenyl)ethenyl>-5-benzofuranol 
• 622863-31-4 5-methoxy-2-[(E,Z)-2-(2-chlorophenyl)ethenyl]-1-benzofuran 
• 622863-29-0 5-methoxy-2-[(E,Z)-2-phenylethenyl]-1-benzofuran 
• 622863-32-5 4-(2-chlorophenyl)-9-methoxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione 
• 622863-30-3 9-methoxy-4-phenyl-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione 

Relevant articles and documents

alpha-SYNUCLEIN AGGREGATE BINDING AGENT AND IMAGING METHOD

The present invention provides an α-synuclein aggregate binding agent that has high binding selectivity for an α-synuclein aggregate. The α-synuclein aggregate binding agent contains a compound represented by a formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof: in the formula (I), R1 and R2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, and hydroxyalkyl; R3 is hydrogen or halogen; the ring A is a benzene or pyridine ring; the ring B is represented by the following formula (i) or (ii): R4 and R5 are each independently selected from the group consisting of hydrogen, hydroxy, alkoxy, haloalkoxy, halohydroxyalkoxy, and aminoalkyl.

Synthesis, anti-inflammatory evaluation in vivo and docking studies of some new 5-(benzo[b]furan-2-ylmethyl)-6-methyl-pyridazin-3(2H)-one derivatives

Seven novel 5-(benzo[b]furan-2-ylmethyl)-6-methyl-pyridazin-3(2H)-one derivatives (6a to 6g) have been synthesized by the condensation of appropriate 3-(benzofuran-2-ylmethylene)-4-oxopentanoic acid and hydrazine hydrate in ethanol. Structures of all compounds were elucidated by elemental analysis, IR, 1H NMR and 13C NMR. These compounds were tested for their anti-inflammatory activity in carrageenan-induced rat paw edema model. In silico molecular docking study has been executed to study the binding interactions of the synthesized compounds with COX-2 protein. Compounds 6a, 6b, 6e and 6g showed a good anti-inflammatory activity at 50 mg/kg compared with the indometacin at 10 mg/kg and the aspirin at 150 mg/kg and good binding affinity with COX-2.

In Vitro Antitumor Activity of Newly Synthesized Pyridazin-3(2H)-One Derivatives via Apoptosis Induction

Systemic toxicity associated with drug resistance continues to be the major obstacle to curative therapy of cancer. Tumor cell resistance to chemotherapeutic drugs often results in coordinate resistance to other structurally and functionally unrelated drugs and the subsequent development of cross resistance phenotype. Therefore, it seems necessary to identify new molecules as anticancer agents. In this process, we synthesized a series of new pyridazin-3(2H)-one derivatives and evaluated their antitumor potential. These cyclic molecules were synthesized and designed as a combination of benzofuran with pyridazinones. All final compounds have been characterized by spectral and elemental analyses to confirm successful synthesis reactions. To evaluate their anticancer activity, all derivatives were assessed against the human breast adenocarcinoma cell line (MCF-7) and the murine mastocytoma cell line (P815) using the methyl tetrazolium Test (MTT assay). The cytotoxic activity was found to be dose-dependent and the IC50 values of the synthesized compounds ranged from 14.5 to 40 μM against MCF-7 and from 35 to 82.5 μM against P815. At the same time, no cytotoxic activity was observed against normal cells. In order to investigate the molecular mechanism of the most cytotoxic product (6f), apoptosis induction was measured against MCF-7 cells. Using the annexin-V FITC staining technique, we showed that the cytotoxic effect of this product is associated with apoptosis induction.

Synthesis and antidepressant activity of 5-(benzo[b]furan-2-ylmethyl)-6-methylpyridazin-3(2H)-one derivatives

A new series of pyridazin-3-one derivatives were designed, synthesized and evaluated for their preclinical antidepressant effect on Swiss mice. Among the series, compounds 6c, 6d and 6f exhibited significant activity profile in forced swimming test. Compounds 6c and 6d were most efficacious, which at dose of 50 mg kg-1 reduced the time of immobility by 42.85 and 38.09 %, respectively, as compared to the standard drug fluoxetine which reduced the immobility time by 45.23 % at the dose of 32 mg kg-1. All the test and standard compounds were administered orally 60 min before the test. Interestingly, all active compounds did not cause any significant alteration of locomotor activity in mice as compared to control, indicating that the hybrids did not produce any motor impairment effects. The results indicate that pyridazin-3(2H)-one derivatives may have potential therapeutic value for the management of mental depression.

TREATMENT OR PROPHYLAXIS OF PROLIFERATIVE CONDITIONS

The invention relates to novel compounds for use in the treatment or prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express cytochrome P450 1B1 (CYP1B1) and allelic variants thereof. The invention also provides pharmaceutical compositions comprising one or more such compounds for use in medical therapy, for example in the treatment of prophylaxis of cancers or other proliferative conditions, as well as methods for treating cancers or other conditions in human or non-human animal patients. The invention also provides methods for identifying novel compounds for use in the treatment of prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express CYP1 B1 and allelic variants thereof. The invention also provides a method for determining the efficacy of a compound of the invention in treating cancer.

A study of the Claisen-Eschenmoser reaction for hydroxymethylbenzofurans and-indoles

N,N-Dimethylacetamide dimethyl acetal reacted with 5(7)-substituted 2-(hydroxy-methyl)benzofurans to give N,N-dimethyl-2-(2-methylbenzofuran-3-yl) acetamides. Analogous reactions with 3-(hydroxymethyl)indole and 1-hydroxy-6-methyl-1,2,3,4-tetrahydro-carbazole afforded N,N-dimethyl-3-(3- indolyl)propionamide and N, N-dimethyl-2-(6-methyl-1,2,3,4-tetrahydrocarbazol-1- yl)acetamide, respectively.

ISOTHIAZOLE DIOXIDES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (IA): and the pharmaceutically acceptable salts and solvates thereof. D and E are different groups wherein one is N and the other is CR50. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of formula IA.

THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).

3,4-DI-SUBSTITUTED CYCLOBUTENE-1, 2-DIONES AS CXC-CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (I)or a pharmaceutically acceptable salt or solvate thereof. Also disclosed is the treatment of chemokine-mediated diseases using compounds of the formula (II)

Development of 2,3-Dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-5-benzofuranol (L-670,630) as a Potent and Orally Active Inhibitor of 5-Lipoxygenase

Leukotrienes are potent biological mediators of allergic and antiinflammatory diseases and are derived from arachidonic acid through the action of the 5-lipoxygenase.In this study, the syntheses and comparative biological activities of three series of 2,3-dihydro-2,6-disubstituted-5-benzofuranols with various substituents on position 3 are described.Compounds from each series were evaluated for their ability to inhibit the production of leukotriene B4 (LTB4) in human peripheral blood polymorphonuclear (PMN) leukocytes and the 5-lipoxygenase reaction in cell-free preparations from rat PMN leukocytes.The structure-activity relationships of each series in vitro and in vivo are presented.The bioavailability, metabolism, and toxicity profile of each series are discussed.The series with no substituent at position 3 was the most potent and among the compounds in that series 2,3-dihydro-6-(3-phenoxypropyl)2-(2-phenylethyl)-5-benzofuranol (46, L-670,630) was chosen for further development.