Solid-Phase Synthesis of 2-Benzothiazolyl and 2-(Aminophenyl)benzothiazolyl Amino Acids and Peptides

2-benzothiazoles and 2-(aminophenyl)benzothiazoles represent biologically interesting heterocycles with high pharmacological activity. The combination of these heterocycles with amino acids and peptides is of special interest, as such structures combine the advantages of amino acids and peptides with the advantages of the 2-benzothiazolyl and 2-(aminophenyl)benzothiazolyl pharmacophore group. In this work, we developed an easy and efficient method for the solid-phase synthesis of 2-benzothiazolyl (BTH) and 2-(aminophenyl)benzothiazolyl (AP-BTH) C-terminal modified amino acids and peptides with high chiral purity.

[1]  B. Shainyan,et al.  Synthetic Approaches to Biologically Active C-2-Substituted Benzothiazoles , 2022, Molecules.

[2]  T. Walsh,et al.  Thiazole/Thiadiazole/Benzothiazole Based Thiazolidin-4-One Derivatives as Potential Inhibitors of Main Protease of SARS-CoV-2 , 2022, Molecules.

[3]  C. Supuran,et al.  Repurposing FDA-approved sulphonamide carbonic anhydrase inhibitors for treatment of Neisseria gonorrhoeae , 2021, Journal of enzyme inhibition and medicinal chemistry.

[4]  M. Shahar Yar,et al.  Recent advances and SAR study of 2-substituted benzothiazole scaffold based potent chemotherapeutic agents , 2021, Results in Chemistry.

[5]  S. Mahajan,et al.  Riluzole: A neuroprotective drug with potential as a novel anti-cancer agent (Review) , 2021, International journal of oncology.

[6]  V. Chudasama,et al.  Cysteine protecting groups: applications in peptide and protein science. , 2021, Chemical Society reviews.

[7]  M. Kannavou,et al.  Liposomes Decorated with 2-(4'-Aminophenyl)benzothiazole Effectively Inhibit Aβ1-42 Fibril Formation and Exhibit in Vitro Brain-Targeting Potential. , 2020, Biomacromolecules.

[8]  Sumit,et al.  Advancement in Pharmacological Activities of Benzothiazole and its Derivatives:An Up to Date Review. , 2020, Mini reviews in medicinal chemistry.

[9]  Y. Mabkhot,et al.  Benzothiazoles as potential antiviral agents , 2020, The Journal of pharmacy and pharmacology.

[10]  M. Yar,et al.  Free radical scavengers: An overview on heterocyclic advances and medicinal prospects. , 2020, European journal of medicinal chemistry.

[11]  E. Pioro,et al.  Real-world evidence of riluzole effectiveness in treating amyotrophic lateral sclerosis , 2020, Amyotrophic lateral sclerosis & frontotemporal degeneration.

[12]  Tian-Yi Zhang,et al.  Synthesis, biological evaluation of benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents. , 2020, Bioorganic & medicinal chemistry letters.

[13]  Xiang Gao,et al.  Recent Advances in Synthesis of Benzothiazole Compounds Related to Green Chemistry , 2020, Molecules.

[14]  B. C. Uzuegbunam,et al.  PET Radiopharmaceuticals for Alzheimer’s Disease and Parkinson’s Disease Diagnosis, the Current and Future Landscape , 2020, Molecules.

[15]  Zhi‐Bing Dong,et al.  A Review on Domino Condensation/Cyclization Reactions for the Synthesis of 2-Substituted 1,3-Benzothiazole Derivatives , 2020 .

[16]  M. Yar,et al.  Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review. , 2019, European journal of medicinal chemistry.

[17]  C. Supuran,et al.  Benzothiazole derivatives as anticancer agents , 2019, Journal of enzyme inhibition and medicinal chemistry.

[18]  A. Abadi,et al.  Structure-activity relationships of thiazole and benzothiazole derivatives as selective cannabinoid CB2 agonists with in vivo anti-inflammatory properties. , 2019, European journal of medicinal chemistry.

[19]  A. Husain,et al.  Novel hybrids of benzothiazole-1,3,4-oxadiazole-4-thiazolidinone: Synthesis, in silico ADME study, molecular docking and in vivo anti-diabetic assessment. , 2019, Bioorganic chemistry.

[20]  Dongyu Zhang,et al.  Recent developments in benzothiazole-based iridium(Ⅲ) complexes for application in OLEDs as electrophosphorescent emitters , 2019, Organic Electronics.

[21]  V. Psycharis,et al.  Remarkable Brain Penetration of Cyclopentadienyl M(CO)3+ (M = 99mTc, Re) Derivatives of Benzothiazole and Benzimidazole Paves the Way for Their Application as Diagnostic, with Single-Photon-Emission Computed Tomography (SPECT), and Therapeutic Agents for Alzheimer's Disease. , 2019, Journal of medicinal chemistry.

[22]  M. Amir,et al.  Design, Synthesis, and Screening of Hybrid Benzothiazolyl-Oxadiazoles as Anticonvulsant Agents , 2018 .

[23]  G. Loudos,et al.  2-(4'-Aminophenyl)benzothiazole Labeled with 99mTc-Cyclopentadienyl for Imaging β-Amyloid Plaques. , 2017, ACS medicinal chemistry letters.

[24]  Mengchao Cui,et al.  Recent progress in the development of metal complexes as β-amyloid imaging probes in the brain. , 2017, MedChemComm.

[25]  M. Gioia,et al.  One-pot synthesis of amides from carboxylic acids activated using thionyl chloride , 2016 .

[26]  Y. Keum,et al.  Chrysin-benzothiazole conjugates as antioxidant and anticancer agents. , 2015, Bioorganic & medicinal chemistry letters.

