Pyrrolo [2,1-c] [1,4] benzodiazepine (PBD) is a class of natural products obtained from various actinomycetes which have both anti-tumor and antibiotic activities. They can bind to specific sequences of DNA that can trigger a biological response which is of pharmacological interest. PBD can also prevent cell division leading to death of the bacteria. This research focuses on the synthesis of novel 11-hydrazinyl PBD derivatives using a multi-step synthesis. PBD-dilactam was initially produced using isatoic anhydride and (L)-proline which was then converted to the PBD-thiolactam using Lawesson's reagent. Reaction of thiolactam with hydrazine in ethanol afforded PBD-11-hydrazinyl in good yield. Condensation of 11-hydrazinyl PBD with aldehydes possessing various substitutions was performed to generate (S, E)-11-[2-(phenylmethylene) hydrazono]-1,2,3,10,11,11a-hexahydro-5H benzo[e]pyrrolo[1,2-a] [1,4] diazepin-5-one. 1H-NMR, 13C-NMR, DEPT, IR, GC-MS and X-ray Crystallography were used to characterize the products. Inhibition activity of the products were carried out using TEM-1, AmpC and p99 β-lactamases. National cancer Institute tested some selected compounds on 60 NCI- cell lines
| Identifer | oai:union.ndltd.org:ETSU/oai:dc.etsu.edu:asrf-1256 |
| Date | 12 April 2019 |
| Creators | Mingle, David, Shilabin, Abbas G, Dr |
| Publisher | Digital Commons @ East Tennessee State University |
| Source Sets | East Tennessee State University |
| Detected Language | English |
| Type | text |
| Source | Appalachian Student Research Forum |
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