A facile one-pot, three component synthesis of a new series of 1,3,4-thiadiazines: Anticancer evaluation and molecular docking studies

Mamidala, Srikanth; Vangala, Venugopal; Peddi, Saikiran Reddy; Chedupaka, Raju; Manga, Vijjulatha; Vedula, Rajeswar Rao

doi:10.1016/j.molstruc.2021.130111

Cited by 16 publications

(8 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 8 was followed by derivatives 6 (21.8 for HepG-2 and 25.6 for Caco-2) and 4 (18.1 for HepG-2 and 23 for Caco-2), as indicated in Table 1. The superior antitumor activity of compound 8 could be attributed to the presence of a thiazolyl-pyrazole moiety, which per the literature exhibits strong anticancer activity [49][50][51] . In addition, the presence of acetonitrile, incorporated into the pyrazole ring (at position 3), may reveal anticancer activity, as reported through other authors 52,53 .…”

Section: Bioactivity Of the Synthesized Indazolylthiazole-based Heterocyclic Compounds 221 Antitumor Activitymentioning

confidence: 59%

Synthesis, and Docking Studies of Novel Heterocycles Incorporating the Indazolylthiazole Moiety as Antimicrobial and Anticancer Agents

Dawoud

El‐Gendi

Abdallah

et al. 2021

Preprint

View full text Add to dashboard Cite

The current study was directed toward developing a new series of fused heterocycles incorporating an indazolylthiazole moiety. The newly synthesized compounds were characterized through elemental analysis and spectral data (IR, 1H-NMR, 13C-NMR, and mass spectrometry). The cytotoxic effect of the newly synthesized compounds was evaluated against normal human cells (HFB-4) and cancer cell lines (HepG-2 and Caco-2). Among the synthesized compounds, derivatives 4, and 6 revealed significant selective antitumor activity, in a dose-dependent manner, against both HepG-2 and Caco-2 cell lines, with a lower risk toward HFB-4 cells (normal cells). Derivative 8 revealed the maximum antitumor activity toward both tumor cell lines, with an SI value of about approximately 26 and an IC50 value of approximately 5.9 µg/ml. The effect of these derivatives (8, 4, and 6) on the expression of 5 tumor regulating genes was studied through quantitative real-time PCR, where their interaction with these genes was simulated through a molecular docking study. Furthermore, the antimicrobial activity results revealed that compounds 2, 7, 8, and 9 have potential antimicrobial activity, with maximum broad spectrum activity through compound 3 against the three tested pathogens: Streptococcus mutans, Pseudomonas aeruginosa, and Candida albicans. The newly prepared compounds also revealed antibiofilm formation activity with maximum activity against Streptococcus mutans, Pseudomonas aeruginosa, and Candida albicans.

show abstract

Section: Bioactivity Of the Synthesized Indazolylthiazole-based Heterocyclic Compounds 221 Antitumor Activitymentioning

confidence: 59%

Synthesis, and Docking Studies of Novel Heterocycles Incorporating the Indazolylthiazole Moiety as Antimicrobial and Anticancer Agents

Dawoud

El‐Gendi

Abdallah

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…[35] When 3-bromoacetylcoumarin ( 2) is treated with quinoline (8) the 3-coumarinoyl quinolinium bromides ( 9) is formed in good yields. [36] Compound 2 also develops the 3-(2-(1H-1,2,4triazol-1-yl) acetyl)-coumarin (11) in good yield upon reaction with 1H-1,2,4-triazole (10) in dioxane. [37] Under reflux conditions in pyridine, 3-bromoacetylcoumarin (2), isoindole-dione (12) and thioacetic acid ( 14) form coumarin-isoindoline-dione ( 13) and coumarin-ethyl-thioacetic acid (15) in good yields, respectively.…”

Section: Nucleophilic Substitutions Of 3-bromoacetylcoumarinmentioning

confidence: 99%

“…[9] 3-(Bromoacetyl)coumarin has gained a reputation as a crucial structural class that is able to take part in the synthesis of diverse bioactive scaffolds. [10,11] Accumulated studies showed a broad range of 3-(bromoacetyl)coumarin biological activity including anti-proliferative, antimicrobial, [12] and type 2 diabetes mellitus inhibitory activities. [13] A comprehensive review on different aspects on bi-heterocyclic coumarins was published by Anand.…”

Section: Introductionmentioning

confidence: 99%

“…Coumarins are considered to be a privileged scaffold for medicinal chemists due to their ability to transform into a large variety of functionalized coumarins via relatively easy synthetic methods [9] . 3‐(Bromoacetyl)coumarin has gained a reputation as a crucial structural class that is able to take part in the synthesis of diverse bioactive scaffolds [10,11] . Accumulated studies showed a broad range of 3‐(bromoacetyl)coumarin biological activity including anti‐proliferative, antimicrobial, [12] and type 2 diabetes mellitus inhibitory activities [13] .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

et al. 2022

View full text Add to dashboard Cite

Compounds containing the coumarin scaffold are widely used in the pharmaceutical and medicinal industries. The biological activities of coumarin containing derivatives make the attractive for the develop new drugs. Different methods and techniques are developed to synthesize new drugs using coumarin as a starting material. This review summarized various methods, techniques and reaction conditions for synthesis of coumarins containing compounds from 3‐bromoacetylcoumarin. A total of 79 coumarin intermediates and products are reported herein. The different reactions include nucleophilic substitutions, one‐pot and multi‐step synthesis for preparation of coumarin containing compounds through different mechanisms and the outcomes achieved through such reactions are discussed. The prepared compounds showed a range of activities resulting in antifungal, antimicrobial, anti‐inflammatory, antidiabetic and cholinesterase inhibitors. The nucleophilic substitution reactions involving urea related compounds, followed by intramolecular cyclization lead to imidazole and thiazole moieties, which exhibit antibacterial activities. It is hoped that this review provides useful insight for researchers engaged in this field to expand the knowledge gained in this area.

show abstract

“…Among these compounds, 3-(bromoacetyl)coumarin 1 and its derivatives are a prominent structural class in the synthesis of various bioactive heterocyclic scaffolds, 17,18 they also are important components in drug discovery on account of their biological activities such as antiproliferative, antimicrobial activities, 19 and are promising inhibitors of type 2 diabetes mellitus. 20 In addition, numerous chemosensors are based on polyfunctional coumarin platforms used to detect multianalyte detection, such as different bioactive elements and various environmental pollutants.…”

Section: Introductionmentioning

confidence: 99%

3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

et al. 2021

View full text Add to dashboard Cite

show abstract

A facile one-pot, three component synthesis of a new series of 1,3,4-thiadiazines: Anticancer evaluation and molecular docking studies

Cited by 16 publications

References 56 publications

Synthesis, and Docking Studies of Novel Heterocycles Incorporating the Indazolylthiazole Moiety as Antimicrobial and Anticancer Agents

Synthesis, and Docking Studies of Novel Heterocycles Incorporating the Indazolylthiazole Moiety as Antimicrobial and Anticancer Agents

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

Contact Info

Product

Resources

About