69353-11-3

Basic information

• Product Name: 3-Benzylcarbazic acid methyl ester
• Synonyms: 3-Benzylcarbazic acid methyl ester
• CAS NO: 69353-11-3
• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 0
• Mol File: 69353-11-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.127g/cm³
• Refractive Index: 1.53
• Solubility: DMSO; Chloroform; Ethyl Acetate; Ethanol
• CAS DataBase Reference: 3-Benzylcarbazic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Benzylcarbazic acid methyl ester(69353-11-3)
• EPA Substance Registry System: 3-Benzylcarbazic acid methyl ester(69353-11-3)

Safety Data

• Hazardous Substances Data: 69353-11-3(Hazardous Substances Data)

Usage

Uses

Methyl 2-benzylhydrazinecarboxylate is an intermediate for the synthesis of CFM 1571 Hydrochloride (C291720), which acts as a soluble guanylyl cyclase (sGC) activator while ignoring adenylyl cyclase. Inhibits collagen-stimulated platelet aggregation in vitro.

InChI:InChI=1/C9H12N2O2/c1-13-9(12)11-10-7-8-5-3-2-4-6-8/h2-6,10H,7H2,1H3,(H,11,12)

Upstream product

• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 21732-13-8 methyl 3-benzylidenecarbazate 

Downstream Products

• 132611-20-2 N¹-methoxycarbonyl-N²-benzyl-N²-(1-benzyl-5-chloro-4-imidazolylcarbonyl)hydrazine 
• 132611-17-7 N¹-methoxycarbonyl-N²-benzyl-N²-(1-benzyl-5-nitro-4-imidazolylcarbonyl)hydrazine 
• 132611-18-8 N¹-methoxycarbonyl-N²-benzyl-N²-(5-amino-1-benzyl-4-imidazolylcarbonyl)hydrazine 
• 1378284-51-5 methyl 2-benzyl-2-(3-phenylnaphthalen-1-yl)hydrazinecarboxylate 
• 51627-42-0 2-methoxy-5-phenyl-1,3,4-oxadiazole 
• 21732-13-8 methyl 3-benzylidenecarbazate 
• 1352123-71-7 methyl 2-benzyl-3-isopropyl-4-propyl-2,3-dihydro-1H-benzo[g]indazole-1-carboxylate 

Relevant articles and documents

Gold-catalyzed three-component spirocyclization: A one-pot approach to functionalized pyrazolidines

An efficient, highly atom economic synthesis of hitherto unknown spirocyclic pyrazolidines in a one-pot process was developed. The gold-catalyzed three-component coupling of alkynols, hydrazines and aldehydes or ketones likely proceeds via cycloisomerization of the alkynol to an exocyclic enol ether and subsequent [3 + 2]-cycloaddition of an azomethine ylide. A library of 29 derivatives with a wide range of functional groups was synthesized in up to 97% yield. With this new method, every position in the final product can be substituted which renders the method ideal for applications in combinatorial or medicinal chemistry.

Chiral 1,3,4-oxadiazol-2-ones as highly selective FAAH inhibitors

In the present study, identification of chiral 1,3,4-oxadiazol-2-ones as potent and selective FAAH inhibitors has been described. The separated enantiomers showed clear differences in the potency and selectivity toward both FAAH and MAGL. Additionally, the importance of the chirality on the inhibitory activity and selectivity was proven by the simplification approach by removing a methyl group at the 3-position of the 1,3,4-oxadiazol-2-one ring. The most potent compound of the series, the S-enantiomer of 3-(1-(4-isobutylphenyl)ethyl) -5-methoxy-1,3,4-oxadiazol-2(3H)-one (JZP-327A, 51), inhibited human recombinant FAAH (hrFAAH) in the low nanomolar range (IC50 = 11 nM), whereas its corresponding R-enantiomer 52 showed only moderate inhibition toward hrFAAH (IC50 = 0.24 μM). In contrast to hrFAAH, R-enantiomer 52 was more potent in inhibiting the activity of hrMAGL compared to S-enantiomer 51 (IC 50 = 4.0 μM and 16% inhibition at 10 μM, respectively). The FAAH selectivity of the compound 51 over the supposed main off-targets, MAGL and COX, was found to be >900-fold. In addition, activity-based protein profiling (ABPP) indicated high selectivity over other serine hydrolases. Finally, the selected S-enantiomers 51, 53, and 55 were shown to be tight binding, slowly reversible inhibitors of the hrFAAH.