Synthesis, spectral investigation, molecular docking and biological evaluation of Cu(II), Ni(II) and Mn(II) complexes of (E)-2-((2-butyl-4-chloro-1H-imidazol-5-yl)methylene)-N-methylhydrazinecarbothioamide (C10H16N5ClS) and its DFT studies

Reddy, A. Sreenath; Mao, Jincheng; Krishna, L. Sivarama; Badavath, Vishnu Nayak; Maji, Siddhartha

doi:10.1016/j.molstruc.2019.06.085

Cited by 19 publications

(6 citation statements)

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“…The synthesized compounds in the present work were screened for cytotoxicity using MTT assay against a panel of cancer cell lines including HEK(human embryonic kidney 293 cells), DU145(human prostate cancer), MCF‐7(human breast adenocarcinoma), MDA‐MB‐231(human breast cancer), Miapaca‐2 (human pancreatic cancer), HeLa(cervical cancer cell) and HepG2 (human liver cancer cell line) at 10 μM concentration (Table ) . Compounds with more than 50% inhibition were considered as active compounds and IC 50 values were determined from the dose response curves.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

et al. 2019

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Designed, synthesized a series of novel imidazo[1,2-a]pyridine derivatives and evaluated for their in vitro cytotoxicity. Fluorine containing compounds, (2-fluorophenyl)(4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)methanone (7 e),(4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)(2-(trifluoromethyl)phenyl)methanone (7 h) and (3-fluorophenyl) (4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)methanone (7 i) were found to have an effective cytotoxic profile against HepG2, HeLa and MDA-MB-231. Compounds 7 h (IC 50 = 5.8 μM) and 7 i (IC 50 = 3.5 μM) were found potent when compared with control Paclitaxel (IC 50 = 2.8 μM), against HeLa. Compound 7 h also found to be potent against HepG2 (IC 50 = 2.0 μM) and MDAMB-231(IC 50 = 6.9 μM) respectively, when compared with Paclitaxel (HepG2, IC 50 = 0.56 μM; MDAMB-231, IC 50 = 1.9 μM). Compound 7 e also found to be potent against HepG2 (IC 50 = 9.8 μM) cell lines. Synthesized piperazine linked imidazo[1,2-a]pyridine derivatives (7 i, IC 50 = 3.5 μM) and (7 h, IC 50 = 5.8 μM) showed 1.74 fold, 1.12 fold increase in antiproliferative activity than reported homopiperazine linked imidazo [1,2-a]pyrimidine derivatives (4-Fluorophenyl)(4-(2-(4fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl)-1,4-diazepan-1-yl)methanone(10 f, IC 50 = 6.12 μM) and (4-(2-(4-Fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl)-1,4-diazepan-1-yl)(3methoxyphenyl)methanone (12, IC 50 = 6.54 μM) against Hela cell lines. Molecular docking studies showed that designed compounds occupy at the active site of both colchicine and human estrogen receptor which demonstrated that the designed compounds were able to bind with multiple targets, the biological activity of these compounds hold promise to find application in considering for treatment protocol.[a] M.

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Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

et al. 2019

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“…Jabbi et al stated that when their Schiff base ligand was coordinated with metals, there was a shift to lower frequencies of 1573 and 1614 cm −1 for the metal Schiff base complexes [3]. Reddy et al reported the range for the infrared vibrational frequencies for azomethine groups to be between 1550 and 1650 cm -1 , and Sadi et al stated the infrared vibrational frequency for the synthesized Schiff base as 1561 cm -1 , while Xavier et al confirmed the formation of azomethine (-C=N-) with a medium to strong stretching frequency range between 1587 and 1620 cm -1 [8,17,62].…”

Section: Elemental Analysis (Ea)mentioning

confidence: 99%

Ease to Challenges in Achieving Successful Synthesized Schiff Base, Chirality, and Application as Antibacterial Agent

