17686-89-4Relevant academic research and scientific papers
A green, chemoselective, and practical approach toward N-(2-azetidinonyl) 2,5-disubstituted pyrroles
Bandyopadhyay, Debasish,Rhodes, Elvira,Banik, Bimal K.
, p. 16756 - 16764 (2013/09/23)
Pyrrole and 2-azetidinone are two essential heterocyclic scaffolds, which are being broadly used in medicinal chemistry and drug discovery field. A green and practical method to synthesize novel N-(2-azetidinonyl) 2,5-disubstituted pyrroles, which are com
Remarkable iodine-catalyzed synthesis of novel pyrrole- bearing n-polyaromatic β-lactams
Bandyopadhyay, Debasish,Rivera, Gildardo,Salinas, Isabel,Aguilar, Hector,Banik, Bimal K.
experimental part, p. 1082 - 1088 (2010/04/29)
Because of their interesting biological properties various methods for the synthesis of substituted pyrroles are described in the literature. However, synthesis of pyrroles fused with a β-lactam ring has not been reported. Our group has demonstrated synth
Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
Banik, Bimal K.,Banik, Indrani,Becker, Frederick F.
, p. 3611 - 3622 (2007/10/03)
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
Banik, Bimal K.,Becker, Frederick F.,Banik, Indrani
, p. 2523 - 2528 (2007/10/03)
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.
