Research Journal of Pharmacy and Technology

Open Access Open Access  Restricted Access Subscription Access
Open Access Open Access Open Access  Restricted Access Restricted Access Subscription Access

Biological Screening and Structure Activity Relationship of Benzothiazole


Affiliations
1 Dr. Subhash Technical Campus, Faculty of Pharmacy, Khamdhrol Road, Junagadh, Gujarat,, India
2 Nobel Pharmacy College, Bhesan Road, Junagadh, Gujarat,, India
     

   Subscribe/Renew Journal


Benzothiazole is a heterocyclic compound having nitrogen and sulphur. It's a bicyclic compound with a thiazole with benzene ring fused together. As per a review of the literature, benzothiazole is a primary moiety for the development of anticancer, antidiabetic, antioxidant, analgesic, and anti-inflammatory, antibacterial, antifungal, antiviral, anticonvulsant, antidepressant, antioxidant, and hepatoprotective agents. As a result, a list of biologically active benzothiazole derivatives has indeed been compiled in this study. The structure-activity relationship is analyzed based on the biological activities of benzothiazole derivatives and their substitution pattern. We also examined the mechanism of action of various benzothiazole derivatives, which can benefit researchers in the creation of new benzothiazole derivatives.

Keywords

Anticancer, Antidiabetic, Antioxidant, Benzothiazole, Hepatoprotective, SAR.
Subscription Login to verify subscription
User
Notifications
Font Size


  • Shaista A, Amrita P. Benzothiazole-A magic molecule. International Journal Of Pharmaceutical Sciences And Research. 2017 Dec 1;8(12):4909-29. Benzothiazole – A Magic Molecule | International Journal Of Pharma Ceutical Sciences and Research (ijpsr.com)

  • Bhuva HA, Kini SG. Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors. Journal of Molecular Graphics and Modelling. 2010 Aug 24;29(1):32-7. https://doi.org/10.1016/j.jmgm.2010.04.003

  • Kumar SU, Rathore DS, Garg G, Khatri KA, Saxena R, Sahu SK. Synthesis and evaluation of some benzothiazole derivatives as antidiabetic agents. Int. J. Pharm. Pharm. Sci. 2017;9(2):60. http://dx.doi.org/10.22159/ijpps.2017v9i2.14359

  • Kim MJ, Park CH, Kim DH, Park MH, Park KC, Hyun MK, Lee AK, Moon HR, Chung HY. Hepatoprotective effects of MHY3200 on high-fat, diet-induced, non-alcoholic fatty liver disease in rats. Molecules. 2018 Aug;23(8):2057. https://doi.org/10.3390/molecules23082057

  • Hazra K, Nargund LV, Rashmi P, Chandra NS, Nandha B. Synthesis and antioxidant activity of some novel Fluorobenzothiazolopyrazoline. Der Chemica Sinica. 2011;2(2):149-57. 227 (imedpub.com)

  • Selvakumar K, Madhan R, Srinivasan G, Baskar V. Antioxidant assays in pharmacological research. Asian Journal of Pharmacy and Technology. 2011;1(4):99-103. Antioxidant Assays in Pharmacological Research-Indian Journals

  • Siddiqui N, Rana A, Khan SA, Ahsan W, Alam MS, Ahmed S. Analgesic and antidepressant activities of benzothiazole-benzamides. Biomedical & Pharmacology Journal. 2008;1(2):297. Analgesic and antidepressant activities of benzothiazole-benzamides - ProQuest

  • Kumar KR, Karthik KN, Begum PR, Rao CM. Synthesis, characteristics and biological evaluation of benzothiazole derivatives as potential antimicrobial and analgesic agents. Asian J. Res. Pharm. Sci. 2017 Jun 28;7(2):115. DOI: 10.5958/2231-5659.2017.00018.2

  • Pattan SR, Pujar VD, Dighe NS, Musmade DS, Hiremath SN, Shinde HV, Laware RB. Synthesis and Anti-Inflammatory Activity of 2-Amino Substituted Benzothiazoles. Asian Journal of Research in Chemistry. 2010 Mar 28;3(1):113-5. https://ajrconline.org/HTML_Papers/Asian Journal of Research in Chemistry__PID__2010-3-1-29.html

  • Azam MA, Dharanya L, Mehta CC, Sachdeva S. Synthesis and biological evaluation of some novel pyrazolopyrimidines incorporating a benzothiazole ring system. Acta pharmaceutica. 2013 Mar 1;63(1):19-30. https://doi.org/10.2478/acph-2013-0001

