Synthesis, DFT Studies, Antioxidant and Anticancer Activities of Newly Synthesized Compounds Containing Lawsone Using Different Halo Reagents.

Authors

  • Gulam Muheyuddeen
  • Dr. Stuti Verma
  • Saquib Tanweer
  • Dr. Anoop Sirbaiya
  • Jishan Ahmad

DOI:

https://doi.org/10.53555/jaz.v43i1.4399

Keywords:

Lawsone, Halo-reagents, DFT studies, anti-oxidant, anti-tumor

Abstract

A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4- hydroxy-7-methoxy-2-oxo-1,2 dihydroquinolin-3-yl)naphthalene-1,4-dione (7) and naphtha [2,3-b]furan-3,4,9(2H)-trione (6) based on Lawsone ‘that plays as important precursor’ was synthesized by reaction with 1,3- diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2- chloro-acetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds.

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Author Biographies

Gulam Muheyuddeen

Assistant Professor, Department of Pharmaceutical Chemistry, Faculty of pharmacy, Jahangirabad institute of technology, Jahangirabad fort, Barabanki, Affiliated to Dr. AKTU, Lucknow Uttar Pradesh, Orchid ID- 0000-0001-6317-1630

Dr. Stuti Verma

Aryakul College of Pharmacy & Research Sitapur- Village- Jajjaur, Post- Manawa, (Near Krishi Vigyan Kendra Sitapur) Sidhauli, Dist- Sitapur- 261303 U.P

Saquib Tanweer

Department of pharmaceutical chemistry, Faculty of pharmacy, Jahangirabad institute of technology, Jahangirabad fort, Jahangirabad, Barabanki, Uttar Pradesh, India, 225203.

Dr. Anoop Sirbaiya

KPS Memorial Institute of Pharmacy Sitapur 261207

Jishan Ahmad

Department of pharmaceutical chemistry, Faculty of pharmacy, Jahangirabad institute of technology, Jahangirabad fort, Jahangirabad, Barabanki, Uttar Pradesh, India, 225203

References

Mourad Jridi, Sabrine Sellimi, Khaled Ben Lassoued, Sabrine Beltaief, Nabil Souissi, Leticia Mora, Fidel Toldra, Abdelfatteh Elfeki, Moncef Nasri, and Rim Nasri, “Wound Healing Activity of Cuttlefish Gelatin Gels and Films Enriched by Henna (Lawsonia Inermis) Extract,” Colloids and Surfaces A: Physicochemical and Engineering Aspects 512, (2017): 71–9. 2016.10.014

Balagani Sathish Kumar, Kusumoori Ravi, Amit Kumar Verma, Kaneez Fatima, Mohammad Hasanain, Arjun Singh, Jayanta Sarkar, Suaib Luqman, Debabrata Chanda, and Arvind S. Negi, “Synthesis of Pharmacologically Important Naphthoquinones and Anticancer Activity of 2-Benzyllawsone through DNA topoisomerase-II Inhibition,” Bioorganic & Medicinal Chemistry 25, no. 4 (2017): 1364–73.

Aamir Ahmad, Katharina Mahal, Subhash Padhye, Fazlul H. Sarkar, Rainer Schobert, and Bernhard Biersack, “New Ferrocene Modified Lawsone Mannich Bases with anti-Proliferative Activity against Tumor Cells,” Journal of Saudi Chemical Society 21, no. 1 (2017): 105–10.

Shi-Bin Wang, Zhenzhou Tao, and Ping Li, “Lawsone Suppresses Azoxymethane Mediated Colon Cancer in Rats and Reduces Proliferation of DLD-1 Cells via NF-jB Pathway,” Biomedicine & Pharmacotherapy¼Biomedecine & Pharmacotherapie 89, (2017): 152–61.

