Synthesis and Biological Evaluation of Novel Fused [1,2,3]Triazolo[4',5':3,4] pyrrolo[2,1-f]purines as Potent Anti-Proliferative Agents

Sucharitha, E. Ramya; Kumar, Naveen; Ravinder, M.; Reddy, N. Vasudeva; Narsimha, Sirassu

doi:10.1134/s1068162021040208

Cited by 11 publications

(2 citation statements)

References 38 publications

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“…[70] Another possible CH functionalization instead of an interrupted click was reported (Scheme 64). [71] Triazolophenanthridines 180 were prepared through a three-component reaction using cyclic aryl iodonium compounds 179, sodium azide, and terminal alkynes in the presence of catalytic CuI, sodium bicarbonate, anhydrous DMSO at 50 °C under inert atmosphere (Scheme 65). Mechanistically, the initial step involves the exchange between the triflate anion of iodonium and the azide to form derivative 181, which then undergoes oxidative addition with copper to form intermediate 182 and subsequent reductive elimination with incorporation of the azide onto the aromatic ring 183.…”

Section: Insertion Of a Carbon Atommentioning

confidence: 99%

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Each Interruption is an Opportunity: Novel Synthetic Strategies Explored Through Interrupted Click Reactions

Brunelli,

Russo,

Giustiniano

et al. 2024

Chemistry A European J

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The particular and unique mechanism of the copper‐catalyzed reaction between azides and alkynes (CuAAC) has not only allowed for the efficient synthesis of 1,2,3‐trisubstituted 1,4‐triazoles in excellent yields and under mild conditions, becoming the quintessential click reaction, but it has also enabled the straightforward formation of a metallocycle intermediate, the copper triazolyl. This, under suitable reaction conditions able to suppress its protonolysis, can be used either for the creation of new bicyclic triazolyl structures or for the generation of novel three or four‐component reactions. The aim of this review is to rationalize and unify all these transformations, which are collectively referred to as “interrupted click reactions”.

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Section: Insertion Of a Carbon Atommentioning

confidence: 99%

“…Another possible CH functionalization instead of an interrupted click was reported (Scheme 64). [71] …”

Section: Interrupted Click Transformations In the Following Yearsmentioning

confidence: 99%

Each Interruption is an Opportunity: Novel Synthetic Strategies Explored Through Interrupted Click Reactions

Brunelli,

Russo,

Giustiniano

et al. 2024

Chemistry A European J

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Cu(I)‐Catalyzed One‐Pot Synthesis of [1,2,3]Triazolo[5,1‐a] isoquinolin‐6(5H)‐one Derivatives as EGFR‐Targeting Anticancer Agents

Samala¹,

Nukala²,

Thirukovela³

et al. 2022

ChemistrySelect

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The CuI promoted one‐pot multi‐component synthesis of new fused [1,2,3]triazolo[5,1‐a]isoquinoline derivatives (4 a–4 h, 8 a–8 f & 9 a–9 f) without isolating unsafe azides and their in vitro cytotoxic activity against MCF‐7 & MDA‐MB‐231 (breast cancer cells) and A‐549 (alveolar carcinoma) was reported herein. Out of all, compounds 9‐chloro‐1‐(morpholinomethyl)‐[1,2,3]triazolo[5,1‐a]isoquinolin‐6(5H)‐one (8 d), 9‐fluoro‐1‐(morpholinomethyl)‐[1,2,3]triazolo[5,1‐a]isoquinolin‐6(5H)‐one (8 e), 9‐chloro‐1‐((1,1‐dioxidothiomorpholino)methyl)‐[1,2,3]triazolo[5,1‐a]isoquinolin‐6(5H)‐one (9 d), and 1‐((1,1‐dioxidothiomorpholino)methyl)‐9‐fluoro‐[1,2,3]triazolo[5,1‐a]isoquinolin‐6(5H)‐one (9 e) showed superior potency against all the cell lines than the standard drug erlotinib with IC50 values ranging from 2.45 to 7.19 μM. The most active compounds 8 d, 8 e, 9 d, and 9 e were also screened for their efficacy in inhibiting tyrosine kinase EGFR and results revealed that compound 9 d showed comparable activity with standard drug erlotinib, whereas, compounds 8 d, 8 e, and 9 e showed superior activity than the erlotinib. Molecular modeling studies for active compounds on EGFR (PDB‐ID‐4HJO) were also conducted and the obtained free energies were observed to be in agreement with the in vitro activity data. Finally, compounds 8 d, 8 e, 9 d, and 9 e didn't show AMES toxicity and followed the rules of Egan, Ghose, Veber, Lipinski, and Muegge rules without any deviation.