  • Bhusari KP, Amnerkar ND, Khedekar PB, Kale MK, Bhole RP. Synthesis and in vitro antimicrobial activity of some new 4-amino-N-(1, 3-benzothiazol-2-yl) benzenesulphonamide derivatives. Asian Journal of Research in Chemistry. 2008 Oct;1(2):53-8. https://www.researchgate.net/publication/236695001

  • Akhtar T, Hameed S, Al-Masoudi N, Loddo R, Colla P. In vitro antitumor and antiviral activities of new benzothiazole and 1, 3, 4-oxadiazole-2-thione derivatives. Acta pharmaceutica. 2008 Jun 1;58(2):135-49. https://www.researchgate.net/publication/5336236

  • Pareek V, Paliwal P, Kushwaha A, Jetti SR, Jain S. Biological Activity of some benzothiazolopyrazolines and Their Photoproducts: A Comparative Study. 26-32.pdf (d1wqtxts1xzle7.cloudfront.net)

  • Bele DS, Singhvi I. Synthesis and Antimicrobial Activity of Some Mannich Bases of 6-Substituted-2-Aminobenzothiazole. Synthesis. 2009 Jun 28;9:12. Asian Journal of Research in Chemistry (ajrconline.org)

  • Gupta YK, Agarwal SC. Synthesis and antimicrobial activity of new 4-thiazolidinone derivatives containing 2-amino-6-ethoxybenzothiazole. Asian Journal of Research in Chemistry. 2011 Dec 28;4(12):1245-52. https://ajrconline.org/HTML_Papers/Asian Journal of Research in Chemistry__PID__2011-4-12-30.html

  • Priyadarsini R, Tharani CB, Aruna AA. Docking studies, Synthesis, Characterisation of Substituted Benzothiazoles as DHFR inhibitors and Evaluation of their Antitubercular Activities. Asian Journal of Research in Chemistry. 2012 Sep 28;5(9):1136-42. https://ajrconline.org/HTML_Papers/Asian Journal of Research in Chemistry__PID__2012-5-9-8.html

  • Bryson HM, Fulton B, Benfield P. Riluzole. Drugs. 1996 Oct;52(4):549-63. https://doi.org/ 10.2165/00003495-199652040-00010

  • Johnson BK, Colvin CJ, Needle DB, Mba Medie F, Champion PA, Abramovitch RB. The carbonic anhydrase inhibitor ethoxzolamide inhibits the Mycobacterium tuberculosis PhoPR regulon and Esx-1 secretion and attenuates virulence. Antimicrobial agents and chemotherapy. 2015 Aug 1;59(8):4436-45. https://doi.org/ 10.1128/AAC.00719-15

  • Prabhu PP, Panneerselvam T, Shastry CS, Sivakumar A, Pande SS. Synthesis and anticancer evaluation of 2-phenyl thiaolidinone substituted 2-phenyl benzothiazole-6-carboxylic acid derivatives.Journal of Saudi Chemical Society. 2015 Mar 1;19(2):181-5. http://dx.doi.org/10.1016/j.jscs.2012.02.001

  • Pathak N, Rathi E, Kumar N, Kini SG, Rao CM. A review on anticancer potentials of benzothiazole derivatives. Mini reviews in medicinal chemistry. 2020 Jan 1;20(1):12-23. http://doi.org/ 10.2174/1389557519666190617153213

  • Siddiqui N, Pandeya SN, Khan SA, Stables J, Rana A, Alam M, Arshad MF, Bhat MA. Synthesis and anticonvulsant activity of sulfonamide derivatives-hydrophobic domain. Bioorganic & medicinal chemistry letters. 2007 Jan 1;17(1):255-9. https://doi.org/10.1016/j.bmcl.2006.09.053

  • Akhilesh G, Swati R. Therapeutic importance of Benzothiazole. Asian Journal of Research in Chemistry. 2010 Dec 28;3(4):821-36. https://doi.org/10.1517/13543776.2014.999764

  • Hunasnalkar SG, Gazi S, Patil SM, Surwase US. Synthesis and biological activities of some benzothiazole derivatives. Asian Journal of Research in Chemistry. 2010;3(2):421-7. Asian Journal of Research in Chemistry (ajrconline.org)

