One-pot synthesis of sulfonyl-1<i>H</i>-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity

Sreerama, Rakesh; Swamy, T. Narasimha; Ravinder, M.; Reddy, N. Vasudeva; Narsimha, Sirassu

doi:10.1080/10426507.2020.1854257

Cited by 14 publications

(5 citation statements)

References 33 publications

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“…The synthesis of benzo[ d ]thiazolyl‐sulfonyl‐benzo[4,5]isothiazolo[2,3‐ c ][1,2,3]triazoles ( 3 a – 3 h & 4 a – 4 h ) outlined in Scheme 2. The previously reported intermediate iodoalkyne ( 1 ) [17] reacts with different freshly prepared sulfonyl azides [18] ( 2 ) under [3+2]cycloaddition followed by a C−C bond coupling reaction.…”

Section: Chemistrymentioning

confidence: 99%

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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

ChemistrySelect

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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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Section: Chemistrymentioning

confidence: 99%

“…The previously reported intermediate iodoalkyne (1) [17] reacts with different freshly prepared sulfonyl azides [18] (2) under [3 + 2]cycloaddition followed by a CÀ C bond coupling reaction.…”

Section: Chemistrymentioning

confidence: 99%

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

ChemistrySelect

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“…23 Very recently, we have developed an efficient method for the synthesis of a novel class of 1,2,3-triazole containing sulfonyl derivatives. [24][25][26][27][28][29][30][31] Based on the previous reports, we envisaged that the synthesized 1,2,3-triazole as well as their sulfone derivatives might show potent antibacterial (Fig. 1) hemolytic and in silico TLR4 protein inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2,3-triazole-piperazin-benzo[b][1,4]thiazine 1,1-dioxides: antibacterial, hemolytic and in silico TLR4 protein inhibitory activities

Ramu,

Krishna,

Kapavarapu

et al. 2024

RSC Adv.

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“…Anticancer, antibacterial, antioxidant, anti-HIV, and anti-inflammatory characteristics are among the biological properties. [5][6][7][8][9][10][11][12] Some sulfonyl 1,2,3-triazoles have also been shown to have effective anticancer properties. [13][14][15][16] Furthermore, imidazoles are a significant class of nitrogen-containing heterocyclic chemicals with numerous uses, particularly anticancer properties.…”

Section: Introductionmentioning

confidence: 99%

“…The wide range of pharmacological activities of 1,2,3‐triazoles has piqued the interest of synthetic and medicinal chemists. Anticancer, antibacterial, antioxidant, anti‐HIV, and anti‐inflammatory characteristics are among the biological properties [5–12] . Some sulfonyl 1,2,3‐triazoles have also been shown to have effective anticancer properties [13–16] .…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic [3+2] Cycloaddition Reaction: Synthesis of Fully Decorated Sulfonyl 1,2,3‐Triazoles as Potent EGFR Targeting Anticancer Agents**

Reddy Dodlapati,

Madhukar Reddy,

Azam

et al. 2023

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A general strategy was developed for the synthesis of new fully decorated sulfonyl1,2,3‐triazolyl imidazoles from β‐ketosulfones and several aryl sulfonyl azides using the ramachary organocatalytic cycloaddition method. Organocatalytic [3+2] cycloaddition reaction of β‐ketosulfone acts as an internal alkyne, as reported for the synthesis of sulfonyl‐1,2,3‐triazolyl imidazoles at 80 °C in good to excellent yields of products in the presence of catalytic amounts of pyrrolidine (10 mol %). In vitro anticancer activity of all these derivatives revealed that four compounds like 4‐((5‐(4‐methoxyphenyl)‐4‐((1‐methyl‐1H‐imidazol‐2‐yl) sulfonyl)‐1H‐1,2,3‐triazol‐1‐yl)sulfonyl) benzonitrile, 5‐(4‐methoxyphenyl)‐4‐((1‐methyl‐1H‐imidazol‐2‐yl)sulfonyl)‐1‐((4‐nitro phenyl) sulfonyl)‐1H‐1,2,3‐triazole,4‐((4‐((1‐methyl‐1H‐imidazol‐2‐yl) sulfonyl)‐5‐(4‐nitrophenyl)‐1H‐1,2,3‐triazol‐1‐yl)sulfonyl)benzonitrile, and 1‐((4‐chlorophenyl)sulfonyl)‐4‐((1‐methyl‐1H‐imidazol‐2‐yl) sulfonyl)‐5‐(4‐nitrophenyl)‐1H‐1,2,3‐triazole was active against three human cancer cell lines: MCF‐7, MDA‐MB‐231, and A‐549. Later, the results of the inhibitory assay of potent compounds against the tyrosine kinase epidermal growth factor receptor revealed that compounds 1‐((4‐chlorophenyl)sulfonyl)‐5‐(4‐methoxyphenyl)‐4‐((1‐methyl‐1H‐imidazol‐2‐yl)sulfonyl)‐1H‐1,2,3‐triazole and 1‐((4‐chlorophenyl) sulfonyl)‐4‐((1‐methyl‐1H‐imidazol‐2‐yl) sulfonyl)‐5‐(4‐nitrophenyl)‐1H‐1,2,3‐triazole showed more potency than the reference drug erlotinib.

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One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity

Cited by 14 publications

References 33 publications

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

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

Synthesis of 1,2,3-triazole-piperazin-benzo[b][1,4]thiazine 1,1-dioxides: antibacterial, hemolytic and in silico TLR4 protein inhibitory activities

Organocatalytic [3+2] Cycloaddition Reaction: Synthesis of Fully Decorated Sulfonyl 1,2,3‐Triazoles as Potent EGFR Targeting Anticancer Agents**

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