Design, Synthesis and Docking Studies of Novel 1, 2, 3-Triazolyl Phenylthiazole Analogs as Potent Anti-HIV-1 NNRT Inhibitors

Kasralikar, Hanmant M.; Jadhavar, Suresh C.; Bhansali, Sujit G.; Patwari, Shivaji B.; Bhusare, Sudhakar R.

doi:10.4172/2161-0444.1000467

Cited by 4 publications

(3 citation statements)

References 21 publications

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“…The newly characterized compounds were evaluated for their antimicrobial, as well as anti-inflammatory, properties [45]. A number of organic and synthetic compounds with a thiazole core are being studied for their potential antibacterial [46,47], anti-human immunodeficiency viruses [48], anticoagulant [49], anti-inflammatory [50], and antioxidant [51] properties.…”

Section: Introductionmentioning

confidence: 99%

Anticancer Studies of Newly Synthesized Thiazole Derivatives: Synthesis, Characterization, Biological Activity, and Molecular Docking

Al-Salmi,

Alrohaimi,

Behery

et al. 2023

Crystals

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Thiazole and its derivatives have received a lot of attention from researchers due to its wide biological, pharmacological, and anticancer properties. A novel series of 2-[2-[4-Hydroxy-3-substituted benzylidene hydrazinyl]-thiazole-4[5H]-ones (4a–c) and acetoxy derivative (5) were synthesized via using thiosemicarbazones (2a–c). The structure of the thiazole derivatives (4a–c) and 5 in these compounds was confirmed by spectroscopic techniques (IR and NMR), as well as elemental investigations. The synthesized derivatives biological activity was assessed based on their capacity to suppress the growth of the cancer cell lines MCF-7 and HepG2, as well as to halt the cell cycle and trigger apoptosis. Among the synthesized thiazole derivatives, compound 4c was found the most active derivative, with inhibitory concentrations IC50 = 2.57 ± 0.16 and 7.26 ± 0.44 µM in MCF-7 and HepG2, respectively, compared to Staurosporine as the standard drug with IC50 6.77 ± 0.41 and 8.4 ± 0.51 µM, respectively. Additionally, compound 4c blocked vesicular endothelial growth factor receptor-2 (VEGFR-2), according to our results (IC50 = 0.15 µM), compared to Sorafenib (IC50 = 0.059 µM) as the standard drug. Moreover, compound 4c induced cell cycle arrest at the G1/S phase, increasing the percentage and accumulation of cancer cells (DNA content) in the pre-G1 phase by 37.36% in MCF-7 cancer cells compared to untreated MCF-7 cells at 2.02%. Also, compound 4c increased the percentage of early and late apoptosis from 0.51% and 0.29%, respectively, in the case of the MCF-7 untreated control sample to 22.39% and 9.51%, respectively, in the MCF-7 treated sample. Furthermore, molecular docking studies of compounds 4a–c and 5 were conducted with four key proteins (aromatase, epidermal growth factor receptor (EGFR), cyclin-dependent kinase 2 (CDK2), and B-cell lymphoma 2 (Bcl-2)) that stimulate the growth, proliferation, and development of cancer cells. Compound 4c exhibited good docking scores with a promising and potential binding affinity toward the active site of selected docked proteins. According to these results, compound 4c showed efficient cytotoxic activity against the tested cancer cells.

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Section: Introductionmentioning

confidence: 99%

Anticancer Studies of Newly Synthesized Thiazole Derivatives: Synthesis, Characterization, Biological Activity, and Molecular Docking