  • Sasikala M, Sundaraganapathy R, Mohan S. MTT Assay on Anticancer Properties of Phytoconstituents from Ipomoea aquatica forsskal using MCF–7 cell lines for breast cancer in Women. Research Journal of Pharmacy and Technology. 2020 Mar 1;13(3):1356-60. Doi: 10.5958/0974-360X.2020.00250.4

  • Prasad PR, Shinde SD, Waghmare GS, Naik VL, Bhuvaneswari K, Kuberkar SV. Synthesis and in vitro anticancer activity of 9-chloro-3-cyano-8-fluoro-2-methylthio-4-oxo-4H-pyrimido [2, 1-b][1, 3] benzothiazole and its 2-substituted derivatives. J Chem Pharm Res. 2011;3:20-7. Synthesis and in vitro anticancer activity of 9-chloro-3-cyano-8-fluoro-2- methylthio-4-oxo-4H-pyrimido [2, 1-b] [1, 3] benzothiazole and its 2- substituted derivatives | Abstract (jocpr.com)

  • Uremis N, Uremis MM, Tolun FI, Ceylan M, Doganer A, Kurt AH. Synthesis of 2-substituted benzothiazole derivatives and their in vitro anticancer effects and antioxidant activities against pancreatic cancer cells. Anticancer research. 2017 Nov 1;37(11):6381-9. http://doi.org/ 10.21873/anticanres.12091

  • Sadhasivam G, Kulanthai K, Natarajan A. Synthesis and anti-cancer studies of 2, 6-disubstituted benzothiazole derivatives. Oriental Journal of Chemistry. 2015;31(2):819. http://dx.doi.org/10.13005/ojc/310224

  • Shi XH, Wang Z, Xia Y, Ye TH, Deng M, Xu YZ, Wei YQ, Yu LT. Synthesis and biological evaluation of novel benzothiazole-2-thiol derivatives as potential anticancer agents. Molecules. 2012 Apr;17(4):3933-44. http://doi.org/ 10.3390/molecules17043933.

  • M Youssef A, Malki A, H Badr M, Y Elbayaa R, S Sultan A. Synthesis and anticancer activity of novel benzimidazole and benzothiazole derivatives against HepG2 liver cancer cells. Medicinal Chemistry. 2012 Mar 1;8(2):151-62.http://doi.org/ 10.2174/157340612800493719

  • Singh M, Modi A, Narayan G, Singh SK. Benzothiazole derivatives bearing amide moiety: potential cytotoxic and apoptosis-inducing agents against cervical cancer. Anti-cancer drugs. 2016 Jul 1;27(6):519-32. http://doi.org/10.1097/CAD.0000000000000357

  • Devmurari VP, Shivanand P, Goyani MB, Jivani NP. Synthesis and anticancer activity of some novel 2-substituted benzothiazole. International Journal of Chemical Sciences. 2010; 8(1): 663-75. Synthesis and Anticancer Activity of Some Novel 2-Substituted Benzothiazole| Abstract (tsijournals.com)

  • Ma H, Zhuang C, Xu X, Li J, Wang J, Min X, Zhang W, Zhang H, Miao Z. Discovery of benzothiazole derivatives as novel non-sulfamide NEDD8 activating enzyme inhibitors by target-based virtual screening. European journal of medicinal chemistry. 2017 Jun 16;133:174-83. http://doi.org/:10.1016/j.ejmech.2017.03.076

  • Kaya B, Hussin W, Yurttaş L, Turan-Zitouni G, Karaca Kaya B, Hussin W, Yurttaş L, Turan-Zitouni G, Gençer HK, Baysal M, Karaduman AB, Kaplancıklı ZA. Design and Synthesis of New 1, 3, 4-Oxadiazole–Benzothiazole and Hydrazone Derivatives as Promising Chemotherapeutic Agents. Drug research. 2017 May;67(05):275-82. http://dx.doi.org/10.1055/s-0042-119070

  • Patil VS, Nandre KP, Ghosh S, Rao VJ, Chopade BA, Sridhar B, Bhosale SV, Bhosale SV. Synthesis, crystal structure and antidiabetic activity of substituted (E)-3-(Benzo [d] thiazol-2-ylamino) phenylprop-2-en-1-one. European journal of medicinal chemistry. 2013 Jan 1;59:304-9. http://dx.doi.org/10.1016/j.ejmech.2012.11.020

