Scientific Publication List

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Selected List of Published Research and Review Articles and Patents

The following is a selected list of peer-reviewed research articles authored by Hamari Chemicals, Ltd.

  1. Optical Resolution of Rimantadine. Molecules 2019, 24, 1828.
  2. Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine. Symmetry 2019, 11, 578.
  3. Expedient Asymmetric Synthesis of (S)‑2-Amino-4,4,4-trifluorobutanoic Acid via Alkylation of Chiral Nucleophilic Glycine Equivalent. Org. Process Res. Dev. 2019, 23, 629–634.
  4. Large Scale Synthesis of Chiral (3Z,5Z)‑2,7-Dihydro‑1H‑azepine-Derived Hamari Ligand for General Asymmetric Synthesis of Tailor-Made Amino Acids. Org. Process Res. Dev. 2019, 23, 619–628.
  5. Tandem alkylation−second-order asymmetric transformation protocol for the preparation of phenylalanine-type tailor-made α‑amino acids. ACS Omega 2018, 3, 9729–9737.
  6. Second-order asymmetric transformation and its application for the practical synthesis of α-amino acids. Org. Biomol. Chem. 2018, 16, 4968–4972.
  7. 2-Pyrrolidinecarboxamide, N-(2-Benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-,(2R)- and (2S)-. e-EROS reagent article.
  8. Axially chiral Ni(II) complexes of α‐amino acids: Separation of enantiomers and kinetics of racemization. Chirality 2018, 30, 498–508.
  9. Identification of novel plasminogen activator inhibitor-1 inhibitors with improved oral bioavailability: Structure optimization of N-acylanthranilic acid derivatives. Bioorg. Med. Chem. Lett. 2018, 28, 809–813.
  10. An N-protection free ligation of the peptide thioester and the peptide with an N-alkoxy- or N-aryloxyamino group at its N-terminus. Tetrahedron Lett. 201758, 4638–4641.  
  11. Analysis of crystallographic structures of Ni(II) complexes of α-amino acid Schiff bases: Elucidation of the substituent effect on stereochemical preferences. Dalton Trans. 2017, 46, 4191–4198.
  12. Operationally convenient and scalable asymmetric synthesis of (2S)- and (2R)-α-(methyl)cysteine derivatives through alkylation of chiral alanine schiff base NiII complexes Eur. J. Org. Chem. 2017, 14, 1931–1939.
  13. Scale-up synthesis of (R)- and (S)-N-(2-Benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl) pyrrolidine-2-carboxamide hydrochloride, a versatile reagent for the preparation of tailor-made α- and β-amino acids in an enantiomerically pure form. Org. Process Res. Dev. 2017, 21, 732–739.
  14. Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes. Amino Acids 2017, 49, 1487–1520.
  15. Asymmetric synthesis of α-deuterated α-amino acids. Org. Biomol. Chem. 2017, 15, 6978–6983.
  16. Unprecedented property of 4,6-di(substituted)amino-1,2-dihydro-1,3,5-triazines: Formation of acid salts by simple treatment with alkali metal salts of protic acids. Bull. Chem. Soc. Jpn. 2017, 90, 178–187.
  17. Purely chemical approach for preparation of D-α-amino acids via (S)-to-(R)-interconversion of unprotected tailor-made α-amino acids. J. Org. Chem. 2016, 81, 3501–3508.
  18. Asymmetric synthesis of aromatic and heteroaromatic α-amino acids using a recyclable axially chiral ligand. Eur. J. Org. Chem. 2016, 5, 999–1006.
  19. Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base. Amino Acids 2016, 48, 973–986.
  20. Recyclable ligands for the non-enzymatic dynamic kinetic resolution of challenging α-amino acids. Angew. Chem. Int. Ed. 2015, 54, 12918–12922.
  21. Chemical dynamic thermodynamic resolution and S/R interconversion of unprotected unnatural tailor-made α-amino acids. J. Org. Chem. 2015, 80, 9817–9830.
  22. Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2–SN2’ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(II) complex. RSC Adv. 2015, 5, 1051–1058.
  23. Synthesis of (2S,3S)-β-(trifluoromethyl)-α,β-diamino acid by Mannich addition of glycine Schiff base Ni(II) complexes to Ntert-butylsulfinyl-3,3,3-trifluoroacetaldimine. J. Fluorine Chem. 2015, 171, 67–72.
  24. Chemical dynamic kinetic resolution and S/R interconversion of unprotected α-amino acids. Angew. Chem. Int. Ed. 2014, 53, 12214–12217.
  25. Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine. Chem. Commun. 2014, 50, 10295–10298.
  26. Design and synthesis of (S)- and (R)-α-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of α-amino acids. Org. Biomol. Chem. 2014, 12, 6239–6249.
  27. Asymmetric synthesis of α-amino acids under operationally convenient conditions. Adv. Synth. Catal. 2014, 356, 2203–2208.
  28. Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations. Amino Acids 2014, 46, 2047–2073.
  29. Inexpensive chemical method for preparation of enantiomerically pure phenylalanine. Amino Acids 2014, 46, 945–952.
  30. Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)amino]acetyl}amino)benzophenone; A case of configurationally stable stereogenic nitrogen. Beilstein J. Org. Chem. 2014, 10, 442–448.
  31. NH-type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications. Org. Biomol. Chem. 2014, 12, 1278–1291.
  32. Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: Aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of α-amino acids. Amino Acids 2013, 45, 1017–1033.
  33. Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: alkyl halide alkylations. Amino Acids 2013, 45, 691–718.
  34. Chemical deracemization and (S) to (R) interconversion of some fluorine-containing α-amino acids. J. Fluorine Chem. 2013, 152, 114–118.
  35. Synthesis of bis-α,α’-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine. Org. Biomol. Chem. 2013, 11, 4508–4515.
  36. Chemical approach for interconversion of (S)- and (R)-α-amino acids. Org. Biomol. Chem. 2013, 11, 4503–4507.
  37. Structure-Activity Relationships of New N-Acylanthranilic Acid Derivatives as Plasminogen Activator Inhibitor-1 Inhibitors. Chem. Pharm. Bull. 2011, 59, 215–224.
  38. Effect of Carnosine and its Trolox-Modified Derivatives on Life Span of Drosophila melanogaster. Rejuvenation Res. 2010, 13, 453–457.
  39. Structure–Activity Relationships of New 2-Acylamino-3-thiophenecarboxylic Acid Dimers as Plasminogen Activator Inhibitor-1 Inhibitors. Chem. Pharm. Bull. 2010, 58, 615–619.
  40. Bactericidal Effect of HM-242, a Novel Disinfectant, against Pseudomonas aeruginosaBiocontrol Sci. 2010, 15, 7–13.
  41. A novel inhibitor of plasminogen activator inhibitor-1 provides antithrombotic benefits devoid of bleeding effect in nonhuman primates.  J. Cereb. Blood Flow Metab. 2010, 30, 904–912.
  42. Biological Activity of Novel Synthetic Derivatives of Carnosine.  Cell. Mol. Neurobiol. 2010, 30, 395–404.
  43. Synthesis of Novel 4,6-Di(substituted)amino-1,2-dihydro-1,3,5-triazine Derivatives as Topical Antiseptic Agents. J. Med. Chem. 2009, 52, 597–600.
  44. In vitro evaluation of the antimicrobial activity of HM-242, a novel antiseptic compound. J. Antibiot. 2009, 62, 489–493.
  45. A New Synthetic Method of Zinc(II) Complexes Based on Mixing.  Yakugaku Zasshi 2005, 125, 829–832.
  46. L-Carnosine and Close Derivatives Accelerate Zinc Uptake from the lntestine in Rats.  Biomed.Res.Trace.Elements. 2001, 12, 159–167.
  47. Characterization of Crystalline L-carnosine Zn(II) Complex (Z-103), a Novel Anti-gastric Ulcer Agent: Tautomeric Change of Imidazole Moiety upon Complexation. Chem. Pharm. Bull. 1990, 38, 2140–3146.
  48. A simple ring-expansion of 1,4-benzothiazines to give 1,5-benzothiazepines. J. CHEM. SOC., CHEM. COMMUN. 1983, 8, 450–451.

