1355328-30-1

Basic information

• Product Name: N-(3,3-difluorocyclobutyl)formamide
• Synonyms: N-(3,3-difluorocyclobutyl)formamide;Formamide, N-(3,3-difluorocyclobutyl)-
• CAS NO: 1355328-30-1
• Molecular Formula: C₅H₇F₂NO
• Molecular Weight: 135.1119864
• Mol File: 1355328-30-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 239.3±40.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• PKA: 14.13±0.40(Predicted)
• CAS DataBase Reference: N-(3,3-difluorocyclobutyl)formamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,3-difluorocyclobutyl)formamide(1355328-30-1)
• EPA Substance Registry System: N-(3,3-difluorocyclobutyl)formamide(1355328-30-1)

Safety Data

• Hazardous Substances Data: 1355328-30-1(Hazardous Substances Data)

Usage

General Description

N-(3,3-difluorocyclobutyl)formamide is a chemical compound with the molecular formula C5H7F2NO. It is a formamide derivative containing a difluorocyclobutyl group. N-(3,3-difluorocyclobutyl)formamide is used in organic synthesis and medicinal chemistry as a building block to create other complex molecules. It has also been studied for its potential pharmacological properties, including anti-inflammatory and analgesic effects. N-(3,3-difluorocyclobutyl)formamide may also have applications in the development of new drugs and materials due to its unique chemical structure and properties.

Upstream product

• 1029720-19-1 tert-butyl (3,3-difluorocyclobutyl)carbamate 
• 637031-93-7 3,3-difluorocyclobutylamine hydrochloride 
• 154748-49-9 3-(tert-butyloxycarbonylamino)cyclobutan-1-one 
• 791061-00-2 3,3-difluorocyclobutyl-1-amine 
• 109-94-4 formic acid ethyl ester 
• 64-18-6 formic acid 

Downstream Products

• 1448345-75-2 (S)-N-((R)-1-(2-chlorophenyl)-2-(3,3-difluorocyclobutylamino)-2-oxoethyl)-N-(3-fluorophenyl)-2-oxo-3-(pyrimidin-2-yl)oxazolidine-4-carboxamide 
• 1448346-14-2 (S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-N-(3-fluorophenyl)-5-oxo-4-(pyrimidin-2-yl)morpholine-3-carboxamide 
• 1448348-39-7 5-((2S)-N-(1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyano pyridin-2-yl)-5-oxopyrrolidine-2-carboxamido)isophthalamide 
• 1448347-64-5 (2S)-N-(1-(2-Chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-dicyanophenyl)-5-oxopyrrolidine-2-carboxamide 
• 1448348-13-7 (2S)-4-(tert-Butyldimethylsilyloxy)-N-(1-(2-chlorophenyl)-2-(3,3-difluorocyclobut-ylamino)-2-oxoethyl)-N-(3-fluorophenyl)-4-methyl-5-oxopyrrolidine-2-carboxamide 
• 1448348-14-8 (2S)-4-(tert-Butyldimethylsilyloxy)-N-(1-(2-chlorophenyl)-2-(3,3-difluorocyclobutyl-amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3-fluorophenyl)-4-methyl-5-oxopyrrolidine-2-carboxamide 
• 1448348-22-8 (4S)-N-(1-(2-Chlorophenyl)-2-(3,3-difluorocyclobutylamino)-2-oxoethyl)-N-(3-fluoro-phenyl)-1-methyl-2-oxoimidazolidine-4-carboxamide 
• 1448348-21-7 Ethyl 2-((4S)-4-((1-(2-chlorophenyl)-2-(3,3-difluorocyclobutylamino)-2-oxoethyl)(3-fluorophenyl)carbamoyl)-2-oxoimidazolidin-1-yl)acetate 
• 1448345-68-3 C₂₄H₂₃ClF₃N₃O₃ 
• 1448346-52-8 (S)-N-((S)-1-(2-Chlorophenyl)-2-(3,3-difluorocyclo butylamino)-2-oxoethyl)-3-(4-cyanopyridin-2-yl)-N-(3-fluorophenyl)-2-oxoimidazolidine-4-carboxamide 
• 1448346-43-7 (S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-5-oxopyrrolidine-2-carboxamide 
• 1448347-43-0 (2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide 
• 1448347-30-5 (S)-N-((S)-1-(2-Chlorophenyl)-2-(3,3-difluorocyclobutylamino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3-fluoro-5-sulfamoylphenyl)-5-oxopyrrolidine-2-carboxamide 
• 1448347-49-6 (2S)-N-{(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl}-1-(4-cyanopyridin-2-yl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide 

Relevant articles and documents

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Mutations in isocitrate dehydrogenase 1 (IDH1) are commonly found in various human malignancies. Inhibitors of several mutant IDH1 enzymes have entered clinical trials as target therapeutic drugs for the treatment of patients with IDH1 mutations. Herein, we report the synthesis and evaluation of two 18F-labeled tracers, [18F]AG120 and [18F]AG135 for imaging expression of mutated IDH1 in positron emission tomography (PET). [18F]AG120 and [18F]AG135 were synthesized in decay-corrected radiochemical yield of 1 % and 3 %, respectively, high molar activity (52–66 MBq/nmol and 216–339 MBq/nmol, respectively) and high radiochemical purity (>99%). Both tracers showed good in vitro stability, selective uptake into mutated IDH1-expressing cells and good pharmacokinetic profiles with low uptake in most organs/tissues. Furthermore, [18F]AG120 micro-PET/CT imaging displayed significantly greater uptake in IDH1-mutant than in wild-type tumors, Relatively, uptake of [18F]AG135 was observed neither in IDH1-mutant tumor xenografts nor in wild-type tumors. This study suggests that [18F]AG120 is a promising radiotracer for PET imaging of IDH1 mutation, However, further optimization and investigation are necessary for [18F]AG135 due to the limited uptake in mutated IDH1-expressing tumors.

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Somatic point mutations at a key arginine residue (R132) within the active site of the metabolic enzyme isocitrate dehydrogenase 1 (IDH1) confer a novel gain of function in cancer cells, resulting in the production of d-2-hydroxyglutarate (2-HG), an oncometabolite. Elevated 2-HG levels are implicated in epigenetic alterations and impaired cellular differentiation. IDH1 mutations have been described in an array of hematologic malignancies and solid tumors. Here, we report the discovery of AG-120 (ivosidenib), an inhibitor of the IDH1 mutant enzyme that exhibits profound 2-HG lowering in tumor models and the ability to effect differentiation of primary patient AML samples ex vivo. Preliminary data from phase 1 clinical trials enrolling patients with cancers harboring an IDH1 mutation indicate that AG-120 has an acceptable safety profile and clinical activity.