Synthesis of Putrescine Bisamides as Antimicrobial and Anti-Inflammatory Agents with Molecular Docking Studies | Chapter 2 | Science and Technology: Developments and Applications Vol. 9

Putrescine bis amides are one of the subclasses of naturally occurring polyamides. During the last two decades, several symmetrical and unsymmetrical putrescine bisamides have been isolated from Aglaia, Liberica, and Carydalis species. In this study, a new naturally occurring N1, N6-dihydrocinnamyl putrescine bisamide, JBIR-94, along with nine structural analogs and a series of substituted phenyl and alkyl putrescine bisamides have been synthesized from putrescine and appropriately substituted carboxylic acids, through carboxylic acid chlorides. Antimicrobial, 5-Lipooxygenase enzyme inhibitory, and antioxidant studies were performed for all synthesized compounds. Antimicrobial assay performed against human pathogenic bacteria and fungi. Zone of inhibition was determined using agar well diffusion method, and minimum inhibitory concentration (MIC) was determined by broth dilution assay. The 5-Lipoxygenase (PDB ID 308Y) X-Ray crystal structure was obtained from the Protein Data Bank and used in docking studies. Antioxidant activities of putrescine bisamides were performed through radical scavenging assay using DPPH and Superoxide radicals. Dihydrocinnamyl series of putrescine bisamides (4a-4i) showed good bioactivities compared to substituted phenyl (6a-6g) and diakyl (6h-6j) series of compounds. Among all compounds, 4h (methylenedioxy analog) and 4a (JBIR-94) showed good antimicrobial, anti-inflammatory, and antioxidant activities.

 

Author (s) Details

Siddaiah Vidavalur
Department of Chemistry, Andhra University, Visakhapatnam, India.

 

Sunanda Kumari Kadiri
Department of Microbiology, Andhra University, Visakhapatnam, India.

 

Kumari Yettula
Department of Chemistry, Andhra University, Visakhapatnam, India.

 

Srinuvasarao Rayavarapu
Department of Chemistry, Andhra University, Visakhapatnam, India.

 

Mahaboob Basha Gajula
Department of Chemistry, Andhra University, Visakhapatnam, India.

 

Mangarao Nakka
Department of Chemistry, Andhra University, Visakhapatnam, India.

Ramu Tadikonda
Department of Chemistry, Andhra University, Visakhapatnam, India.

 

Please see the book here:- https://doi.org/10.9734/bpi/stda/v9/4995

2,6-Diaryl-4-Indolylpyridines as Novel 5-LOX Inhibitors | Chapter 7 | Chemistry and Biochemistry: Research Progress Vol. 5

 3-Substituted indole is a privileged structural motif found in many biologically active compounds and natural products. 3-Substituted indole derivatives exhibit several biological activities such as antibacterial, anti-inflammatory, antitumor, anticancer, anti-hypertensive, anti-depressant, and antiviral activities. The study aims to synthesize a series of 2,6-diaryl-4-indolylpyridines from substituted acetophenones and 1H-indole-3-carbaldehydes using ammonium acetate as a nitrogen source in the presence of acetic acid and 5-LOX activities of several 2,6-diaryl-4-indolylpyridines. A series of 2,6-diaryl substituted-4-indolylpyridines has been synthesized from indole-3-carboxaldehyde and acetophenones, and all the compounds have been characterized by spectroscopic techniques. 5-Lipoxygenase enzyme inhibitory activities were performed for all the compounds. 1H-Indole-3-carboxaldehyde and 5-bromo-1H-indole-3-carboxaldehyde were prepared from indole using phosphorus oxychloride in DMF. The reaction of indole-3-carboxaldehyde (1a-b) with substituted acetophenones (2a-i) in the presence of ammonium acetate in acetic acid at reflux conditions furnished 2,6-diaryl-4-indolylpyridines (3aa-3bf) in 63-84% yield. Based on this protocol, 14 derivatives of all the compounds were purified by column chromatography on silica gel. The chemical structures of the target compounds were confirmed by 1H NMR, 13C NMR, and MS spectra Among the 2, 6-diaryl substituted-4-indolylpyridine derivatives, 3ad and 3aa showed good activity.

 

Author (s) Details

Berihu Tekluu
Department of Organic Chemistry and FDW, College of Science and Technology, Andhra University, Visakhapatnam, Andhra Pradesh, India.

 

Kumari Yettula
Department of Organic Chemistry and FDW, College of Science and Technology, Andhra University, Visakhapatnam, Andhra Pradesh, India.

 

 

Sunanda Kumari Kadiri
Department of Microbiology, College of Science and Technology, Andhra University, Visakhapatnam, Andhra Pradesh, India.

 

Siddaiah Vidavalur
Department of Organic Chemistry and FDW, College of Science and Technology, Andhra University, Visakhapatnam, Andhra Pradesh, India.

Please see the book here:- https://doi.org/10.9734/bpi/cbrp/v5/4997