Solvent free Synthesis of 2-[(5-methyl-1,3-benzoxazol-2-yl)sulfanyl] Acetohydrazide Derivatives as Novel Antimicrobial and Antitumor Agents

J. Paveendra

Department of Chemistry, Sahyadri Science College, Shivamogga-577203, India.

H. M. Vagdevi *

Sahyadri Science College, Shivamogga-577203, India.

Dyamanna Thippeswamy

Department of Chemistry, School of Chemical Sciences, Kuvempu University, Jnana-Sahyadri, Shankaraghatta-577 451, Karnataka, India.

Yanjerappa Arthobha Nayaka

Department of Chemistry, School of Chemical Sciences, Kuvempu University, Jnana-Sahyadri, Shankaraghatta-577 451, Karnataka, India.

*Author to whom correspondence should be addressed.


Abstract

In pursuit of designing novel chemical entities with antitumor and antimicrobial activities, 2-[(5-methyl-1,3-benzoxazol-2-yl)sulfanyl]acetohydrazidederivatives have been synthesized as a scaffold of a series of amine derivatives, these analogs were on reductive amination with solvent free condition. All the synthesized compounds were assessed for antibacterial, antifungal, and antitumor activities against standard strains. The compounds 3a, 3b and 3g showed highest degree of inhibition against A. flavus and compounds 3a, 3b, 3d and 3h Showed highest degree of inhibition against C. albicans, compounds 3a,3e and 3g has shown the encouraging antibacterial activityresults against E. coli and compounds 3a, 3b and 3h exhibited a promising activity against  B. subtilis. Compounds 3a, 3b and 3c exhibited promising antitumor activity.

Keywords: Benzoxazole, solvent free condition, antitumor, antimicrobial


How to Cite

Paveendra , J., Vagdevi , H. M., Thippeswamy, D. and Nayaka , Y. A. (2023) “Solvent free Synthesis of 2-[(5-methyl-1,3-benzoxazol-2-yl)sulfanyl] Acetohydrazide Derivatives as Novel Antimicrobial and Antitumor Agents”, Journal of Pharmaceutical Research International, 35(13), pp. 36–45. doi: 10.9734/jpri/2023/v35i137368.

Downloads

Download data is not yet available.

References

Gajanan S. Shanbhan, Amit Bhargavagiridhar, Pal Singh Shrinivas D. Joshinarendra chundawat, synthesis, molecular simulation studies, in vitro biological assessment of 2-substituted benzoxazole derivatives as promising antimicrobial agents. Turkish Journal of Chemistry: 2023;47:263-279.

D. M. Livermore. Antibiotic resistance in staphylococci. International Journal of Antimicrobial Agents. 2000;16:S3–S10.

McKee ML, Kerwin SM. Synthesis, metal ion binding, and biological evaluation of new anticancer 2-(2’-Hydroxyphenyl)benzoxazole Analogs of UK-1. BioorgMedChem. 2008;16:1775-1783.

Mohamed A Abdelgawad. New benzoxazole derivatives as antiprotozoal agents: In silico studies, synthesisand biological evaluation. Hindawi Journal of Chemistry; 2021.

Dadmal TL, Appalanaidu, Killari, Kumbhare RM, Mondal T, Ramaiah MJ, Bhadra, Manika Pal. Synthesis and biological evaluation of triazole and isoxazole tagged Benzothiazole/Benzoxazole derivatives as potentcytotoxic agents. New J. Chem. 2018;42:15546-15551.

Ravikumar P, Raolji GSB, Venkata Sastry K, Kalidasua S, Balaaraju T. Design, synthesis, and anticancer evaluation of tetrazole-fused benzoxazolederivatives as tubulin binding agents. Russ J Gen Chem. 2018;88(10):2183–218.

Maruthamuthu, Shameela Rajam.The chemistry and biological significance of imidazole, benzimidazole, benzoxazole, tetrazole and quinazolinone nucleus. Journal of Chemical and Pharmaceutical Research. 2016;8(5):505-526.

ChandaK, Rajasekhar S, Maiti B A. Decade Update on Benzoxazoles, a Privileged Scaffold in Synthetic Organic Chemistry.Synlett. 2017;28:521−541.

Taylor AP, Robinson RP, Fobian, YM Blakemore, DC Jones, LHand Fadeyi O. Modern advances in heterocyclic chemistry in drug discovery. Organic & Biomolecular Chemistry. 2016;14: 6611-6637.

The Thai Nguyen, Xuan-Trang Thi Nguyen, Thuy-Linh Ho Nguyen, Phuong Hoang Tran. Synthesis of benzoxazoles, benzimidazoles, and benzothiazolesusing a bronsted acidic ionic liquid gel as an efficientheterogeneous catalyst under a solvent-free condition. ACS Omega 2019;4;368−373.

Laliteshwar P Singh, Viney Chawla, Pooja Chawla and Shailendra K Saraf. Synthesis and antimicrobial activity of some 2-phenyl-benzoxazole derivatives.Der Pharma Chemica. 2010;2(4):206-212.

lumenschein GR, Jr Smit EF, Planchard D. A randomized phase II study of the MEK1/MEK2inhibitor trametinib (GSK1120212) compared with docetaxel in KRAS-mutant advanced non-small-cell lung cancer (NSCLC)dagger. Ann Oncol. 2015;26:894–901.

Surendra Kumar R, Ibrahim A Arif , Anis Ahamed , Akbar Idhayadhulla. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues.Saudi J Biol Sci. 2016;23(5):614-20.

