Synthesis and characterization of a new spirooxindole grafted pyrrolidino/piperidine moiety

Abdel Aziz, Yasmine; Gehad Lotfy, Gehad Lotfy; Mohamed M. Said, Mohamed M. Said; El Sayed H. El Ashry, El Sayed H. El Ashry; El Sayed H. El Tamany, El Sayed H. El Tamany; Saied M. Soliman, Saied M. Soliman; Matti Haukka, Matti Haukka; Assem Barakat, Assem

doi:10.21608/rpbs.2021.50391.1079

Synthesis and characterization of a new spirooxindole grafted pyrrolidino/piperidine moiety

Document Type : Original Article

Authors

¹ pharmaceutical organic chemistry faculty of pharmacy Suez canal university

² Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt

³ 2Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, Egypt.

⁴ Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt.

⁵ 4Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland

⁶ 5Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia.

10.21608/rpbs.2021.50391.1079

Abstract

In this text, we synthesized and characterized a new spirooxindole grafted pyrrolidino/piperidine moieties. The new hit obtained via one-pot reaction of the chalcone based cyclohexanone with the isatin and (R)-piperidine-2-carboxylic acid in MeOH under reflux for 48 h. The compound exclusively obtained in regio-selective and diastereo-selective manner. The chemical feature of the target compound is confirmed by ¹H NMR and ¹³C NMR spectroscopy. In addition, we reported for the first time the X-ray single crystal structure of isatin. Its molecular packing depends mainly on strong O…H hydrogen bonds and π-π stacking interactions as well as weak H…H and H…C contacts. Using DFT calculations, isatin is a polar molecule with a net dipole moment of 5.912 Debye. Also, the calculated structure agreed very well with the experimental one. The charge distribution at the different atomic sites is calculated using NBO calculations.

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