6939-12-4

Usage

InChI:InChI=1/C3H4N2O2/c1-5-2-3(6)7-4-5/h2H,1H3/p+1

Upstream product

• 13256-22-9 N-nitrososarcosine 
• 108-24-7 acetic anhydride 
• 107-97-1 sarcosine 
• 17590-38-4 3-methyl-N-nitroso-5-sydnone imine 

Downstream Products

• 33549-57-4 4-(hydroxy-diphenyl-methyl)-3-methyl-sydnone 
• 145161-65-5 2-Methyl-6-(N-methylanilino)-4,7(2H)-indazolchinon 
• 197226-81-6 ethyl 1-methyl-4-(trifluoromethyl)-1H-pyrazole-3-carboxylate 
• 111493-74-4 ethyl 3-(trifluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 
• 62102-92-5 (Z)-3-methyl-4-styrylsydnone 
• 1173658-38-2 3-methyl-4-(1-phenylvinyl)sydnone 
• 1315168-19-4 C₁₁H₈N₂O₂ 
• 3463-26-1 1-methyl-3-phenyl-1H-pyrazole 
• 1002334-06-6 1-methyl-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 
• 1146143-79-4 4-(4-methoxyphenyl)-3-methylsydnone 
• 1146143-76-1 3-methyl-4-(3-nitrophenyl)sydnone 
• 35431-71-1 3-methyl-4-phenylsydnone 
• 93029-87-9 3-methyl-4-(4-nitrophenyl)sydnone 
• 1005788-16-8 N-(5-hydroxy-2-methylphenyl)-1,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 

Relevant academic research and scientific papers

Formation of Liquid-Crystal Phases in the Binary System Cetylpyridinium Bromide/N-Methylsydnone Studied by Light Microscopy and Small-Angle X-ray Diffraction

Liquid-crystal phases were detected in the binary system cetylpyridinium bromide/N-methylsydnone by optical microscopy and small-angle X-ray diffraction.Surfactant self-aggregation can thus occur in aprotic solvents.Hydrogen bonding in solvents is thus not an essential requirement for molecular aggregation.

New NO-donors with antithrombotic and vasodilating activities, II: 3-Alkyl-N-nitroso-5-sydnone imines

Fifteen 3-alkyl-, four 3-cycloalkyl-N-nitroso-5-sydnone imines and five 3-alkyl-N-nitro-5-sydnone imines were synthesized and their ability to inhibit platelet aggregation induced by collagen (Born-test) was studied in vitro. Dependent on the chemical structure, the IC50-values for the inhibition of platelet aggregation were in the range of 0.2-140 μmol/L. It is suggested that this scale reflects different binding properties of the nitrosimines with respect to the platelet membrane. Highest activities were observed for the 3-hexyl (2f) and the 3-cyclohexyl (2p) derivative. Three nitrimines (3e, 3f, 3i) also showed IC50 values below 10 μmol/L. For the nitrosimines 2a, 2f, and 2m antithrombotic activity was demonstrated in vivo. They inhibited laser induced arterial thrombosis in anesthetized rats up to 70% two h after oral administration. In conscious renal-hypertensive dogs, the decrease in systolic blood pressure and left ventricular enddiastolic pressure suggests an antianginal activity of the compound 2a similar to that of molsidomine (M). The smoother onset and the longer duration of action of the new compound as compared to M could be a significant advantage of 2a in the therapy of angina pectoris.

Visible-light induced photo-click and release strategy between monoarylsydnone and phenoxylfumarate

We report a visible-light induced photo-click and release platform between monoarylsydnone (MASyd) and phenoxylfumarates. The pyrazoline produced by the cycloaddition undergoes a photo-aromatization to form a fluorescent pyrazole. Meanwhile, the photo-aro

Expanding available pyrazole substitution patterns by sydnone cycloaddition reactions

We report the use of alkynylsilanes for the regiocontrolled synthesis of pyrazoles from functionalised sydnones. The strategies outlined herein allow a range of pyrazoles to be accessed with substitution patterns that are otherwise not directly obtained with high selectivity by alkyne cycloadditions. Moreover, this study serendipitously highlighted a simple and convenient procedure for the synthesis of aryl monofluoromethyl ethers through the combination of TBAF and dichloromethane.

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

Sydnone Cycloaddition Route to Pyrazole-Based Analogs of Combretastatin A4

The combretastatins are an important class of tubulin-binding agents. Of this family, a number of compounds are potent tumor vascular disrupting agents (VDAs) and have shown promise in the clinic for cancer therapy. We have developed a modular synthetic r

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.

Synthesis of 2 H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes

A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupl

Zwitterionic and mesoionic liquids: Molecular aggregation in 3-methylsydnone

Ionic liquids are green solvents with interesting properties: displaying low melting points and high boiling points. They offer a new approach applicable in many instances. Nevertheless, the presence of free ions can be a matter in some cases, e.g. for the study of nucleophilic reactions, in electrochemistry, and in each situation where there is a competition between counter ions, as in micellization of ionic surfactants. Neutral compounds having formal unit electrical charges of opposite sign, and the same physical properties than ionic liquids would be a nice alternative to these latter solvents. There are two classes of chemical compounds having these characteristics: zwitterionic liquids (with no uncharged canonical representation) and mesoionic liquids (in which the negative and the positive charges are delocalized). In that last class we have chosen to work with 3-methylsydnone in order to examine, in this aprotic solvent, if it was possible to observe aggregation of surfactants in the same manner as in water. With all kinds of surfactants studied (ionic, zwitterionic and mesoionic) we have been able to demonstrate the formation of direct micelles: hydrogen bonding is thus not mandatory for molecular aggregation. Comparison of the behavior in water and in formamide showed that solvophobic interactions were qualitatively comparable but with a lower intensity.

Synthesis and reactions of 9,10-diazatetracyclo-[6.3.0.0.4,110.5.9]undecanes

The tandem 1,3-dipolar cycloaddition between sydnones and 1,5-cyclooctadiene provides 9,10-diazatetracyclo[6.3.0.0.4,110.5,9]undecanes (the Weintraub reaction) in modest to good yields.