The following is a selected review article authored by Hamari Chemicals, Ltd.

  1. The Second-generation of Highly Potent Hepatitis C Virus (HCV) NS3/4A Protease Inhibitors: Evolutionary Design Based on Tailor-made Amino Acids, Synthesis and Major Features of Bio-activity. Curr. Pharm. Des. 2017, 23, 4493–4554.
  2. New routes to tailor-made amino acids. Speciality Chemicals Magazine March 2016, 36, 42–43.
  3. Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas. Chem. Rev. 2016, 116, 422–518.
  4. Small-molecule therapeutics for Ebola virus (EBOV) disease treatment. Eur. J. Org. Chem. 2016, 1, 8–16.
  5. Tailor-Made α-Amino Acids in the Pharmaceutical Industry: Synthetic Approaches to (1R,2S)-1-Amino-2-vinylcyclopropane-1-carboxylic Acid (Vinyl-ACCA). Eur. J. Org. Chem. 2016, 16, 2757–2774.
  6. Recent advances in the trifluoromethylation methodology and new CF3-containing drugs. J. Fluorine Chem. 2014, 167, 37–54.
  7. Synthesis of fluorine-containing α-amino acids in enantiomerically pure form via homologation of Ni(II) complexes of glycine and alanine Schiff bases. J. Fluorine Chem. 2013, 155, 21–38.

The following is a selected list of patents by Hamari Chemicals, Ltd.

  1. METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID. WO2014188783.
  2. AXIAL-ASYMMETRIC N-(2-ACYLARYL)-2-[5, 7-DIHYDRO-6H-DIBENZO [C, E] AZEPINE-6-YL] ACETAMIDE COMPOUND AND CHIRALITY CONVERSION METHOD FOR [Alpha]-AMINO ACID USING SAME. WO2014098063.
  3. METHOD FOR PRODUCING OPTICALLY ACTIVE ALCOHOL. WO2013061999.
  4. METHOD FOR PRODUCING OPTICALLY ACTIVE TETRAHYDROQUINOLINE. WO2013011930.
  5. METHOD FOR PRODUCING FINE POWDER OF LOXOPROFEN SODIUM DIHYDRATE FOR PHARMACEUTICAL PREPARATIONS. WO2012137667.
  6. NOVEL DIHYDROTRIAZINE DERIVATIVE. WO2010024225.
  7. PROCESS FOR PRODUCTION OF ETHYNYLTHYMIDINE COMPOUND USING 5-METHYLURIDINE AS STARTING RAW MATERIAL. WO2009125841.
  8. METHOD FOR PURIFYING ETHYNYLTHYMIDINE COMPOUND. WO2009119785.
  9. METHOD FOR SYNTHESIZING L-ANSERINE. JP2005082571.
  10. NOVEL 2,4-DIAMINO-1,3,5-TRIAZINE DERIVATIVE. WO2004054989.