An In-Depth Analysis of Benzothiazole Derivatives: Structure, Properties, and Applications

Gaurav Kumar; Sanjay Singh; Manisha Negi; Abhishek

doi:10.32628/IJSRST24114141

Authors

Gaurav Kumar Siddhartha Institute of Pharmacy, VMSBUTU, Dehradun, India Author
Sanjay Singh Siddhartha Institute of Pharmacy, VMSBUTU, Dehradun, India Author
Manisha Negi Siddhartha Institute of Pharmacy, VMSBUTU, Dehradun, India Author
Abhishek Siddhartha Institute of Pharmacy, VMSBUTU, Dehradun, India Author

DOI:

https://doi.org/10.32628/IJSRST24114141

Keywords:

Benzothiazole, Pharmacological Applications, Biological Activities

Abstract

Benzothiazole and its derivatives indeed have a rich presence in natural products and pharmaceuticals. They're fascinating due to their diverse biological activities and structural versatility. These compounds exhibit various pharmacological characteristics and structural diversity, making them a focal point in the advancement of new therapeutic agents. Present study aims to consolidate current information on the pharmacological activities of benzothiazole derivatives, emphasizing their therapeutic potential and underlying mechanisms of action. Benzothiazole derivatives are known for their broad range of biological activities: providing insights into how modifications in their chemical structure can enhance their pharmacological efficacy and selectivity. Given the broad pharmacological profile and therapeutic potential of benzothiazole derivatives, ongoing research and development are likely to yield new and effective drugs for various medical conditions. This review underscores the importance of benzothiazole as a scaffold in drug discovery and encourages further investigation into its diverse pharmacological applications.

Downloads

Download data is not yet available.

References

Taylor AP, Robinson RP, Fobian YM, Blakemore DC, Jones LH, Fadeyi O. Modern advances in heterocyclic chemistry in drug discovery. Organic & biomolecular chemistry. 2016;14(28):6611-37. DOI: https://doi.org/10.1039/C6OB00936K

Sharma PC, Sinhmar A, Sharma A, Rajak H, Pathak DP. Medicinal significance of benzothiazole scaffold: an insight view. Journal of enzyme inhibition and medicinal chemistry. 2013 Apr 1;28(2):240-66. DOI: https://doi.org/10.3109/14756366.2012.720572

Arella S, Thanyasri P, Bhavana P, Reddy MS. REVIEW ON BIOACTIVE HETEROCYCLIC COMPOUNDS. EPRA International Journal of Research and Development (IJRD). 2023 Nov 30;8(11):291-306.

Kumar A, Mishra AK. Advancement in pharmacological activities of benzothiazole and its derivatives: An up to date review. Mini Reviews in Medicinal Chemistry. 2021 Feb 1;21(3):314-35. DOI: https://doi.org/10.2174/1389557520666200820133252

Zajac M, Hrobárik P, Magdolen P, Foltínová P, Zahradník P. Donor–π-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity. Tetrahedron. 2008 Nov 10;64(46):10605-18.

Liao C, Kim UJ, Kannan K. A review of environmental occurrence, fate, exposure, and toxicity of benzothiazoles. Environmental science & technology. 2018 Mar 26;52(9):5007-26. DOI: https://doi.org/10.1021/acs.est.7b05493

Gao X, Liu J, Zuo X, Feng X, Gao Y. Recent advances in synthesis of benzothiazole compounds related to green chemistry. Molecules. 2020 Apr 5;25(7):1675. DOI: https://doi.org/10.3390/molecules25071675

Joseph J, Janaki GB. Synthesis, structural characterization and biological studies of copper complexes with 2-aminobenzothiazole derivatives. Journal of Molecular Structure. 2014 Apr 24;1063:160 DOI: https://doi.org/10.1016/j.molstruc.2014.01.028

https://www.who.int/healthtopics/cancer#:~:text=Cancer%20is%20the%20second%20leading,the%20most%20common%20among%20women.

Kataria, B., Jethva, H.B., Shinde, P.V., Banait, S.S., Shaikh, F., Ajani, S. (2023). SLDEB: Design of a secure and lightweight dynamic encryption bio-inspired model for IoT networks. International Journal of Safety and Security Engineering, Vol. 13, No. 2, pp. 325-331. https://doi.org/10.18280/ijsse.130214 DOI: https://doi.org/10.18280/ijsse.130214

Siamof CM, Goel S, Cai W. Moving beyond the pillars of cancer treatment: perspectives from nanotechnology. Frontiers in Chemistry. 2020 Nov 10;8:598100. DOI: https://doi.org/10.3389/fchem.2020.598100

Irfan A, Batool F, Zahra Naqvi SA, Islam A, Osman SM, Nocentini A, Alissa SA, Supuran CT. Benzothiazole derivatives as anticancer agents. Journal of enzyme inhibition and medicinal chemistry. 2020 Jan 1;35(1):265-79. DOI: https://doi.org/10.1080/14756366.2019.1698036

