Synthesis and antioxidant screening of Novel indole amines

Rubab, Syeda Laila; Nisar, Bushra; Raza, Abdul Rauf; Saadia, Mubshara; Tahir, Muhammad Nawaz; Sajjad, Noreen; Shanavas, S.; Sharmila, V.; Acevedo, R.

doi:10.1007/s13738-021-02482-8

Cited by 5 publications

(3 citation statements)

References 35 publications

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“…Indoles are promising scaffolds in the medicinal world. Due to versatile applications of natural and synthetic indole derivatives in biological and pharmacological fields, they are being used as drugs, e.g., anti-HIV [4], anticancer [5][6], antimicrobial [7], antioxidant [8][9], anti-inflammatory [10], anticholinesterase [11], antidepressant [12], antihistaminic [13], antiparkinson [14], antitumor [15,16], tubulin inhibitors [17] and receptor inhibitors [18].…”

Section: Applications Of Indole Derivativesmentioning

confidence: 99%

A Brief Review of the Medicinally Important Indole Derivatives

Dube,

Chaudhari,

Thakare

et al. 2023

JAZ

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Indole is an exceptional heterocyclic molecule with a broad spectrum of pharmacological activity owing to various modes of action. It is also a versatile pharmacophore and a favored scaffold. For drug development, it is an excellent moiety whose only characteristic is that it resembles many protein structures. Plenty of research has been taking place in recent years to synthesize and explore the various therapeutic prospective of this moiety. This review summarizes some of the recent effective chemical synthesis (2014-2018) for indole ring. Some of the most recent efficient chemical synthesis for the indole ring (from 2014 to 2018) is compiled in this review. The structure-activity relationship (SAR) was also given a lot of weight in this review in order to pinpoint the active pharmacophores of different indole analogues that have been the subject of studies for the past five years and are responsible for a variety of effects, including antiviral, antitubercular, anticancer, and anticonvulsant ones. The goals and framework of every research issue are explained in detail to help medicinal chemists have a deeper understanding of the circumstances contextually. Researchers will undoubtedly use this review as a platform to strategically design a variety of novel indole derivatives with lower toxicity and side effects and a range of intriguing pharmacological activity.

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Section: Applications Of Indole Derivativesmentioning

confidence: 99%

A Brief Review of the Medicinally Important Indole Derivatives

Dube,

Chaudhari,

Thakare

et al. 2023

JAZ

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“…Reactive oxygen species (ROS), which are commonly generated as byproducts of chemical reactions within the human body, in ict harmful effects on living cells. Oxidative stress occurs when the body's natural antioxidant defense system cannot effectively neutralize the free radicals produced within the body [11][12][13]. The antioxidant activity is a biological property of small molecules that have been widely studied and is related to the treatment and prevention of several diseases, including in ammatory diseases (e.g., rheumatoid arthritis), diabetes and neurodegenerative diseases (e.g., Alzheimer's disease) [14,15].…”

Section: Introductionmentioning

confidence: 99%

Standalone methodology for building QSAR models: an antioxidant QSAR model of di(hetero)aryl amines and amides as a case study

Mateus,

Abreu

2024

Preprint

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QSAR modeling is a methodology used in various scientific fields to correlate molecular descriptors to the properties or biological activities of compounds of interest. Several steps are needed to construct a QSAR model, including chemical structure preparation, molecular descriptor calculation and selection, and model building and validation. We present a complete methodology for preparing QSAR models using free and open-source software tools. A detailed step-by-step protocol is provided with the complete process of QSAR modeling, from compound library preparation to statistical validation. A QSAR model was developed as a case study to model the antioxidant activity, particularly the radical scavenging activity of 70 di(hetero)aryl amine and amide compounds. The OCHEM platform was used to calculate the 12,072 molecular descriptors. These molecular descriptors and the experimental pIC50 for each compound were introduced in PyQSAR software, and a genetic algorithm was used to select four molecular descriptors to build the QSAR model: B06[C-O], Eig04_AEA(dm), JGI2 and J_Dz(p). The QSAR model was then implemented by applying multiple linear regression, and a final equation was obtained. The QSAR model presents excellent statistical parameters that verify its robustness and predictability, namely, the correlation coefficient (R2 = 0.8905), the mean score value of the MLR method (Q2CV = 0.8676) and the relative standard deviation of the residuals (RSR = 0.3320 and RSRCV=0.3518). This QSAR model will guide the synthesis of new di(hetero)aryl amines or amides with improved antioxidant activities. All files and the complete protocol are provided to replicate the building of the presented antioxidant QSAR model, and researchers will be able to prepare other QSAR models using different compound libraries and different biological activities.

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“…Indoles are promising scaffolds in the medicinal world. Due to versatile applications of natural and synthetic indole derivatives in biological and pharmacological fields, they are being used as drugs, e.g., anti-HIV [ 1 ], anticancer [ 2 , 3 ], antimicrobial [ 4 ], antioxidant [ 5 , 6 ], anti-inflammatory [ 7 ], anticholinesterase [ 8 ], antidepressant [ 9 ], antihistaminic [ 10 ], anti-Parkinson [ 11 ], antitumor [ 12 , 13 ], tubulin inhibitors [ 14 ] and receptor inhibitors [ 15 ]. We have already successfully synthesized and published many series of indole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Antimicrobial, Anticholinesterase Potential of Indole Derivatives and Unexpectedly Synthesized Novel Benzodiazine: Characterization, DFT and Hirshfeld Charge Analysis

et al. 2023

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The pharmacological effectiveness of indoles, benzoxazepines and benzodiazepines initiated our synthesis of indole fused benoxazepine/benzodiazepine heterocycles, along with enhanced biological usefulness of the fused rings. Activated indoles 5, 6 and 7 were synthesized using modified Bischler indole synthesis rearrangement. Indole 5 was substituted with the trichloroacetyl group at the C7 position, yielding 8, exclusively due to the increased nucleophilic character of C7. When trichloroacylated indole 8 was treated with basified ethanol or excess amminia, indole acid 9 and amide 10 were yielded, respectively. Indole amide 10 was expected to give indole fused benoxazepine/benzodiazepine 11a/11b on treatment with alpha halo ester followed by a coupling agent, but when the reaction was tried, an unexpectedly rearranged novel product, 1,3-bezodiazine 12, was obtained. The synthetic compounds were screened for anticholinesterase and antibacterial potential; results showed all products to be very important candidates for both activities, and their potential can be explored further. In addition, 1,3-bezodiazine 12 was explored by DFT studies, Hirshfeld surface charge analysis and structural insight to obrain a good picture of the structure and reactivity of the products for the design of derivatised drugs from the novel compound.

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Synthesis and antioxidant screening of Novel indole amines

Cited by 5 publications

References 35 publications

A Brief Review of the Medicinally Important Indole Derivatives

A Brief Review of the Medicinally Important Indole Derivatives

Standalone methodology for building QSAR models: an antioxidant QSAR model of di(hetero)aryl amines and amides as a case study

Evaluation of Antimicrobial, Anticholinesterase Potential of Indole Derivatives and Unexpectedly Synthesized Novel Benzodiazine: Characterization, DFT and Hirshfeld Charge Analysis

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