A REVIEW OF BENZOPYRAN DERIVATIVES IN PHARMACOTHERAPY OF BREAST CANCER

Authors

  • Kumar Piyush Faculty of Pharmacy, Integral University, Lucknow – 226 026, Uttar Pradesh, India.
  • Singh Kuldeep Faculty of Pharmacy, Integral University, Lucknow – 226 026, Uttar Pradesh, India.
  • Rahman Md. Azizur Faculty of Pharmacy, Integral University, Lucknow – 226 026, Uttar Pradesh, India.
  • Hasan Syed Misbahul Faculty of Pharmacy, Integral University, Lucknow – 226 026, Uttar Pradesh, India.
  • Wal Pranay Department of Pharmacy, Pranveer Singh Institute of Technology, Kanpur – 209 305, Uttar Pradesh, India.

DOI:

https://doi.org/10.22159/ajpcr.2018.v11i7.26017

Keywords:

Anticancer, Benzopyran, Breast cancer, Estrogen, Estrogen receptor

Abstract

One of the naturally occurring compounds containing oxygen moiety is benzopyran. Depending on its substitution pattern, different biological effects are shown. The benzopyran ring system is present in many natural products (such as genistein, hesperidin, and warfarin) as well as synthetic products. It displays pharmacological properties such as antitumor, anti-HIV, antimicrobials, anti-inflammatory, and anticoagulants. The sufficient literature support and the fact that benzopyran has potential as a pharmacophore particularly as anti-breast cancer, etc, current research seemed pertinent keeping in view the mechanism of anti-breast cancer activity. Therefore, the objective of this review is to focus on important benzopyran analogs with anti-breast cancer activity and highlight their mechanisms of action.

Downloads

Download data is not yet available.

References

Pierpaoli E, Viola V, Pilolli F, Piroddi M, Galli F, Provinciali M. γ-and δ-tocotrienols exert a more potent anticancer effect than α-tocopheryl succinate on breast cancer cell lines irrespective of HER-2/neu expression. Life Sci 2010;86:668-75.

Middleton E, Kandaswami C, Theoharides TC. The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol Rev 2000;52:673-751.

Lee H, Lee K, Jung JK, Cho J, Theodorakis EA. Synthesis and evaluation of 6-hydroxy-7-methoxy-4-chromanone- and chroman-2- carboxamides as antioxidants. Bioorg Med Chem Lett 2005;15:2745-8.

Costantino L, Rastelli G, Gamberini MC, Vinson JA, Bose P, Iannone A, et al. 1-benzopyran-4-one antioxidants as aldose reductase inhibitors. J Med Chem 1999;42:1881-93.

Kraus GA, Mengwasser J, Maury W, Oh C. Synthesis of chroman aldehydes that inhibit HIV. Bioorg Med Chem Lett 2011;21:1399-401.

Tummino PJ, Ferguson D, Hupe L, Hupe D. Competitive inhibition of HIV-1 protease by 4-hydroxy-benzopyran-2-ones and by 4-hydroxy-6-phenylpyran-2-ones. Biochem Biophys Res Commun 1994;200:1658 64.

Koufaki M, Kiziridi C, Alexi X, Alexis MN. Design and synthesis of novel neuroprotective 1,2-dithiolane/chroman hybrids. Bioorg Med Chem 2009;17:6432-41.

Hong KW, Kim KY, Lee JH, Shin HK, Kwak YG, Kim SO, et al. Neuroprotective effect of (2S,3S,4R)-Nâ€-cyano-N-(6-amino-3, 4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-benzopyran-4- yl)-N’-benzylguanidine (KR-31378), a benzopyran analog, against focal ischemic brain damage in rats. J Pharmacol Exp Ther 2002;301:210-6.

Rawat P, Verma SM. Synthesis and pharmacological evaluation of 6-hydroxy-2,5,7,8-tetramethyl-N’-(2-oxoindolin-3-ylidene)chroman- 2-carbohydrazide derivatives as antimicrobial agents. J Chem Pharm Res 2016;8:149-54.

Bhat M, Siddiqui N, Khan S. Synthesis of novel 3-(4-acetyl-5h/methyl- 5-substituted phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2h-chromen-2- ones as potential anticonvulsant agents. Acta Pol Pharm 2008;65:235-9.

Patil RB, Sawant SD. Synthesis, docking studies and evaluation of antimicrobial and in vitro antiproliferative activity of 5h-chromeno 4,3- d pyrimidin-2-amine derivatives. Int J Pharm Pharm Sci 2015;7:304-8.

Ahmed HA. Synthesis of some novel benzopyranes derivatives and evaluation their biological activity. Asian J Pharm Clin Res 2015;8:7 12.

Nayak Y, Hillemane V, Daroji VK, Jayashree BS, Unnikrishnan MK. Antidiabetic activity of benzopyrone analogues in nicotinamide-streptozotocin induced Type 2 diabetes in rats. Sci World J 2014. Article ID 854267:1-12.

Unlusoy MC, Verspohl EJ, Erta R. Synthesis and antidiabetic activity of some new chromonyl-2, 4-thiazolidinediones. J Enzyme Inhib Med Chem 2010;25:784-9.

Bano M, Barot KP, Ahmed SM, Nikolova S, Ivanov I, Ghate MD. Benzopyran derivatives as cardio-selective ATP-sensitive potassium channel openers: A review. Mini Rev Med Chem 2013;13:1744-60.

Evans JM, Cassidy F. Benzopyran Derivatives, their Preparation and Anti-Hypertensive Pharmaceutical Compositions Containing them; 1983;EP 0126311 A3.

Rawat P, Verma SM. Design and synthesis of chroman derivatives with dual anti-breast cancer and antiepileptic activities. Drug Des Devel Ther 2016;10:2779-88.