Montero V, Montana M, Carré M, Vanelle P. Quinoxaline derivatives: Recent discoveries and development strategies towards anticancer agents. European Journal of Medicinal Chemistry. 2024 Apr 7:116360. DOI: https://doi.org/10.1016/j.ejmech.2024.116360

Yoshida M, Hayakawa I, Hayashi N, Agatsuma T, Oda Y, Tanzawa F, Iwasaki S, Koyama K, Furukawa H, Kurakata S, Sugano Y. Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents. Bioorganic & medicinal chemistry letters. 2005 Jul 15;15(14):3328-32.

Patil, P., Kataria, B., Redkar, V., Banait, A., Shilpa, C., Patil, & Khetani, V. (08 2024). Automated Detection of Tuberculosis Using Deep Learning Algorithms on Chest X-rays. Frontiers in Health Informatics, 13, 218–229.

Ahmed K, Yellamelli Valli Venkata S, Mohammed NA, Sultana F, Methuku KR. Recent advances on structural modifications of benzothiazoles and their conjugate systems as potential chemotherapeutics. Expert Opinion on Investigational Drugs. 2012 May 1;21(5):619-35. DOI: https://doi.org/10.1517/13543784.2012.676043

Xu X, Zhu Z, Chen S, Fu Y, Zhang J, Guo Y, Xu Z, Xi Y, Wang X, Ye F, Chen H. Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticancer and antiinflammatory agents. Frontiers in Chemistry. 2024 Mar 18;12:1384301. DOI: https://doi.org/10.3389/fchem.2024.1384301

Shivadekar, S., Kataria, B., Limkar, S. et al. Design of an efficient multimodal engine for preemption and post-treatment recommendations for skin diseases via a deep learning-based hybrid bioinspired process. Soft Comput (2023). https://doi.org/10.1007/s00500-023-08709-5

Al-Sanea MM, Hamdi A, Mohamed AA, El-Shafey HW, Moustafa M, Elgazar AA, Eldehna WM, Ur Rahman H, Parambi DG, Elbargisy RM, Selim S. New benzothiazole hybrids as potential VEGFR-2 inhibitors: design, synthesis, anticancer evaluation, and in silico study. Journal of enzyme inhibition and medicinal chemistry. 2023 Dec 31;38(1):2166036. DOI: https://doi.org/10.1080/14756366.2023.2166036

Frasinyuk M, Chhabria D, Kartsev V, Dilip H, Sirakanyan SN, Kirubakaran S, Petrou A, Geronikaki A, Spinelli D. Benzothiazole and chromone derivatives as potential ATR kinase inhibitors and anticancer agents. Molecules. 2022 Jul 20;27(14):4637. DOI: https://doi.org/10.3390/molecules27144637

Zhao T, Yang Y, Yang J, Cui Y, Cao Z, Zuo D, Zhai X. Harmine-inspired design and synthesis of benzo [d] imidazo [2, 1-b] thiazole derivatives bearing 1, 3, 4-oxadiazole moiety as potential tumor suppressors. Bioorganic & Medicinal Chemistry. 2021 Sep 15;46:116367. DOI: https://doi.org/10.1016/j.bmc.2021.116367

Sultana F, Saifi MA, Syed R, Mani GS, Shaik SP, Osas EG, Godugu C, Shahjahan S, Kamal A. Synthesis of 2-anilinopyridyl linked benzothiazole hydrazones as apoptosis inducing cytotoxic agents. New Journal of Chemistry. 2019;43(18):7150-61. DOI: https://doi.org/10.1039/C8NJ06517A

Saipriya D, Prakash A, Kini SG, Pai K, Biswas S. Design, Synthesis, Antioxidant and Anticancer Activity of Novel Schiff's Bases of 2-Amino Benzothiazole. Indian Journal of Pharmaceutical Education & Research. 2018 Oct 3;52. DOI: https://doi.org/10.5530/ijper.52.4s.114

Prasad P, Bhuwnashwer K, Kuberker SV; International Journal of Research in Pharmaceutical and Biomedical Sciences 2012, 3(2): 882-886.

Khan KM, Rahim F, Halim SA, Taha M, Khan M, Perveen S, Mesaik MA, Choudhary MI. Synthesis of novel inhibitors of β-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking. Bioorganic & medicinal chemistry. 2011 Jul 15;19(14):4286-94. DOI: https://doi.org/10.1016/j.bmc.2011.05.052

Prabhu PP, Shastry CS, Pande S, Pai A; Journal of Pharmacy Research 2011, 4(7): 2209-2211.