Odularu

2023

BioMed Research International

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This study reports how to overcome the challenges experienced in achieving successful synthesized Schiff base via types of Schiff base (chiral and achiral), synthesis, nature of products, and its antibacterial applications. Schiff base is a versatile ligand which is useful in asymmetric reactions to prepare chiral catalysts. It is also used in symmetric reactions to prepare achiral compounds. In line with the achiral compounds, conventional (room temperature and refluxing) and microwave irradiation methods are the two main types of methods to synthesize achiral Schiff base as reported in this review. Among various experimental approaches, this study supports the green chemistry microwave approach to synthesize Schiff base because of its benefits environmental sustainability. Problems relating to the nature of products formed from the synthesized Schiff bases were examined and resolved. Herein, the products could either be solid (crystals, powder, and precipitate), oily, or viscous (sticky) products. Some familiar characterization techniques used to identify and confirm the successful syntheses of Schiff bases, such as solubility test, melting point (MP), Fourier transform infrared (FTIR), ultraviolet-visible (UV-Vis), and nuclear magnetic resonance (NMR, 1H NMR, and 13C NMR), were discussed. In addition, the antibacterial studies on Schiff base and corresponding metal complexes confirmed their biological relevance to the human.

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“…Synthesis and characterization of CHz ( 1 H NMR, 13 C NMR, FTIR, MS, and TGA) and characterization of CuCHz (FTIR, MS, and TGA); spectroscopic studies of the inclusion complex between CuCHz and DMβCD; and interaction studies between the Cu(II) complex and ctDNA in the presence and absence of heptakis-2,6-Odimethyl-β-cyclodextrin, DMβCD (PDF)…”

Section: ■ Associated Contentmentioning

confidence: 99%

“…They have attracted attention in recent years because of their diverse pharmacological properties such as antimycobacterial, antifungal, anticancer, antioxidant, antihypertensive, and anti-inflammatory effects. , Transition-metal complexes obtained from 3-formylchromone Schiff bases have still received considerable attention, in view of their chelating ability exhibiting efficient ct DNA binding. − This type of compounds bearing N and O donors has structural similarities to neutral biological systems in which the CN linkage of azomethine derivatives is essential for their displayed biological activity. Also, it has been demonstrated that this chelating activity is enhanced on chelation with metal atoms due to the increase in the planarity of the intercalators, allowing the insertion of the complexes and their stacking between the base pairs of double-helical ct DNA more easier than the free ligands. , A number of metal complexes (Cu(II), Zn(II), Pd(II), Pt(II), Ni(II), La(III), Ru(II), Sm(III), and Nd(III)) with Schiff base derivative have been reported, and their ct DNA-binding properties have been studied. − Nevertheless, these metal complexes have a disadvantage due to their water solubility, which is still unsatisfactory, restricting their use as anticancer agents. , …”

Section: Introductionmentioning

confidence: 99%

Influence of DMβCD on the Interaction of Copper(II) Complex of 6-Hydroxychromone-3-carbaldehyde-3-hydroxybenzoylhydrazine with ctDNA

et al. 2020

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The interaction mechanism between a scarcely soluble copper(II) complex of Cu(II)-6-hydroxychromone-3-carbaldehyde-(3′-hydroxy)benzoylhydrazone (CuCHz) in aqueous solution and its DMβCD complex was studied in the presence of ctDNA through spectroscopy and thermodynamic methods. The thermodynamic results indicate that the binding process of the CuCHz–DMβCD inclusion complex is a spontaneous process and the inclusion is enthalpy-driven. The binding constants of CuCHz and CuCHz–DMβCD with ctDNA are 2.69 × 103 and 14.7 × 103 L mol–1, respectively. The stoichiometry of the complex is 1:1, and the determined thermodynamic indicates that the process of binding is spontaneous and entropy-driven. A competitive binding titration with ethidium bromide revealed that CuCHz efficiently displaces EB from the EB–DNA system. In addition to the thermal denaturation experiments and docking studies, we can confirm that the mode of binding of this complex to ctDNA is intercalation mode. The presence of DMβCD enhances the aqueous solubility of CuCHz; nevertheless, the cyclodextrin did not affect the interaction of CuCHz with ctDNA because the inclusion complex breaks down when it binds with ctDNA.

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Synthesis, spectral investigation, molecular docking and biological evaluation of Cu(II), Ni(II) and Mn(II) complexes of (E)-2-((2-butyl-4-chloro-1H-imidazol-5-yl)methylene)-N-methylhydrazinecarbothioamide (C10H16N5ClS) and its DFT studies

Cited by 19 publications

References 50 publications

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

Ease to Challenges in Achieving Successful Synthesized Schiff Base, Chirality, and Application as Antibacterial Agent

Influence of DMβCD on the Interaction of Copper(II) Complex of 6-Hydroxychromone-3-carbaldehyde-3-hydroxybenzoylhydrazine with ctDNA

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