146829-56-3

Basic information

• Product Name: 2-AMINO-5-FLUOROBENZALDEHYDE
• Synonyms: 2-AMINO-5-FLUOROBENZALDEHYDE
• CAS NO: 146829-56-3
• Molecular Formula: C₇H₆FNO
• Molecular Weight: 139.13
• Mol File: 146829-56-3.mol

Chemical Properties

• Boiling Point: 260℃
• Flash Point: 111℃
• Appearance: /
• Density: 1.293
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2-AMINO-5-FLUOROBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-FLUOROBENZALDEHYDE(146829-56-3)
• EPA Substance Registry System: 2-AMINO-5-FLUOROBENZALDEHYDE(146829-56-3)

Safety Data

• Hazardous Substances Data: 146829-56-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-FLUOROBENZALDEHYDE is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
2-AMINO-5-FLUOROBENZALDEHYDE is used as a reactant in the stereoselective preparation of aryltetrahydroquinolines via gold-phosphine catalyzed heterocyclization of aminobenzaldehyde with alkynes. This process demonstrates its utility in the synthesis of complex organic molecules, which can be further utilized in various applications.

Upstream product

• 287121-32-8 (5-Fluoro-2-nitrophenyl)-methanol 
• 94569-84-3 2-bromo-5-fluorobenzaldehyde 
• 748805-85-8 (2-amino-5-fluorophenyl)methanol 
• 395-81-3 5-fluoro-2-nitrobenzaldehyde 
• 446-08-2 2-amino-5-fluorobenzoic acid 

Downstream Products

• 1128-61-6 6-fluoro-2-methyl-quinoline 
• 71083-44-8 6-fluoroquinoline-3-carbonitrile 
• 10173-67-8 4-fluoro-2-(2-fluorobenzo[4,5]imidazo[1,2-c]quinazolin-6-yl)aniline 

Relevant articles and documents

Design, synthesis and in vitro anticancer activity of novel quinoline and oxadiazole derivatives of ursolic acid

A series of new quinoline derivatives of ursolic acid were designed and synthesized in an attempt to develop potential anticancer agents. The structures of these compounds were identified by 1H NMR, 13C NMR, IR and ESI-MS spectra analysis. The target compounds were evaluated for their in vitro cytotoxicity against three human cancer cell lines (MDA-MB-231, Hela and SMMC-7721). From the results, compounds 3a–d displayed significant antitumor activity against three cancer cell lines. Especially, compound 3b was found to be the most potent derivative with IC50 values of 0.61 ± 0.07, 0.36 ± 0.05, 12.49 ± 0.08 μM against MDA-MB-231, HeLa and SMMC-7721 cells, respectively, stronger than positive control etoposide. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3b could significantly induce the apoptosis of MDA-MB-231 cells in a dose-dependent manner. The cell cycle analysis also indicated that compound 3b could cause cell cycle arrest of MDA-MB-231 cells at G0/G1 phase.

Design, synthesis, and anticancer evaluation of novel quinoline derivatives of ursolic acid with hydrazide, oxadiazole, and thiadiazole moieties as potent MEK inhibitors

In this article, a series of novel quinoline derivatives of ursolic acid (UA) bearing hydrazide, oxadiazole, or thiadiazole moieties were designed, synthesised, and screened for their in vitro antiproliferative activities against three cancer cell lines (MDA-MB-231, HeLa, and SMMC-7721). A number of compounds showed significant activity against at least one cell line. Among them, compound 4d exhibited the most potent activity against three cancer cell lines with IC50 values of 0.12 ± 0.01, 0.08 ± 0.01, and 0.34 ± 0.03 μM, respectively. In particular, compound 4d could induce the apoptosis of HeLa cells, arrest cell cycle at the G0/G1 phase, elevate intracellular reactive oxygen species level, and decrease mitochondrial membrane potential. In addition, compound 4d could significantly inhibit MEK1 kinase activity and impede Ras/Raf/MEK/ERK transduction pathway. Therefore, compound 4d may be a potential anticancer agent and a promising lead worthy of further investigation.

Silver-Catalyzed Three-Component Coupling Reaction of Amines, 2-Isocyanobenzaldehydes, and 2,2,2-Trifluorodiazoethane and Synthesis of Trifluoromethyl-Substituted Indolo[1,2-c]quinazolines

A silver-catalyzed three-component coupling reaction of amines, 2-isocyanobenzaldehydes, and 2,2,2-trifluorodiazoethane has been developed. This reaction provides an efficient method for the construction of CF3-containing dihydroquinazolines. On the basis of this reaction, using trifluorodiazoethyl-substituted dihydroquinazolines as synthons, trifluoromethyl-substituted indolo[1,2-c]quinazolines were prepared in high yields via a TBHP/KI-mediated sequential intramolecular cyclization and aromatization process. (Figure presented.).