Racané L, Kralj M, Šuman L, Stojković R, Tralić-Kulenović V, Karminski-Zamola G. Novel amidino substituted 2-phenylbenzothiazoles: Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo. Bioorganic & medicinal chemistry. 2010 Feb 1;18(3):1038-44. DOI: https://doi.org/10.1016/j.bmc.2009.12.054

Devmurari VP, Shivanand P,Goyani NP, Nandanwar RR, Jiwani NP, Pramul P; International Journal of ChemTech Research 2010, 2(1): 681-689.

Kamal A, Reddy KS, Khan MN, Shetti RV, Ramaiah MJ, Pushpavalli SN, Srinivas C, Pal-Bhadra M, Chourasia M, Sastry GN, Juvekar A. Synthesis, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole–pyrrolo [2, 1-c][1, 4] benzodiazepine conjugates. Bioorganic & medicinal chemistry. 2010 Jul 1;18(13):4747-61. DOI: https://doi.org/10.1016/j.bmc.2010.05.007

Tzanopoulou S, Sagnou M, Paravatou-Petsotas M, Gourni E, Loudos G, Xanthopoulos S, Lafkas D, Kiaris H, Varvarigou A, Pirmettis IC, Papadopoulos M. Evaluation of Re and 99mTc complexes of 2-(4′-aminophenyl) benzothiazole as potential breast cancer radiopharmaceuticals. Journal of medicinal chemistry. 2010 Jun 24;53(12):4633-41. DOI: https://doi.org/10.1021/jm1001293

Caleta I, Kralj M, Marjanović M, Bertosa B, Tomić S, Pavlović G, Pavelić K, Karminski-Zamola G. Novel cyano-and amidinobenzothiazole derivatives: synthesis, antitumor evaluation, and X-ray and quantitative structure− activity relationship (QSAR) analysis. Journal of medicinal chemistry. 2009 Mar 26;52(6):1744-56. DOI: https://doi.org/10.1021/jm801566q

Luzina EL, Popov AV. Synthesis and anticancer activity of N-bis (trifluoromethyl) alkyl-N′-thiazolyl and N-bis (trifluoromethyl) alkyl-N′-benzothiazolyl ureas. European journal of medicinal chemistry. 2009 Dec 1;44(12):4944-53. DOI: https://doi.org/10.1016/j.ejmech.2009.08.007

Mosula L, Zimenkovsky B, Havrylyuk D, Missir AV, Chirita IC, Lesyk R. Synthesis and antitumor activity of novel 2-thioxo-4-thiazolidinones with benzothiazole moieties. Farmacia. 2009 May 1;57(3):321-0.

Akhtar T, Hameed S, A AL-MASOUDI NA, Loddo R, La 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. DOI: https://doi.org/10.2478/v10007-008-0007-2

Kok S, Gambari R, Chui C, Yuen M, Lin E, Wong R, Lau F, Cheng G, Lam W, Chan S, LamK, Cheng C, Lai P, Yu M, Cheung F, Tang J and Chan A; Bioorganic & Medicinal Chemistry 2008, 16: 3626-3631. DOI: https://doi.org/10.1016/j.bmc.2008.02.005

Al-Soud YA, Doni AS, Saeed B, Jaber IH, Khalid B, Al-Masoudi NA, Kadir TA, Colla PL, Busonera B, Sena T, Loddo R; ARKIVOK 2008, XV: 225-238. DOI: https://doi.org/10.3998/ark.5550190.0009.f20

Choi SJ, Park HJ, Lee SK, Kim SW, Han G, Choo HY. Solid phase combinatorial synthesis of benzothiazoles and evaluation of topoisomerase II inhibitory activity. Bioorganic & medicinal chemistry. 2006 Feb 15;14(4):1229-35. DOI: https://doi.org/10.1016/j.bmc.2005.09.051

Mortimer CG, Wells G, Crochard JP, Stone EL, Bradshaw TD, Stevens MFG and Westwell AD; J. Med. Chem 2006, 49: 179-185. DOI: https://doi.org/10.1021/jm050942k

Yoshida M, Hayakawa I, Hayashi N, Agatsuma T, Oda Y, Tanzawa F, Iwasaki S, Koyama K, Furukawa H, Kurakata S, Sugano Y. Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents. Bioorganic & medicinal chemistry letters. 2005 Jul 15;15(14):3328-32. DOI: https://doi.org/10.1016/j.bmcl.2005.05.077

Song BA, Liu XH, Yang S, Hu DY, Jin LH, Zhang H. Synthesis and Anticancer Activity of 2, 3, 4‐Trimethoxyacetophenoxime Ester Containing Benzothiazole Moiety. Chinese Journal of Chemistry. 2005 Sep;23(9):1236-40. DOI: https://doi.org/10.1002/cjoc.200591236

Hose CD, Hollingshead M, Sausville EA, Monks A. Induction of CYP1A1 in tumor cells by the antitumor agent 2-[4-amino-3-methylphenyl]-5-fluoro-benzothiazole: a potential surrogate marker for patient sensitivity. Molecular cancer therapeutics. 2003 Dec 1;2(12):1265-72.

