5901-56-4

Usage

InChI:InChI=1/C7H8N4O2/c8-7(9)10-5-1-3-6(4-2-5)11(12)13/h1-4H,(H4,8,9,10)

Upstream product

• 420-04-2 CYANAMID 
• 100-01-6 4-nitro-aniline 
• 506-93-4 guanidine nitrate 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 42249-51-4 N-(4-nitrobenzenesulfonyl)guanidine 
• 67-64-1 acetone 
• 152120-58-6 N,N′-bis(tert-butoxycarbonyl)-N′′-(4-nitrophenyl)guanidine 
• 18905-24-3 p-aminophenylguanidine 
• 636-98-6 p-nitrobenzene iodide 
• 867-44-7 S-Methylisothiourea sulfate 

Downstream Products

• 21226-34-6 N-(4-nitrophenyl)-4-nitrobenzenesulfonamide 
• 858501-16-3 N-(4-nitro-benzenesulfonyl)-N'-(4-nitro-phenyl)-guanidine 
• 127099-85-8 N-Cyanoguanidine 
• 32503-05-2 1-(4-chlorophenyl)-3-(4-nitrophenyl)guanidine 
• 1381848-15-2 1-(2-methoxyphenyl)-3-(4-nitrophenyl)guanidine 
• 1381848-14-1 1-(4-nitrophenyl)-3-(m-tolyl)guanidine 
• 1381848-13-0 1-(4-methoxyphenyl)-3-(4-nitrophenyl)guanidine 
• 1381848-16-3 methyl 4-(3-(4-Nitrophenyl)guanidino)benzoate 
• 1415509-23-7 C₁₈H₁₄N₆O₂ 
• 1415509-29-3 C₁₉H₁₆N₆O₂ 
• 1612217-65-8 4-(4-fluorophenyl)-N-(4-nitrophenyl)pyrimidin-2-amine 
• 1612217-70-5 C₁₆H₁₁BrN₄O₂ 
• 1612217-73-8 C₁₆H₁₀Cl₂N₄O₂ 
• 1612217-77-2 C₁₆H₁₀Cl₂N₄O₂ 

Relevant academic research and scientific papers

The utilization of ball milling in synthesis of aryl guanidines through guanidinylation and N-Boc-deprotection sequence

Solid state ball milling was used in guanidinylation reactions of aromatic amines with N,N′-Di-Boc-1H-pyrazole-1-carboxamidine reagent. Reaction conditions are advantageous, and in general reactions proceed in significantly shorter reaction times and in higher yields than under the conventional solution conditions. Mechanochemical conditions were also successfully applied to the cleavage of N-Boc protecting group.

Design and synthesis of a novel series of N,4-diphenylpyrimidin-2-amine derivatives as potent and selective PI3Kγ inhibitors

Due to the increasing evidence linking the PI3Kγ pathway to various disease states, PI3Kγ is becoming an important target for cancer treatment. Herein we designed and synthesized a novel series of N,4-diphenylpyrimidin-2-amine derivatives with low CDOCKER-INTERACTION-ENERGY and then evaluated their PI3Kγ in vitro inhibitory activities and in vitro antiproliferation assays against four human cancer cells. Among the compounds we synthesized, compound C8 (IC50 = 65 nM) demonstrated the most potent inhibitory activity against PI3Kγ kinase as well as at the cellular level, compared to the control drug TG100713 (IC50 = 127 nM). Moreover, molecular docking analysis was also performed to determine possible binding modes between PI3Kγ and the target compounds.

Synthesis of symmetrical and unsymmetrical N, N ′-diaryl guanidines via copper/N-methylglycine-catalyzed arylation of guanidine nitrate

CuI/N-methylglycine-catalyzed coupling reaction of guanidine nitrate with both aryl iodides and bromides takes place at 70-100 °C, affording symmetrical N,N′-diaryl guanidines with good to excellent yields. Unsymmetrical N,N′-diaryl guanidines can be assembled via monoarylation of guanidine nitrate with aryl iodides bearing a strong electron-withdrawing group and subsequent coupling with another aryl iodide.

Palladium-catalyzed C-H functionalization using guanidine as a directing group: Ortho arylation and olefination of arylguanidines

Palladium-catalyzed C-H functionalization using guanidine as the directing group was achieved under mild reaction conditions. Various guanidine derivatives were produced in moderate to good yields by using simple unactivated arenes or ethyl acrylate as the source of arylation or olefination, respectively.

Structural and biochemical basis for the firm chemo- and regioselectivity of the nitro-forming N-oxygenase AurF

Site-directed mutagenesis based on the crystal structure of AurF, a nitro group forming monooxygenase from Streptomyces thioluteus, revealed that AurF variants are capable of selectively transforming guanidyl- and amidinyl-substituted anilines into the corresponding nitro compounds. Our results provide new insights into the biochemical basis of regioselective N-oxygenation. The Royal Society of Chemistry.

Solid-phase synthesis of N-aryl-N′-carboalkoxy guanidines by the mitsunobu reaction of Fmoc-guanidines

A new method for the solid-phase synthesis of N-aryl-N′-carboalkoxy guanidines is described. Aromatic amines were reacted with Fmoc-isothiocyanate to provide Fmoc-thioureas, which were coupled with Rink amide resin to provide the corresponding resin-bound Fmoc-guanidines. Subsequent Mitsunobu alkylation with a variety of alcohols delivered N-aryl-N′ carboalkoxy guanidines in good to high purity after resin cleavage.

A novel, facile methodology for the synthesis of N,N′-bis(tert-butoxycarbonyl)-protected guanidines using polymer-supported carbodiimide

A novel methodology for the synthesis of guanidines from amines has been developed using polymer assisted synthesis, potentially allowing the preparation of series of compounds in a high throughput manner. The methodology comprises the use of polymer-supported carbodiimide as the activating agent for N,N′-bis(tert-butoxycarbonyl) thiourea with polymer-supported trisamine as a scavenger, followed by deprotection with trifluoroacetic acid. For the first time, polymer-supported carbodiimide has been utilized as an activating agent to synthesize guanidines.