Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in vitro exploration for therapeutic potential against HeLa cancer cell lines

Lad, Nitin P.; Kulkarni, Surendra U.; Sharma, Rajiv; Mascarenhas, Malcolm; Kulkarni, Mahesh R.; Pandit, S. S.

doi:10.1016/j.ejmech.2016.12.022

Cited by 26 publications

(14 citation statements)

References 26 publications

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“…[25]. Compound (E)-ethyl 3-(2-fluorophenyl)acrylate was synthesized by the Wittig reaction of the commercially available 2-fluorobenzaldehyde (10) with ethyl 2-(triphenyl-phosphoranylidene)acetate (11) according to the procedure described in the literature [26]. (E)-3-(2-Fluorophenyl)prop-2-en-1-ol (13) was synthesized by reducing (E)-ethyl 3-(2-fluorophenyl)acrylate (12) with diisobutylaluminium hydride (DIBAL) based on the procedure reported in the literature [27].…”

Section: Synthesismentioning

confidence: 99%

“…Starting materials 22 and 9 were synthesized using the procedure previously described by us [23]. (E)-ethyl 3-(2-fluorophenyl)acrylate (12) was prepared from commercially available 2-fluorobenzaldehyde (10, CAS 446-52-6) according to the reported procedure [26]. (E)-3-(2-Fluorophenyl)prop-2-en-1-ol (13) was synthesized by reducing (E)-ethyl 3-(2-fluorophenyl)acrylate (12) with DIBAL based on the procedure reported in the literature [27].…”

Section: General Proceduresmentioning

confidence: 99%

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New Zampanolide Mimics: Design, Synthesis, and Antiproliferative Evaluation

et al. 2020

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Zampanolide is a promising microtubule-stabilizing agent (MSA) with a unique chemical structure. It is superior to the current clinically used MSAs due to the covalent nature of its binding to β-tubulin and high cytotoxic potency toward multidrug-resistant cancer cells. However, its further development as a viable drug candidate is hindered by its limited availability. More importantly, conversion of its chemically fragile side chain into a stabilized bioisostere is envisioned to enable zampanolide to possess more drug-like properties. As part of our ongoing project aiming to develop its mimics with a stable side chain using straightforward synthetic approaches, 2-fluorobenzyl alcohol was designed as a bioisosteric surrogate for the side chain based on its binding conformation as confirmed by the X-ray structure of tubulin complexed with zampanolide. Two new zampanolide mimics with the newly designed side chain have been successfully synthesized through a 25-step chemical transformation for each. Yamaguchi esterification and intramolecular Horner–Wadsworth–Emmons condensation were used as key reactions to construct the lactone core. The chiral centers at C17 and C18 were introduced by the Sharpless asymmetric dihydroxylation. Our WST-1 cell proliferation assay data in both docetaxel-resistant and docetaxel-naive prostate cancer cell lines revealed that compound 6 is the optimal mimic and the newly designed side chain can serve as a bioisostere for the chemically fragile N-acetyl hemiaminal side chain in zampanolide.

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Section: Synthesismentioning

confidence: 99%

Section: General Proceduresmentioning

confidence: 99%

New Zampanolide Mimics: Design, Synthesis, and Antiproliferative Evaluation

et al. 2020

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“…6 Piperlongumine derived cyclic sulfonamide 2 significantly reduced the HeLa cells growth. 7 Chromone-based sulfonamide 3 ( Figure 1) showed IC 50 of 0.72 and 0.50 μmol against MCF-7 and A-549 cell lines, respectively. 8 On the other hand, two series of 1, 2, 3-triazole derivatives in our group have revealed their anticancer activity: Chalcone-1, 2, 3-triazole-azole 4 showed the potent antiproliferative activity with an IC 50 value of 1.52 μmol against SK-N-SH cancer cells and induced morphological changes; 9 1, 2, 3-Triazole-chalcone 5 (Figure 2) inhibited the proliferation of SK-N-SH cancer cells by inducing apoptosis and arresting the cell cycle at the G1 phase.…”

Section: Introductionmentioning

confidence: 99%

Efficient click reaction towards novel sulfonamide hybrids by molecular hybridization strategy as antiproliferative agents

Hou

Zhang

et al. 2018

J Chem Sci

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Twelve novel sulfonamide hybrids were designed by molecular hybridization strategy. The target sulfonamide hybrids were obtained in the click reaction of azide derivatives and commerciallly available alkynes. All sulfonamide hybrids were evaluated for their antiproliferative activity against three selected cancer cell lines (MGC-803, EC-109 and PC-3). Most of the synthesized compounds exhibited moderate to good activity against all the cancer cell lines selected. Particularly, compound 8c showed the potent antiproliferative activity with an IC 50 value of 0.7 μmol against MGC-803 cancer cells. These sulfonamide hybrids might be promising lead compounds to develop antitumor agents in the clinical practice.

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“…Sulfonamides have a functional group (R-SO 2 -NH 2 ) called the sulfonamide group; sulfonamide scaffolds are also very important structural motifs that are present in diverse pharmaceuticals ( Figure 1 ), showing important and extensive biological activities, such as antitumor [ 8 , 9 , 10 , 11 , 12 ], anti-inflammatory [ 13 , 14 ], and antiviral activities [ 15 , 16 ]. However, due to the structural particularity, natural products that contain a primary sulfonamide group in their structures are rare.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Cytotoxic Activity of Novel Natural Arylsulfonamide-Inspired Molecules

et al. 2022

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Primary arylsulfonamide functional groups feature prominently in diverse pharmaceuticals. However, natural arylsulfonamides are relatively infrequent. In this work, two novel arylsulfonamide natural products were first synthesized, and then a series of novel molecules derived from natural arylsulfonamides were designed and synthesized, and their in vitro cytotoxic activities against A875, HepG2, and MARC145 cell lines were systematically evaluated. The results indicate that some of these arylsulfonamide derivatives exhibit significantly good cytotoxic activity against the tested cell lines compared with the control 5-fluorouracil (5-FU), such as compounds 10l, 10p, 10q, and 10r. In particular, the potential molecule 10q, containing a carbazole moiety, exhibited the highest inhibitory activity against all tested cell lines, with IC50 values of 4.19 ± 0.78, 3.55 ± 0.63, and 2.95 ± 0.78 μg/mL, respectively. This will offer the potential to discover novel drug-like compounds from the sparsely populated area of natural products that can lead to effective anticancer agents.

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Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in vitro exploration for therapeutic potential against HeLa cancer cell lines

Cited by 26 publications

References 26 publications

New Zampanolide Mimics: Design, Synthesis, and Antiproliferative Evaluation

New Zampanolide Mimics: Design, Synthesis, and Antiproliferative Evaluation

Efficient click reaction towards novel sulfonamide hybrids by molecular hybridization strategy as antiproliferative agents

Design, Synthesis, and Cytotoxic Activity of Novel Natural Arylsulfonamide-Inspired Molecules

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