33342-18-6

Usage

Uses

Used in Organic Synthesis:
5-(3-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE is utilized as a key building block in organic synthesis for the creation of a variety of pharmaceuticals and biologically active molecules. Its presence in these syntheses is attributed to its reactive aldehyde group and the electron-withdrawing fluorine atom on the phenyl ring, which can influence the reactivity and selectivity of chemical reactions.
Used in Medicinal Chemistry:
In the realm of medicinal chemistry, 5-(3-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE serves as a versatile intermediate for the preparation of new drugs. Its unique structural features allow it to be incorporated into drug candidates that target specific biological pathways or receptors, potentially leading to the development of novel therapeutic agents.
Used in Chemical Biology Research:
5-(3-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE is also employed in chemical biology for research purposes. Its distinctive structure allows it to be a useful probe in studying the interactions between small molecules and biological targets, contributing to a better understanding of molecular mechanisms and the discovery of new bioactive compounds.
Used in Pharmaceutical Industry:
5-(3-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE is used as a synthetic intermediate for the development of new pharmaceuticals. Its incorporation into drug molecules can enhance their pharmacological properties, such as potency, selectivity, and metabolic stability, thereby improving their therapeutic potential.
Used in Agrochemical Industry:
Although not explicitly mentioned in the provided materials, given its utility in organic synthesis, 5-(3-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE could potentially be used in the agrochemical industry as a precursor for the synthesis of bioactive compounds with pesticidal or herbicidal properties, contributing to the development of more effective and environmentally friendly agrochemicals.

Upstream product

• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 768-35-4 3-fluorophenylboronic acid 
• 33756-24-0 tris(3-flourophenyl)bismuthine 
• 27329-70-0 5-formylfurane-2-boronic acid 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 98-01-1 furfural 
• 372-19-0 meta-fluoroaniline 

Downstream Products

• 1259371-02-2 (E)-5-(3'-fluorophenyl)furan-2-carbaldehyde 4-bromobenzoylhydrazone 
• 1338232-97-5 (Z)-5-((5-(3-fluorophenyl)furan-2-yl)methylene)-2-iminothiazolidin-4-one 
• 33342-27-7 [5-(3-fluoro-phenyl)-furan-2-yl]-methanol 
• 1032337-86-2 C₁₉H₁₂F₃NO₄ 
• 1032338-36-5 C₁₉H₁₃ClFNO₄ 
• 1032338-11-6 C₁₉H₁₂Cl₂FNO₄ 

Relevant academic research and scientific papers

Access to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan-Yne Cyclization of N -(2-Furanylmethyl) Alkynamides under Air

A protocol for synthesis of chalcone derivatives with a 2-pyridone subunit from N-(2-furanylmethyl) alkynamides is reported. This synthesis involves Pd/Cu-catalyzed oxidative furan-yne cyclization at room temperature in air and may proceed via nucleopalladation of the alkyne to form a vinylpalladium intermediate, with a furan ring acting as the nucleophile.

Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations

Protein arginine methyltransferase 5 (PRMT5) is an important protein arginine methyltransferase that catalyzes the symmetric dimethylation of arginine resides on histones or non-histone substrate proteins. It has been thought as a promising target for many diseases, particularly cancer. Despite the potential applications of PRMT5 inhibitors in cancer treatment, very few of PRMT5i have been publicly reported. In this investigation, virtual screening and structure–activity relationship studies were carried out to discover novel PRMT5i, which finally led to the identification of a number of new PRMT5i. The most active compound, P5i-6, exhibited a considerable inhibitory potency against PRMT5 with an IC50 value of 0.57?μm, and a high selectivity for PRMT5 against other tested PRMTs. It displayed a very good antiviability activity against two colorectal cancer cell lines, HT-29 and DLD-1, and one hepatic cancer cell line, HepG2, in a sensitivity assay against 36 different cancer cell lines. Western blot assays indicated that P5i-6 selectively inhibited the symmetric dimethylations of H4R3 and H3R8 in DLD-1 cells. Overall, P5i-6 could be used as a chemical probe to investigate new functions of PRMT5 in biology and also served as a good lead compound for the development of new PRMT5-targeting therapeutic agents.

