A Review on Anti-Cancer Activity of Benzopyrazole and Thiazolidine-4-One Nucleus

Authors

  • Babita Patial Assistant Professor, Department of Pharmaceutical Chemistry, School of Pharmacy, Career Point University, Himachal Pradesh, INDIA.
  • Anshul Chawla Vice-Principal, CT College of Pharmacy, Jalandhar, Punjab, INDIA.
  • Rajiv Sharma Department of Pharmaceutical Chemistry, University Institute of Pharmaceutical Sciences, Chandigarh University, Mohali, INDIA.
  • Rubeena Akhter Department of Pharmacy, School of Pharmacy, Career Point University, Himachal Pradesh, INDIA.
  • Priya Sharma Department of Pharmacy, School of Pharmacy, Career Point University, Himachal Pradesh, INDIA.
  • Saksham Department of Pharmacy, School of Pharmacy, Career Point University, Himachal Pradesh, INDIA.
  • Ritesh Kumar Department of Pharmacy, School of Pharmacy, Career Point University, Himachal Pradesh, INDIA.

Keywords:

Benzoxazole, Thiazolidin-4-ones, Anticancer drug, Isolated Natural Product

Abstract

The review covers recent information about antioxidant, anticancer, anti-inflammatory, analgesic, anticonvulsant, antidiabetic, antiparasitic, antimicrobial, antitubercular and antiviral properties of thiazolidin-4-ones. Additionally, the influence of different substituents in molecules on their biological activity was discussed in this paper. Thus, this study may help to optimize the structure of thiazolidin-4-one derivatives as more efficient drug agents. Presented information may be used as a practical hint for rational design of new small molecules with biological activity, especially among thiazolidin-4-ones. The anticancer drug research and development is taking place in the direction where the new entities are developed which are low in toxicity and are with improved activity. Benzoxazole and its derivative represent a very important class of heterocyclic compounds, which have a diverse therapeutic area. Recently, many active compounds synthesized are very effective; natural products isolated with benzoxazole moiety have also shown to be potent towards cancer.

Downloads

Download data is not yet available.

References

Baxevanis, C. N., Perez, S. A., Papamichail, M. (2009). Combinatorial treatments including vaccines, chemotherapy and monoclonal antibodies for cancer therapy. Cancer Immunol. Immunother. 58, 317–324. doi: 10.1007/s00262-008-0576-4

Benedec, D., Vlase, L., Oniga, I., Toiu, A., Tămaş, M., Brindusa, T. (2012). Isoflavonoids from Glychrrhiza sp. and Ononis spinosa. Farmacia 60, 615–620

Awuchi, C. G., Amagwula, I. O., Priya, P., Kumar, R., Yezdani, U., & Khan, M. G. (2020). Aflatoxins in foods and feeds: A review on health implications, detection, and control. Bull. Environ. Pharmacol. Life Sci, 9, 149-155.

Sahana, S. (2020). Purabi saha, Roshan kumar, Pradipta das, Indranil Chatterjee, Prasit Roy, Sk Abdur Rahamat. A Review of the 2019 Corona virus (COVID-19) World Journal of Pharmacy and Pharmaceutical science, 9(9), 2367-2381.

Bromberg, J. (2002). Stat proteins and oncogenesis. J. Clin. Invest. 109, 1139–1142. doi: 10.1172/JCI15617

Umama, Y., Venkatajah, G., Shourabh, R., Kumar, R., Verma, A., Kumar, A., & Gayoor, M. K. (2019). Topic-The scenario of pharmaceuticals and development of microwave as; sisted extraction technique. World J Pharm Pharm Sci, 8(7), 1260-1271.

Carnero, A., Blanco-Aparicio, C., Renner, O., Link, W., Leal, J. F. (2008). The PTEN/PI3K/AKT signalling pathway in cancer, therapeutic implications. Curr. Cancer Drug Targets 8, 187–198. doi: 10.2174/156800908784293659

Chang, Y.-C., Nair, M. G., Santell, R. C., Helferich, W. G. (1994). Microwave-mediated synthesis of anticarcinogenic isoflavones from soybeans. J. Agric. Food Chem. 42, 1869–1871. doi: 10.1021/jf00045a007

Chen, J., Sun, L. (2012). Formononetin-induced apoptosis by activation of Ras/p38 mitogen-activated protein kinase in estrogen receptor-positive human breast cancer cells. Horm. Metab. Res. 44, 943–948. doi: 10.1055/s-0032-1321818

