Physical Science International Journal

Synthesis, Spectroscopic and Docking Studies of Napthyl Substituted Di-Spiro Octahydroindolizine

R. Vishnu Priya

Department of Physics, The Madura College (Autonomous), Madurai – 625 011, India

J. Suresh *

Department of Physics, The Madura College (Autonomous), Madurai – 625 011, India

S. Sivakumar

Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625 021, India

R. Ranjith Kumar

Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625 021, India

R. Sankaranarayanan

Centre of Excellence in Bioinformatics, School of Biotechnology, Madurai Kamaraj University, Madurai-625021, India

*Author to whom correspondence should be addressed.

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Abstract

The crystal structure of spiro[2.2"]acenaphthene-1"-onespiro[3.3']-5'-(naphthylmethylidine)-1'-methylpiperidin-4'-one-4-(naphthyl)octahydroindolizine has been elucidated  by modern spectroscopic technique including, ¹H and ¹³C NMR spectroscopy and unequivocally confirmed by single crystal X-ray diffraction. The title compound C₄₅H₃₈N₂O₂, crystallizes in the tetragonal system, space group I41/a with a=39.692(5) Å, b= 39.692(5) Å,   c= 8.793(5) Å, α = β = γ = 90°, V = 13852.98(83) A³. The central piperidine ring adopts twisted conformation, the piperidine of octahydroindolizine ring is in chair conformation and the pyrrole ring is in slightly twisted envelope conformation.  Details of the synthesis, NMR, crystal structure determination and intra-molecular interaction of the compound are given. The molecular docking study of synthesized compound with an enzyme, namely, N-acetyl-gamma-glutamyl-phosphate reductase that is involved in arginine biosynthesis in M. tuberculosis (MtbAGPR) has also been carried out.

 

Keywords: Single crystal structure, conformation, hydrogen bond, NMR spectra, docking studies

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