93681-36-8

Basic information

• Product Name: 2-Azetidinone, 3-amino-1-phenyl-4-(2-phenylethenyl)-, cis-
• CAS NO: 93681-36-8
• Molecular Formula: C17H16N2O
• Molecular Weight: 264.327
• Mol File: 93681-36-8.mol

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 3-amino-1-phenyl-4-(2-phenylethenyl)-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 3-amino-1-phenyl-4-(2-phenylethenyl)-, cis-(93681-36-8)
• EPA Substance Registry System: 2-Azetidinone, 3-amino-1-phenyl-4-(2-phenylethenyl)-, cis-(93681-36-8)

Safety Data

• Hazardous Substances Data: 93681-36-8(Hazardous Substances Data)

Upstream product

• 953-21-9 N-(3-phenylallylidene)benzenamine 
• 104-55-2 3-phenyl-propenal 
• 62-53-3 aniline 
• 953-21-9 Phenyl-[(E)-3-phenyl-prop-2-en-(Z)-ylidene]-amine 
• 79006-93-2 (Z)-3-[(3S,4R)-2-Oxo-1-phenyl-4-((E)-styryl)-azetidin-3-ylamino]-but-2-enoic acid methyl ester 

Relevant articles and documents

4-Aminoquinoline-β-lactam conjugates: Synthesis, antimalarial, and antitubercular evaluation

A library of quinoline-β-lactam-based hybrids was synthesized and tested for their antimalarial and antitubercular activities. The present antimalarial data showed the dependence of activity on the nature of linker, N-1 substituent of the β-lactam ring as well as the length of alkyl chain. Most of the compounds are not as efficient as chloroquine in inhibiting the culture growth of Plasmodium falciparum W2 strain. Nevertheless, the synthesized hybrids showed better antitubercular activities (up to five times) compared with cephalexin (up to three times) and ethionamide. Thirty four 4-aminoquinoline-β-lactam conjugates have been synthesized and evaluated for their antimalarial and anti-TB profiles.

Discovery of highly selective 7-chloroquinoline-thiohydantoins with potent antimalarial activity

A series of C-3 thiourea functionalized β-lactams, β-lactam-7-chloroquinoline conjugates and 7-chloroquinoline-thiohydantoin derivatives were prepared with the aim of probing antimalarial structure-activity relationships. 7-Chlorquinoline-thiohydantoin derivatives were found to be potent inhibitors of cultured Plasmodium falciparum, with the most potent and non-cytotoxic compound exhibiting an IC50 of 39.8 nM. Studies of β-hematin formation suggested that inhibition of haemozoin formation could be primary mechanism of action, with IC50 values comparable to those of chloroquine. Evaluation of cytotoxicity against HeLa cells demonstrated high selective indices.

Diastereoselective synthesis of 2,3-disubstituted 1-arylazetidines via NaBH4-promoted facile reduction of C-3 functionalized azetidin-2-ones

A facile diastereoselective synthesis of 2,3-disubstituted 1-arylazetidines has been reported via NaBH4-promoted reduction of C-3 functionalized azetidin-2-ones. Since the developed protocol does not involve the use of a Lewis acid, the methodo

β-Lactam-synthon-interceded diastereoselective synthesis of functionally enriched thioxo-imidazolidines, imidazolidin-2-ones, piperazine-5,6-diones and 4,5-dihydroimidazoles

The manuscript explicates simple and convenient protocols for the diastereoselective synthesis of functionally decorated thioxo-imidazolidines, imidazolidin-2-ones, piperazine-5,6-diones and 4,5-dihydroimidazoles using β-lactam synthon approach with an ex

Antiplasmodial and cytotoxicity evaluation of 3-functionalized 2-azetidinone derivatives

3-Azido-, 3-amino- and 3-(1,2,3-triazol-1-yl)-β-lactams were synthesized and evaluated for their antiplasmodial activity against four strains of Plasmodium falciparum and KB cells for their cytotoxicity profiles. The presence of a cyclohexyl substituent at N-1 and a phenyl group on the triazole ring markedly improved the activity profiles of triazole-tethered β-lactam exhibiting IC50 values of 1.13, 1.21 and 1.00 μM against 3D7, K1 and W2 strains respectively.

Synthesis of β-lactams from acetic acids and imines induced by phenyl dichlorophosphate reagent

The development of a practical method for the preparation of vinylamino-β-lactams from Dane salts and Schiff bases is described. Among the reagents known to produce β-lactams from imines and acetic acids, only phenyl dichlorophosphate and 1-methyl-2-chloropyridinium iodide are suitable for the synthesis of vinylamino-β-lactams. Reaction of acetic acids with ethanolimine derivatives promoted by phenyl dichlorophosphate affords oxazolidines instead of β-lactams. Protection of the hydroxyl group as the trimethylsilyl ether in the starting Schiff bases provides a convenient route to the corresponding β-lactams instead of oxazolidines. Some observations on the scope of the method are made.