Chen, J., Zeng, J., Xin, M., Huang, W., Chen, X. (2011). Formononetin induces cell cycle arrest of human breast cancer cells via IGF1/PI3K/Akt pathways in vitro and in vivo. Horm. Metab. Res. 43, 681–686. doi: 10.1055/s-0031-1286306

Chen, J., Zhang, X., Wang, Y., Ye, Y., Huang, Z. (2018a). Differential ability of formononetin to stimulate proliferation of endothelial cells and breast cancer cells via a feedback loop involving MicroRNA-375, RASD1, and ERalpha. Mol. Carcinog. 57, 817–830. doi: 10.1002/mc.22531

Chen, J., Zhao, X., Ye, Y., Wang, Y., Tian, J. (2013). Estrogen receptor beta-mediated proliferative inhibition and apoptosis in human breast cancer by calycosin and formononetin. Cell. Physiol. Biochem. 32, 1790–1797. doi: 10.1159/000356612

Nyarko, R. O., Kumar, R., Sharma, S., Chourasia, A., Roy, A., & Saha, P. (2022). ANTIBACTERIAL ACTIVITY OF HERBAL PLANT-TINOSPORA CORDIFOLIA AND CATHARNTHUS ROSEUS.

Cheng, X., Yan, H., Jia, X., Zhang, Z. (2016). Preparation and in vivo/in vitro evaluation of formononetin phospholipid/vitamin E TPGS micelles. J. Drug Target 24, 161–168. doi: 10.3109/1061186X.2015.1064435

Kumar, R., Saha, P., Lokare, P., Datta, K., Selvakumar, P., & Chourasia, A. (2022). A Systemic Review of Ocimum sanctum (Tulsi): Morphological Characteristics, Phytoconstituents and Therapeutic Applications. International Journal for Research in Applied Sciences and Biotechnology, 9(2), 221-226.

Cooke, R. G., Rae, I. D. (1964). Isoflavonoids. I. Some new constituents of Pterocarpus indicus heartwood. Aust. J. Chem. 17, 379–384. doi: 10.1071/CH9640379

Dubey, A., Yadav, P., Verma, P., & Kumar, R. (2022). Investigation of Proapoptotic Potential of Ipomoea carnea Leaf Extract on Breast Cancer Cell Line. Journal of Drug Delivery and Therapeutics, 12(1), 51-55.

Bind, A., Das, S., Singh, V. D., Kumar, R., Chourasia, A., & Saha, P. NATURAL BIOACTIVES FOR THE POTENTIAL MANAGEMENT OF GASTRIC ULCERATION. Turkish Journal of Physiotherapy and Rehabilitation, 32, 3.

Cui, X., Guo, J., Lai, C.-S., Pan, M.-H., Ma, Z., Guo, S., et al. (2017). Analysis of bioactive constituents from the leaves of Amorpha fruticosa L. J. Food Drug Anal. 25, 992–999. doi: 10.1016/j.jfda.2016.10.006

Saha, P., Kumar, R., Nyarko, R. O., Kahwa, I., & Owusu, P. (2021). HERBAL SECONDARY METABOLITE FOR GASTRO-PROTECTIVE ULCER ACTIVITY WITH API STRUCTURES.

Dakora, F. D., Joseph, C. M., Phillips, D. A. (1993). Alfalfa (Medicago sativa L). Root exudates contain lsof lavonoids in the presence of Rhizobium meliloti. Plant Physiol., 101, 819–824. doi: 10.1104/pp.101.3.819

kumar, R., Saha, P., Nyarko, R., Lokare, P., Boateng, A., Kahwa, I., Owusu Boateng, P., & Asum, C. (2022). Effect of Covid-19 in Management of Lung Cancer Disease: A Review. Asian Journal of Pharmaceutical Research and Development, 10(3), 58-64. https://doi.org/https://doi.org/10.22270/ajprd.v10i3.1131

Deponte, M. (2013). Glutathione catalysis and the reaction mechanisms of glutathione-dependent enzymes. Biochim. Biophys. Acta 1830, 3217–3266. doi: 10.1016/j.bbagen.2012.09.018

Kumar, R., & Dubey, A. Phytochemical Investication and Heptoprotective Evalution Acacia Rubica Extract Isonized and Paracetamol Indused Animal Toxicity. Turkish Journal of Physiotherapy and Rehabilitation, 32, 3.

