New horizons in benzothiazole scaffold for cancer therapy: Advances in bioactivity, functionality, and chemistry
Source abstract
Abstract
Abstract In the pasture of oncology, anticancer agents having advanced modes of action are of great interest because of increasing chronicity of resistance against anticancer drugs. Heterocyclic scaffolds like benzothiazoles are reported to display an extensive range of pharmacological activities including anticancer, anti-tubercular, antiviral, fungicidal, etc. and are indispensable tools for the researchers involved in vistas of chemistry for proposing of novel anticancer drugs. Benzothiazole scaffold is a bicyclic organic compound having benzene ring fused with heterocyclic nucleus (thiazole) containing sulphur and nitrogen atoms that possess a wide range of different pharmacological activities and are still of grand and logical concern nowadays. Interesting pharmacological activities are exhibited by benzothiazoles and they were developed as successful inhibitors of a variety of biological targets such as tubulin polymerase inhibitor, DNA topoisomerase-inhibitor, an Abl kinase inhibitor, HDAC inhibitor, Aurora-B kinase inhibitor. This review highlights the latest research on the structure-activity relationship of benzothiazole scaffold against different biological targets for their anticancer activity. This survey additionally addresses the recent patents granted and novel advancement made through the application of nanocarriers in recent decades with thorough talk of benzothiazoles as conceivable anticancer mediators which may be helpful for the emerging scientific pursuits.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Synthesis and biological activity · Quinazolinone synthesis and applications · Cancer therapeutics and mechanisms
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (100+)
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1. B.G. Katzung, Basic & Clinical Pharmacology, 9th edition, Section VIII. Chemotherapeutic Drugs-Chapter 55. Published by Lange Medical Books, December 15th2003, pp. 1276.
2. H.P. Rang, M.M. Dale, J.M. Ritter, R.J. Flower, Rang and Dale's Textbook of Pharmacology6th ed., pp-718.
3. Ganglioside GD3 synthase (GD3S), a novel cancer drug target10.1016/j.apsb.2018.07.009 ↗
4. American cancer society. Cancer facts and figures2018, pp 1–76. [https://www.cancer.org/content/dam/cancer-org/research/cancer-facts-andstatistics/annual-cancer-facts-and-figures/2018/cancer-facts-and-figures-2018.pdf] (accessed on January 25, (2018).
5. Thiazole-containing compounds as therapeutic targets for cancer therapy10.1016/j.ejmech.2019.112016 ↗
6. Pharmacological significance of triazole scaffold, J10.3109/14756360903524304 ↗
7. Synthesis and characterization of N-Mannich based prodrugs of ciprofloxacin and norfloxacin: in vitro anthelmintic and cytotoxic evaluation, J10.1016/j.jare.2017.06.003 ↗
8. A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry10.1016/j.ejmech.2014.10.059 ↗
9. Benzothiazole: different methods of synthesis and biological activities
10. Synthesis and anticancer evaluation of bis (- benzimidazoles), bis (benzoxazoles), and benzothiazoles10.1016/j.bmc.2006.05.007 ↗
11. Design, synthesis and mode of action of some benzothiazole derivatives bearing an amide moiety as antibacterial agents10.1039/C4RA02649G ↗
12. Synthesis and anticonvulsant activity of sulphonamide derivatives hydrophobic domain10.1016/j.bmcl.2006.09.053 ↗
13. In vitro antitumor and antiviral activities of new benzothiazole and 1, 3, 4 oxadiazole 2 thione derivatives10.2478/v10007-008-0007-2 ↗
14. Benzothiazolines as antituberculous agent, J10.1021/jm00285a022 ↗
