Indole-3-Glyoxylamide- An Important Scaffold for Anticancer Activity

Authors

  • C. Buvana Department of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.
  • Avinash Raveendran Department of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.
  • R. Suresh Department of Pharmacy, Faculty of Engineering and Technology, Annamalai University, Chidambaram, Tamilnadu, India
  • Y. Haribabu Department of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.

DOI:

https://doi.org/10.22270/ajprd.v8i4.803

Keywords:

Indole-3-glyoxylamide, Anticancer activity, Indibulin (D-24851)

Abstract

Synthetic indolylglyoxyl amides were identified as a new group of microtubule destabilizing anticancer agents, with the most active derivative N-(pyridine-4-yl)-[1-(4-chlorobenzyl)indol-3-yl]glyoxylamide (Indibulin, D-24851, ) possessing the promising in vitro activity against SKOV3 ovarian cancer, U87 glioblastoma and ASPC-1 pancreatic cancer cells. Indole-3-glyoxylamides are an attractive lead series for continuing development as potential therapeutic agents. A number of Indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors; exert a cytotoxic effect against multiple cancer cell lines. Recently, substituted indolylglyoxylamides were found to exhibit anticancer, antiprion and anti HIV activity. This developed an interest in reviewing lead based on indole-3-glyoxylamide. This review focused on overview of drug molecule of indole-3-glyoxylamide. We hope that the review could give a guide to develop newer anti-cancer agents with greater potency against drug-sensitive and drug-resistant cancers in the future.

 

Downloads

Download data is not yet available.

Author Biographies

C. Buvana, Department of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.

Department of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.

Avinash Raveendran, Department of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.

Deparment of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.

R. Suresh, Department of Pharmacy, Faculty of Engineering and Technology, Annamalai University, Chidambaram, Tamilnadu, India

Department of Pharmacy, Faculty of Engineering and Technology, Annamalai University, Chidambaram, Tamilnadu, India

Y. Haribabu, Department of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.

Department of Pharmaceutical chemistry, Grace College of Pharmacy, Palakkad, Kerala.

References

1. Molecular Targets and Cancer Therapeutics-- Oct 22-26, 2007;
2. file:///C:/Users/mafsa/Desktop/Indole-3-glyoxylamide%20_%20CAS_5548-10-7%20_%20Manufacturer%20ChemFaces.html
3. Ebrahim Saeedian Moghadam Design, synthesis and cytotoxicity evaluation of indibulin analogs.Heterocycl. Commun. 2018; 24(4): 211–217
4. Ebrahim Saeedian Moghadam and Mohsen Amini.2-[2-Methyl-5-phenyl-1-(3,4,5-trimethoxyphenyl)-1Hpyrrol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide.Molbank 2018;M1002 1-8.
5. Sonia Kapoor, Shalini Srivastava &Dulal Panda Indibulin dampens microtubule dynamics and produces synergistic antiproliferative efect with vinblastine in MCF-7 cells: Implications in cancer chemotherapy http://www.nature.com/scientificreports 17 august 2018.
6. Sravanthi Devi Guggilapu. Synthesis of thiazole linked indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors.European Journal of Medicinal Chemistry 138 • June 2017

