Design-based synthesis, molecular docking analysis of an anti-inflammatory drug, and geometrical optimization and interaction energy studies of an indole acetamide derivative

Al-Ostoot, Fares Hezam; Geetha, D. V.; Mohammed, Yasser Hussein Eissa; Akhileshwari, P.; Sridhar, M. A.

doi:10.1016/j.molstruc.2019.127244

Cited by 34 publications

(13 citation statements)

References 47 publications

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“…Futher the ligand molecule structures were drawn using Chem Draw Professional 16.0, and the energies minimization were performed using Chem3D 16.0. All molecular docking was carried out with the AutoDockTools-1.5.6 (ADT) [ 28 ]. This is one of the docking engines with the most common use.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, structural characterization, and DFT studies of anti-cancer drug N-(2-Aminophenyl)-2-(4-bromophenoxy)acetamide

Chandana¹,

Al-Ostoot

Mohammed

et al. 2021

Heliyon

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Drug design is an integrated and developing system that portends an era of a novel and safe tailored drugs. It involves studying the effects of biologically active synthetic, semi-synthetic, and natural compounds based on molecular interactions in terms of molecular structure with activated functional groups or its unique physicochemical properties involved. The title compound, N -(2-aminophenyl)-2-(4-bromophenoxy) acetamide ( c ), was synthesized in a good yield and characterized by different spectroscopic techniques ( 1 H, 13 CNMR, and LC-MS) and finally, the structure was confirmed by X-ray diffraction (XRD) studies. The XRD data confirms that the cryatal structure is orthorhombic with space group of Pca2 1 . The intermolecular interactions (N–H … O and N–H … Cg) inside the molecule stabilizes the crystal structure. The existence of this intermolecular interactions are computed by the Hirshfeld surfaces (HS) and two-dimensional (2D) fingerprints plot analysis. In addition to this, Energy frame work analysis is performed to quantify the interaction energies between the molecular pairs in a crystal by incorporating new version of CrystalExplorer17 using the energy model of HF/3-21G. Also to calculate the HOMO and LUMO energies, DFT calculations were carried out.

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Section: Methodsmentioning

confidence: 99%

Synthesis, structural characterization, and DFT studies of anti-cancer drug N-(2-Aminophenyl)-2-(4-bromophenoxy)acetamide

Chandana¹,

Al-Ostoot

Mohammed

et al. 2021

Heliyon

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“…The indole nucleus as a versatile and unique scaffold is frequently found in the medicinal chemistry and experimental drug design field with marvellous characteristics [ 140 ]. Due to the presence of an electron-rich pyrrole moiety [ 141 , 142 ], that can use non-covalent interactions with various other molecules through hydrogen bonding formation between NH moiety and π–π system [ 143 ]. Because of this ideal property, indole and its diverse derivatives are widely used for the design and development of novel drugs [ 144 ].…”

Section: An Overview Of Heterocycles Containing Nitrogen As Possible mentioning

confidence: 99%

“…Quinoline-based Schiff base derivatives (144) have been introduced by Muhammad Taha et al [188] by refluxing methanolic mixture of methyl quinoline-6-carboxylate (142) and hydrazine hydrate for 6 h to obtain quinoline-6-carbohydarzide (143). The intermediate ( 143) was then refluxed for 3 h with various aromatic aldehydes in the presence of 5-6 drops of glacial acetic acid to obtain quinoline derivatives (Z)-N'-ethylidenequinoline-6-carbohydrazide (144) as shown in Scheme 24.…”

Section: Introduction To Synthesis Of Quinoline and Its Derivativesmentioning

confidence: 99%

Recent investigations into synthesis and pharmacological activities of phenoxy acetamide and its derivatives (chalcone, indole and quinoline) as possible therapeutic candidates