Al-Salmi,

Alrohaimi,

Behery

et al. 2023

Crystals

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“…Nonsteroidal anti-inflammatory drugs (NSAIDs) that act on the affected tissues 3,4 by inhibiting the cyclooxygenase (COX) involved in the synthesis of prostaglandins are one of the major class of drugs used to treat inflammation. 5−9 Various natural as well as synthetic compounds containing the thiazole core moiety have been explored for their antitumor, 10,11 antimicrobial, anti-HIV, 12 anticoagulant, 13 anti-inflammatory, 14 and antioxidant 15 properties since many decades. The available literature also supports the bioactivities of thiazole scaffolds (Figure 1).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Various natural as well as synthetic compounds containing the thiazole core moiety have been explored for their antitumor, , antimicrobial, anti-HIV, anticoagulant, anti-inflammatory, and antioxidant properties since many decades. The available literature also supports the bioactivities of thiazole scaffolds (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Pyridine- and Thiazole-Based Hydrazides with Promising Anti-inflammatory and Antimicrobial Activities along with Their In Silico Studies

et al. 2020

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A new class of compounds formed by the linkage of −C(O)–NH– with pyridine and thiazole moieties was designed, synthesized, and characterized by various spectral approaches. The newly characterized compounds were evaluated for their antimicrobial as well as anti-inflammatory properties. The in vitro anti-inflammatory activity of these compounds was evaluated by denaturation of the bovine serum albumin method and showed inhibition in the range of IC 50 values—46.29–100.60 μg/mL. Among all the tested compounds, compound 5l has the highest IC 50 value and compound 5g has the least IC 50 value. On the other hand, antimicrobial results revealed that compound 5j showed the lowest MIC values and compound 5a has the highest MIC values. Furthermore, molecular docking of the active compounds demonstrated a better docking score and interacted well with the target protein. Physicochemical parameters of the titled compounds were found suitable in the reference range only. The in silico molecular docking study revealed their COX-inhibitory action. Compound 5j emerged as a significant bioactive molecule among the synthesized analogues.

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Molecular and Electronic Structures, Spectra, Electrochemistry and Anti‐bacterial Efficacy of Novel Heterocyclic Hydrazones of Phenanthrenequinone and Their Nickel(II) Complexes

et al. 2022

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A pair of tridentate ligands incorporating heterocyclic hydrazones of 9,10‐phenanthrenequinone viz,. pyridyl‐hydrazino‐phenathrenequinone HLPy 1a and benzothiazolyl‐hydrazino‐phenathrenequinone HLBenz 1b have been synthesized and both behave as monoanionic towards nickel(II), forming meridional octahedral complexes of type [Ni(LPy)2] 2a and [Ni(LBenz)2] 2b as evident from single crystal X‐ray diffraction studies. The complexes are electro‐active in solution and nature of redox orbitals has been analysed by theoretical means. They display two oxidative and two reductive responses that have been ascribed to the redox processes of coordinated ligands. The electronic absorption spectral patterns of two complexes are analogous barring the fact that lower energy transition for 2b is marginally bathochromically shifted relative to that of 2a and it has been clarified by TD‐DFT studies. Anti‐bacterial efficacy of the ligands HLPy 1a, HLBenz 1b and complexes [Ni(LPy)2] 2a, [Ni(LBenz)2] 2b against four Gram‐positive and four Gram‐negative strains has been explored. [Ni(LPy)2] 2a exhibits more pronounced efficacy than [Ni(LBenz)2] 2b and these are greater than those of the corresponding ligands. The mode of action of 2a is essential via DNA damage while protein leakage and membrane lipid damage were observed upon treatment with 2b.

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Design, Synthesis and Docking Studies of Novel 1, 2, 3-Triazolyl Phenylthiazole Analogs as Potent Anti-HIV-1 NNRT Inhibitors

Cited by 4 publications

References 21 publications

Anticancer Studies of Newly Synthesized Thiazole Derivatives: Synthesis, Characterization, Biological Activity, and Molecular Docking

Anticancer Studies of Newly Synthesized Thiazole Derivatives: Synthesis, Characterization, Biological Activity, and Molecular Docking

Pyridine- and Thiazole-Based Hydrazides with Promising Anti-inflammatory and Antimicrobial Activities along with Their In Silico Studies

Molecular and Electronic Structures, Spectra, Electrochemistry and Anti‐bacterial Efficacy of Novel Heterocyclic Hydrazones of Phenanthrenequinone and Their Nickel(II) Complexes

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