Click Chemistry Approach to Isoindole-1,3-dione Tethered 1,2,3-Triazole Derivatives

Kaur, Rajneesh; Singh, Raman P.; Kumar, Antresh; Singh, Kuldeep

doi:10.1055/s-0039-1690326

Cited by 6 publications

(4 citation statements)

References 11 publications

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“…General procedure for click reaction [36,37] To a solution of N-propargyated azetidin-2-one (17 or 18), substituted azide 10, cupric acetate (10 mol%), and sodium ascorbate (20% mol) were added in a solution of water (4 mL) and tert-butyl alcohol (4 mL) at room temperature with stirring for 24 h. Upon completion of the reaction (monitored by TLC), the mixture was diluted with water, extracted with ethyl acetate, and dried over anhydrous Na 2 SO 4 . After evaporation of the solvent, the final compounds were chromatographed (DCM/Methanol) to yield pure products (6 or 7).…”

Section: 2mentioning

confidence: 99%

1,2,3-Triazole β-lactam conjugates as antimicrobial agents

Kaur

Singh

Kumar

et al. 2020

Heliyon

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A convenient and efficient synthesis of new triazole β-lactam conjugates using click chemistry is described. β-lactam 15 and 16 were prepared using cycloaddition strategy and propargylated at N-1 to afford compounds 17 and 18. Cu-catalyzed click reaction of these β-lactams 17 and 18 with different aryl azides provided 1,2,3-triazole conjugates 6 and 7, respectively. The products were fully characterized spectroscopically and tested against Gram-(þ) and Gram-(-) bacteria. Compound 7a and 7c were found to be most active.

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Section: 2mentioning

confidence: 99%

1,2,3-Triazole β-lactam conjugates as antimicrobial agents

Kaur

Singh

Kumar

et al. 2020

Heliyon

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“…These compounds have a typical chemical structure, including a CO‐ N (R)‐CO motif. The deliberate hydrophobic nature of substituent (‐R) makes them able to penetrate through the cell membranes in vivo (Bansode et al, 2009) with a wide range of interesting biological activity in the fields of pharmaceuticals (Kaur et al, 2019). Among these biological activities are anti‐inflammatory (A Qinna, 2012; Machado et al, 2005; Raghupathy & Billett, 2009), anticonvulsant (Kadi, 2006), anti‐HIV (El‐Barbary, 2004), antibacterial (Mohamed et al, 2021; Mohamed, 2017), antitumor (Donarska et al, 2021; Lentzsch et al, 2002; Philoppes & Lamie, 2019), anti‐Alzheimer (Azimi et al, 2017; Panek et al, 2018), antimalarial (Singh et al, 2015), antidiabetic (Mobinikhaledi et al, 2015; Pascale et al, 2010; Wang et al, 2017), and analgesic agents (Said et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of novel tetrabromophthalimide derivatives as potential tubulin inhibitors endowed with apoptotic induction for cancer treatment

Abdel‐Motaal,

Aldakhili,

Abo Elmaaty

et al. 2024

Drug Development Research

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Although various approaches exist for treating cancer, chemotherapy continues to hold a prominent role in the management of this disease. Besides, microtubules serve as a vital component of the cellular skeleton, playing a pivotal role in the process of cell division making it an attractive target for cancer treatment. Hence, the scope of this work was adapted to design and synthesize new anti‐tubulin tetrabromophthalimide hybrids (3‐17) with colchicine binding site (CBS) inhibitory potential. The conducted in vitro studies showed that compound 16 displayed the lowest IC50 values (11.46 µM) at the FaDu cancer cell lines, whereas compound 17 exhibited the lowest IC50 value (13.62 µM) at the PC3 cancer cell line. However, compound 7b exhibited the lowest IC50 value (11.45 µM) at the MDA‐MB‐468 cancer cell line. Moreover, compound 17 was observed to be the superior antitumor candidate against all three tested cancer cell lines (MDA‐MB‐468, PC3, and FaDu) with IC50 values of 17.22, 13.15, and 13.62 µM, respectively. In addition, compound 17 showed a well‐established upregulation of apoptotic markers (Caspases 3, 7, 8, and 9, Bax, and P53). Moreover, compound 17 induced downregulation of the antiapoptotic markers (MMP2, MMP9, and BCL‐2). Furthermore, the colchicine binding site inhibition assay showed that compounds 15a and 17 exhibited particularly significant inhibitory potentials, with IC50 values of 23.07 and 4.25 µM, respectively, compared to colchicine, which had an IC50 value of 3.89 µM. Additionally, cell cycle analysis was conducted, showing that compound 17 could prompt cell cycle arrest at both the G0‐G1 and G2‐M phases. On the other hand, a molecular docking approach was applied to investigate the binding interactions of the examined candidates compared to colchicine towards CBS of the β‐tubulin subunit. Thus, the synthesized tetrabromophthalimide hybrids can be regarded as outstanding anticancer candidates with significant apoptotic activity.

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“…It requires only a light click to accomplish a conversion rate close to 100% . The “Click” is fast, gentle, thorough, and even unassisted; thus, it is utilized in many fields such as material preparation, bioimaging, and chemical synthesis . Motivated by the strengths of click chemistry, the efficient connectivity properties of clicks are employed in the sensing field to pioneer novel and superior technologies.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous Detection of Micro-RNAs by a Disposable Biosensor via the Click Chemistry Connection Strategy

Liu,

Wang,

et al. 2024

Anal. Chem.

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Click Chemistry Approach to Isoindole-1,3-dione Tethered 1,2,3-Triazole Derivatives

Abstract: A convenient and efficient approach for the synthesis of novel 1,2,3-triazole tethered isoindol-1,3-dione conjugates by a nucleophilic substitution reaction of phthalic anhydride with 1,2,3-triazole containing carbohydrazide is described. The latter were prepared by using click chemistry.

Cited by 6 publications

References 11 publications

1,2,3-Triazole β-lactam conjugates as antimicrobial agents

1,2,3-Triazole β-lactam conjugates as antimicrobial agents

Design and synthesis of novel tetrabromophthalimide derivatives as potential tubulin inhibitors endowed with apoptotic induction for cancer treatment

Simultaneous Detection of Micro-RNAs by a Disposable Biosensor via the Click Chemistry Connection Strategy

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