1208311-07-2Relevant academic research and scientific papers
Amino acids derived benzoxazepines: Design, synthesis and antitumor activity
Dwivedi, Shailendra Kumar Dhar,Samanta, Krishnananda,Yadav, Manisha,Jana, Amit Kumar,Singh, Abhishek Kumar,Chakravarti, Bandana,Mondal, Sankalan,Konwar, Rituraj,Trivedi, Arun Kumar,Chattopadhyay, Naibedya,Sanyal, Sabyasachi,Panda, Gautam
, p. 6816 - 6821 (2014/01/06)
Two series of new benzoxazepines substituted with different alkyl amino ethyl chains were synthesized comprising synthetic steps of inter and intramolecular Mitsunobu reaction, lithium aluminium hydride (LAH) reduction, debenzylation, bimolecular nucleophilic substitution (SN2) reaction. The present study investigates the effect of a tyrosine-based benzoxazepine derivative in human breast cancer cells MCF-7 and MDA-MB-231 and in breast cancer animal model. The anti-proliferative effect of 15a on MCF-7 cells was associated with G1 cell-cycle arrest. This G1 growth arrest was followed by apoptosis as 15a dose dependently increased phosphatidylserine exposure, PARP cleavage and DNA fragmentation that are hallmarks of apoptotic cell death. Interestingly, 15a activated components of both intrinsic and extrinsic pathways of apoptosis characterized by activation of caspase-8 and -9, mitochondrial membrane depolarization and increase in Bax/Bcl2 ratio. However, use of selective caspase inhibitors revealed that the caspase-8-dependent pathway is the major contributor to 15a-induced apoptosis. Compound 15a also significantly reduced the growth of MCF-7 xenograft tumors in athymic nude mice. Together, 15a could serve as a base for the development of a new group of effective breast cancer therapeutics.
Amino acid based enantiomerically pure 3-substituted benzofused heterocycles: A new class of antithrombotic agents
Mishra, Jitendra Kumar,Samanta, Krishnananda,Jain, Manish,Dikshit, Madhu,Panda, Gautam
supporting information; experimental part, p. 244 - 247 (2010/04/02)
A diverse group of novel medium ring heterocycles derived from naturally abundant proteinogenic amino acids were evaluated for their potency towards antithrombotic activity. The more potent benzofused oxazepine and oxazocine scaffolds were diversified by incorporating different amino acids at the position number 3. Further the effect of ring size has also been taken into account and it was observed that the eight-membered oxazocines ane more potent compared to the corresponding oxazepines.