  • Pattan SR, Suresh CH, Pujar VD, Reddy VV, Rasal VP, Koti BC. Synthesis and antidiabetic activity of 2-amino [5'(4-sulphonylbenzylidine)-2, 4-thiazolidinedione]-7-chloro-6-fluorobenzothiazole. NOPR: Synthesis and antidiabetic activity of 2-amino [5'(4-sulphonylbenzylidine)-2,4-thiazolidinedione]-7-chloro-6-fluorobenzothiazole (niscair.res.in)

  • Ahmadi A, Khalili M, Ghaderi P, Rastegar G, Nahri-Niknafs B. Synthesis and blood glucose and lipid-lowering effects of benzothiazole-substituted benzenesulfonylurea derivatives. Monatshefte für Chemie-Chemical Monthly. 2015 Dec;146(12):2059-65. Synthesis and blood glucose and lipid-lowering effects of benzothiazole-substituted benzenesulfonyl urea derivatives | SpringerLink

  • Moreno-Díaz H, Villalobos-Molina R, Ortiz-Andrade R, Díaz-Coutiño D, Medina-Franco JL, Webster SP, Binnie M, Estrada-Soto S, Ibarra-Barajas M, Leon-Rivera I, Navarrete-Vázquez G. Antidiabetic activity of N-(6-substituted-1, 3-benzothiazol-2-yl) benzenesulfonamides. Bioorganic & Medicinal Chemistry Letters. 2008 May 1;18(9):2871-7. https://doi.org/10.1016/j.bmcl.2008.03.086

  • Kharbanda C, Alam MS, Hamid H, Javed K, Bano S, Ali Y, Dhulap A, Alam P, Pasha MQ. Novel Piperine derivatives with Antidiabetic effect as PPAR‐γ agonists. Chemical biology & drug design. 2016 Sep;88(3):354-62. Novel benzothiazole based sulfonylureas/sulfonylthioureas: design, synthesis and evaluation of their antidiabetic potential - New Journal of Chemistry (RSC Publishing)

  • Sadhasivam G, Kulanthai K. Synthesis, characterization, and evaluation of anti-inflammatory and anti-diabetic activity of new benzothiazole derivatives. J. Chem. Pharm. Res. 2015;8:425-31. http://dx.doi.org/10.13005/ojc/310224

  • Puranik NV, Puntambekar HM, Srivastava P. Antidiabetic potential and enzyme kinetics of benzothiazole derivatives and their non-bonded interactions with α-glucosidase and α-amylase. Medicinal Chemistry Research. 2016 Apr 1;25(4):805-16. Antidiabetic potential and enzyme kinetics of benzothiazole derivatives and their non-bonded interactions with α-glucosidase and α-amylase | SpringerLink

  • Kim SM, Lee B, An HJ, Kim DH, Park KC, Noh SG, Chung KW, Lee EK, Kim KM, Kim DH, Kim SJ. Novel PPARα agonist MHY553 alleviates hepatic steatosis by increasing fatty acid oxidation and decreasing inflammation during aging. Oncotarget. 2017 Jul 11;8(28):46273. doi: 10.18632/oncotarget.17695

  • Paramashivappa R, Kumar PP, Rao PS et al. Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors. Bio organic & medicinal chemistry letters. 2003 Feb 1;13(4):657-60. https://doi.org/10.1016/S0960-894X(02)01006-5

  • Verma AK, Martin A, Singh AK. Synthesis, Characterization and evaluation of Anti-inflammatory and Analgesic activity of Benzothiazole derivatives. Indian Journal of Pharmaceutical and Biological Research. 2014 Sep 30;2(03):84-9. https://doi.org/10.30750/ijpbr.2.3.14

  • Gurupadayya BM, Gopal M, Padmashali B, Manohara YN. Synthesis and pharmacological evaluation of azetidin-2-ones and thiazolidin-4-ones encompassing benzothiazole. Indian journal of pharmaceutical sciences. 2008 Sep;70(5):572. doi: 10.4103/0250-474X.45393

  • Ugwu DI, Okoro UC, Ukoha PO, Gupta A, Okafor SN. Novel anti-inflammatory and analgesic agents: synthesis, molecular docking and in vivo studies. Journal of enzyme inhibition and medicinal chemistry. 2018 Jan 1;33(1):405-15. https://doi.org/10.1080/14756366.2018.1426573

  • Russo F, Romeo G, Santagati NA, Caruso A, Cutuli V, Amore D.Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties. European journal of medicinal chemistry. 1994 Jan 1;29(7-8):569-78. https://doi.org/10.1016/0223-5234(94)90149-X