Dhillon, A. S., Hagan, S., Rath, O., Kolch, W. (2007). MAP kinase signalling pathways in cancer. Oncogene 26, 3279–3290. doi: 10.1038/sj.onc.1210421

Dickinson, J. M., Smith, G. R., Randel, R. D., Pemberton, I. J. (1988). In vitro metabolism of formononetin and biochanin A in bovine rumen fluid. J. Anim. Sci. 66, 1969–1973. doi: 10.2527/jas1988.6681969x

Donnelly, D. M. X., Thompson, J. C., Whalley, W. B., Ahmad, S. (1973). Dalbergia species. Part IX. Phytochemical examination of Dalbergia stevensonii standl. J. Chem. Soc. Perkin I, 16, 1737–1745. doi: 10.1039/p19730001737

Duronio, R. J., Xiong, Y. (2013). Signaling pathways that control cell proliferation. Cold Spring Harb. Perspect. Biol. 5, a008904. doi: 10.1101/cshperspect.a008904

El-Bakoush, A., Olajide, O. A. (2018). Formononetin inhibits neuroinflammation and increases estrogen receptor beta (ERβ) protein expression in BV2 microglia. Int. Immunopharmacol. 61, 325–337. doi: 10.1016/j.intimp.2018.06.016

Eling, T. E., Baek, S.-J., Shim, M.-S., Lee, C.-H. (2006). NSAID activated gene (NAG-1), a modulator of tumorigenesis. BMB Rep. 39, 649–655. doi: 10.5483/BMBRep.2006.39.6.649

Daharia, A., Jaiswal, V. K., Royal, K. P., Sharma, H., Joginath, A. K., Kumar, R., & Saha, P. (2022). A Comparative review on ginger and garlic with their pharmacological Action. Asian Journal of Pharmaceutical Research and Development, 10(3), 65-69.

Erasto, P., Bojase-Moleta, G., Majinda, R. R. T. (2004). Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus. Phytochemistry 65, 875–880. doi: 10.1016/j.phytochem.2004.02.011

Esquela-Kerscher, A., Slack, F. J. (2006). Oncomirs—microRNAs with a role in cancer. Nat. Rev. Cancer 6, 259–269. doi: 10.1038/nrc1840

Ewen, M. E., Sluss, H. K., Sherr, C. J., Matsushime, H., Kato, J.-Y., Livingston, D. M. (1993). Functional interactions of the retinoblastoma protein with mammalian D-type cyclins. Cell 73, 487–497. doi: 10.1016/0092-8674(93)90136-E

Fang, S., Qu, Q., Zheng, Y., Zhong, H., Shan, C., Wang, F., et al. (2016). Structural characterization and identification of flavonoid aglycones in three Glycyrrhiza species by liquid chromatography with photodiode array detection and quadrupole time-of-flight mass spectrometry. J. Sep. Sci. 39, 2068–2078. doi: 10.1002/jssc.201600073

Kumar, R., Saha, P., Kumar, Y., Sahana, S., Dubey, A., & Prakash, O. (2020). A Review On Diabetes Mellitus: Type1 & Type2.

Fu, X., Yuan, J., Chen, X., Qiu, Y., Qi, G. (2011). Method for synthesis of formononetin. CN 2010-10570613.

Guo, B., Liao, C., Liu, X., Yi, J. (2018). Preliminary study on conjugation of formononetin with multiwalled carbon nanotubes for inducing apoptosis via ROS production in HeLa cells. Drug Des. Devel. Ther. 12, 2815–2826. doi: 10.2147/DDDT.S169767

Goh, J.X.H., Tan, L.T.H., Goh, J.K., Chan, K.G., Pusparajah, P., Lee, L.H., et al. (2019). Nobiletin and Derivatives: Functional Compounds from Citrus Fruit Peel for Colon Cancer Chemoprevention. Cancers (Basel) 11, 867. doi:10.3390/cancers11060867

Guo, B., Xu, D., Liu, X., Liao, C., Li, S., Huang, Z., et al. (2017a). Characterization and cytotoxicity of PLGA nanoparticles loaded with formononetin cyclodextrin complex. J. Drug Deliv. Sci. Technol. 41, 375–383. doi: 10.1016/j.jddst.2017.08.010

Guo, W., Xiao, J., Xiao, H., Wang, X. (2011). Method for total synthesis of formononetin from resorcinol and p-methoxyphenylacetic acid. CN 2010-10600926.

