Synthesis, Characterization and Antimicrobial Evaluation of New Compounds Derived from 2-Mercaptobenzoxazole

Authors

  • Zainab Dhia.k Ministry of Health, Department of Health in Baghdad , Russafa, Baghdad, Iraq.
  • Mohammed K.Hadi Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad, Iraq.

DOI:

https://doi.org/10.31351/vol34iss3pp12-17

Abstract

The synthesis of a novel series of 2-mercaptobenzoxazole hydrazide(2-benzo[d]oxazol-2-ylthio) acetohydrazide) derivatives (3a-c, 4a, and 4b) through the use of various  sulfonyl chlorides in dichloromethane  and triethyl amine for the compounds (3a-c) and different aromatic aldehydes in the presence of glacial acetic acid for the compounds (4a, b). The novel compounds' anti-microbial effectiveness has been evaluated in vitro against two of (G+Ve) and two of (G-Ve) bacteria and for fungal activity. In comparison to other compounds, compounds (3a and 3b) had the most anti-microbial action against  Candida albicans and pseudomonas aeruginosa, respectively, while compound (3c)   was more effective against gram-positive bacteria (Streptococcus pyogenes) compare with other compounds. By using their ((melting point,  Thin Layer Chromato-graphy , attenuated total reflectance-Fourier transform infrared  (ATR-FTIR), and 1 HNMR, the target compounds were identified.

How to Cite

1.
Dhia.k Z, Mohammed K.Hadi. Synthesis, Characterization and Antimicrobial Evaluation of New Compounds Derived from 2-Mercaptobenzoxazole. Iraqi Journal of Pharmaceutical Sciences [Internet]. 2025 Sep. 20 [cited 2025 Sep. 20];34(3):12-7. Available from: https://www.bijps.uobaghdad.edu.iq/index.php/bijps/article/view/2958

Publication Dates

Received

2023-09-01

Revised

2023-09-30

Accepted

2024-03-13

Published Online First

2025-09-20

References

Chan AC, Ager D, Thompson IP. Resolving the mechanism of bacterial inhibition by plant secondary metabolites employing a combination of whole-cell biosensors. Journal of microbiological methods. 2013 Jun 1;93(3):209-17.

Sahib HA, Dakhel ZA, Hadi MK. Synthesis and Preliminary Antimicrobial Activity Evaluation of New Amide Derivatives of 2-aminobenzothiazole. International Journal of Drug Delivery Technology. 2021; 11(4):1258-1261.

Sachdeva H, Mathur J, Guleria A. Indole derivatives as potential anticancer agents: A review. Journal of the Chil. Chem. Soc. 2020 Sep;65(3):4900-4907.

Abduljabbar TT, Hadi MK. Synthesis, Characterization and Antibacterial Evaluation of Some Coumarin Derivatives. Iraqi Journal of Pharmaceutical Sciences, 2021, 30(1):249-257.

Sharma PK, Amin A, Kumar M. A Review: Medicinally Important Nitrogen Sulphur Containing Heterocycles. Open J. Med. Chem. 2020 Sep 14;14(1).49-64.

Bozdag M., Supuran, C. T., Esposito, D., Angeli, A., Carta, F., Monti, S. 2-Mercaptobenzoxazoles: a class of carbonic anhydrase inhibitors with a novel binding mode to the enzyme active site. Chemical Communications, 2020, 56.59: 8297-8300.‏

Srikanth, L., Usha, N., Ramesh, J., Raghunandan, N., Rao, J. V., & Manohar, K. R. Synthesis and evaluation of new phenylamino-thiadiazolo-oxadiazolo-1, 3-benzoxazoles for their antifungal and anti-inflammatory activity. Der Pharma Chemica, 2010, 2.4: 231-240.‏

Jiang, Jie, Tang, X., Dou, W., Zhang, H., Liu, W., Wang, C., & Zheng, J. Synthesis and characterization of the ligand based on benzoxazole and its transition metal complexes: DNA-binding and antitumor activity. Journal of Inorganic Biochemistry, 2010, 104.5: 583-591.‏

Sondhi, S. M., Singh, N., Kumar, A., Lozach, O., & Meijer, L. Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff’s bases. Bioorganic & medicinal chemistry, 2006, 14.11: 3758-3765.‏

Klimešová, V., Kočí, J., Waisser, K., Kaustová, J., & Möllmann. Preparation and in vitro evaluation of benzylsulfanyl benzoxazole derivatives as potential antituberculosis agents. European journal of medicinal chemistry, 2009, 44.5: 2286-2293.‏

Azam, Mohammed Afzal; Suresh, Bhojraj. Biological activities of 2-mercaptobenzothiazole derivatives: a review. Scientia pharmaceutica, 2012, 80.4: 789-824.‏

Sadawarte, Sadawarte, G., Jagatap, S., Patil, M., Jagrut, V., & Rajput, J. D. Synthesis of substituted pyridine based sulphonamides as an antidiabetic agent. European Journal of Chemistry, 2021, 12.3: 279-283.‏

Al-Mudhafar, M. M. J., Abdulkadir, M. Q., Mohammed, A. A., Al-hilli, F. A., & Hussian, A. M. Synthesis and microbiological study of new sulfonamides. Pharmacie Globale. 2012, 3(6), 1.‏

Kołaczek, A., Fusiarz, I., Ławecka, J., & Branowska, D. Biological activity and synthesis of sulfonamide derivatives: a brief review. Chemik, 2014, 68.7: 620-628.

