75907-83-4

Basic information

• Product Name: 2-FLUORO-N-HYDROXY-BENZAMIDINE
• Synonyms: 2-FLUORO-N-HYDROXY-BENZAMIDINE;ART-CHEM-BB B034860;VITAS-BB TBB010693
• CAS NO: 75907-83-4
• Molecular Formula: C₇H₇FN₂O
• Molecular Weight: 154.1416832
• Product Categories: pharmacetical
• Mol File: 75907-83-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-FLUORO-N-HYDROXY-BENZAMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUORO-N-HYDROXY-BENZAMIDINE(75907-83-4)
• EPA Substance Registry System: 2-FLUORO-N-HYDROXY-BENZAMIDINE(75907-83-4)

Safety Data

• Hazardous Substances Data: 75907-83-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluoro-N-hydroxy-benzamidine is used as a building block for the synthesis of various pharmaceuticals, leveraging its unique properties to create novel drug candidates with improved efficacy and selectivity.
Used in Organic Synthesis:
2-FLUORO-N-HYDROXY-BENZAMIDINE serves as a reagent in organic synthesis, enabling the creation of a wide range of organic compounds for various applications, including the development of new materials and the synthesis of complex organic molecules.
Used in Research and Development:
2-Fluoro-N-hydroxy-benzamidine is utilized as a research tool in the study of biological processes, aiding scientists in understanding the mechanisms of action and potential applications of 2-FLUORO-N-HYDROXY-BENZAMIDINE in biological systems.

Upstream product

• 394-47-8 2-fluorobenzonitrile 
• 75907-82-3 2-fluorobenzothioamide 

Downstream Products

• 75907-99-2 5-(3,3-Dinitrobutyl)-3-(2-fluorophenyl)-1,2,4-oxadiazole 
• 75907-89-0 O-(4,4-Dinitropentanoyl)-2-fluorobenzamidoxime 
• 16672-12-1 3-(2-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one 
• 110722-41-3 {3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 110703-57-6 {3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid 
• 110704-45-5 5-Chloromethyl-3-(2-fluoro-phenyl)-[1,2,4]oxadiazole 
• 844498-75-5 C₉H₈ClFN₂O₂ 
• 685525-40-0 3-[3-(2-fluorphenyl)-1,2,4-oxadiazol-5-yl]-propanoic acid 
• 71204-93-8 2-fluorobenzimidamide 

Relevant articles and documents

Novel O-acylated amidoximes and substituted 1,2,4-oxadiazoles synthesised from (+)-ketopinic acid possessing potent virus-inhibiting activity against phylogenetically distinct influenza A viruses

This article describes the synthesis and antiviral activity evaluation of new substituted 1,2,4-oxadiazoles containing a bicyclic substituent at position 5 of the heterocycle and O-acylated amidoximes as precursors for their synthesis. New compounds were

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators

Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing py

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Structure-activity and structure-property relationships of novel Nrf2 activators with a 1,2,4-oxadiazole core and their therapeutic effects on acetaminophen (APAP)-induced acute liver injury

The antioxidant function induced by Nrf2 protects the liver from damage. We found a novel Nrf2 activator named compound 25 via structural modification of compound 1 we previously reported. In vitro, compound 25 induced Nrf2 transport into the nucleus and protected hepatocyte L02 cells from APAP-induced cytotoxicity via activating the Nrf2-ARE signaling pathway. In vivo, 25 exhibited therapeutic effects in a mouse model of acute liver injury induced by acetaminophen (APAP) by up-regulating Nrf2-dependent antioxidases and down-regulating liver injury markers in serum. Together, these results indicated that 25 is a potent Nrf2/ARE activator both in vitro and in vivo. The drug-like properties of compound 25 further revealed its potential for development as a therapeutic drug against acute liver injury.

