[Home ] [Archive]   [ فارسی ]  
:: Main :: About :: Current Issue :: Archive :: Search :: Submit :: Contact ::
Main Menu
Home::
Journal Information::
Articles archive::
For Authors::
For Reviewers::
Subscription::
Contact us::
Site Facilities::
Webmail::
::
Search in website

Advanced Search
..
Receive site information
Enter your Email in the following box to receive the site news and information.
..
Journal Citation Index

 

Citation Indices from GS

AllSince 2019
Citations89785395
h-index3725
i10-index235137

 

..
Central Library of Kurdistan University of Medical Sciences
AWT IMAGE
..
Vice-Chancellery for Research and Technology
AWT IMAGE
..
SCImago Journal & Country Rank
:: Volume 27, Issue 3 (Scientific Journal of Kurdistan University of Medical Sciences 2022) ::
SJKU 2022, 27(3): 23-35 Back to browse issues page
Synthesis, Molecular Docking Study and Evaluation of Cytotoxic Activity of Two Homoisoflavonoids Containing Morpholinoethoxy Substitution
Touba Eslaminejad1 , Khalil Eskandari2 , Fatemeh Abedinezhad3 , Bagher Amirheidari4 , Ali Asadipour5 , Yaghoub Pourshojaei 6
1- Assistant Professor, Pharmaceutics Research Centre, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran.
2- Researcher, Department of Medicinal Chemistry, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran
3- Pharm. D. Herbal and Traditional Medicines Research Center, Kerman University of Medical Sciences, Kerman, Iran.
4- Assistant Professor, Department of Biotechnology, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Kerman University of Medical Sciences, Kerman, Iran
5- Professor, Department of Medicinal Chemistry, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran
6- Assistant Professor, Department of Medicinal Chemistry, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran , pourshojaei@yahoo.com
Abstract:   (1581 Views)
Background and Aim: Chemotherapy is one of the most common methods available for the treatment of cancer. Resistance to anticancer drugs can result in failures in chemotherapy of cancers. Therefore, investigation is necessary for the discovery of new drugs. Homoisoflavonoids are well-known natural products that possess a wide range of pharmacological activities. Hence, synthesis and assessment of cytotoxicity of homoisoflavonoids containing morpholinoethoxy moiety and their molecular docking simulation were taken into consideration.
Materials and Methods: Two 7-morpholinoethoxyhomoisoflavonoids synthesized via three steps including SN2 reaction of 7-hydroxychromanine with morpholino ethyl chloride hydrochloride in the basic media under reflux condition to produce intermediate 3. The second step included aldol condensation of the intermediate with suitable aldehydes in the presence of gaseous HCl in ethanol, and finally neutralization with NaOH 5%. The structures of the products were confirmed using IR, 13CNMR, and 1HNMR techniques. Cytotoxic effects of final products on HT-29 and 3T3 cell lines were assessed. To evaluate the binding mode of compounds with tubulin protein, docking simulation was performed by using MOE.
Results: Two morpholinoethoxy homoisiflavonoids were prepared with moderate to good production yield. Cytotoxic evaluation of these compounds showed satisfactory results. The results of molecular docking simulation showed an acceptable binding energy of the interaction between the ligands with the tubulin protein binding site: (E)-7-(2-morpholinoethoxy)-3-(3,4,5-trimethoxybenzylidene) chroman-4-one= -7.3727 Kcal/mol and (E)-3-(4-methoxybenzylidene)-7-(2-morpholinoethoxy) chroman-4-one released -7.6838 Kcal/mol per mole of energy.
Conclusion:The results showed that compound (E)-3-(4-methoxybenzylidene)-7-(2-morpholinoethoxy) chroman-4-one has higher cytotoxicity than (E)-7-(2-morpholinoethoxy)-3-(3,4,5-trimethoxybenzylidene) chroman-4-one against HT-29 and 3T3 cell lines. The in-silico results confirmed the results obtained from in vitro experiments and showed three interactions between ligand (E)-3-(4-methoxybenzylidene)-7-(2-morpholinoethoxy)chroman-4-one and αThr179, αThr145, and αTyr224 amino acids in tubulin active site.
 
Keywords: Molecular docking, cytotoxic activity, Homoisoflavonoids
Full-Text [PDF 667 kb]   (368 Downloads)    
Type of Study: Original Research | Subject: Pharmacology
Received: 2021/03/9 | Accepted: 2021/11/1 | Published: 2022/09/11
Send email to the article author

Add your comments about this article
Your username or Email:

CAPTCHA

Ethics code: IR.KMU.REC.1399.672



XML   Persian Abstract   Print


Download citation:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:

Eslaminejad T, Eskandari K, Abedinezhad F, Amirheidari B, Asadipour A, Pourshojaei Y. Synthesis, Molecular Docking Study and Evaluation of Cytotoxic Activity of Two Homoisoflavonoids Containing Morpholinoethoxy Substitution. SJKU 2022; 27 (3) :23-35
URL: http://sjku.muk.ac.ir/article-1-6643-en.html


Rights and permissions
Creative Commons License This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Volume 27, Issue 3 (Scientific Journal of Kurdistan University of Medical Sciences 2022) Back to browse issues page
مجله علمی دانشگاه علوم پزشکی کردستان Scientific Journal of Kurdistan University of Medical Sciences
مجله علمی دانشگاه علوم پزشکی کردستان Scientific Journal of Kurdistan University of Medical Sciences
Persian site map - English site map - Created in 0.06 seconds with 45 queries by YEKTAWEB 4645