  • Tariq S, Kamboj P, Alam O, Amir M. 1, 2, 4-Triazole-based benzothiazole/benzoxazole derivatives: Design, synthesis, p38α MAP kinase inhibition, anti-inflammatory activity and molecular docking studies. Bioorganic chemistry. 2018 Dec 1;81:630-41. https://doi.org/10.1016/j.bioorg.2018.09.015

  • Kumar V, Sharma S, Husain A. Synthesis and in vivo Anti-inflammatory and Analgesic activities of Oxadiazoles clubbed with Benzothiazole nucleus. International Current Pharmaceutical Journal. 2015 Nov 7;4(12):457-61. https://doi.org/10.3329/icpj.v4i12.25597

  • Shafi S, Alam MM, Mulakayala N, Mulakayala C, Vanaja G, Kalle AM, Pallu R, Alam MS. Synthesis of novel 2-mercapto benzothiazole and 1, 2, 3-triazole based bis-heterocycles: their anti-inflammatory and anti-nociceptive activities. European journal of medicinal chemistry. 2012 Mar 1;49:324-33. https://doi.org/10.1016/j.ejmech.2012.01.032

  • Siddiqui N. Design, synthesis and anticonvulsant screening of newer benzothiazole-semicarbazones. Asian Journal of Biomedical and Pharmaceutical Sciences. 2012 Jan 1;2(10):8 Analgesic and antidepressant activities of benzothiazole-benzamides - ProQuest

  • Nath R, Yar MS, Pathania S, Grover G, Debnath B, Akhtar MJ. Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide. Journal of Molecular Structure. 2021 Mar 15;1228:129742. https://doi.org/10.1016/j.molstruc.2020.129742

  • Chopade RS, Bahekar RH, Khedekar PB, Bhusari KP, Ram Rao AR. Synthesis and Anticonvulsant Activity of 3‐(6‐Substituted‐benzothiazol‐2‐yl)‐6‐phenyl‐[1, 3]‐xazinane‐2‐thiones. Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry. 2002 Nov;335(8):381-8. https://doi.org/10.1002/1521-4184(200211)335:8<381::AID-ARDP381>3.0.CO;2-S

  • Ali R, Siddiqui N. Preliminary Anticonvulsant and Toxicity Screening of Substituted Benzylidenehydrazinyl-N-(6-substituted benzo [d] thiazol-2-yl) propanamides. The Scientific World Journal. 2014 Jan 1;2014. http://dx.doi.org/10.1155/2014/194652

  • Amir M, Asif S, Ali I, Hassan MZ. Synthesis of benzothiazole derivatives having acetamido and carbothioamido pharmacophore as anticonvulsant agents. Medicinal Chemistry Research. 2012 Sep;21(9):2661-70. Synthesis of benzothiazole derivatives having acetamido and carbothioamido pharmacophore as anticonvulsant agents | SpringerLink

  • Amnerkar ND, Bhusari KP. Synthesis, anticonvulsant activity and 3D-QSAR study of some prop-2-eneamido and 1-acetyl-pyrazolin derivatives of aminobenzothiazole. European Journal of Medicinal Chemistry. 2010 Jan 1;45(1):149-59. https://doi.org/10.1016/j.ejmech.2009.09.037


Abstract Views: 294

PDF Views: 0




  • Biological Screening and Structure Activity Relationship of Benzothiazole

Abstract Views: 294  |  PDF Views: 0

Authors

Khyati Bhagdev
Dr. Subhash Technical Campus, Faculty of Pharmacy, Khamdhrol Road, Junagadh, Gujarat,, India
Sibaji Sarkar
Nobel Pharmacy College, Bhesan Road, Junagadh, Gujarat,, India

Abstract


Benzothiazole is a heterocyclic compound having nitrogen and sulphur. It's a bicyclic compound with a thiazole with benzene ring fused together. As per a review of the literature, benzothiazole is a primary moiety for the development of anticancer, antidiabetic, antioxidant, analgesic, and anti-inflammatory, antibacterial, antifungal, antiviral, anticonvulsant, antidepressant, antioxidant, and hepatoprotective agents. As a result, a list of biologically active benzothiazole derivatives has indeed been compiled in this study. The structure-activity relationship is analyzed based on the biological activities of benzothiazole derivatives and their substitution pattern. We also examined the mechanism of action of various benzothiazole derivatives, which can benefit researchers in the creation of new benzothiazole derivatives.

Keywords


Anticancer, Antidiabetic, Antioxidant, Benzothiazole, Hepatoprotective, SAR.

References