69353-11-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzylcarbazic acid methyl ester is used as an intermediate in the synthesis of CFM 1571 Hydrochloride (C291720), a soluble guanylyl cyclase (sGC) activator. This activator selectively targets sGC without affecting adenylyl cyclase, making it a valuable compound in the development of drugs for various therapeutic applications.
Used in Cardiovascular Applications:
As a precursor to CFM 1571 Hydrochloride, 3-Benzylcarbazic acid methyl ester contributes to the development of drugs that inhibit collagen-stimulated platelet aggregation in vitro. This property is essential in the treatment and prevention of cardiovascular diseases, such as atherosclerosis and thrombosis, by reducing the risk of blood clot formation.

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

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

Relevant academic research and scientific papers

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.

Metal-Free Synthesis of 1,3,4-Oxadiazoles from N′-(Arylmethyl)hydrazides or 1-(Arylmethyl)-2-(arylmethylene)hydrazines

An efficient and versatile metal-free synthesis of 1,3,4-oxadiazoles from N′-(arylmethyl)hydrazides or 1-(arylmethyl)-2-(arylmethylene)hydrazines through oxidative dehydrogenation is reported. A range of 2,5-disubstituted 1,3,4-oxadiazoles were prepared by treating N′-(arylmethyl)hydrazides with (diacetoxyiodo)benzene in acetonitrile or by treating 1-(arylmethyl)-2-(arylmethylene)hydrazines with [bis(trifluoroacetoxy)iodo]benzene in methyl tert-butyl ether. Aldehyde N-acylhydrazones and aldazines were initially generated in situ as intermediates.

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.

Gold-catalyzed three-component annulation: Efficient synthesis of highly functionalized dihydropyrazoles from alkynes, hydrazines, and aldehydes or ketones

Polysubstituted dihydropyrazoles were directly obtained by a gold-catalyzed three-component annulation. This reaction consists of a Mannich-type coupling of alkynes with N,N′-disubstituted hydrazines and aldehydes/ketones followed by intramolecular hydroa