PURABISAHA, R. K., RAWAT, S. S. N., & PRAKASH, A. (2021). A REVIEW ON NOVEL DRUG DELIVERY SYSTEM.

Guo, Y. H., Wang, Y., Xin, M. (2016). Low concentration of formononetin stimulates the proliferation of nasopharyngeal carcinoma cell line CNE2 by upregulating bcl-2 and p-ERK1/2 expression. Pharm. Biol. 54, 1841–1846. doi: 10.3109/13880209.2015.1129546

Gyémánt, N., Tanaka, M., Antus, S., Hohmann, J., Csuka, O., Mandoky, L., et al. (2005). In vitro search for synergy between flavonoids and epirubicin on multidrug-resistant cancer cells. In Vivo 19, 367–374.

He, Y., Jin, J., Wang, L., Hu, Y., Liang, D., Yang, H., et al. (2017). Evaluation of miR-21 and miR-375 as prognostic biomarkers in oesophageal cancer in high-risk areas in China. Clin. Exp. Metastasis 34, 73–84. doi: 10.1007/s10585-016-9828-4

Heinonen, S.-M., Wähälä, K., Adlercreutz, H. (2004). Identification of urinary metabolites of the red clover isoflavones formononetin and biochanin A in human subjects. J. Agric. Food Chem. 52, 6802–6809. doi: 10.1021/jf0492767

KUMAR, R., SAHA, P., SARKAR, S., RAWAT, N., & PRAKASH, A. (2021). A REVIEW ON NOVEL DRUG DELIVERY SYSTEM. IJRAR-International Journal of Research and Analytical Reviews (IJRAR), 8(1), 183-199.

Hinds, P. W., Mittnacht, S., Dulic, V., Arnold, A., Reed, S. I., Weinberg, R. A. (1992). Regulation of retinoblastoma protein functions by ectopic expression of human cyclins. Cell 70, 993–1006. doi: 10.1016/0092-8674(92)90249-C

Hollander, M. C., Blumenthal, G. M., Dennis, P. A. (2011). PTEN loss in the continuum of common cancers, rare syndromes and mouse models. Nat. Rev. Cancer 11, 289–301. doi: 10.1038/nrc3037

Hu, W., Xiao, Z. M. (2015). Formononetin induces apoptosis of human osteosarcoma cell line U2OS by regulating the expression of Bcl-2, Bax and MiR-375 in vitro and in vivo. Cell. Physiol. Biochem. 37, 933–939. doi: 10.1159/000430220

Kumar, R., & Saha, P. (2022). A Review on Artificial Intelligence and Machine Learning to Improve Cancer Management and Drug Discovery. International Journal for Research in Applied Sciences and Biotechnology, 9(3), 149-156.

Huang, J., Xie, M., Gao, P., Ye, Y., Liu, Y., Zhao, Y., et al. (2015). Antiproliferative effects of formononetin on human colorectal cancer via suppressing cell growth in vitro and in vivo. Process Biochem. 50, 912–917. doi: 10.1016/j.procbio.2015.03.001

KumarR., SahaP., KahwaI., BoatengE. A., BoatengP. O., & NyarkoR. O. (2022). Biological Mode of Action of Phospholipase A and the Signalling and Pro and Anti Inflammatory Cytokines: A Review. Journal of Advances in Medicine and Medical Research, 34(9), 1-10. https://doi.org/10.9734/jammr/2022/v34i931342

Saha, P., Kumar, R., Nyarko, R. O., Kahwa, I., & Owusu, P. (2021). HERBAL SECONDARY METABOLITE FOR GASTRO-PROTECTIVE ULCER ACTIVITY WITH API STRUCTURES.

Ingham, J. L. (1976). Induced and constitutive isoflavonoids from stems of chickpeas (Cicer arietinum L). inoculated with spores of Helminthosporium carbonum Ullstrup. J. Phytopathol. 87, 353–367. doi: 10.1111/j.1439-0434.1976.tb01741.x

Sahana, S. (2020). Purabi saha, Roshan kumar, Pradipta das, Indranil Chatterjee, Prasit Roy, Sk Abdur Rahamat. A Review of the 2019 Corona virus (COVID-19) World Journal of Pharmacy and Pharmaceutical science, 9(9), 2367-2381.

Awuchi, C. G., Amagwula, I. O., Priya, P., Kumar, R., Yezdani, U., & Khan, M. G. (2020). Aflatoxins in foods and feeds: A review on health implications, detection, and control. Bull. Environ. Pharmacol. Life Sci, 9, 149-155.