15. Antimalarials. III. Benzothiazole amino alcohols10.1021/jm00308a018 ↗
16. Synthesis and anthelmintic activity of 3-(2-hydrozinobenzothiazole) substituted indole-2-one
17. Synthesis and analgesic activity of some 2-[{4 (alkylthioureido) phenyl} sulphonamido]-6-substituted benzothiazoles
18. Synthesis and biological activities of fuorobenzothiazoles
19. Synthesis and anti-diabeticactivity of 2-amino-[(4 sulphonylbenzylidene-2, 4 thiazolidenedinone]-7-chloro-6-flourobenzothiazole
20. Study of fungicidal activities of some benzothiazoles
21. Metabolically stabilized benzothiazoles for imaging of amyloid plaques, J10.1021/jm061466g ↗
22. Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents, J10.1021/jm030026b ↗
23. Synthesis and evaluation of benzothiazole-based analogues as novel, potent and selective fatty acid amide hydrolase inhibitors, J10.1021/jm801042a ↗
24. Search for histamine H3 receptor antagonists with combined inhibitory potency at N-tau-methyltransferase: ether derivatives
25. N-{[(6-substituted-1, 3-benzothiazole-2-yl)amino]carbonothioyl} 2/4 substituted benzamides: synthesis and pharmacological evaluation10.1016/j.ejmech.2007.07.008 ↗
26. Synthesis of azulen-1-yl-benzothiazol-2-yl aiazenes10.1016/j.dyepig.2006.01.041 ↗
27. Preparation of benzothiazoles as intermediates for dyes, plant protectants and pharmaceuticals
28. Benzothiazole schiff bases as potential imaging agents for b-amyloid plaques in Alzheimer's disease10.1007/s00044-012-0416-0 ↗
29. Synthesis of novel inhibitors of b-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking10.1016/j.bmc.2011.05.052 ↗
30. Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56lck inhibitors10.1016/S0960-894X(03)00511-0 ↗
31. Novel antiallergic and anti-inflammatory agents. Part I: synthesis and pharmacology of glycolic amide derivatives10.1016/S0968-0896(98)00065-0 ↗
32. Investigations on the mechanism of action of the novel antitumor agents 2-benzothiazolyl, 2-benzoxazolyl, and 2-benzimidazolyl hydrazones derived from 2-acetylpyridine10.1002/(SICI)1521-4184(19994)332:4<115::AID-ARDP115>3.0.CO;2-G ↗
33. The therapeutic potential of aryl Hydrocarbon Receptor (AhR) agonists in anticancer drug development10.1358/dof.2004.029.05.804556 ↗
34. Antitumour benzothiazoles. Part 10: the synthesis and antitumour activity of benzothiazole substituted quinol derivatives10.1016/S0960-894X(00)00027-5 ↗
35. Induction of CYP1A1 in tumor cells by the antitumor agents 2-[4-amino-3-methylphenyl]-5-flourobenzothiazole: a potential surrogate marker for patient sensitivity
36. Antitumour 2-(4aminophenyl)benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo10.1038/sj.bjc.6600719 ↗
37. The antitumor drug candidate 2(4-amino-3-methylphenyl)-5-fluorobenzothiazole induces NF-[kappa] B activity in drug-sensitive MCF-7 cells10.1097/00001813-200502000-00004 ↗
38. Synthesis and biological evaluation of triazole and isoxazole tagged Benzothiazole/Benzoxazole derivatives as potent cytotoxic agents10.1039/C8NJ01249K ↗
39. Chua · J. Med. Chem · 1999 · 42 · 38110.1021/jm981076x ↗
40. DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells10.1038/sj.bjc.6600722 ↗
41. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo, J10.1021/jm9600959 ↗
42. The development of theantitumourbenzothiazole prodrug, phortress, as a clinical candidate10.2174/0929867043455530 ↗
43. Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides, J10.1021/jm031057+ ↗
44. Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells, J
45. The vesosome-a multi-compartment drug delivery vehicle10.2174/0929867043456197 ↗
46. Synthesis and anti-cancer activity of benzothiazole containing phthalimide on human carcinoma cell lines10.1016/j.bmc.2008.02.005 ↗
