302595-58-0

Upstream product

• 13831-31-7 Acetoxyacetyl chloride 
• 17686-89-4 6--chrysen 
• 108-24-7 acetic anhydride 
• 1357362-60-7 (3R,4R)-3-{[(1S,3R,4R,6R)-4-bromo-3,7,7-trimethylbicyclo[4.1.0]hept-3-yl]oxy}-1-(chrysen-6-yl)-4-phenylazetidin-2-one 
• 1215310-72-7 (3R,4R)-1-(chrysen-6-yl)-3-hydroxy-4-phenylazetidin-2-one 
• 75-36-5 acetyl chloride 
• 1215310-71-6 C₂₇H₁₉NO₂ 

Relevant academic research and scientific papers

Microwave-Induced Enantiospecific Synthesis of trans-(3R,4R)-3-Acetoxy-4-aryl-1-(chrysen-6-yl)azetidin-2-ones via the Staudinger Cycloaddition Reaction of (+)-Car-3-ene with Polyaromatic Imines

Abstract: The enantiospecific synthesis of 3-acetoxy-trans-β-lactams via the Staudinger [2+2] cycloaddition reaction of polyaromatic imines with bicyclic (+)-car-3-ene was investigated. The sterically hindered polyaromatic substituent at the N1 position in the imines plays a significant role, directing the cycloaddition reaction to stereoselective formation of trans-(3R,4R)-N-azetidin-2-ones. The results as described herein are highly unprecedented, since the synthesis of a single optically active trans-β-lactam, starting from a chiral ketene, has never been reported previously.

Stereoselective synthesis of β-lactams with polyaromatic imines: Entry to new and novel anticancer agents

We present herein stereoselective synthesis of novel β-lactams using polyaromatic imines following the Staudinger reaction. Consistent mechanisms for these results have been advanced. As a measure of cytotoxicity, some of these compounds have been assayed against nine human cancer cell lines. Structure - activity study has revealed that 1-N-chrysenyl and 1-N-phenanthrenyl 3-acetoxy-4-aryl-2-azetidinones have potent anticancer activity. The presence of the acetoxy group at C3 of the β-lactams has proven to be obligatory for their anticancer activity.

Bismuth nitrate-induced microwave-mediated deglycosylation of O-glycosides: Synthesis of enantiopure 3-hydroxy β-lactams

Bismuth nitrate-induced microwave-mediated cleavages of O-glycosidic bond in β-lactams are achieved to afford their corresponding hydroxyl derivatives in excellent yields.

An efficient synthesis of optically active trans-(3R,4R)-3-acetoxy-4-aryl- 1-(chrysen-6-yl)azetidin-2-ones using (+)-car-3-ene as a chiral auxiliary

An efficient enantioselective synthesis of 3-acetoxy trans-β-lactams 7a and 7b via [2+2] cycloaddition reactions of imines 4a and 4b, derived from a polycyclic aromatic amine and bicyclic chiral acid obtained from (+)-car-3-ene, is described. The cycloadd

Asymmetric synthesis of anticancer β-lactams via Staudinger reaction: Utilization of chiral ketene from carbohydrate

We describe herein asymmetric synthesis of a novel anticancer β-lactam following Staudinger reaction with chiral carbohydrate as the ketene component with an achiral imine. The in vitro cytotoxicity studies of these β-lactams are also reported here.

Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction

Stereocontrolled synthesis of novel β-lactams using polyaromatic imines following the Staudinger reaction has been accomplished. The effects of domestic microwave irradiation on this type of reaction have been investigated. Formation of trans-β-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride (equivalent) with imines in the presence of triethylamine. A donor-acceptor complex pathway is believed to be involved in the formation of cis-β-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the resulting β-lactams. SAR has identified β-lactams with anticancer activity. The presence of an acetoxy group has proven obligatory for their anticancer activity.

Synthesis of anticancer β-lactams: Mechanism of action

Synthesis of the trans 1-N-chrysenyl and 1-N-phenanthrenyl 3-acetoxy-4-phenyl-2-azetidinones has been achieved. Microwave-assisted reaction has proved useful in the synthesis of these compounds. Cell growth inhibition study has indicated selective anticancer activity against two leukemia and colon carcinoma cell lines. A mechanistic correlation of their anticancer activity has been described. Striking G2 blockade that is clearly distinct in cell cycle analysis and demonstrated only in sensitive cell lines has been observed. They do not induce apoptosis in sensitive or resistant lines. They also do not inhibit topoisomerases. Ames test has shown they are nonmutagenic.

Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines

Cycloaddition of imines derived from polycyclic aromatic amines with acid chloride (or equivalent) in the presence of triethylamine at -78°C to room temperature unexpectedly produced trans-β-lactams. (C) 2000 Elsevier Science Ltd.