24091-06-3

Upstream product

• 79-19-6 thiosemicarbazide 
• 66-99-9 β-naphthaldehyde 

Downstream Products

• 1335143-53-7 [BiCl₃(1-(2-methoxybenzylidene)thiosemicarbazide)(H₂O)]*H₂O 
• 1427161-65-6 2-naphthaldehyde-[4-(2-hydroxy-5-methoxyphenyl)-1,3-thiazol-2-yl]hydrazone 

Relevant academic research and scientific papers

Design and efficient synthesis of novel 4,5-dimethylthiazole-hydrazone derivatives and their anticancer activity

Background: Recently, researchers have been warning about the increased mortality of the various cancer types. Also, the lung adenocarcinoma and the glioma types are burning issues for world's health due to late or wrong diagnosis and/or insufficient treatment methods. For this purpose, our research group designed and synthesized novel 4,5-dimethyl thiazole-hydrazone derivatives which were tested against cancer and normal cell lines to understand the structure-activity relationship (SAR). Methods: The lead compounds were obtained by reacting 2-(substituted aryl-2-ylmethylene) hydrazin-1-carbothioamide with 3-chloro-2-butanone derivatives. The structural elucidation of the compounds was performed by1H-NMR,13C-NMR, and LC/MS-IT-TOF spectral and elemental analyses. The synthesized compounds were tested in vitro for the anticancer activity against A549 human lung adenocarcinoma and C6 rat glioma cells and investigated for which pathway to induce cell death. Also, the docking study of the active compounds was achieved to understand the SAR. Results: The targeted compounds (2a-2l) were synthesized successfully above 70% yields, and the analysis findings proved their purity. In general, the results of activity studies displayed significant effects against at least one cell line, except compounds 2e (indol-3-yl) and 2h (4-dimethylaminophenyl). Furthermore, compounds 2b and 2f displayed potential anticancer activity. With the help of molecular docking study, a potential selectivity of compound 2f was observed for type II protein kinase. On the other hand, compound 2b interacted with the active site nearly the same as Dasatinib. Therefore, these two compounds could be used as a base on developing selective anticancer drugs. Conclusion: Pyridin-2-yl (2b) derivative was found to be a favorable molecule with high anticancer potency against C6 and A549 cell lines. Additionally, 1-naphthyl (2f) derivative was a worthy compound for potential selectivity. In future studies, it will be our priority to focus on developing derivatives of these two compounds (2b and 2f) and elucidate their mechanisms.

Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-D-hexosaminidase and chitinase

Insect chitinase and N-acetyl-β-D-hexosaminidases (Hex) are potential targets for developing new pesticides. Here, a series of thiazolylhydrazones I (with substituted group R1 at N3) and II (with substituted group R1 at N2) were designed, synthesised and evaluated as competitive inhibitors of OfHex1 and OfChi-h, from the agricultural pest Ostrinia furnacalis. Derivatives I-3d and II-3d, with phenoxyethyl group at R1, demonstrated the best inhibitory activities against OfHex1 and OfChi-h. Molecular docking analysis indicated that the branched conformation compound II-3d (Ki = 1.5 μmol/L) formed more hydrogen bonds with OfHex1 than the stretched conformation compound I-3d (Ki = 5.9 μmol/L). The differences in compounds’ binding conformations with OfChi-h explained differences in inhibitory activity of compounds I-3d (Ki = 1.9 μmol/L) and II-3d (Ki = 4.1 μmol/L). This work suggests a novel scaffold for developing specific Hex and Chi-h inhibitors.

Design and synthesis of thiazolylhydrazone derivatives as inhibitors of chitinolytic N-acetyl-β-D-hexosaminidase

N-acetyl-β-D-hexosaminidase (Hex) is potential target for pesticide design. Here, a series of thiazolylhydrazone derivatives were designed, synthesized and evaluated as competitive inhibitors of OfHex1, a Hex from the agricultural pest Ostrinia furnacalis. The derivative 3k, with a (benzyloxy)methyl group at the N3 atom, demonstrated greater potency with a Ki of 10.2 μM. Molecular docking analysis indicated that the (benzyloxy)methyl group of 3k was bound to a previously unexplored pocket formed by Loop478-496. Then further optimization around naphthalene ring led to find the more potency substituent phenyl. The derivative 7, with phenoxyethyl group at R1 and a phenyl group at R2, demonstrated an augmented potency with a Ki of 2.1 μM. Molecular docking analysis indicated that 7 was bound to the active pocket of OfHex1 more favorably than 3k. This work suggests a novel scaffold for developing specific Hex inhibitors.

Microwave-assisted synthesis and antitumor evaluation of a new series of thiazolylcoumarin derivatives

A new series of thiazolylcoumarin derivatives was synthesized. The designed strategy embraced a molecular hybridization approach which involves the combination of the thiazole and coumarin pharmacophores together. The new hybrid compounds were tested for

Synthesis, molecular docking, acetylcholinesterase and butyrylcholinesterase inhibitory potential of thiazole analogs as new inhibitors for Alzheimer disease

A series of thirty (30) thiazole analogs were prepared, characterized by 1H NMR, 13C NMR and EI-MS and evaluated for Acetylcholinesterase and butyrylcholinesterase inhibitory potential. All analogs exhibited varied butyrylcholinester

Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives

Eighteen new hydrazino-1,3-thiazole derivatives were evaluated against 8 strains of multi-resistant Candida spp. Introduction of an indolyl moiety linked to the hydrazone function enhanced the in vitro anti-Candida activity, with an activity spectrum towards Candida albicans strains. Introduction of a (S)-2-aminoethyl chain on the thiazole nucleus largely enhanced the in vitro antifungal activity, with a selectivity oriented towards non-C. albicans species.

Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase

Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the transformation of tyrosine into l-dopaquinone. The aim of the present study was to study molecules able to inhibit tyrosinase to be used in treating depigmentation-related disorders. In this study, we targeted arylthiosemicarbazone analogs with the aim to contribute to the identification of the optimal aryl ring to be linked to the thiosemicarbazone moiety. The biological activity was evaluated on commercial mushroom tyrosinase which was purified prior use. The results demonstrated that several of our compounds (1a-h, 1j, 1r and 5) had more potent inhibitory activities than kojic acid which was used as the reference inhibitor.

Elaborated 1H NMR study for the ligitional behavior of two thiosemicarbazide derivatives towards some heavy metals (Sn(II), Sb(III), Pb(II) and Bi(III)), thermal, antibacterial and antifungal studies

A new series of heavy metal complexes are prepared. Sn(II), Sb(III), Pb(II) and Bi(III) are the metal ions used in complexation with two thiosemicarbazide ligands. The IR and 1H NMR spectra of the free ligands display their presence in thiole-thione forms coincide with each other. The IR spectra of the complexes support the presence of 2:2 molar ratio (M:HL) with HL1 ligand and 1:1 beside 1:2 with HL2. The ligand coordinates as bi molecules in some complexes and displays two tautomer forms at the same complex molecule 1H NMR spectra of Sn(II) and Sb(III) complexes were done and comes coincide with IR data. The electronic spectral analysis displays a lower shift appearance in n → π* charge transfer band in most isolated complexes. As well as, a new band is shinned in visible region with Sb(III), Bi(III) complexes and Sn(II)-HL2. This band is pointed to its use in spectrophotometric analysis for these metal ions. The TG analysis for all isolated compounds was briefly discussed. The molecular modeling parameters support the stability of thiole form of the free ligands in comparing with their thiones by a small difference. The antibacterial and antifungal activities were studied against some organisms and reveal the priority of most investigated complexes.