Abu-Yamin, A. A., Abduh, M. S., Saghir, S. A. M., & Al-Gabri, N. Synthesis, characterization and biological activities of new Schiff base compound and its lanthanide complexes. Pharmaceuticals, 2022, 15.4: 454.‏

Badihian, S.; Shaygannejad, V.; Soleimani, P.; Mirmosayyeb, O.; Samee, Z.; Manouchehri, N.; Esmaeil, N. Decreased serum levels of interleukin-35 among multiple sclerosis patients may be related to disease progression. J. Biol. Regul. Homeost. Agents 2018, 32, 1249–1253.

Song, X.-Q.; Wang, Z.-G.; Wang, Y.; Huang, Y.-Y.; Sun, Y.-X.; Ouyang, Y.; Xie, C.-Z.; Xu, J.-Y. Syntheses, characterization, DNA/HSA binding ability and antitumor activities of a family of isostructural binuclear lanthanide complexes containing hydrazine Schiff base. J. Biomol. Struct. Dyn. 2020, 38, 733–743.

Kafi-Ahmadi, L.; Marjani, A.P. Mononuclear Schiff base complexes derived from 5-azophenylsalicylaldehyde with Co (ii), Ni (ii) ions: Synthesis, characterization, electrochemical study and antibacterial properties. S. Afr. J. Chem. 2019, 72, 101–107.

Kaczmarek, M.T.; Zabiszak, M.; Nowak, M.; Jastrzab, R. Lanthanides: Schiff base complexes, applications in cancer diagnosis, therapy, and antibacterial activity. Coord. Chem. Rev. 2018, 370, 42–54.

El-Gammal, O.A.; Mohamed, F.S.; Rezk, G.N.; El-Bindary, A.A. Structural characterization and biological activity of a new metal complexes based of Schiff base. J. Mol. Liq. 2021, 330, 115522.

Halah A. Sahib, Mohammed K. Hadi, Maadh Qusay Abdulkadir. Synthesis, and Antimicrobial Evaluation of New hydrazone Derivatives of (2,4-dinitrophenyl) hydrazine. Research Journal of Pharmacy and Technology. 2022; 15(4):1743-8

Keshavayya, J.; Pandurangappa, M.; Ravi, B. Synthesis, characterization and electrochemical investigations of azo dyes derived from 2-Amino-6-ethoxybenzothiazole. Chem. Data Collect. 2018, 17, 13–29.

Hassan OM, Sarsam SW. Synthesis, characterization and preliminary anti-inflammatory evaluation of new etodolac derivatives. Iraqi Journal of Pharmaceutical Sciences. 2019;28(1):106–12

Hadi MK, Abdulkadir MQ, Abdul-Wahab AH. Synthesis and Antimicrobial Evaluation of Sulfonylhydrazide Derivatives of Etodolac. International Journal of Drug Delivery Technology. 2021;11(3):1000-1003.

Kamms, Zainab Dhia; HADI, Mohammed K. Synthesis, Characterization and preliminary Anti-Microbial Evaluation of New Ibuprofen Hydrazide Derivatives. Pakistan Journal of Medical & Health Sciences, 2022, 16.03: 693-693.‏

Saour YK, Al-Bayati IR, and Hadi KM. Synthesis of New Coumarin and 2-quinolone Derivatives with Expected Biological Activities. Iraqi J Pharm Sci. 2012; 21(2).

Abdulraheem SS, Hadi MK. Synthesis and Characterization of New Coumarin Derivatives as Possible Antimicrobial Agents. International Journal of Drug Delivery Technology. 2021; 11(4):1484-1490.

Mohammed Kamil Hadi, Nedaa A. Hameed A. Rahim, Ahmed T. Sulaiman, Rusul Mohammed Hasan Ali. Synthesis, Characterization and Preliminary Antimicrobial Evaluation of New Schiff bases and Aminothiadiazole Derivatives of N- Substituted Phthalimide. Research Journal of Pharmacy and Technology. 2022; 15(9):3861-5.

Kamms ZD, Hadi MK. Synthesis, Characterization and Preliminary Antimicrobial and Anti-inflammatory Evaluation of New Ibuprofen Hydrazide Derivatives. International Journal of Drug Delivery Technology. 2023;13(1):376-38.

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Published

2025-09-20