Flaviano M. Ottoni, Eliza R. Gomes, Rodrigo M. P_adua, M^onica C. Oliveira, Izabella T. Silva, and Ricardo J. Alves, “Synthesis and Cytotoxicity Evaluation of Glycosidic Derivatives of Lawsone against Breast Cancer Cell Lines,” Bioorganic & Medicinal Chemistry Letters 30, no. 2 (2020): 126817.

Katharina Mahal, Aamir Ahmad, Florian Schmitt, Julia Lockhauserb€aumer, Kathrin Starz, Rohan Pradhan, Subhash Padhye, Fazlul H. Sarkar, Waleed S. Koko, Rainer Schobert, et al. “Improved Anticancer and Antiparasitic Activity of New Lawsone Mannich bases,” European Journal of Medicinal Chemistry 126, (2017): 421–31.

Morgana V. de Ara_ujo, Cibelle Cabral David, Jos_e Clementino Neto, Luiz A. P. L. de Oliveira, Karoline Cristina Jatob_a da Silva, Jefferson Miguel Dos Santos, Jo~ao Kayke S. da Silva, Victoria B. C. de A Brand~ao, Tania M. S. Silva, Celso A. Camara, et al. “Evaluation on the Leishmanicidal Activity of 2-N,N’-dialkylamino-1,4-naphthoquinoneDerivatives,” Experimental Parasitology 176, (2017): 46–51.

Pooja Gaur, Jyotshna, Dhananjay Kumar Singh, Suaib Luqman, and Karuna Shanker, “Validated Method for Quality Assessment of Henna, (Lawsonia Inermis L.) Leaves after Postharvest Blansssssching and Its Cosmetic Application,” Industrial Crops and Products 95, (2017): 33–42.

Om P. S. Patel, Richard M. Beteck, and Lesetja J. Legoabe, “Antimalarial Application of Quinones: A Recent Update,” European Journal of Medicinal Chemistry 210, (2021): 113084–110.

Gabriel Adetoye Adedeji, Olukayode Yekin Ogunsanwo, and Taiwo Olayemi Elufioye, “Quantifications of Phytochemicals and Biocide Actions of Lawsonia Inermis Linn. Extracts against Wood Termites and Fungi,” International Biodeterioration & Biodegradation 116, (2017): 155–62.

Gayoung Kim, and Sung-Eun Lee, “Antifungal and Antiaflatoxigenic Properties of Naphthoquinones toward Aspergillus flavus and Their Mode of Inhibitory Action on Aflatoxin Biosynthesis,” Food Control 119, (2021): 107506–13.

F. Zulkifli, Nora’aini. Ali, M. Sukeri, Yusof, M. I. N. Isa, A. Yabuki, and W B. Wan Nik, “Henna Leaves Extract as a Corrosion Inhibitor in Acrylic Resin Coating,” Progress in Organic Coatings 105, (2017): 310–9.

Geetam Richhariya, Anil Kumar, Perapong Tekasakul, and Bhupendra Gupta, “Natural Dyes for Dye Sensitized Solar Cell: A Review,” Renewable and Sustainable Energy Reviews 69, (2017): 705–18.

I. Jinchu, C. O. Sreekala, and K. S. Sreelatha, “Lawsone Metal Complex as an Effective Sensitizer for Dye Sensitized Solar Cells,” Materials Today: Proceedings 33, no. 2 (2020): 1356–60.

M. A. Holgado, J. L. Arias, M. J. Cozar, J. Alvarez-Fuentes, A. M. Ganan-Calvo, and M. Fern_andez-Ar_evalo, “Synthesis of Lidocaine-loaded PLGA Microparticles by Flow Focusing. Effects on Drug Loading and Release Properties,” International Journal of Pharmaceutics 358, no. 1–2 (2008): 27–35.

Fanzhi Qu, Chen Zhao, Yafei Liu, Jiaqing Cao, Wei Li, and Yuqing Zhao, “Semi-Synthesis and anti-Tumor Evaluation of Novel 25-Hydroxyprotopanaxadiol Derivatives as Apoptosis Inducing Agents,” MedChemComm 6, no. 11 (2015): 2004–11.