47. Synthesis, characterization and biological evaluation of some benzimidazole clubbed benzothiazole derivatives
48. Benzothiazole: different methods of synthesis and diverse biological activities10.25004/IJPSDR.2011.030101 ↗
49. I.Caleta, M.Kralj, M.Marjanovic, B.Bertoša, S.Tomic, G.Pavlovic, K.Pavelić, G.Karminski-Zamola. Novel cyano-and amidinobenzothiazole derivatives: synthesis, antitumor evaluation, and X-ray and Quantitative Structure-Activity Relationship (QSAR) analysis. J. Med. Chem.200952(6) 1744–56.10.1021/jm801566q ↗
50. Convenient synthesis of benzothiazoles and benzimidazoles through brønstedacid catalyzed cyclization of 2-amino thiophenols/anilines with β-diketones10.1021/ol403475v ↗
51. Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles and benzimidazoles catalyzedby4-methoxy-TEMPO10.1002/anie.200803381 ↗
52. Copper-catalyzed thiolation annulations of 1,4-dihalides with sulfides leading to 2-trifluoromethyl benzothiophenes and benzothiazoles10.1021/jo101675f ↗
53. Recent advances in the chemistry and biology of benzothiazoles10.1002/ardp.201400340 ↗
54. A novel practical synthesis of benzothiazoles via Pd-catalyzed thiol cross-coupling10.1021/ol7015737 ↗
55. Organocatalytic synthesis of benzoxazoles and benzothiazoles using aryl iodide and oxone via C-H functionalization and C-O/S bond formation, J10.1021/jo501216h ↗
56. Facile synthesis of benzothiazoles via cascade reactions of 2-iodoanilines, acid chlorides and lawesson'sreagent, J10.1021/cc900085p ↗
57. Methanesulfonic acid/SiO2 as an efficient combination for the synthesis of 2-substituted aromatic and aliphatic benzothiazoles from carboxylic acids10.1080/00397910802431214 ↗
58. Copper-catalyzed double C-S bonds formation via different paths: synthesis of benzothiazoles from N-benzyl-2-iodoaniline and potassium sulfide10.1021/ol403638d ↗
59. ZnO nanoparticles: a green efficient catalyst for the room temperature synthesis of biologically active 2-aryl-1,3-benzothiazole and 1,3-benzoxazole derivatives10.1016/j.tetlet.2014.07.123 ↗
60. Magnetically recoverable and reusable CuFeO nanoparticle-catalyzed synthesis of benzoxazoles, benzothiazoles and benzimidazoles using dioxygen as oxidant10.1039/C4RA00559G ↗
61. Direct C-H arylation of benzothiazoles by magnetically separable nano copper ferrite, a recyclable catalyst10.1016/j.tetlet.2015.07.002 ↗
62. Synthesis of benzimidazoles/benzothiazoles by using recyclable, magnetically separable nano-Fe2O3 in aqueous medium, J10.1007/s13738-017-1107-z ↗
63. A heterogeneous and recyclable catalyst for the one-pot synthesis of benzimidazoles, benzoxazoles and benzothiazoles under solvent-free conditions,J10.1002/jccs.201700060 ↗
64. FeO@SiO2/collagen: an efficient magnetic nanocatalyst for the synthesis of benzimidazole and benzothiazole derivatives10.1016/j.crci.2016.05.003 ↗
65. Hajipour · RSC Adv. · 2015 · 5 · 10782210.1039/C5RA22207A ↗
66. Advantages and risks of nanotechnologies in cancer patients and occupationally exposed workers10.1517/17425247.2014.913568 ↗
67. Nanoparticles as an emerging tool to alter the gene expression: preparation and conjugation methods
68. Nanoparticles in cancer treatment: opportunities and obstacles10.2174/1389450119666180326122831 ↗
69. ZnO nanoparticles: a green efficient catalyst for the room temperature synthesis of biologically active 2-aryl-1, 3-benzothiazole and 1, 3-benzoxazole derivatives10.1016/j.tetlet.2014.07.123 ↗
70. Nanotechnology in cancer therapy10.3109/1061186X.2013.837469 ↗
71. Nanomaterial-enabled cancer therapy10.1016/j.ymthe.2017.04.026 ↗
72. Importance of Benzothiazole Motif in Modern Drug Discovery: introduction
