Design, synthesis and biological evaluation of substituted 2-amino-1,3-thiazine derivatives as antituberculosis and anti-cancer agents

Prasad, Tangella Nagendra; Reddy, Eeda Koti; Gudise, Veera Babu; Basha, Shaik Firoj

doi:10.1080/00397911.2019.1597125

Cited by 13 publications

(6 citation statements)

References 27 publications

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“…In continuation of our perpetual study on heterocycles and spirocycles, 19 we have demonstrated an AB 2 C type four-component reaction 20 between 1,3-indanedione, aryl aldehydes, and β-nitrostyrene derived MBH acetates via [1 + 1 + 1 + 3] cyclization strategy ( Scheme 2 ).…”

Section: Introductionmentioning

confidence: 73%

Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation

Gudise,

Anwar

2023

RSC Adv.

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Section: Introductionmentioning

confidence: 73%

Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation

Gudise,

Anwar

2023

RSC Adv.

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“…[129] β-carbolines' have a planar structure that allows them to attach to DNA and cause DNA damage. [130] Clinical studies and phytochemical screening have proven the anticancer activity of herbal remedies. [131] The need to create novel anticancer and chemopreventive drugs is clinically unfulfilled.…”

Section: Discussionmentioning

confidence: 99%

“…In addition, some of these substances exhibit anti-cancer action by photocleaving DNA and inhibiting histone deacetylase (HDAC). [130] The search for novel plant-derived anticancer compounds is continuing on a global scale. Increasingly, people are choosing to use natural plant items for cancer treatment in recent years due to concern over the side effects of oral and chemotherapeutic anticancer drugs.…”

Section: Discussionmentioning

confidence: 99%

“…They are a vast class of chemical compounds that exist in nature and contain one or more nitrogen atoms in their structures [129] . β‐carbolines′ have a planar structure that allows them to attach to DNA and cause DNA damage [130] . Clinical studies and phytochemical screening have proven the anticancer activity of herbal remedies [131] .…”

Section: Discussionmentioning

confidence: 99%

“…According to published research on β‐carbolines, these compounds show cytotoxic activity via a variety of mechanisms of action. In addition, some of these substances exhibit anti‐cancer action by photocleaving DNA and inhibiting histone deacetylase (HDAC) [130] . The search for novel plant‐derived anticancer compounds is continuing on a global scale.…”

Section: Discussionmentioning

confidence: 99%

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Anticancer Potential of β‐Carboline Alkaloids: An Updated Mechanistic Overview

Tshikhudo,

Mabhaudhi,

Koorbanally

et al. 2024

Chemistry & Biodiversity

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This comprehensive review is designed to evaluate the anticancer properties of β‐carbolines derived from medicinal plants, with the ultimate goal of assessing their suitability and potential in cancer treatment, management, and prevention. An exhaustive literature survey was conducted on a wide array of β‐carbolines including, but not limited to, harmaline, harmine, harmicine, harman, harmol, harmalol, pinoline, tetrahydroharmine, tryptoline, cordysinin C, cordysinin D, norharmane, and perlolyrine. Various analytical techniques were employed to identify and screen these compounds, followed by a detailed analysis of their anticancer mechanisms. Natural β‐carbolines such as harmaline and harmine have shown promising inhibitory effects on the growth of cancer cells, as evidenced by multiple in vitro and in vivo studies. Synthetically derived β‐carbolines also displayed noteworthy anticancer, neuroprotective, and cognitive‐enhancing effects. The current body of research emphasizes the potential of β‐carbolines as a unique source of bioactive compounds for cancer treatment. The diverse range of β‐carbolines derived from medicinal plants can offer valuable insights into the development of new therapeutic strategies for cancer management and prevention.

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2‐Aminoaryl‐3,5‐diaryl pyrazines: Synthesis, biological evaluation against Mycobacterium tuberculosis and docking studies

Gangarapu

Ranganatham

Reddy

et al. 2020

Archiv der Pharmazie

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Rationally designed Mycobacterium tuberculosis (Mtb) inhibitors were synthesized under Buchwald conditions using Pd2(dba)3/xantphos and the compounds were investigated for their biological activity against the Mtb standard strain H37Rv and two other clinically isolated multidrug‐resistant strains with different drug resistance patterns. Compounds 5e, 6e, 7e, and 8e exhibited excellent antituberculosis activity against H37Rv with a minimum inhibitory concentration (MIC) value of 15 μg/ml. Compounds 5a, 6c, 7b, 8a, 8b, and 8d also displayed their potency with a MIC value in the range of 15–25 μg/ml. In addition to the Mtb studies, compounds 4e, 5e, 7e, and 8e were tested for cytotoxicity on HEK‐293 cells and compounds 7e and 8e were identified to have low toxicities of up to 200 and 300 μM, respectively. The synthesized compounds docked with the 2FUM protein of Mtb and the docking studies revealed that compounds 5e, 6e, 7e, and 8e can bind strongly in the active site of the enzyme and showed binding energies of −9.62, −10.7, −11.48, and −12.06 kcal/mol, respectively. Compound 7e forms four hydrogen bonds, whereas compound 8e forms five hydrogen bonds with amino acids, respectively. Based on these results, compounds 7e and 8e might be considered potential lead compounds with good anti‐Mtb potency.

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Design, synthesis and biological evaluation of substituted 2-amino-1,3-thiazine derivatives as antituberculosis and anti-cancer agents

Cited by 13 publications

References 27 publications

Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation

Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation

Anticancer Potential of β‐Carboline Alkaloids: An Updated Mechanistic Overview

2‐Aminoaryl‐3,5‐diaryl pyrazines: Synthesis, biological evaluation against Mycobacterium tuberculosis and docking studies

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