[27]  Rangappa S. Keri,et al.  A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry. , 2015, European journal of medicinal chemistry.

[28]  T. Pabst,et al.  Short Synthesis of a Proline Amide Orexin Receptor Antagonist on the Pilot Plant Scale , 2014 .

[29]  Rajesh H. Vekariya,et al.  Recent advances in the synthesis of 2-substituted benzothiazoles: a review , 2014 .

[30]  A. McNeil,et al.  Enzyme-triggered gelation: targeting proteases with internal cleavage sites. , 2014, Chemical communications.

[31]  Y. Kimura,et al.  Novel Synthetic Method for the Vilsmeier-Haack Reagent and Green Routes to Acid Chlorides, Alkyl Formates, and Alkyl Chlorides , 2013 .

[32]  Xiaopeng Hu,et al.  Zopolrestat as a Human Glyoxalase I Inhibitor and Its Structural Basis , 2013, ChemMedChem.

[33]  Andreas F. M. Kilbinger,et al.  Tuning the solubility of hepta(p-benzamide)s via the monomer sequence , 2013 .

[34]  T. Kawase,et al.  An Effective Synthesis of N,N-Dimethylamides from Carboxylic Acids and a New Route from N,N-Dimethylamides to 1,2-Diaryl-1,2-diketones. , 2011 .

[35]  T. Kawase,et al.  An effective synthesis of N,N-dimethylamides from carboxylic acids and a new route from N,N-dimethylamides to 1,2-diaryl-1,2-diketones , 2010 .

[36]  F. Albericio,et al.  PyOxP and PyOxB: the Oxyma-based novel family of phosphonium salts. , 2010, Organic & biomolecular chemistry.

[37]  D. Gatos,et al.  Synthesis of the very acid-sensitive Fmoc-Cys(Mmt)-OH and its application in solid-phase peptide synthesis. , 2009, International journal of peptide and protein research.

[38]  T. Singh,et al.  Synthesis of New Thiazolylthiazolidinylbenzothiazoles and Thiazolylazetidinylbenzothiazoles as Potential Insecticidal, Antifungal, and Antibacterial Agents , 2006, Archiv der Pharmazie.

[39]  P. K. Basniwal,et al.  2-(4-aminophenyl) benzothiazole: a potent and selective pharmacophore with novel mechanistic action towards various tumour cell lines. , 2006, Mini reviews in medicinal chemistry.

[40]  A. Westwell,et al.  The development of the antitumour benzothiazole prodrug, Phortress, as a clinical candidate. , 2004, Current medicinal chemistry.

[41]  M. Stevens,et al.  Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs. , 2002, Journal of medicinal chemistry.

[42]  S. Mourtas,et al.  Solid phase synthesis of benzothiazolyl compounds , 2001 .

[43]  D. Gatos,et al.  Convergent Peptide Synthesis , 2000 .

[44]  G. Dozeman,et al.  Chemical Development of a Pilot Scale Process for the ACAT Inhibitor 2, 6-Diisopropylphenyl ((2,4,6-Triisopropylphenyl)acetyl)sulfamate. , 1997 .

[45]  S Wrigley,et al.  Antitumor benzothiazoles. 3. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo. , 1996, Journal of medicinal chemistry.

[46]  L. A. Carpino.  1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive , 1993 .

[47]  F. Higashi,et al.  Direct polyamidation with thionyl chloride in N‐methyl‐pyrrolidone , 1986 .

[48]  P. M. Hardy.  PROTECTING GROUPS IN PEPTIDE SYNTHESIS , 1980 .

[49]  N. Semenov,et al.  A New Look at the Chalcogen Bond: π-Hole-based Chalcogen (Se, Te) Bonding Which Does Not Include a σ-Hole Interaction , 2023, Inorganic Chemistry Frontiers.

[50]  R. Liu,et al.  Panchromatic luminescent D-π-A benzothiazoles with different π-bridging modulation: design, synthesis and application in WLEDs devices , 2023, Materials Chemistry Frontiers.

[51]  A. Cherkasov,et al.  Metal-involving C···dz2-PtII Tetrel Bonding as a Principal Component of Stacking Interaction between Arenes and the Platinum(II) Square-plane , 2023, Inorganic Chemistry Frontiers.

[52]  É. Tóth,et al.  Metal complexes for the visualisation of amyloid peptides , 2022, Sensors & Diagnostics.

[53]  E. Rathi,et al.  A review on anticancer potentials of benzothiazole derivatives. , 2019, Mini reviews in medicinal chemistry.

[54]  Ashish A. Gawai,et al.  Synthesis, Preliminary Pharmacological and Acute Toxicity Studies of a New Series of 7-(2-(Benzo[d]thiazol-2-ylamino)ethoxy)-4-methyl-2H-chromen-2-one Derivatives with Atypical Antipsychotic Activity , 2019, Indian Journal of Pharmaceutical Sciences.

[55]  C. P. Rao,et al.  Synthesis, characterization and biological evaluation of benzothiazole derivatives as potential antimicrobial and analgesic agents , 2017 .

[56]  S. Mourtas,et al.  Resin-bound aminothiols: synthesis and application , 2003 .

[57]  W. Chan,et al.  Fmoc Solid Phase Peptide Synthesis: A Practical Approach (Practical Approach Series) , 2019 .

[58]  B. Merrifield,et al.  Concept and early development of solid-phase peptide synthesis. , 1997, Methods in enzymology.

[59]  E. Giralt,et al.  Convergent solid-phase peptide synthesis. , 1997, Methods in enzymology.

[60]  B. Mylari,et al.  Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl] methyl]-1-phthalazineacetic acid (zopolrestat) and congeners. , 1991, Journal of medicinal chemistry.