SYNTHESIS OF PYRROLO[2,1-c] [1,4] BENZODIAZEPINE -11- HYDRAZINYL DEVRIVATIES AS A POTENTIAL ANTIMICROBIAL AGENT

Authors' Affiliations

DEPARTMENT OF CHEMISTRY COLLEGE OF ART AND SCIENCE

Location

Ballroom

Start Date

4-5-2018 8:00 AM

End Date

4-5-2018 12:00 PM

Poster Number

67

Name of Project's Faculty Sponsor

Abbas G. Shilabin

Faculty Sponsor's Department

chemistry

Classification of First Author

Graduate Student-Master’s

Type

Poster: Competitive

Project's Category

Natural Sciences

Abstract or Artist's Statement

SYNTHESIS OF PYRROLO[2,1-c] [1,4] BENZODIAZEPINE -11- HYDRAZINYL DEVRIVATIES AS A POTENTIAL ANTIMICROBIAL AGENT

David Mingle and Abbas G. Shilabin Department of Chemistry, East Tennessee State University, Johnson City, TN 37614, USA

ABSTRACT 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 PBD-11-hydrazinyl derivatives using a multi step synthesis. PBD-dilactam was initialy produced using isatoic anhydride and (S)-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 PBD-11-hydrazinyl 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 and GC-MS were used to characterize the products. Inhibition activity of the products were carried out using TEM-1 and p99 β-lactamases. Microbial activity will be conducted in collaboration with Natural Product Center at University of Mississippi on the final products.

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Apr 5th, 8:00 AM Apr 5th, 12:00 PM

SYNTHESIS OF PYRROLO[2,1-c] [1,4] BENZODIAZEPINE -11- HYDRAZINYL DEVRIVATIES AS A POTENTIAL ANTIMICROBIAL AGENT

Ballroom

SYNTHESIS OF PYRROLO[2,1-c] [1,4] BENZODIAZEPINE -11- HYDRAZINYL DEVRIVATIES AS A POTENTIAL ANTIMICROBIAL AGENT

David Mingle and Abbas G. Shilabin Department of Chemistry, East Tennessee State University, Johnson City, TN 37614, USA

ABSTRACT 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 PBD-11-hydrazinyl derivatives using a multi step synthesis. PBD-dilactam was initialy produced using isatoic anhydride and (S)-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 PBD-11-hydrazinyl 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 and GC-MS were used to characterize the products. Inhibition activity of the products were carried out using TEM-1 and p99 β-lactamases. Microbial activity will be conducted in collaboration with Natural Product Center at University of Mississippi on the final products.