Rawat P, Verma SM. Docking studies of substituted chroman analogs at estrogen receptor. Asian J Pharm Clin Res 2015;8:88-92.

Lal J. Clinical pharmacokinetics and interaction of centchroman–a mini review. Contraception 2010;81:275-80.

Xu L, Farmer R, Haung X, Pavese J, Voll E, Irene O, et al. Discovery of a novel drug KBU2046 that inhibits conversion of human prostate cancer to a metastatic phenotype. Cancer Prev Res 2010;3:B58.

Chen CL, Levine A, Rao A, O’Neill K, Messinger Y, Myers DE, et al. Clinical pharmacokinetics of the CD19 receptor-directed tyrosine kinase inhibitor B43-genistein in patients with B-lineage lymphoid malignancies. J Clin Pharmacol 1999;39:1248-55.

Purushothaman A, Nandhakumar E, Sachdanandam P. Anticancer effect of shemamruthaa (a phytochemical formulation) on 7, 12-dimethylbenz(a)anthracene induced mammary carcinoma in rats. Asian J Pharm Clin Res 2012;5:101-7.

Solomon VR, Hu C, Lee H. Hybrid pharmacophore design and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity. Bioorg Med Chem 2009;17:7585-92.

Kaushik S, Rikhi M. Docking and cytotoxicity studies of 2-vinylchromone derivatives on human breast cancer cell lines. Int J Pharm Pharm Sci 2015;7:113-7.

Ciocca DR, Roig V. Estrogen receptors in human nontarget tissues: Biological and clinical implications. Endocr Res 1995;16:35-62.

Jordan VC. Antiestrogens and selective Estrogen receptor modulators as multifunctional medicines. Clinical considerations and new agents. J Med Chem 2003;46:1081-11.

Kumar S, Deshpande S, Chandra V, Kitchlu S, Dwivedi A, Nayak VL, et al. Synthesis and biological evaluation of 2,3,4-triarylbenzopyran derivatives as SERM and therapeutic agent for breast cancer. Bioorg Med Chem 2009;17:6832-40.

Muftuoglu Y, Mustata G. Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). Bioorg Med Chem Lett 2010;20:3050-64.

Bonfield K, Amato E, Bankemper T, Agard H, Steller J, Keeler JM, et al. Development of a new class of aromatase inhibitors: Design, synthesis and inhibitory activity of 3-phenylchroman-4-one (isoflavanone) derivatives. Bioorg Med Chem 2012;20:2603-13.

Shah AA, Ito A, Nakata A, Yoshida M. Identification of a selective SIRT2 inhibitor and its anti-breast cancer activity. Biol Pharm Bull 2016;39:1739-42.

Seifert T, Malo M, Kokkola T, Engen K, Saxin MF, WalleÌn EA, et al. Chroman-4-one- and chromone-based sirtuin 2 inhibitors with antiproliferative properties in cancer cells. J Med Chem 2014;57:9870 88.

McGlynn P, Lloyd B. Recombinational repair and restart of damaged replication forks. Nat Rev Mol Cell Biol 2002;3:859-70.

Yu SW, Andrabi SA, Wang H, Kim NS, Poirier GG, Dawson TW, et al. Apoptosis-inducing factor mediates poly(ADP-ribose) (PAR) polymer-induced cell death. Proc Natl Acad Sci U S A 2006;103:18314-9.

Singh S, Ahmad A, Raghuvanshi DS, Hasanain M, Agarwal K, Dubey V, et al. Synthesis of. 3,5-dihydroxy-7,8-dimethoxy-2-(4- methoxyphenyl) benzopyran-4-one derivatives as anticancer agents. Bioorg Med Chem Lett 2016;26:5322-7.

Brown JM, Wilson WR. Exploiting tumour hypoxia in cancer treatment. Nat Rev Cancer 2004;4:437-47.

Tan C, Noronha RG, Roecker AJ, Pyrzynska B, Khwaja F, Zhang Z, et al. Identification of a novel small-molecule inhibitor of the hypoxia-inducible factor 1 pathway. Cancer Res 2005;65:605-12.

Vara JA, Casado E, Castro J, Cejas P, Belda-Iniesta C, González- Barón M. PI3K/AKT signalling pathway and cancer. Cancer Treat Rev 2004;30:193-204.

Lee SH, Johnson D, Luong R, Sun Z. Crosstalking between androgen and PI3K/AKT signaling pathways in prostate cancer cells. J Biol Chem 2015;290:2759-68.

Saxena R, Fatima I, Chandra V, Blesson CS, Kharkwal G, Hussain MK, et al. Benzopyran derivative CDRI-85/287 induces G2-M arrest in estrogen receptor-positive breast cancer cells via modulation of estrogen receptors α- and β-mediated signaling, in parallel to EGFR signaling and suppresses the growth of tumor xenograft. Steroids 2013;78:1071-86.

Feldmann H. Protease signalling in cell death: Caspases versus cysteine cathepsins. FEBS Lett 2007;581:2761-7.

Sashidhara KV, Avula SR, Sharma K, Palnati GR, Bathula SR. Discovery of coumarin-monastrol hybrid as potential antibreast tumor-specific agent. Eur J Med Chem 2013;60:120-7.

Published

07-07-2018

How to Cite

Piyush, K., S. Kuldeep, R. Md. Azizur, H. S. Misbahul, and W. Pranay. “A REVIEW OF BENZOPYRAN DERIVATIVES IN PHARMACOTHERAPY OF BREAST CANCER”. Asian Journal of Pharmaceutical and Clinical Research, vol. 11, no. 7, July 2018, pp. 43-46, doi:10.22159/ajpcr.2018.v11i7.26017.

Issue

Section

Review Article(s)