Gurmeet Kaur P, Balamurugan, Sahana Vasudevan, Saikiran Jadav, Princy SA. Antimicrobial and antibiofilm potential of acyclic amines and diamines against multi-drug resistant Staphylococcus aureus. Fmicb. 2017;8:1767.

Raghunath B.Toche, Ravindra A, Janaro. Synthesis, Characterization and antimicrobial evaluation of novel urea, sulfonamide and acetamide 3,4- dihydropyrazino[1,2-α]indol-1(2H)-one derivatives. Arabian journal of chemistry. 2015;12(8):1-11.

Azizian J, Torabi P, Noei J. Synthesis of benzimidazoles and benzoxazoles using TiCl3OTf in ethanol at room temperature.Tetrahedron Lett. 2016;57: 185−188.

Jayanna ND, Vagdevi HM, Dharshan, JC, Prashith Kekuda TR, Hanumanthappa BC, Gowdarshivannanavar BC. Synthesis and Biological Evaluation of Novel 5,7-Dichloro-1,3-benzoxazole Derivatives.Journal of Chemistry Hindawi. 2013;1-9.

Naruti Longkumer, Kikoleho Richa, Rituparna Karmaker, Visekhonuo Kuotsu. Green synthesis of bromo organic molecules and investigations on their antibacterial properties: An experimental and computational approach. Acta Chim. Slov. 2019;66: 276–283.

Satyendra RV, Vishnumurthy KA, Vagdevi HM, Rajesh KP, Manjunatha H, Shruthi A. Synthesis, In vitro antioxidant, anthelmintic and molecular docking studies of novel dichloro substituted benzoxazole-triazolo-thione derivatives. Eur J Med Chem. 2011;46:3078- 3084.

MohdAmir, Kumar Shikha. Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino) phenyl]acetic acid derivatives.European Journal of Medicinal Chemistry. 2004;39:535–545.

Dinesh R Godhani, Anand A Jogel, Anil M, Sanghani, Jignasu P Mehta. Thermal study of synthesized 1,2,4-triazole compounds and their kinetic parameter evaluation. Journal of Chemical and Pharmaceutical Research. 2014;6(6):1034-1041.

Abdelgawad MA, Bakr RB, Ahmad W, Al-Sanea MM, Elshemy HAH. New pyrimidine-benzoxazole/benzimidazole hybrids: Synthesis, Antioxidant, Cytotoxic Activity, in vitro Cyclooxygenase, and phospholipaseA2-V Inhibition. Bioorganic Chemistry. 2019;92:103218.

Mahbubur Rahman MD, Badrul Islam MD ,Mohitosh Biswas, Khurshid Alam AHM. In vitro antioxidant and free radical scavenging activity of different parts of Tabebuia pallida growing in Bangladesh. BMC ResearchNotes. 2015;8:621

Ingle V, Gorepatil P, Mane Y. Samarium (III) triflate as an efficient and reusable catalyst for facile synthesis of benzoxazoles and benzothiazoles in aqueous medium. Synlett. 2013;24:2241−2244.

Chauhan PMS, Martins CJA, Horwell DC. Syntheses of novelheterocycles as anticancer agents. Bioorg Med Chem. 2005;13:3513–3518.

Therese Horch, Evelyn M. Molloy, Florian Bredy, Veit G. Haensch, Kirstin Scherlach, Kyle L. Dunbar, Jonathan Franke, Christian Hertweck. Alternative benzoxazole assembly discovered in anaerobic bacteria provides access to privileged heterocyclic scaffold. Angew. Chem. 2022;134:1521-3757.

Jiatao Yu, Ming Lu. [C12mim]Br: A temperature-dependent phase transfer catalyst and its application for aerobic oxidative synthesis of 2-Aryl benzimidazoles, benzoxazoles or benzothiozoles catalyzed by TEMPO based ionic liquid. J Chin. Chem. Soc. 2014;61:578-582.

Ajay BN, Govindasamy S. Synthesis of benzoxazoles by an efficient Ullmann-type intramolecular C(aryl)–O bond-formingcoupling cyclization with a BINAM-copper(II) catalyst. Synthesis. 2010;4:579–586.

Easmon J, Purstinger G, Thies KS, Heinisch G, Hofmann J. Synthesis, structure-activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acylheteroaromatics. J Med Chem. 2006;49:6343–6350.

P K Jauhari,A. Bhavani,Subhash Varalwar, Kiran Singhal, Prem Raj. Synthesis of some novel 2-substituted benzoxazoles asanticancer, antifungal, and antimicrobial agents.Med Chem Res. 2008;17:412–424.

Vinsova J, Horak V, Buchta V, Kaustova J. Highly lipophilicbenzoxazoles with potential antibacterial activity. Molecules.2005;10:783–793.

Neelima D Tangellamudia, Suchita B Shindea, Venkatesh Pooladandab, Chandraiah Godugub, Sridhar Balasubramanian. Facile synthesis of 2-aryl 5-hydroxy benzo[d]oxazoles and their in vitro antiproliferative effects on various cancer cell lines.Bioorganic & Medicinal Chemistry Letters. 2018;28:3639–3647.

ElHelby AA, Sakr H, Eissa I, Abulkhair H, Al‐Karmalawy H, A A & ElAdl K. Design, synthesis, molecular docking, and anticancer activity of benzoxazole derivatives as VEGFR‐2 inhibitors. Archiv Der Pharmazie. 2019;10:352.

Cheng-Juan Wu, Xin-Yu Li, Ting-Rui Li, et al. Natural sunlight photocatalytic synthesis of benzoxazole-bridged covalent organic framework for photocatalysis. J. Am. Chem. Soc. 2022;144:41;18750–18755.