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135060

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

Article

Last updated: 22 Jan 2023

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Subjects

-

Tags

Drug discovery and development

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.

DOI

10.21608/rpbs.2021.50391.1079

Keywords

Spirooxindole, pyrrolidino/piperidine DFT, Hirshfeld analysis

Authors

First Name

yasmine

Last Name

abdel Aziz

MiddleName

-

Affiliation

pharmaceutical organic chemistry faculty of pharmacy Suez canal university

Email

yassmin_morsy@pharm.suez.edu.eg

City

-

Orcid

0000-0003-2861-4605

First Name

Gehad Lotfy

Last Name

Gehad Lotfy

MiddleName

-

Affiliation

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

Email

gehadlotfy@yahoo.com

City

ismailia

Orcid

-

First Name

Mohamed M. Said

Last Name

Mohamed M. Said

MiddleName

-

Affiliation

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

Email

msaid123eg@yahoo.com

City

ismailia

Orcid

-

First Name

El Sayed H. El Ashry

Last Name

El Sayed H. El Ashry

MiddleName

-

Affiliation

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

Email

elashry@yahoo.com

City

ismailia

Orcid

-

First Name

El Sayed H. El Tamany

Last Name

El Sayed H. El Tamany

MiddleName

-

Affiliation

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

Email

s.eltamany51@yahoo.com

City

-

Orcid

-

First Name

Saied M. Soliman

Last Name

Saied M. Soliman

MiddleName

-

Affiliation

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

Email

saiedsoliman@hotmail.com

City

ismailia

Orcid

-

First Name

Matti Haukka

Last Name

Matti Haukka

MiddleName

-

Affiliation

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

Email

mattihaukka@hotmail.com

City

-

Orcid

-

First Name

Assem

Last Name

Assem Barakat

MiddleName

-

Affiliation

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

Email

assembarakat5@yahoo.com

City

-

Orcid

-

Volume

5

Article Issue

Chemistry

Related Issue

16063

Issue Date

2021-01-01

Receive Date

2020-12-05

Publish Date

2021-01-01

Page Start

1

Page End

7

Print ISSN

2536-9857

Online ISSN

2535-2091

Article File

RPBS_Volume 5_Issue Chemistry_Pages 1-7.pdf

PDF . 1.2MB

Link

https://rpbs.journals.ekb.eg/article_135060.html

Detail API

https://rpbs.journals.ekb.eg/service?article_code=135060

Order

3

Type

Original Article

Type Code

532

Publication Type

Journal

Publication Title

Records of Pharmaceutical and Biomedical Sciences

Publication Link

https://rpbs.journals.ekb.eg/

MainTitle

-

Details

Type

Article

Created At

22 Jan 2023