73. Chitosan-based advanced materials for docetaxel and paclitaxel delivery: recent advances and future directions in cancer theranostics10.1016/j.ijbiomac.2019.12.145 ↗
74. Hadef · 2018 · 14 · 1
75. Applications of nanomaterials based on magnetite and mesoporous silica on the selective detection of zinc ion in live cell imaging10.3390/nano8060434 ↗
76. A review on nanotechnology and plant mediated metal nanoparticles and its applications
77. A novel method for the synthesis of benzothiazole heterocycles catalyzed by copper-diamsar complex loaded on SBA-15 in water media
78. The protein kinase family: conserved features and deduced phylogeny of the catalytic domains10.1126/science.3291115 ↗
79. Tyrosine kinase-role and significance in cancer10.7150/ijms.1.101 ↗
80. The protein tyrosine kinase family of the human genome10.1038/sj.onc.1203957 ↗
81. Receptor tyrosine kinase signalling as a target for cancer intervention strategies10.1677/erc.0.0080161 ↗
82. Receptor tyrosine kinases: mechanisms of activation and signalling10.1016/j.ceb.2007.02.010 ↗
83. Microtubule-associated proteins as targets in cancer chemotherapy10.1158/1078-0432.CCR-06-3040 ↗
84. Synthesis and SAR of [1,2,4]-triazolo[1,5-a]pyrimidines, a class of anticancer agents with a unique mechanism of tubulin inhibition, J10.1021/jm060717i ↗
85. Microtubule-binding natural products for cancer therapy10.1055/s-0030-1250073 ↗
86. 6-Alkylamino and 2,3-dihydro-3′-methoxy-2-phenyl-4-quinazolinones and related compounds: their synthesis, cytotoxicity and inhibition of tubulin polymerization, J
87. Arylthioindoles, Potent inhibitors of tubulin polymerization, J10.1021/jm049360d ↗
88. Synthesis and biological evaluation of cis-restricted triazole/tetrazole mimics of combretastatin-benzothiazole hybrids as tubulin polymerization inhibitors and apoptosis inducers10.1016/j.bmc.2016.12.010 ↗
89. Synthesis and biological evaluation of combretastatin-amidobenzothiazole conjugates as potential anticancer agents10.1016/j.ejmech.2012.08.021 ↗
90. Design and synthesis of cis-restricted benzimidazole and benzothiazole mimics of combretastatin A-4 as antimitotic agents with apoptosis inducing ability10.1016/j.bmcl.2016.06.044 ↗
91. Rational design and synthesis of 2-anilinopyridinyl-benzothiazole schiff bases as antimitotic agents10.1016/j.bmcl.2017.03.089 ↗
92. Kaur P., Kaur V., Kaur S. DNA Topoisomerase II: promising target for anticancer drugs. InMulti-Targeted Approach to Treatment of Cancer (2015) pp. 323–338.10.1007/978-3-319-12253-3_20 ↗
93. Chemistry, biology and interfacial inhibition10.1021/cr900097c ↗
94. Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex10.1021/jm049146p ↗
95. Topoisomerase-I inhibitors for human malignant glioma: differential modulation of p53, p21, bax and bcl-2 expression and of CD95-mediated apoptosis by camptothecin and b-lapachone10.1002/(SICI)1097-0215(19971127)73:5<707::AID-IJC16>3.0.CO;2-2 ↗
96. An efficient one-pot synthesis of benzothiazolo-4β-anilino-podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity10.1016/j.bmcl.2010.11.002 ↗
97. PF-114, a novel selective inhibitor of BCR-ABL tyrosine kinase, is a potent inducer of apoptosis in chronic myelogenous leukemia cells
98. Structure of the kinase domain of an Imatinib-resistant Ablmutant in complex with the aurora kinase inhibitor VX-68010.1158/0008-5472.CAN-05-2788 ↗
99. Ph+ acute lymphoblastic leukemia resistant to the tyrosine kinase inhibitor STI571 has a unique BCR-ABLgene mutation10.1182/blood.V99.5.1860 ↗
100. ABL kinase inhibitory and antiproliferative activity of novel picolinamide based benzothiazoles10.1016/j.bmcl.2015.03.067 ↗