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Synthesis and Biological Evaluation of Benzo[d] thiazolyl‐Sulfonyl‐Benzo[4,5]isothiazolo [2,3‐c][1,2,3] triazole Derivatives as EGFR Targeting Anticancer Agents

Sucharitha¹,

Nukala²,

Thirukovela³

et al. 2023

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A one‐step procedure for the synthesis of new fused Benzo[d]thiazolo‐1,2,3‐triazoles (3 a–3 h and 4 a–4 h) in good yields using sulfonylazides (2) and iodoalkyne (1) through from the 5‐iodo 1,2,3‐triazole generated in situ was developed. Among all, compounds 5‐chloro‐3‐(((1,1‐dioxidobenzo[d]thiazol‐2‐yl)sulfonyl)methyl)benzo[4,5]isothiazolo[2,3‐c] [1,2,3]triazole 8,8‐dioxide (3 e), 3‐(((1,1‐dioxidobenzo[d]thiazol‐2‐yl)sulfonyl)methyl)‐5‐fluorobenzo[4,5]isothiazolo [2,3‐c][1,2,3]triazole 8,8‐dioxide (3 f), 5‐bromo‐3‐(((5‐bromo‐1,1‐dioxidobenzo[d]thiazol‐2‐yl)sulfonyl)methyl)benzo [4,5]isothiazolo[2,3‐c][1,2,3]triazole 8,8‐dioxide (4 d), 3‐(((5‐bromo‐1,1‐dioxidobenzo[d]thiazol‐2‐yl)sulfonyl)methyl)‐5‐chlorobenzo [4,5]isothiazolo[2,3‐c][1,2,3]triazole 8,8‐dioxide (4 e) and 3‐(((5‐bromo‐1,1‐dioxidobenzo[d]thiazol‐2‐yl)sulfonyl)methyl)‐5‐fluorobenzo [4,5] isothiazolo[2,3‐c][1,2,3]triazole 8,8‐dioxide (4 f) showed superior activity against A‐549 and good activity against the MCF‐7. Later, in vitro EGFR results revealed that compounds 4 e and 4 f indicated promising potency with IC50 values of 0.316±0.07 and 0.211±0.09 μM respectively. In silico studies of five potent compounds were also carried out to identify interactions against EGFR receptors and found that the energy calculations were consistent with the IC50 values obtained. In silico pharmacokinetic profile was predicted for potent compounds 3 e, 3 f, 4 d, 4 e, and 4 f using SWISS/ADME and pkCSM, where, all the compounds followed the Lipinski rule without any deviation.

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Synthesis and Biological Evaluation of Novel Fused [1,2,3]Triazolo[4',5':3,4] pyrrolo[2,1-f]purines as Potent Anti-Proliferative Agents

Cited by 11 publications

References 38 publications

Each Interruption is an Opportunity: Novel Synthetic Strategies Explored Through Interrupted Click Reactions

Each Interruption is an Opportunity: Novel Synthetic Strategies Explored Through Interrupted Click Reactions

Cu(I)‐Catalyzed One‐Pot Synthesis of [1,2,3]Triazolo[5,1‐a] isoquinolin‐6(5H)‐one Derivatives as EGFR‐Targeting Anticancer Agents

Synthesis and Biological Evaluation of Benzo[d] thiazolyl‐Sulfonyl‐Benzo[4,5]isothiazolo [2,3‐c][1,2,3] triazole Derivatives as EGFR Targeting Anticancer Agents

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