7. Sravanthi Devi Guggilapu Synthesis of C5-tethered indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors. European Journal of Medicinal Chemistry 128 January 2017.
8. Renukadevi Patil. Indole molecules as inhibitors of tubulin polymerization: potential new anticancer agents, an update (2013–2015)Future Med. Chem. 2016; 8(11):1291–1316
9. Hong-Yu Hu , Xu-Dong Yu, Novel N-Substituted 2-(2-(Adamantan-1-yl)-1H-Indol3-yl)-2-Oxoacetamide Derivatives: Synthesis and Biological Evaluation.Molecules 2016; 21, 530
10. Mukund P. Tantaka ,Vishakha Gupta a , Kumar Nikhil.Sequential one-pot synthesis of bis(indolyl)glyoxylamides: Evaluation of antibacterial and anticancer activities.Bioorg. Med. Chem. Lett. 2016; 1-5
11. Helen E. Colley, MunittaMuthana, Sarah J. Danson.An orally bioavailable, indole-3-glyoxylamide based series of tubulin polymerization inhibitors showing tumor growth inhibition in a mouse xenograft model of head and neck cancer.
12. Mardia T. El Sayed , Nehal A. Hamdy , Dalia A.Indoles as anti-cancer agents.Adv Mod Oncol Res 2015; 1(1):20–35;
13. Yang Zheng, Ren-Jun Li, Zhen Zhan, Yan Zhou, Li Hai.Fe-catalyzed regioselective Friedel–Crafts hydroxyalkylation of 4 N-substituted glyoxylamide with indoles.Chin. Chem. Lett. 2015; 3447 1-6.
14. N. M. Jagadeesh1, K. M. Mahadevan1 M. N Kumara, N. Prashantha.Synthesis And Molecular Docking Study Of N-Alkyl/Aryl-2-Aryl Indol-3-Yl Glyoxylamides As Novel Anticancer Agents.Int J Pharm Pharm Sci, Vol 6, Suppl 2, 921-926.
15. Nagendra Kumar Kaushik , Neha Kaushik , Pankaj Attri.Biomedical Importance of Indoles. Molecules 2013; 18, 6620-6662;
16. Vijayakumar N. Sonar. ndole Inhibitors of Human Nonpancreatic Secretory Phospholipase A2. 3. Indole-3-glyoxamides.J. Med. Chem. 2012; 39:5159-5175
17. Shivaputra A Patil, Renukadevi Patil.Indole molecules as inhibitors of tubulin polymerization: potential new anticancer agents.Future Med. Chem. 2012; 4(16):2085–2115
18. Ran Cao, Minyu Liu Min Yin. Discovery of Novel Tubulin Inhibitors via Structure-Based Hierarchical Virtual Screening.J. Chem. Inf. Model. 2012, 52, 2730−2740.
19. Tien-Heng Huang1, Shu-Jun Chiu2,3, Pei-Hsiuang Chiang.Antiproliferative Effects of N-Heterocyclic Indolyl Glyoxylamide Derivatives on Human Lung Cancer Cells. ANTICANCER RESEARCH 2011; 31:3407-3416.
20. Chih-Bo Hu, Ching-Ping Chen, Teng-Kuang Yeh.BPR0C261 is a novel orally active antitumor agent with antimitotic and anti-angiogenic activities.Cancer Sci 2011; January vol. 102| no. 1 182–191.
21. Peter KUTSCHYa1, Andrej SÝKORAb, Zuzana ČURILLOVÁ.Glyoxyl Analogs of Indole Phytoalexins: Synthesis And Anticancer Activity.Collect. Czech. Chem. Commun. 2010; 75(8):887–903
22. BeiningChen.The synthesis of a library of indole-3-glyoxylamides and their evaluation as potential antiprion agents 2009; 1:250-256.
23. Anke Wienecke, and Gerald Bacher.Indibulin, a Novel Microtubule Inhibitor, Discriminates between Mature Neuronal and Nonneuronal Tubulin.American Association for Cancer Research.Cancer Res 2009; 69(1):171-177.
24. Pascal Marchand , Maud Antoine , Guillaume Le Baut.Synthesis and structure–activity relationships of N-aryl(indol-3-yl)glyoxamides as antitumor agents.Bioorganic & Medicinal Chemistry 17 2009; 6715–6727
25. Mark J. Thompson, VincianeBorsenberger.Design, Synthesis, and Structure-Activity Relationship of Indole-3-glyoxylamide Libraries Possessing Highly Potent Activity in a Cell Line Model of Prion Disease.J. Med. Chem. 2009; 52:7503–7511 7
26. Maud Antoine, Pascal Marchand, Guillaume Le Baut.Side chain modifications of (indol-3-yl)glyoxamides as antitumor agents.Journal of Enzyme Inhibition and Medicinal Chemistry, October 2008; 23(5):686–695.
27. David A. James, KeizoKoya, Hao Li.Indole- and indolizine-glyoxylamides displaying cytotoxicity against multidrug resistant cancer cell lines.Bioorganic & Medicinal Chemistry Letters, 2008; 18:1784–1787.
28. Marina N. Semenova, Alex S. Kiselyov , Ilia Y. Titov.In vivo Evaluation of Indolyl Glyoxamides in the Phenotypic Sea Urchin Embryo Assay.Chem Biol Drug Des 2007; 70:485–490.
29. Andrea Brancale, Romano Silvestri. Indole, a Core Nucleus for Potent Inhibitors of Tubulin Polymerization. Medicinal Research Reviews, 2007; 27(2):209:238,
30. Wen-Tai Li, Der-Ren Hwang, Ching-Ping Chen.Synthesis and Biological Evaluation of N-Heterocyclic Indolyl Glyoxylamides as Orally Active Anticancer Agents.J. Med. Chem. 2003; 46:1706-1715.

Published

2020-08-15

How to Cite

Buvana, C., Raveendran, A., Suresh, R., & Haribabu, Y. (2020). Indole-3-Glyoxylamide- An Important Scaffold for Anticancer Activity. Asian Journal of Pharmaceutical Research and Development, 8(4), 218–230. https://doi.org/10.22270/ajprd.v8i4.803