PPTS-Catalyzed Bicyclization Reaction of 2-Isocyanobenzaldehydes with Various Amines: Synthesis of Diverse Fused Quinazolines

A PPTS (pyridinium p-toluenesulfonate)-catalyzed bicyclization reaction of 2-isocyanobenzaldehydes as 1,5-dielectrophiles with various amines has been developed. The reaction not only provides a simple and efficient strategy for the assembly of structurally diverse fused quinazoline derivatives from readily available substrates under metal-free and mild conditions in a single step with only water and hydrogen as the by-products, but also opens the way to the application of o-formyl arylisocyanides in the synthesis of nitrogen-containing heterocycles. (Figure presented.).

Repurposing an Aldolase for the Chemoenzymatic Synthesis of Substituted Quinolines

Quinoline derivatives are important natural products and pharmaceuticals, but their synthesis can be challenging due to poor yields, harsh reaction conditions, and instability of starting materials. Here we report the chemoenzymatic synthesis of quinaldic acids under mild conditions using an aldolase, trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (NahE, or HBPA). A series of 2-aminobenzaldehydes derived from reduction of the corresponding nitro analogue were reacted with pyruvate in the presence of NahE to give substituted quinolines in up to 93% isolated yield. This reaction differs from the aldol condensation catalyzed by NahE in vivo, instead resembling the heterocycle formation catalyzed by its homologue, dihydrodipicolinate synthase.

Identification of Inhibitors of Cholesterol Transport Proteins Through the Synthesis of a Diverse, Sterol-Inspired Compound Collection

Cholesterol transport proteins regulate a vast array of cellular processes including lipid metabolism, vesicular and non-vesicular trafficking, organelle contact sites, and autophagy. Despite their undoubted importance, the identification of selective modulators of this class of proteins has been challenging due to the structural similarities in the cholesterol-binding site. Herein we report a general strategy for the identification of selective inhibitors of cholesterol transport proteins via the synthesis of a diverse sterol-inspired compound collection. Fusion of a primary sterol fragment to an array of secondary privileged scaffolds led to the identification of potent and selective inhibitors of the cholesterol transport protein Aster-C, which displayed a surprising preference for the unnatural-sterol AB-ring stereochemistry and new inhibitors of Aster-A. We propose that this strategy can and should be applied to any therapeutically relevant sterol-binding protein.

INHIBITORS OF CYCLIN-DEPENDENT KINASES

Provided herein are inhibitors of cyclin-dependent kinases (CDKs), pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of diseases.

Enantioselective Organocatalytic Intramolecular Aza-Diels–Alder Reaction

A highly efficient catalytic enantioselective intramolecular Povarov reaction was developed with primary anilines as 2-azadiene precursors. A wide variety of angularly fused azacycles were obtained without column chromatography in high to excellent yields and with excellent diastereo- and enantioselectivity (d.r.>99:1 and up to e.r. 99:1). Furthermore, the catalyst loading could be lowered to 1 mol %, and the obtained azacycles could be used as key intermediates for further transformations to generate additional molecular diversity.

Easy Access to Quinolin-2(1 H)-ones via a One-Pot Tandem Oxa-Michael-Aldol Sequence

An efficient strategy for the synthesis of a variety of quinolin-2(1 H)-one derivatives has been developed. The reaction proceeded from cinnamide derivatives via a tandem reaction in the presence of NaOH to afford the corresponding 2- quinolin-2(1 H)-one derivatives in good to excellent yields.

Ursolic acid quinolinyl hydrazide derivative with anti-tumor activity as well as preparation method and application thereof

The invention discloses an ursolic acid quinolinyl hydrazide derivative with anti-tumor activity as well as a preparation method and application thereof. The invention provides an ursolic acid quinolinyl hydrazide heterocyclic derivative with a structure shown as a general formula I and pharmaceutically acceptable salt thereof: the formula I is shown in the description, wherein I-a: R1 is equal to H and R2 is equal to CH3; I-b: R1 is equal to OMe and R2 is equal to CH3; I-c: R1 is equal to F and R2 is equal to CH3; I-d: R1 is equal to C1 and R2 is equal to CH3; I-e: R1 is equal to H1 and R2 is equal to n-C4H9; I-f: R1 is equal to OMe and R2 is equal to n-C4H9; I-g: R1 is equal to F and R2 is equal to n-C4H9; I-h: R1 is equal to C1 and R2 is equal to n-C4H9. The ursolic acid quinolinyl hydrazide heterocyclic derivative and the pharmaceutically acceptable salt thereof, provided by the invention, have the remarkable anti-tumor activity; a pharmacology experiment shows that the ursolic acid quinolinyl hydrazide derivative disclosed by the invention has a remarkable inhibition effect on human breast cancer cells MDA-MB-231, human cervical cancer cells HeLa and human hepatoma cells SMMC-7721, has low toxicity on human normal epithelial cells QSG-7701 and has a potential of being used for developing anti-tumor drugs.