Jin, S., Zhang, Q. Y., Kang, X. M., Wang, J. X., Zhao, W. H. (2010). Daidzein induces MCF-7 breast cancer cell apoptosis via the mitochondrial pathway. Ann. Oncol. 21, 263–268. doi: 10.1093/annonc/mdp499

Jin, Y.-M., Xu, T.-M., Zhao, Y.-H., Wang, Y.-C., Cui, M.-H. (2014). In vitro and in vivo anti-cancer activity of formononetin on human cervical cancer cell line HeLa. Tumour Biol. 35, 2279–2284. doi: 10.1007/s13277-013-1302-1

Kannan, K., Jain, S. K. (2000). Oxidative stress and apoptosis. Pathophysiology 7, 153–163. doi: 10.1016/S0928-4680(00)00053-5

Kumar, R., & Dubey, A. Phytochemical Investication and Heptoprotective Evalution Acacia Rubica Extract Isonized and Paracetamol Indused Animal Toxicity. Turkish Journal of Physiotherapy and Rehabilitation, 32, 3.

Roshan, K. (2020). Priya damwani, Shivam kumar, Adarsh suman, Suthar Usha. An overview on health benefits and risk factor associated with coffee. International Journal Research and Analytical Review, 7(2), 237-249.

Kumar, R., Saha, P., Kumar, Y., Sahana, S., Dubey, A., & Prakash, O. (2020). A REVIEW ON DIABETES MELLITUS: TYPE1 & TYPE2.

Nyarko, R. O., Prakash, A., Kumar, N., Saha, P., & Kumar, R. (2021). Tuberculosis a globalized disease. Asian Journal of Pharmaceutical Research and Development, 9(1), 198-201.

Kim, Y. S., Ryu, Y. B., Curtis-Long, M. J., Yuk, H. J., Cho, J. K., Kim, J. Y., et al. (2011). Flavanones and rotenoids from the roots of Amorpha fruticosa L. that inhibit bacterial neuraminidase. Food Chem. Toxicol. 49, 1849–1856. doi: 10.1016/j.fct.2011.04.038

Klein, B., Zhang, X. G., Lu, Z. Y., Bataille, R. (1995). Interleukin-6 in human multiple myeloma. Blood 85, 863–872.

Raj, A., Tyagi, S., Kumar, R., Dubey, A., & Hourasia, A. C. (2021). Effect of isoproterenol and thyroxine in herbal drug used as cardiac hypertrophy. Journal of Cardiovascular Disease Research, 204-217.

Safi, S. Z., Qvist, R., Kumar, S., & Ismail, I. S. B. (2013). Molecular mechanisms of Diabetic Retinopathy, general preventive strategies and novel therapeutic targets. Experimental and Clinical Endocrinology & Diabetes, 121(03), P109.

Nyarko, R. O., Kumar, R., Sharma, S., Chourasia, A., Roy, A., & Saha, P. (2022). ANTIBACTERIAL ACTIVITY OF HERBAL PLANT-TINOSPORA CORDIFOLIA AND CATHARNTHUS ROSEUS.

Krueger, J. S., Keshamouni, V. G., Atanaskova, N., Reddy, K. B. (2001). Temporal and quantitative regulation of mitogen-activated protein kinase (MAPK) modulates cell motility and invasion. Oncogene 20, 4209–4218. doi: 10.1038/sj.onc.1204541

PURABISAHA, R. K., RAWAT, S. S. N., & PRAKASH, A. (2021). A REVIEW ON NOVEL DRUG DELIVERY SYSTEM.

Bind, A., Das, S., Singh, V. D., Kumar, R., Chourasia, A., & Saha, P. Natural Bioactives for The Potential Management of Gastric Ulceration. Turkish Journal of Physiotherapy and Rehabilitation, 32, 3.

Downloads

Published

2022-06-22

How to Cite

Babita Patial, Anshul Chawla, Rajiv Sharma, Rubeena Akhter, Priya Sharma, Saksham, & Ritesh Kumar. (2022). A Review on Anti-Cancer Activity of Benzopyrazole and Thiazolidine-4-One Nucleus. International Journal for Research in Applied Sciences and Biotechnology, 9(3), 166–174. Retrieved from https://ijrasb.com/index.php/ijrasb/article/view/399

Issue

Vol. 9 No. 3 (2022): May Issue

Section

Articles

License

Copyright (c) 2022 International Journal for Research in Applied Sciences and Biotechnology

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.