273216-72-1

Basic information

• Product Name: METHYL 2-(1-[1,1'-BIPHENYL]-4-YLETHYLIDENE)-1-HYDRAZINECARBOXYLATE
• Synonyms: METHYL 2-(1-[1,1'-BIPHENYL]-4-YLETHYLIDENE)-1-HYDRAZINECARBOXYLATE
• CAS NO: 273216-72-1
• Molecular Formula: C16H16N2O2
• Molecular Weight: 268.31
• Mol File: 273216-72-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL 2-(1-[1,1'-BIPHENYL]-4-YLETHYLIDENE)-1-HYDRAZINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-(1-[1,1'-BIPHENYL]-4-YLETHYLIDENE)-1-HYDRAZINECARBOXYLATE(273216-72-1)
• EPA Substance Registry System: METHYL 2-(1-[1,1'-BIPHENYL]-4-YLETHYLIDENE)-1-HYDRAZINECARBOXYLATE(273216-72-1)

Safety Data

• Hazardous Substances Data: 273216-72-1(Hazardous Substances Data)

Upstream product

• 92-91-1 biphenyl-4-acetaldehyde 
• 6294-89-9 hydrazinecarboxylic acid methyl ester 

Relevant articles and documents

Synthetic entry into 1-phosphono-3-azabicyclo[3.1.0]hexanes

3-Azabicyclo[3.1.0]hex-2-en-1-yl phosphonates were prepared in a five-step reaction route from β-ketophosphonates. The key steps in this sequence are an atom-transfer radical cyclization and an unforeseen lithium-halogen exchange with n-BuLi. The cyclization reaction proceeds with excellent diastereoselectivity. The resulting cyclic imines were reduced, and 3-azabicyclo[3.1.0]hexan-1-yl phosphonates were obtained.

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.