Synthesis, characterisation and photophysical studies of oxadiazolyl coumarin: A new class of blue light emitting fluorescent dyes

A library of novel 1, 2, 4-oxadiazole linked coumarin dyes have been synthesised via condensation of corresponding acid 6 and N’-hydroxybenzimidamide 8. This new class of organic compounds were examined for their fluorescent properties and found to emit blue light in the visible region of the spectrum with very high Stoke's shift values. Most of these compounds demonstrated high quantum yields and fluorescence life time in nano-second range which makes them quite lucrative to be used as new fluorescent probes. The highest quantum yield of 0.68 was shown by compound 9j which also shows high Stoke's shift value. The electronic structure of these coumarin-based donor–π–acceptor (D–π–A)-type organic dyes have been examined by Density Functional Theory (DFT). TGA analysis of few of the compounds show that they are stable up to temperature range of 0–245?°C. The synthesised compounds were characterised by NMR and mass spectrometry and the structure of two of these compounds have been confirmed by X-ray crystallography.

NEW AMINOACID DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I): wherein R1, R2, R5, R6, R7, R12, X, Y, A, E and n are as defined in the description. Medicaments.

Nitrobenzofurazan derivatives of N′-hydroxyamidines as potent inhibitors of indoleamine-2,3-dioxygenase 1

Tryptophan metabolism through the kynurenine pathway is considered as a crucial mechanism in immune tolerance. Indoleamine 2,3-dioxygenase 1 (IDO1) plays a key role in tryptophan catabolism in the immune system and it is also considered as an important therapeutic target for the treatment of cancer and other diseases that are linked with kynurenine pathway. In this study, a series of nitrobenzofurazan derivatives of N′-hydroxybenzimidamides (1) and N′-hydroxy-2-phenylacetimidamides (2) were synthesized and their inhibitory activities against human IDO1 enzyme were tested using in-vitro and cellular enzyme activity assay. The optimization leads to the identification of potent compounds, 1d, 2i and 2k (IC50 = 39-80 nM), which are either competitive or uncompetitive inhibitors of IDO1 enzyme. These compounds also showed IDO1 inhibition potencies in the nanomolar range (IC50 = 50-71 nM) in MDA-MB-231 cells with no/negligible amount of cytotoxicity. The stronger selectivity of the potent compounds for IDO1 enzyme over tryptophan 2,3-dioxygenase (TDO) enzyme (312-1593-fold) also makes them very attractive for further immunotherapeutic applications.

Oxadiazolone-Enabled Synthesis of Primary Azaaromatic Amines

Despite their tremendous synthetic and pharmaceutical utility, primary azaaromatic amines remain elusive for access based on a generally applicable C-H functionalization strategy. An oxadiazolone-enabled approach is reported for convenient entry into N-unsubstituted 1-aminoisoquinolines through Co(III)-catalyzed redox-neutral, step-, atom-, and purification-economic C-H functionalization with alkynes. A 15N labeling experiment reveals the effectiveness of both oxadiazolone N atoms as directing sites. The installed primary amine can be harnessed as a synthetically useful handle for attachment of divergent appendages.

Microwave-assisted synthesis, molecular docking and antiproliferative activity of (3/5-aryl-1,2,4-oxadiazole-5/3-yl)(3,4,5-trimethoxyphenyl)methanone oxime derivatives

A series of (3/5-aryl-1,2,4-oxadiazole-5/3-yl)(3,4,5-trimethoxyphenyl)methanone oxime derivatives were synthesized via a rapid and facile microwave-assisted synthesis method of building a 1,2,4-oxadiazole skeleton using mandelic acid as the starting material. Twenty-four target compounds were evaluated for their in vitro antiproliferative activities against three human cancer cell lines (SGC-7901, A549 and HT-1080). Among them, 16b exhibited the highest potency against different tumour cell lines, especially the A549 cell line (IC50 = 87 nM). Structure-activity relationship (SAR) studies revealed that the aryl substituent at the C-5 position on the 1,2,4-oxadiazole ring is superior to that at the C-3 position. An oxime as a connector can obviously increase the potency, contrary to that in SMART derivatives. Moreover, 16b significantly induced a cell cycle arrest in the G2/M phase and caused microtubule destabilization. Molecular docking studies provided a theoretical binding mode of 16b at the colchicine site in the tubulin dimer. Our work laid the foundation for further structure-guided design of novel tubulin polymerization inhibitors.

Design and discovery of 5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide inhibitors of HIV-1 integrase

Raltegravir (RAL) is a first clinically approved integrase (IN) inhibitor for the treatment of HIV but rapid mutation of the virus has led to chemo-resistant strains. Therefore, there is a medical need to develop new IN inhibitors to overcome drug resista