Wells G, Berry JM, Bradshaw TD, Burger AM, Seaton A, Wang B, Westwell AD, Stevens MF. 4-Substituted 4-hydroxycyclohexa-2, 5-dien-1-ones with selective activities against colon and renal cancer cell lines. Journal of medicinal chemistry. 2003 Feb 13;46(4):532-41. DOI: https://doi.org/10.1021/jm020984y

Hutchinson I, Bradshaw TD, Matthews CS, Stevens MF, Westwell AD. Antitumour benzothiazoles. Part 20: 3′-cyano and 3′-alkynyl-substituted 2-(4′-aminophenyl) benzothiazoles as new potent and selective analogues. Bioorganic & medicinal chemistry letters. 2003 Feb 10;13(3):471-4. DOI: https://doi.org/10.1016/S0960-894X(02)00930-7

O'Brien SE, Browne HL, Bradshaw TD, Westwell AD, Stevens MF, Laughton CA. Antitumor benzothiazoles. Frontier molecular orbital analysis predicts bioactivation of 2-(4-aminophenyl) benzothiazoles to reactive intermediates by cytochrome P4501A1. Organic & biomolecular chemistry. 2003;1(3):493-7.. DOI: https://doi.org/10.1039/b209067h

Bradshaw TD, Stevens MF, Westwell AD. The discovery of the potent and selective antitumour agent 2-(4-amino-3-methylphenyl) benzothiazole (DF 203) and related compounds. Current medicinal chemistry. 2001 Feb 1;8(2):203-10. DOI: https://doi.org/10.2174/0929867013373714

Bradshaw TD, Wrigley S, Shi DF, Schultz RJ, Paull KD, Stevens MF. 2-(4-Aminophenyl) benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity. British journal of cancer. 1998 Mar;77(5):745-52. DOI: https://doi.org/10.1038/bjc.1998.122

Wells G, Bradshaw TD, Diana P, Seaton A, Shi DF, Westwell AD, Stevens MF. Antitumour benzothiazoles. Part 10: the synthesis and antitumour activity of benzothiazole substituted quinol derivatives. Bioorganic & medicinal chemistry letters. 2000 Mar 6;10(5):513-5. DOI: https://doi.org/10.1016/S0960-894X(00)00027-5

Bénéteau V, Besson T, Guillard J, Léonce S, Pfeiffer B. Synthesis and in vitro antitumour evaluation of benzothiazole-2-carbonitrile derivatives. European journal of medicinal chemistry. 1999 Dec 1;34(12):1053-60. DOI: https://doi.org/10.1016/S0223-5234(99)00130-0

American Diabetes Association. Diagnosis and classification of diabetes mellitus. Diabetes care. 2010 Jan 1;33(Supplement_1): S62-9. DOI: https://doi.org/10.2337/dc10-S062

Galicia-Garcia U, Benito-Vicente A, Jebari S, Larrea-Sebal A, Siddiqi H, Uribe KB, Ostolaza H, Martín C. Pathophysiology of type 2 diabetes mellitus. International journal of molecular sciences. 2020 Aug 30;21(17):6275. DOI: https://doi.org/10.3390/ijms21176275

Wild S, Roglic G, Green A, Sicree R, King H. Global prevalence of diabetes: estimates for the year 2000 and projections for 2030. Diabetes care. 2004 May 1;27(5):1047-53. DOI: https://doi.org/10.2337/diacare.27.5.1047

Cade WT. Diabetes-related microvascular and macrovascular diseases in the physical therapy setting. Physical therapy. 2008 Nov 1;88(11):1322-35. DOI: https://doi.org/10.2522/ptj.20080008

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

Kharbanda C, Alam MS, Hamid H, Javed K, Bano S, Ali Y, Dhulap A, Alam P, Pasha MA. Novel benzothiazole based sulfonylureas/sulfonylthioureas: design, synthesis and evaluation of their antidiabetic potential. New Journal of Chemistry. 2016;40(8):6777-86. DOI: https://doi.org/10.1039/C5NJ03589A

Kumar RR, Velmurugan V, Aanandhi MV, gururagavan M. Shanthalingam K; International Journal of Pharmaceutical Research and Development 2012; 4(8): 78-83.

