Volume : 09, Issue : 06, June – 2022



Authors :

S S D Bhavani Raja*, Samyuktha.Metta, Rangampally Sindhu, Thurupu Rajendhar, Naveena.R

Abstract :

The present work deals with designing of some novel substituted 2 -amino 3- chloro naphthalene – 1,4 dione derivatives on the basis reaction between 2,3- dichloronaphthalene -1,4-dione and various secondary amine like 5-amino uracil (L1), 5-amino 1,3-dimethyl uracil (L2), 2-amino-chromen (L3), 2-amino- furan (L4) and isonicotinohydrazide (L5) in presence of ethanol. The synthesized compounds were characterized by IR, 1H NMR, 13C NMR, Mass spectrometry and elementary analysis. Preliminary QSAR study was carried out for the synthesized compounds. All the compounds obeyed the Lipnski rule of 5. Solubility characters of synthesized compounds were carried out by using various solvents. The tested compounds are freely soluble in DMSO, soluble in chloroform and methanol, slightly soluble in acetone, ethyl acetate and ethanol and insoluble in water. The structures of the synthesized compounds were studied using Autodock software against Topoisomerease II as a target enzymes. The docking results showed that Compounds L3, L2, L4, and L1 were found to have significant binding score against target enzyme Topoisomerase compared to standard drug Etaposide.
Keywords: Molecular Docking, Naphthoquinone, Synthesis, Characterization

Cite This Article:

Please cite this article in press S S D Bhavani Raja et al, Synthesis, Characterization, Molecular Docking Studies Of Substituted 2-Amino 3-Chloro Naphthoquinone Derivatives.,Indo Am. J. P. Sci, 2022; 09(6).,

Number of Downloads : 10


1. Monks TJ Hanzlık RP Cohen GM Ross D Graham DG Quinone chemistry and toxicity. Toxicology and Applied Pharmacology. 1992;112:2–16. [PubMed] [Google Scholar]
2. Kutyrev AA Nucleophilic reactions of quinones. Tetrahedron report number 298. Tetrahedron 1991;47:8043–8065. [Google Scholar]
3. Delarmelina M Daltoe RD Cerri MF Madeira KP Rangel LBA -(Substituted -naphthoquinone derivatives containing nitrogen, oxygen and sulfur. Synthesis, Antitumor Activity and Docking of 2. 2015;1:3–3. [Google Scholar]
4. Neckers L Schulte TW Mimnaugh E Geldanamycin as a potential anti-cancer agent: its molecular target and biochemical activity. Investigational. New Drugs. 1999;17:361–373. [PubMed] [Google Scholar]
5. Tandon VK Maurya HK Kumar S Rashid A Panda D -naphthoquinones that potently induce apoptosis in cancer cells. Synthesis and evaluation of 2-Heteroaryl and 2. 2014;1:3–3. [Google Scholar]
6. Gafner S Wolfender JL Nianga M Stoeckli-Evans H Hostettmann K. Antifungal and antibacterial naphthoquinones from Newbouldia laevis roots. Phytochemistry. 1996;42:1315–1320. [PubMed] [Google Scholar]
7. Opitz W Pelster B Fruchtmann R Krupka U Gauss W -Naphthoquinone derivatives having anti-inflammatory action. U.S. Patent. 1986;1:062–062. [Google Scholar]
8. Tran T Saheba E Arcerio AV Chavez V Li Q-yi Quinones as antimycobacterial agents. Bioorganic & Medicinal Chemistry. 2004;12:4809–4813. [PubMed] [Google Scholar]
9. Silva TMS Camara CA Barbosa TP Soares AZ Cunha LC Molluscicidal activity of synthetic lapachol amino and hydrogenated derivatives. Bioorganic & Medicinal Chemistry. 2005;13:193–196. [PubMed] [Google Scholar]
10. Ryu CK Lee IK Jung SH Lee CO Synthesis and cytotoxic activities of 6-chloro-7-arylamino-5. 1999;9:8–isoquinolinediones. [PubMed] [Google Scholar]
11. Satheshkumar A Ganesh K Elango KP Charge transfer facilitated direct electrophilic substitution in phenylaminonaphthoquinones: experimental, theoretical and electrochemical studies. New Journal of Chemistry. 2014;38:993–1003. [Google Scholar]
12. Tudor G Gutierrez P Aguilera-Gutierrez A Sausville EA Cytotoxicity and apoptosis of benzoquinones: redox cycling, cytochrome c release, and BAD protein expression. Biochemical Pharmacology. 2003;65:1061–1075. [PubMed] [Google Scholar]
13. Pal S Jadhav M Weyhermüller T Patil Y Nethaji M Molecular structures and antiproliferative activity of side-chain saturated and homologated analogs of 2-chloro-3-(n-alkylamino)-1,4-napthoquinone. Journal of Molecular Structure. 2013;1049:355–361. [Google Scholar]