Novel inhibitors of Plasmodium falciparum based on 2,5-disubstituted furans

Phenotypic HTS campaigns with a blood stage malaria assay have been used to discover novel chemotypes for malaria treatment with potential alternative mechanisms of action compared to existing agents. N1-(5-(3-Chloro-4-fluorophenyl)furan-2-yl)-N3,N3-dimethylpropane-1,3-diamine, 1 was identified as a modest inhibitor of P. falciparum NF54 (IC50= 875 nM) with an apparent long plasma half-life after high dose oral administration to mice, although the compound later showed poor metabolic stability in liver microsomes through ring- and side chain-oxidation and N-dealkylation. We describe here the synthesis of derivatives of 1, exploring the influence of substitution patterns around the aromatic ring, variations on the alkyl chain and modifications in the core heterocycle, in order to probe potency and metabolic stability, where 4k showed a long half-life in rats.

Identification of a small molecule inhibitor that stalls splicing at an early step of spliceosome activation

Small molecule inhibitors of pre-mRNA splicing are important tools for identifying new spliceosome assembly intermediates, allowing a finer dissection of spliceosome dynamics and function. Here, we identified a small molecule that inhibits human pre-mRNA splicing at an intermediate stage during conversion of pre-catalytic spliceosomal B complexes into activated Bact complexes. Characterization of the stalled complexes (designated B028) revealed that U4/U6 snRNP proteins are released during activation before the U6 Lsm and B-specific proteins, and before recruitment and/or stable incorporation of Prp19/CDC5L complex and other Bact complex proteins. The U2/U6 RNA network in B028 complexes differs from that of the Bact complex, consistent with the idea that the catalytic RNA core forms stepwise during the B to Bact transition and is likely stabilized by the Prp19/CDC5L complex and related proteins. Taken together, our data provide new insights into the RNP rearrangements and extensive exchange of proteins that occurs during spliceosome activation.

Mono- and biscouplings using triarylbismuths for the atom-efficient arylations of functionalized furans under palladium catalysis

Palladium-catalyzed cross-coupling reactions of functionalized bromofurans with triarylbismuths have been described for the atom-economic synthesis of functionalized arylfuran systems. The coupling reactions using triarylbismuths with various 2-bromofurans and 2,5-dibromofuran underwent smoothly to afford the corresponding 2-arylfurans and 2,5-diarylfurans in high yields in a short reaction time (one hour). Georg Thieme Verlag Stuttgart · New York.

Synthesis and evaluation of compounds that induce readthrough of premature termination codons

A structure-activity relationship (SAR) study was carried out to identify novel, small molecular weight compounds which induce readthrough of premature termination codons. In particular, analogs of RTC13, 1, were evaluated. In addition, hypothesizing that these compounds exhibit their activity by binding to the ribosome, we prepared the hybrid analogs 13 containing pyrimidine bases and these also showed good readthrough activity.

New class of potent antitumor acylhydrazone derivatives containing furan

A pair of chemical isomeric structures of N-acylhydrazone compounds I and II were designed and synthesized. The reaction was carried out with high diastereoselectivity to obtain one configurational isomer in excellent yields. The exact configuration and conformation of IIa and IIe were confirmed by the X-ray single crystal diffraction. The antitumor bioassay revealed that some compounds exhibited excellent activity against the selected cancer cell lines. In particular, IIf (IC50 = 16.4 μM) was better than doxorubicin (IC50 = 53.3 μM) against human promyelocytic leukemic cells (HL-60). Their toxicities were predicted in silico. The results showed that compounds II were safe and eligible to be development candidates. IIf showed great promise as a novel lead compound for further anticancer discovery.

Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2- furanmethyl ester

Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, 1H NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus, but most compounds exhibited good fungicidal activities against Corynespora cassiicola, Thanatephorus cucumeris, Botrytis cinerea, and Fusarium oxysporum. In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides.

Inhibitors of HCV NS5B polymerase. Part 1: Evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid

A novel series of nonnucleoside HCV NS5B polymerase inhibitors were prepared from (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid, a high throughput screening lead. SAR studies combined with structure based drug design focusing on the southern heterobiaryl region of the template led to the synthesis of several potent and orally bioavailable lead compounds. X-ray crystallography studies were also performed to understand the interaction of these inhibitors with HCV NS5B polymerase.

N-hydroxy-5-phenyl-2-furancarboximidamides useful as cardiotonic agents

The present invention involves certain N-hydroxy-5-phenyl-2-furancarboximidamides, pharmaceutical compositions containing such compounds, and methods for increasing the contractile force of cardiac muscle of a mammal which comprises systemically administering such compounds to a mammal.