Mariappan G, Prabhat P, Sutharson L, Banerjee J, Patangia U, Nath S. Synthesis and antidiabetic evaluation of benzothiazole derivatives. Journal of the Korean Chemical Society. 2012;56(2):251-6. DOI: https://doi.org/10.5012/jkcs.2012.56.2.251

Alang G, Kaur G, Kaur R, Singh A, Tiwari R. Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2 (3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p-Substituted Acetophenones) Hydrazine Analogs. Journal of Young Pharmacists. 2010 Oct 1;2(4):394-8. DOI: https://doi.org/10.4103/0975-1483.71636

Navarrete-Vazquez G, Paoli P, León-Rivera I, Villalobos-Molina R, Medina-Franco JL, Ortiz-Andrade R, Estrada-Soto S, Camici G, Diaz-Coutiño D, Gallardo-Ortiz I, Martinez-Mayorga K. Synthesis, in vitro and computational studies of protein tyrosine phosphatase 1B inhibition of a small library of 2-arylsulfonylaminobenzothiazoles with antihyperglycemic activity. Bioorganic & medicinal chemistry. 2009 May 1;17(9):3332-41. DOI: https://doi.org/10.1016/j.bmc.2009.03.042

De SK, Chen LH, Stebbins JL, Machleidt T, Riel-Mehan M, Dahl R, Chen V, Yuan H, Barile E, Emdadi A, Murphy R. Discovery of 2-(5-nitrothiazol-2-ylthio) benzo [d] thiazoles as novel c-Jun N-terminal kinase inhibitors. Bioorganic & medicinal chemistry. 2009 Apr 1;17(7):2712-7. DOI: https://doi.org/10.1016/j.bmc.2009.02.046

Mithlesh, Pareek PK, Kant R, Shukla SK, Ojha KG. Rapid synthesis and biological evaluation of 1, 4-dihydropyridine derivatives containing a benzothiazolyl moiety. CENTRAL EUROPEAN JOURNAL OF CHEMISTRY. 2010 Feb 1;8(1):163-73. DOI: https://doi.org/10.2478/s11532-009-0114-z

Nitta A, Fujii H, Sakami S, Nishimura Y, Ohyama T, Satoh M, Nakaki J, Satoh S, Inada C, Kozono H, Kumagai H. (3R)-3-Amino-4-(2, 4, 5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy) benzothiazol-2-yl] tetrahydropyran-4-yl} butanamide as a potent dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. Bioorganic & medicinal chemistry letters. 2008 Oct 15;18(20):5435-8. DOI: https://doi.org/10.1016/j.bmcl.2008.09.042

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, León-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.

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, León-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. DOI: https://doi.org/10.1016/j.bmcl.2008.03.086

Su X, Vicker N, Ganeshapillai D, Smith A, Purohit A, Reed MJ, Potter BV. Benzothiazole derivatives as novel inhibitors of human 11β-hydroxysteroid dehydrogenase type 1. Molecular and cellular endocrinology. 2006 Mar 27;248(1-2):214-7. DOI: https://doi.org/10.1016/j.mce.2005.10.022

Pattan SR, Suresh CH, Pujar VD, Reddy VV, Rasal VP, Koti BC. Synthesis and antidiabetic activity of 2-amino [5'(4-sulphonylbe.nzylidine)-2, 4-thiazolidinedione]-7-chloro-6-fluorobenzothiazole.

Van Zandt MC, Jones ML, Gunn DE, Geraci LS, Jones JH, Sawicki DR, Sredy J, Jacot JL, DiCioccio AT, Petrova T, Mitschler A. Discovery of 3-[(4, 5, 7-trifluorobenzothiazol-2-yl) methyl] indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications. Journal of medicinal chemistry. 2005 May 5;48(9):3141-52. DOI: https://doi.org/10.1021/jm0492094

Gjorgjieva M, Tomašič T, Kikelj D, Mašič LP. Benzothiazole-based compounds in antibacterial drug discovery. Current medicinal chemistry. 2018 Nov 1;25(38):5218-36. DOI: https://doi.org/10.2174/0929867324666171009103327

Kashyap P, Verma S, Gupta P, Narang R, Lal S, Devgun M. Recent insights into antibacterial potential of benzothiazole derivatives. Medicinal Chemistry Research. 2023 Aug;32(8):1543-73.. DOI: https://doi.org/10.1007/s00044-023-03077-z

Haroun M, Tratrat C, Petrou A, Geronikaki A, Ivanov M, Ciric A, Sokovic M. 2-Aryl-3-(6-trifluoromethoxy) benzo [d] thiazole-based thiazolidinone hybrids as potential anti-infective agents: Synthesis, biological evaluation and molecular docking studies. Bioorganic & Medicinal Chemistry Letters. 2021 Jan 15; 32:127718. DOI: https://doi.org/10.1016/j.bmcl.2020.127718

Skok Z, Barančoková M, Benek O, Cruz CD, Tammela P, Tomašič T, Zidar N, Mašič LP, Zega A, Stevenson CE, Mundy JE. Exploring the chemical space of benzothiazole-based DNA gyrase B inhibitors. ACS medicinal chemistry letters. 2020 Oct 15;11(12):2433-40. DOI: https://doi.org/10.1021/acsmedchemlett.0c00416

