Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click’ Reaction: DNA Intercalation and Cytotoxic Studies

Shankaraiah, Nagula; Kumar, Nitin; Tokala, Ramya; B, Gayatri; Talla, Venu; Santos, Leonardo S.

doi:10.21577/0103-5053.20180111

Cited by 11 publications

(15 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Quinazolinones are hetero- cyclics represented as quinazoline ring with a keto group. Figure 12 depicts quinazolinones demonstrating various pharmacological properties like anticancer (152), antihypertensive (153) and anti-inflammatory (154) [135,136]. Many quinazolinone ring-containing alkaloids have been widely used in drug discovery and development protocols (155 and 156) [137].…”

Section: Quinazolinonementioning

confidence: 99%

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Gulati¹,

John²,

Shankaraiah³

2021

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

Microwave-assisted (MWA) multicomponent reactions (MCRs) have successfully emerged as one of the useful tools in the synthesis of biologically relevant heterocycles. These reactions are strategically employed for the generation of a variety of heterocycles along with multiple point diversifications. Over the last few decades classical MCRs such as Ugi, Biginelli, etc. have witnessed enhanced yield and efficiency with microwave assistance. The highlights of MWA-MCRs are high yields, reduced reaction time, selectivity, atom economy and simpler purification techniques, such an approach can accelerate the drug discovery process. The present review focuses on the recent advances in MWA-MCRs and their mechanistic insights over the past decade and shed light on its advantage over the conventional approach.

show abstract

Section: Quinazolinonementioning

confidence: 99%

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Gulati¹,

John²,

Shankaraiah³

2021

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…In continuation of our earlier efforts towards the synthesis of new cytotoxic agents, and knowing the cytotoxic properties of these scaffolds (naphthalimides/phthalimides) lately we reported click chemistry mediated 1,2,3‐triazole‐naphthalimide/ phthalimide conjugates as DNA intercalating and potent cytotoxic agents (Scheme ) . Therein, we synthesized the triazoles via traditional CuAAC conditions involving green Cu(I)‐catalyst utilized by our group .…”

Section: 3‐dipolar Cycloadditionmentioning

confidence: 99%

Reliability of Click Chemistry on Drug Discovery: A Personal Account

Shankaraiah

Sakla

Laxmikeshav

et al. 2019

The Chemical Record

Self Cite

View full text Add to dashboard Cite

The unprecedented efficiency, reliability and adaptability in drug discovery, with the growing number of applications and impact, have made Click Chemistry fascinating to the scientific community. The specificity, biocompatibility along with other principles of click chemistry offers a reliable platform for the synthesis of drug-like molecules that can expedite the drug discovery process. This account summarizes such successes of versatile click reactions from our research group towards the development of functional molecules.

show abstract

“…On the other hand, phthalimides, have exhibited remarkable pharmacological effects, including anti-inflammatory, antimycobacterial, analgesic, anticonvulsant, and anticancer activities ( 20 21 22 23 ). Some derivatives of thiadiazole and triazole containing phthalimide pharmacophore were reported as anticancer agents ( 24 25 26 ). The synthesis of some derivatives of naphthalimide substituted triazole with a high affinity towards DNA has been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxic activity evaluation of some new 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4- triazole derivatives attached to phthalimide

et al. 2021

View full text Add to dashboard Cite

Background and purpose: In the last few decades, nitrogen-rich heterocyclic compounds such as 1, 3, 4-thiadiazoles, 1, 2, 4-triazoles and 1, 3, 4-oxadiazoles have received considerable attention because of their notable biological properties, especially cytotoxic effects. The small molecules of mentioned azole derivatives revealed very intensive antitumor activity. In addition, phthalimide-thiadiazole and naphthalimide-triazole hybrid derivatives have shown remarkable cytotoxic effects. According to these observations, some of the hybrid derivatives containing the phthalimide-five-membered azoles were prepared in three steps in this research. Experimental approach: The thiol group of azoles was treated with ethyl chloroacetate which was followed by a reaction with hydrazine hydrate to provide acid hydrazide derivatives. Subsequently, the corresponding acid hydrazides were utilized to prepare the final derivatives through the reaction with phthalic anhydride. Cytotoxic activity of final compounds was evaluated against MCF-7 and HeLa cell lines using MTT assay. Findings/Results: Compound 3d containing two phthalimide moieties in its structure showed a significant improvement in cytotoxic activity with an IC 50 value of 29 μM against HeLa cell line. Compounds 3a-3c showed less cytotoxic effects against both cell lines. Conclusion and implications: The combination of the thiadiazole nucleus with two phthalimide structures increased the cytotoxic activity against the HeLa cell line. This increase in cytotoxic activity is probably due to its being more lipophilic characteristic and interaction of this derivative with the biological targets of two directions.

show abstract

Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click’ Reaction: DNA Intercalation and Cytotoxic Studies

Cited by 11 publications

References 19 publications

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Reliability of Click Chemistry on Drug Discovery: A Personal Account

Synthesis and cytotoxic activity evaluation of some new 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4- triazole derivatives attached to phthalimide

Contact Info

Product

Resources

About