Fan-Zhi Qu, Ya-Fei Liu, Jia-Qing Cao, Xu-De Wang, Xiao-Shu Zhang, Chen Zhao, and Yu-Qing Zhao, “Novel 25-hydroxyprotopanaxadiol Derivatives Incorporating Chloroacetyl Chloride and their Anti-tumor Evaluation,” Bioorganic & Medicinal Chemistry Letters 24, no. 23 (2014): 5390–4.

Akira Fujinami, Takeo Satomi, Akihiko Mine, and Toshio Fujita, “Structure-Activity Study of Herbicidal Nchloroacetyl- N-Phenylglycine Esters,” Pesticide Biochemistry and Physiology 6, no. 3 (1976): 287–95.(76)90072-9.

Shi Ting Liu, Hong Wei Yang, Wen Jun Liu, Yu Zhao, Xiao Mao Wang, and Yuefeng F. Xie, “Evaluation of Backwash Strategies on Biologically Active Carbon Filters by Using Chloroacetic Acids as Indicator Chemicals,” Process Biochemistry 51, no. 7 (2016): 886–94.

Wafaa S. Hamama, Alaa E. Hassanien, and Hanafi H. Zoorob, “Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2-Hydroxynaphthalene-1,4-Dione),” Journal of Heterocyclic Chemistry 54, no. 4 (2017): 2155–96.

Wafaa S. Hamama, Alaa E. Hassanien, and Hanafi H. Zoorob, “Adaptable Access for Naphthaquinone Annulation: Bioactivity and Molecular Modeling Evaluations,” Journal of Heterocyclic Chemistry 54, no. 6 (2017): 3273–81.

Wafaa S. Hamama, Alaa E. Hassanien, Manal G. El-Fedawy, and Hanafi H. Zoorob, “Synthesis and Antimicrobial Evaluation of Novel Polyfused Heterocycles-Based Quinolone,” Journal of Heterocyclic Chemistry 52, no. 2 (2015): 492–6.

Ayoob Bazgir, Zeinab Noroozi Tisseh, and Peiman Mirzaei, “An Efficient Synthesis of Spiro[Dibenzo[b,i]Xanthene-13,30-Indoline]-Pentaones and 5H-Dibenzo[b,i] Xanthene-Tetraones,” Tetrahedron Letters 49, no. 35 (2008): 5165–8.

Amosi Makoye, Alexander Pogrebnoi, and Tatiana Pogrebnaya, “Lawsone Isomers, Lawsone Ether and Bilawsone for Dye-sensitized Solar Cells Applications: DFT and UV-Vis Studies,” Journal of Molecular Graphics & Modelling 94, (2020): 107457. [31586755]

E. A. Lissi, B. Modak, R. Torres, J. Escobar, and A. Urzua, “Total Antioxidant Potential of Resinous Exudates from Heliotropium Species, and a Comparison of the ABTS and DPPH methods,” Free Radical Research 30, no. 6 (1999): 471–7.

K. Karrer, and J. R. Rubini, “On the Fate of Labelled Ehrlich Ascites Cells in Mice, an Autoradiographic Study Using H3 Thymidine,” Medicina et Pharmacologia Experimentalis. International Journal of Experimental Medicine 13, no. 2 (1965): 124–30.

Wafaa S. Hamama, Alaa E. Hassanien, and Hanafi H. Zoorob, “Concise Synthesis and Pharmacological Applications of New a-Lapachone Analogues,” Journal of Heterocyclic Chemistry 55, no. 1 (2018): 282–90.

D. Molho, and C. Mentzer, “Nouveaux Proc_ed_es de Synth_ese de la 2-Hydroxy-1,4- Naphtoquinone,”Experientia 6, no. 1 (1950): 11–2. https://doi.org/10.1007/BF02154043.

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Published

2024-04-08

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