Synthesis and Evaluation of Biological Properties of 2-Amino-thiazole-4-carboxamides: Amide Linkage Analogues of Pretubulysin

Ouyang, Ben; Wang, Linan; Qi, Jianpeng; Fan, Meixia; Wang, Haolin; Yao, Lei

doi:10.1248/bpb.b20-00278

Cited by 4 publications

(3 citation statements)

References 20 publications

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“…2-Aminothiazoles and 2-aminoselenazoles constitute important classes of heterocyclic compounds due to their versatile applications. Thus, the 2-aminothiazole partial structure is a significant pharmacophore 1 of a broad variety of therapeutics and drugs, covering the range from antitumor, 2 3 4 5 6 antibacterial, 7 antitubercular, 8 anti-leishmanial, 9 and antioxidant 10 agents to phosphodiesterase-5 antagonists. 11 As examples, Figure 1 shows some structures of clinical drugs bearing the 2-aminothiazole pharmacophore.…”

Section: Table 1 Yields (%) Of 4aa ...mentioning

confidence: 99%

“…Thus, the amino group is readily susceptible towards acylation, alkylation or condensation reactions. 3 4 , 15 16 17 18 The selenium analogs of 2-aminothiazoles have also attracted much attention as biologically active compounds. 19 Antibiotic and neuroprotective, 20 anticancer, 18 21 antifungal, 22 antimicrobial as well as anticonvulsant 23 24 activities have been reported, and high-affinity inhibitors of kinase CK2 and efficient phosphorescence biomarkers have also been described.…”

Section: Table 1 Yields (%) Of 4aa ...mentioning

confidence: 99%

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One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones

et al. 2022

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Both one-pot and two-step procedures for the synthesis of substituted 2-aminothiazoles and 2-aminoselenazoles are described. Anilines are first converted into arenediazonium bromides, which are then reacted with methyl vinyl ketone or cyclopropyl vinyl ketone in the presence of copper(II) bromide to give 4-aryl-3-bromobutan-2-ones (40–71%) and 3-aryl-2-bromo-1-cyclopropylpropan-1-ones (41–79%), respectively. These products are reacted, without prior isolation, with thiourea or selenourea to prepare 4-methyl- and 4-cyclopropyl-5-(R-benzyl)thiazol-2-amines (14 examples) and their selenium analogs (14 examples). The yields of the one-pot procedure are higher (40–81%) than those of the two-step procedure (32–70%).

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Section: Table 1 Yields (%) Of 4aa ...mentioning

confidence: 99%

Section: Table 1 Yields (%) Of 4aa ...mentioning

confidence: 99%

One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones

et al. 2022

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“…Meanwhile, the Mep and Tup parts were tolerant of many structural modifications (Burkhart et al., 2011; Kubicek et al., 2010; Patterson et al., 2007). In our laboratory, we previously found that the compounds with urea group in Mep part would still possess certain antitumor activity (Ouyang et al., 2020; Peng et al., 2019). For example, Compounds 2 and 3 (Figure 1) exhibited antiproliferative activity against MCF‐7 human breast cell lines with an IC 50 value of 0.2 and 0.47 µM, respectively.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and antitumor activity evaluation of pretubulysin analogs

Fan

et al. 2021

Chem Biol Drug Des

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Pretubulysin, a biosynthetic precursor of the tubulysins, shows potent biological activity in a variety of tumor cell lines. Although there are several total synthesis routes to tubulysin and pretubulysin reported, the commercialization still has been hampered due to the complexity of the structure. To find structurally simpler pretubulysin analogs, a series of 2‐(3‐(methylamino)propyl)thiazole‐4‐carboxamides are designed and synthesized, and their anticancer activities are screened using MCF‐7 (breast cancer), and NCI‐H157 (lung cancer) cell lines. Taxol (IC50 = 0.01 µM) and pretubulysin are used as the control. Compounds 8c (IC50 = 0.05 µM, MCF‐7; 0.09 µM, NCI‐H157) and 8h (IC50 = 0.01 µM, MCF‐7; 0.02 µM, NCI‐H157) exhibited certain antitumor activities comparable to those of Taxol. The urea analogs of pretubulysin might represent a promising scaffold for the further development of novel antitumor drugs.

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Bioenergetic characteristics of the murine Nemeth-Kellner lymphoma cells exposed to thiazole derivative in complex with polymeric nanoparticles

Popovych¹,

Shalai²,

Mazur³

et al. 2023

Ukr.Biochem.J.

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The development of a new anticancer drugs targeted at energy metabolism of tumor cells is a promising approach for cancer treatment. The aim of our study was to investigate the action of thiazole derivative N-(5-benzyl-1,3-thiazol-2-yl)-3,5-dimethyl-1-benzofuran-2-carboxamide (BF1) and its complex with PEG based polymeric nanoparticle (PEG-PN) on respiration and mitochondrial membrane potential in murine NK/Ly tumor cells. The rate of oxygen uptake in NK/Ly cells was recorded by a polarographic method using a Clark electrode. The mitochondrial potential relative values were registered using fluorescence TMRM dye. No changes in glucose-fuelled basal respiration or maximal FCCP-stimulated respiration was detected after 15-min incubation of cells with BF1 (10 µM), PEG-PN or BF1 + PEG-PN complex Fluorescent microscopy data showed that BF1 or PEG-PN separately had no effect on the value of mitochondrial membrane potential, while BF1 + PEG-PN complex caused a significant decrease in mitochondrial membrane potential, indicating on the decrease of NK/Ly cells viability. Keywords: cell respiration, mitochondrial membrane potential, NK/Ly tumor cells, PEG, polymeric nanoparticles, thiazole derivative

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Synthesis and Evaluation of Biological Properties of 2-Amino-thiazole-4-carboxamides: Amide Linkage Analogues of Pretubulysin

Cited by 4 publications

References 20 publications

One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones

One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones

Design, synthesis, and antitumor activity evaluation of pretubulysin analogs

Bioenergetic characteristics of the murine Nemeth-Kellner lymphoma cells exposed to thiazole derivative in complex with polymeric nanoparticles

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