Project Title

Synthesis, Characterization and Biological Evaluation of novel (S, E)-11-[2-(arylmethylene)hydrazono] pyrrolo [2,1-c] [1,4] benzodiazepine derivatives.

Authors' Affiliations

David Mingle, Department of chemistry, college of art and sciences, East Tennessee State university

Location

BEECH MTN. ROOM 120

Start Date

4-12-2019 2:40 PM

End Date

4-12-2019 2:55 PM

Faculty Sponsor’s Department

Chemistry

Name of Project's Faculty Sponsor

Dr. Shilabin Abbas

Type

Oral Presentation

Classification of First Author

Graduate Student-Master’s

Project's Category

Organic Chemistry

Abstract Text

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

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Apr 12th, 2:40 PM Apr 12th, 2:55 PM

Synthesis, Characterization and Biological Evaluation of novel (S, E)-11-[2-(arylmethylene)hydrazono] pyrrolo [2,1-c] [1,4] benzodiazepine derivatives.

BEECH MTN. ROOM 120

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