Synthesis and characterization of a new spirooxindole grafted pyrrolidino/piperidine moiety
abdel Aziz, Y., Gehad Lotfy, G., Mohamed M. Said, M., El Sayed H. El Ashry, E., El Sayed H. El Tamany, E., Saied M. Soliman, S., Matti Haukka, M., Assem Barakat, A. (2021). Synthesis and characterization of a new spirooxindole grafted pyrrolidino/piperidine moiety. EKB Journal Management System, 5(Chemistry), 1-7. doi: 10.21608/rpbs.2021.50391.1079
yasmine abdel Aziz; 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 Assem Barakat. "Synthesis and characterization of a new spirooxindole grafted pyrrolidino/piperidine moiety". EKB Journal Management System, 5, Chemistry, 2021, 1-7. doi: 10.21608/rpbs.2021.50391.1079
abdel Aziz, Y., Gehad Lotfy, G., Mohamed M. Said, M., El Sayed H. El Ashry, E., El Sayed H. El Tamany, E., Saied M. Soliman, S., Matti Haukka, M., Assem Barakat, A. (2021). 'Synthesis and characterization of a new spirooxindole grafted pyrrolidino/piperidine moiety', EKB Journal Management System, 5(Chemistry), pp. 1-7. doi: 10.21608/rpbs.2021.50391.1079
abdel Aziz, Y., Gehad Lotfy, G., Mohamed M. Said, M., El Sayed H. El Ashry, E., El Sayed H. El Tamany, E., Saied M. Soliman, S., Matti Haukka, M., Assem Barakat, A. Synthesis and characterization of a new spirooxindole grafted pyrrolidino/piperidine moiety. EKB Journal Management System, 2021; 5(Chemistry): 1-7. doi: 10.21608/rpbs.2021.50391.1079

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

Records of Pharmaceutical and Biomedical Sciences
Article 3, Volume 5, Chemistry - Serial Number 1, January 2021, Page 1-7  XML PDF (1.16 MB)
Document Type: Original Article
DOI: 10.21608/rpbs.2021.50391.1079
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Authors
yasmine abdel Aziz email orcid 1; Gehad Lotfy Gehad Lotfy2; Mohamed M. Said Mohamed M. Said2; El Sayed H. El Ashry El Sayed H. El Ashry3; El Sayed H. El Tamany El Sayed H. El Tamany4; Saied M. Soliman Saied M. Soliman3; Matti Haukka Matti Haukka5; Assem Assem Barakat6
1pharmaceutical organic chemistry faculty of pharmacy Suez canal university
2Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt
32Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, Egypt.
4Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt.
54Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland
65Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia.
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.
Keywords
Spirooxindole; pyrrolidino/piperidine DFT; Hirshfeld analysis
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