Bhoi MN, Borad MA, Jethava DJ, Acharya PT, Pithawala EA, Patel CN, Pandya HA, Patel HD. Synthesis, biological evaluation and computational study of novel isoniazid containing 4H-Pyrimido [2, 1-b] benzothiazoles derivatives. European journal of medicinal chemistry. 2019 Sep 1;177:12-31. DOI: https://doi.org/10.1016/j.ejmech.2019.05.028

Asundaria ST, Patel KC. Synthesis, characterization and antimicrobial activity of thiazole, benzothiazole and pyrimidine derivatives bearing sydnone moieties. Pharmaceutical Chemistry Journal. 2012 Mar;45:725-31. DOI: https://doi.org/10.1007/s11094-012-0712-5

Prabhat P, Das SK, Shafaat K, Anand JP. EVALUATION OF N-(6-CHLOROBENZOTHIAZOL-2-YL)-2-(SUBSTITUTEDAMINO) ACETAMIDE FOR ITS ANTI-BACTERIAL ACTIVITY. International Journal of Pharmaceutical Sciences and Research. 2012 Aug 1;3(8):2669.

Mote SP, Deshmukh SP. Synthesis and Anti-Microbial Activity Of Novel Acetylated Maltosyl Carbamides, Benzothiazolyl Carbamides And Carbamates. Rasayan Journal of Chemistry. 2011;4(1):29-35.

Chaitanya MS, Nagendrappa G, Vaidya VP. Synthesis, biological and pharmacological activities of 2-methyl-4H-pyrimido [2, 1-b][1, 3] benzothiazoles. Journal of Chemical and Pharmaceutical Research. 2010;2(3):206-13.

Devmurari VP, Ghodasara TJ: Synthesis and antibacterial activity of some substituted 2-phenyl benzothiazole. Archives of Applied Science Research 2010, 2(1): 198-203

Pandurangan A, Sharma A, Sharma N, Sharma PK, Visht S. Synthesis and structural studies of novel benzothiazole derivative and evaluation of their antimicrobial activity. Der Pharma Chemica. 2010;2(3):316-24.

Alang G, Kaur R, Kaur G, Singh A, Singla P. Synthesis and antibacterial activity of some new benzothiazole derivatives. Acta Pharmaceutica Sciencia. 2010;52(2).

Haydon DJ, Bennett JM, Brown D, Collins I, Galbraith G, Lancett P, Macdonald R, Stokes NR, Chauhan PK, Sutariya JK, Nayal N. Creating an antibacterial with in vivo efficacy: synthesis and characterization of potent inhibitors of the bacterial cell division protein FtsZ with improved pharmaceutical properties. Journal of medicinal chemistry. 2010 May 27;53(10):3927-36. DOI: https://doi.org/10.1021/jm9016366

Soni B, Ranawat MS, Sharma R, Bhandari A, Sharma S. Synthesis and evaluation of some new benzothiazole derivatives as potential antimicrobial agents. European Journal of Medicinal Chemistry. 2010 Jul 1;45(7):2938-42. DOI: https://doi.org/10.1016/j.ejmech.2010.03.019

Gajdoš P, Magdolen P, Zahradník P, Foltínová P. New conjugated benzothiazole-N-oxides: synthesis and biological activity. Molecules. 2009 Dec 23;14(12):5382-8. DOI: https://doi.org/10.3390/molecules14125382

Rajeeva, B., Srinivasulu, N., & Shantakumar, SM Synthesis and Antimicrobial Activity of Some New 2Substituted Benzothiazole Derivatives. E-Journal of Chemistry, 6(3), 775-779 DOI: https://doi.org/10.1155/2009/404596

Gupta S, Ajmera N, Gautam N, Sharma R, Gautam DC. Novel synthesis and biological activity study of pyrimido [2, 1-b] benzothiazoles.

Bondock S, Fadaly W, Metwally MA. Enaminonitrile in heterocyclic synthesis: Synthesis and antimicrobial evaluation of some new pyrazole, isoxazole and pyrimidine derivatives incorporating a benzothiazole moiety. European journal of medicinal chemistry. 2009 Dec 1;44(12):4813-8. DOI: https://doi.org/10.1016/j.ejmech.2009.07.024

Zajac M, Hrobaric P, Magdonel P, Foltinova P, Zehradnik P; Tetrahedron 2008, 64: 10608-10618. DOI: https://doi.org/10.1016/j.tet.2008.08.064

Bhusari KP, Amneker ND, Khedekar PB, Kale MK, Bhole RP; Asian J. Research Chem. 2008, 1(2): 53-57.