2021

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Graphical abstract Medicinal chemistry can rightfully be regarded as a cornerstone in the public health of our modern society that combines chemistry and pharmacology with the aim of designing and developing new pharmaceutical compounds. For this purpose, many chemical techniques as well as new computational chemistry applications are used to study the utilization of drugs and their biological effects. In the biological interface, medicinal chemistry constitutes a group of interdisciplinary sciences, as well as controlling its organic, physical and computational pillars. Therefore, medicinal chemists working to design an integrated and developing system that portends an era of novel and safe tailored drugs either by synthesizing new pharmaceuticals or to improving the processes by which existing pharmaceuticals are made. It includes researching the effects of synthetic, semi-synthetic and natural biologically active substances based on molecular interactions in terms of molecular structure with triggered functional groups or the specific physicochemical properties. The present work focuses on the literature survey of chemical diversity of phenoxy acetamide and its derivatives (Chalcone, Indole and Quinoline) in the molecular framework in order to get complete information regarding pharmacologically interesting compounds of widely different composition. From a biological and industrial point of view, this literature review may provide an opportunity for the chemists to design new derivatives of phenoxy acetamide and its derivatives that proved to be the successful agent in view of safety and efficacy to enhance life quality.

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“…In other hand COX-1 is housekeeping enzyme which is helps in homeostatic functions, which includes vascular antithrombotic activity, cytoprotection of such as gastric mucosal [7]. The development of speci c COX-2 inhibitors with non-reactive COX-1 along with fewer or no side effects has been the main attractive target for many researchers for many decades [8][9][10]. Heterocyclic compounds have a versatile role in the area of different elds of sciences such as chemistry, biology, biochemistry, drug design, and medicinal chemistry [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization of Novel N'(2-Phenoxyacetyl)Nicotinohydrazide and N'(2-Phenoxyacetyl)Isonicotinohydrazide Derivatives as Anti-Inflammatory and Analgesic Agents

Al-Ostoot

Vivek

et al. 2021

Preprint

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A new derivatives of isonicotinohydrazide 9 (a-e) and 10(a-e) were designed, synthesized, characterized based on the different spectroscopic analysis FT-IR, -1H, -13C-NMR, mass spectra, and also elemental-analyses, and identified as a remarkable anti-inflammatory along with analgesic effect. In-vitro and in-vivo anti-inflammatory and analgesic actions were performed using analgesic acetic acid-induced squirming and Hot plate latency tests using male Swiss albino mice. The study was supported by the in-silico and ADMET approaches. Among the series, compound (10e) showed the highest IC50 value for COX-1 inhibition, whereas compounds (9e) and (10e) exhibited the highest COX-2 SI. Further, in silico studies provide a putative bind site for the potent compound in a three-dimensional geometrical view. The results revealed that the title compound (10e) with bromo group exhibited potent COX-2 inhibitor at different times which is on par with the normal drug used in the assay system. Substitution of halogens at N’(2-phenoxyacetyl)nicotinohyrazide showed (10e) potent analgesic outcome on acetic acid-induced squirming response and thermal pain among the series 9(a-e) and 10(a-e). The overall pharmacological result suggests that the newly synthesized compounds possess good anti-inflammatory along with analgesic-activity which was evaluated through in-vitro, in-vivo, and --silico studies.

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Design-based synthesis, molecular docking analysis of an anti-inflammatory drug, and geometrical optimization and interaction energy studies of an indole acetamide derivative

Cited by 34 publications

References 47 publications

Synthesis, structural characterization, and DFT studies of anti-cancer drug N-(2-Aminophenyl)-2-(4-bromophenoxy)acetamide

Synthesis, structural characterization, and DFT studies of anti-cancer drug N-(2-Aminophenyl)-2-(4-bromophenoxy)acetamide

Recent investigations into synthesis and pharmacological activities of phenoxy acetamide and its derivatives (chalcone, indole and quinoline) as possible therapeutic candidates

Synthesis, Characterization of Novel N'(2-Phenoxyacetyl)Nicotinohydrazide and N'(2-Phenoxyacetyl)Isonicotinohydrazide Derivatives as Anti-Inflammatory and Analgesic Agents

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