Synthesis and Anti‐Proliferative Activity of a Triazole‐Fused Thymidine Analogue

Rahman, Atikur; Sharma, Priyanka; Kaur, Navneet; Shanavas, Asifkhan; Neelakandan, Prakash P.

doi:10.1002/slct.202001013

Cited by 5 publications

(3 citation statements)

References 56 publications

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“…Rahman et al, in 2020, developed a thymidine analogue with linked triazoles 235 and tested its anti-proliferative activities (Scheme 25). 32 Commercially available thymidine 232 was initially converted into its di-azide derivative 233 in three sequential steps and subsequently exposed to CuAAC reaction with 1,3-diethynyl benzene 234 using a CuI/DIPEA system in acetonitrile for 36 h to afford the macrocyclic thymidine analogue 235 (56%). Biological assessment showed that 235 expressed significant toxicity when tested against C6 glioblastoma cancer cell lines, MCF7…”

Section: Scheme 24 Synthesis Of Triazole-fused Macrocycle 231mentioning

confidence: 99%

Untitled

2024

SynOpen

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A systematic highlight of syntheses reported since 2006 of 1,2,3-triazole-fused macrocycles possessing biological activities such as anticancer, antibacterial, antiviral, anti-inflammatory and antilarval action, is presented in this review. The well-renowned Cu-catalyzed azidealkyne cycloaddition reaction was noted to be highly efficient and is one the most common methods utilized by scientists for the synthesis of 1,4-disubstituted triazole-fused macrocycles, whereas Ru-catalyzed cycloaddition is common for the formation of 1,5-disubstituted bioactive triazoles. This review would thus be extremely beneficial for both synthetic organic and medicinal chemists. 1 Introduction 2 Anticancer Derivatives 3 Antibacterial Derivatives 4 Derivatives with Dual Activity 5 Antilarval Derivatives 6 Anti-inflammatory Derivatives 7 Antiviral Derivatives 8 Anti-trypanosomal Derivatives 9 Derivatives with Miscellaneous Activities 10 Conclusion

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Section: Scheme 24 Synthesis Of Triazole-fused Macrocycle 231mentioning

confidence: 99%

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2024

SynOpen

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“…Rahman et al, in 2020, developed a thymidine analogue with linked triazoles 235 and tested its anti-proliferative activities (Scheme 25). 32 Commercially available thymidine 232 was initially converted into its di-azide derivative 233 in three sequential steps and consecutively exposed to CuAAC reaction with 1,3-diethynyl benzene 234 using a CuI/DIPEA system in acetonitrile for 36 h in order to afford the macrocyclic thymidine analogue 235 (56%). Biological assessment showed that 235 expressed significant toxicity when tested against C6 glioblastoma cancer cell lines, MCF7 breast cancer cell lines and HT29 colorectal adenocarcinoma cell lines.…”

Section: Scheme 23 Synthesis Of Triazole Fused Macrocycle 223mentioning

confidence: 99%

Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition

Ansary,

Jahan,

Pal

2023

SynOpen

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A systematic highlight on the syntheses of 1,2,3-triazole fused macrocycles possessing biological activities like anticancer, antibacterial, antiviral, anti-inflammatory, antilarval and more has been presented in this review since 2006. The well-renowned Cu-catalyzed azide-alkyne cycloaddition reaction was noted to be one of the highly efficient and most common methods utilized by several scientists for the synthesis of 1,4-disubstituted triazole fused macrocycles while the Ru-catalyzed cycloaddition led to the 1,5-disubstituted bioactive triazoles. This review would thus be extremely beneficial for both synthetic organic and medicinal chemists.

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“…1,2,3‐Triazole‐dihydropyrimidinone hybrids 52 (GI 50 : 24–38 µM, SRB assay) and the bis‐1,2,3‐triazole‐dihydropyrimidinone analogs 53 (GI 50 : 37–77 µM) exhibited moderate antiproliferative activity against HBL‐100 and T‐47D breast cancer cell lines, [ 80 ] whereas bis‐1,2,3‐triazole‐thymidine derivative 54 (IC 50 : 1.0 µM) possessed promising antiproliferative activity against MCF‐7 breast cancer cells. [ 81 ] Hence, hybrid 54 could serve as a lead compound for the further structural modifications.…”

Section: 23‐triazole‐pyrimidine/quinazoline Hybridsmentioning

confidence: 99%

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

Song,

Zhang,

Zhang

et al. 2023

Archiv der Pharmazie

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Breast cancer, as one of the most common invasive malignancies and the leading cause of cancer‐related deaths in women globally, poses a significant challenge in the world health system. Substantial advances in diagnosis and treatment have significantly improved the survival rate of breast cancer patients, but the number of incidences and deaths of breast cancer are projected to increase by 40% and 50%, respectively, by 2040. Chemotherapy is one of the principal treatments for breast cancer therapy, but multidrug resistance and severe side effects remain the major obstacles to the success of treatment. Hence, there is a vital need to develop novel chemotherapeutic agents to combat this deadly disease. 1,2,3‐Triazole, which can be effectively constructed by click chemistry, not only can serve as a linker to connect different anti‐breast cancer pharmacophores but also is a valuable pharmacophore with anti‐breast cancer potential and favorable properties such as hydrogen bonding, moderate dipole moment, and enhanced water solubility. Particularly, 1,2,3‐triazole‐containing hybrids have demonstrated promising in vitro and in vivo anti‐breast cancer potential against both drug‐sensitive and drug‐resistant forms and possessed excellent selectivity by targeting different biological pathways associated with breast cancer, representing privileged scaffolds for the discovery of novel anti‐breast cancer candidates. This review concentrates on the latest advancements of 1,2,3‐triazole‐containing hybrids with anti‐breast cancer potential, including work published between 2020 and the present. The structure–activity relationships (SARs) and mechanisms of action are also reviewed to shed light on the development of more effective and multitargeted candidates.

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Synthesis and Anti‐Proliferative Activity of a Triazole‐Fused Thymidine Analogue

Cited by 5 publications

References 56 publications

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Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

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