Huang W, Yang GF. Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles. Bioorganic & medicinal chemistry. 2006 Dec 15;14(24):8280-5. DOI: https://doi.org/10.1016/j.bmc.2006.09.016

Yildiz-Oren I, Yalcin I, Aki-Sener E, Ucarturk N. Synthesis and structure–activity relationships of new antimicrobial active multisubstituted benzazole derivatives. European Journal of Medicinal Chemistry. 2004 Mar 1;39(3):291-8. DOI: https://doi.org/10.1016/j.ejmech.2003.11.014

Gagoria J, Kumar Verma P, Khatkar A. Anticonvulsant and neurological profile of benzothiazoles: a mini-review. Central Nervous System Agents in Medicinal Chemistry (Formerly Current Medicinal Chemistry-Central Nervous System Agents). 2015 Apr 1;15(1):11-6.. DOI: https://doi.org/10.2174/1871524915666150112094206

K. K. Sethi, M. V. Saurabh, P. Naru, M. A. Mathrusri. Lett. Drug Des. Discov., 2011, 8, 774-777. 8. X. Q. Deng, M. X. Song, C. X. Wei, F. N. Li, Z. S. Quan. Med. Chem., 2010, 6, 313-320.

D. C. Liu, H. J. Zhang, C. M. Jin, Z. S. Quan. Molecules, 2016, 21,164. 10. D. C. Liu, X. Q. Deng, S. B. Wang, Z. S. Quan. Arch. Pharm. Chem. Life Sci., 2014, 347 268–275. 11. U. Kabra, C. Chopde, S. Wadodkara. J. Heterocyclic Chem., 2011, 48, 1351-1355

V. G. Ugale, H. M. Patel, S. G. Wadodkar. S. B. Bari. A. A. Shirkhedkar. S. J. Surana. Eur. J. Med. Chem., 2012, 53, 107-113. 13. S. Agarwal, D. Gandhi, P. Kalal. Lett. Org. Chem., 2017, 14(10), 729-742. DOI: https://doi.org/10.1016/j.ejmech.2012.03.045

Agarwal DK, Agarwal S, Gandhi D. Benzothiazole: A Versatile Synthetic Auxillary for Antiepileptic Drugs. Chemistry & Biology Interface. 2018 May 1;8(3).

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. DOI: https://doi.org/10.1016/j.ejmech.2009.09.037

SIDDIQUI N, RANA A, KHAN SA, HAQUE SE, ARSHAD M, Ahmed SH, AHSAN W. Sinteza i preliminarna ispitivanja antikonvulzivnog djelovanja derivata benzotiazol-2-il tiadiazola. Acta Pharmaceutica. 2009 Dec 1;59(4):441-51. DOI: https://doi.org/10.2478/v10007-009-0031-x

Siddiqui N, Rana A, Khan SA, Haque SE, Alam MS, Ahsan W, Arshad MF. Anticonvulsant and Toxicity Evaluation of Newly Synthesized 1-[2-(3, 4-disubstituted phenyl)-3-chloro-4-oxoazetidin-1-yl]-3-(6-substituted-1, 3-benzothiazol-2-yl) ureas. Acta Chimica Slovenica. 2009 Jun 1;56(2).

Rana A, Siddiqui N, Khan SA, Haque SE, Bhat MA. N-{[(6-substituted-1, 3-benzothiazole-2-yl) amino] carbonothioyl}-2/4-substituted benzamides: synthesis and pharmacological evaluation. European journal of medicinal chemistry. 2008 May 1;43(5):1114-22. DOI: https://doi.org/10.1016/j.ejmech.2007.07.008

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. DOI: https://doi.org/10.1016/j.bmcl.2006.09.053

Siddiqui N, Rana A, Khan SA, Bhat MA, Haque SE. Synthesis of benzothiazole semicarbazones as novel anticonvulsants—The role of hydrophobic domain. Bioorganic & medicinal chemistry letters. 2007 Aug 1;17(15):4178-82. DOI: https://doi.org/10.1016/j.bmcl.2007.05.048

Scheetz ME II, Carlson DG, Schinitsky MR. Frentizole, a novel immunosuppressive, and azathioprine: their comparative effects on host resistance to Pseudomonas aeruginosa, Candida albicans, Herpes Simplex virus, and influenza (Ann Arbor) virus. Infection and Immunity. 1977 Jan;15(1):145-8. DOI: https://doi.org/10.1128/iai.15.1.145-148.1977

Sabharwal UK, Vaughan JH, Kaplan RA, Robinson CA, Curd JG. Frentizole therapy in systemic lupus erythematosus. Arthritis & Rheumatism: Official Journal of the American College of Rheumatology. 1980 Dec;23(12):1376-80. DOI: https://doi.org/10.1002/art.1780231208

Wokke J. Riluzole. The Lancet. 1996 Sep 21;348(9030):795-9. DOI: https://doi.org/10.1016/S0140-6736(96)03181-9

Shivadekar, S., Kataria, B., Hundekari, S. ., Kirti Wanjale, Balpande, V. P., & Suryawanshi, R. . (2023). Deep Learning Based Image Classification of Lungs Radiography for Detecting COVID-19 using a Deep CNN and ResNet 50. International Journal of Intelligent Systems and Applications in Engineering, 11(1s), 241–250. Retrieved from https://ijisae.org/index.php/IJISAE/article/view/2499.

Hodson ST, Miller FR. The bicarbonate ion pump in the endothelium which regulates the hydration of rabbit cornea. The Journal of physiology. 1976 Dec 1;263(3):563-77. DOI: https://doi.org/10.1113/jphysiol.1976.sp011645

Kazokaitė J, Aspatwar A, Kairys V, Parkkila S, Matulis D. Fluorinated benzenesulfonamide anticancer inhibitors of carbonic anhydrase IX exhibit lower toxic effects on zebrafish embryonic development than ethoxzolamide. Drug and Chemical Toxicology. 2017 Jul 3;40(3):309-19. DOI: https://doi.org/10.1080/01480545.2016.1223095

Steele JW, Faulds D, Goa KL. Epalrestat: a review of its pharmacology, and therapeutic potential in late-onset complications of diabetes mellitus. Drugs & aging. 1993 Nov;3:532-55. DOI: https://doi.org/10.2165/00002512-199303060-00007

Shivadekar, S., Kataria, B., Limkar, S. et al. Design of an efficient multimodal engine for preemption and post-treatment recommendations for skin diseases via a deep learning-based hybrid bioinspired process. Soft Comput (2023). https://doi.org/10.1007/s00500-023-08709-5 DOI: https://doi.org/10.1007/s00500-023-08709-5

Rosales-Hernández MC, Mendieta-Wejebe JE, Padilla-Martínez II, García-Báez EV, Cruz A. Synthesis and Biological Importance of 2-(thio) ureabenzothiazoles. Molecules. 2022 Sep 19;27(18):6104. DOI: https://doi.org/10.3390/molecules27186104

Studentsov EP, Golovina AA, Krasikova RN, Orlovskaja VV, Vaulina DD, Krutikov VI, Ramsh SM. 2-Arylbenzothiazoles: Advances in Anti-Cancer and Diagnostic Pharmaceuticals Discovery. Russian Journal of General Chemistry. 2021 Jan; 91:1-33. DOI: https://doi.org/10.1134/S1070363221010011

Fichtner I, Monks A, Hose C, Stevens MF, Bradshaw TD. The experimental antitumor agents Phortress and doxorubicin are equiactive against human-derived breast carcinoma xenograft models. Breast cancer research and treatment. 2004 Sep; 87:97-107. DOI: https://doi.org/10.1023/B:BREA.0000041586.64371.88

El‐Helby AG, Sakr H, Eissa IH, Al‐Karmalawy AA, El‐Adl K. Benzoxazole/benzothiazole‐derived VEGFR‐2 inhibitors: design, synthesis, molecular docking, and anticancer evaluations. Archiv Der Pharmazie. 2019 Dec;352(12):1900178. DOI: https://doi.org/10.1002/ardp.201900178

Chacko S, Samanta S. A novel approach towards design, synthesis and evaluation of some Schiff base analogues of 2-aminopyridine and 2-aminobezothiazole against hepatocellular carcinoma. Biomedicine & Pharmacotherapy. 2017 May 1; 89:162-76. DOI: https://doi.org/10.1016/j.biopha.2017.01.108

MA, Dar OA, Gull P, Wani MY, Hashmi AA. Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy. MedChemComm. 2018;9(3):409-36. DOI: https://doi.org/10.1039/C7MD00526A

Fekri R, Salehi M, Asadi A, Kubicki M. Synthesis, characterization, anticancer and antibacterial evaluation of Schiff base ligands derived from hydrazone and their transition metal complexes. Inorganica Chimica Acta. 2019 Jan 1;484:245-54. DOI: https://doi.org/10.1016/j.ica.2018.09.022

Kumar H, Goyal A, Kumar N, Garg P. Design, Synthesis, and biological evaluation of pyrazolo-benzothiazole derivatives as a potential therapeutic agent for the treatment of Alzheimer’s disease. Medicinal Chemistry Research. 2022 Nov;31(11):1931-47. DOI: https://doi.org/10.1007/s00044-022-02953-4

Luo B, Li D, Zhang AL, Gao JM. Synthesis, antifungal activities and molecular docking studies of benzoxazole and benzothiazole derivatives. Molecules. 2018 Sep 25;23(10):2457. DOI: https://doi.org/10.3390/molecules23102457

Mor S, Sindhu S. Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno [1, 2-c] pyrazol-4 (1 H)-ones. Medicinal Chemistry Research. 2020 Jan; 29:46-62. DOI: https://doi.org/10.1007/s00044-019-02457-8