Facile Synthesis of<i>N</i>‐Acylsulfonamide in the Presence of Silica Chloride (SiO<sub>2</sub>‐Cl) both under Heterogeneous and Solvent‐Free Conditions

Massah, Ahmad Reza; Momeni, Ahmad Reza; Dabagh, Mina; Aliyan, Hamid; Naghash, Hamid Javaherian

doi:10.1080/00397910701750185

Cited by 11 publications

(4 citation statements)

References 29 publications

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“…Some of the solid supported acids, e.g., SiO 2 -OSO 3 H [29] and HClO 4 -SiO 2 [42], are utilized as catalysts for the preparation of 1,1-diacetate derivatives from the corresponding aldehydes. Recently, we have demonstrated the applicability of SiO 2 -OSO 3 H [43], H 3 PO 4 /TiO 2 -ZrO 2 [44,45], H 3 PO 4 /ZSM-5 [46], SiO 2 -OPO 3 H [47], and SiO 2 -Cl [48] as solid supported acids in several organic transformations.…”

Section: Introductionmentioning

confidence: 99%

ZSM-5-SO3H as a novel, efficient, and reusable catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

2011

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ZSM-5 has been modified as supported sulfuric acid (ZSM-5-SO 3 H) and introduced for the first time as a mild, convenient, reusable, and heterogeneous catalyst. Various types of aldehydes were efficiently converted to their 1,1-diacetates using a catalytic amount of ZSM-5-SO 3 H in excellent yields under solvent-free and heterogeneous conditions at room temperature. The deprotection of 1,1-diacetates has also been achieved using this novel catalyst in ethanol. The procedure is operationally simple, environmentally benign, and only a stoichiometric amount of anhydride is used.

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Section: Introductionmentioning

confidence: 99%

ZSM-5-SO3H as a novel, efficient, and reusable catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

2011

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“…With the aim to synthesize more soluble derivatives of the envisaged NO-COXIBs, the sulfonamide derivatives 4a , 4b , 4e, and 4f were converted to the respective N -propionamides followed by conversion of the chloromethyl group into the nitroesters 6a-d ( Scheme 2 ). For the N -propionamide synthesis, sulfuric acid on silica gel was utilized as “dry immobilized” acid as previously described by Massah et al [ 51 ]. This furnished the propionamides as crude products, which were directly reacted with silver nitrate to give the final products 6a – d .…”

Section: Resultsmentioning

confidence: 99%

Exploring Nitric Oxide (NO)-Releasing Celecoxib Derivatives as Modulators of Radioresponse in Pheochromocytoma Cells

et al. 2022

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COX-2 can be considered as a clinically relevant molecular target for adjuvant, in particular radiosensitizing treatments. In this regard, using selective COX-2 inhibitors, e.g., in combination with radiotherapy or endoradiotherapy, represents an interesting treatment option. Based on our own findings that nitric oxide (NO)-releasing and celecoxib-derived COX-2 inhibitors (COXIBs) showed promising radiosensitizing effects in vitro, we herein present the development of a series of eight novel NO-COXIBs differing in the peripheral substitution pattern and their chemical and in vitro characterization. COX-1 and COX-2 inhibition potency was found to be comparable to the lead NO-COXIBs, and NO-releasing properties were demonstrated to be mainly influenced by the substituent in 4-position of the pyrazole (Cl vs. H). Introduction of the N-propionamide at the sulfamoyl residue as a potential prodrug strategy lowered lipophilicity markedly and abolished COX inhibition while NO-releasing properties were not markedly influenced. NO-COXIBs were tested in vitro for a combination with single-dose external X-ray irradiation as well as [177Lu]LuCl3 treatment in HIF2α-positive mouse pheochromocytoma (MPC-HIF2a) tumor spheroids. When applied directly before X-ray irradiation or 177Lu treatment, NO-COXIBs showed radioprotective effects, as did celecoxib, which was used as a control. Radiosensitizing effects were observed when applied shortly after X-ray irradiation. Overall, the NO-COXIBs were found to be more radioprotective compared with celecoxib, which does not warrant further preclinical studies with the NO-COXIBs for the treatment of pheochromocytoma. However, evaluation as radioprotective agents for healthy tissues could be considered for the NO-COXIBs developed here, especially when used directly before irradiation.

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“…Intermediate compounds 2 a , 2 c , 21 , and 22 were obtained by the reduction and deprotection of respective hydroxy(nitro)stilbene derivatives 17 – 20 , which were synthesized by a double‐bond‐forming Wittig reaction between suitable benzaldehydes 13 – 16 and 3,4,5‐trimethoxybenzyltriphenylphosphonium bromide ( 12 ) in the presence of sodium hydride in anhydrous dichloromethane; stilbenes 17 – 20 were obtained as a 1:1 v / v mixture of E / Z isomers, as depicted in Scheme , and these isomers were separated by column chromatography. Compounds 10 a – m and 11 a – f (Scheme ) were obtained by the formation of an amide bond between stilbene–acrylic acids 27 a – f and 31 a – c with substituted benzene sulfonamides 28 a – f and 32 a – c by using 1‐ethyl‐3‐(3‐dimethylaminopropyl)carbodiimide/4‐dimethylaminopyridine (EDCI/DMAP) . The intermediates were prepared in good yields by the Claisen–Schmidt condensation of different phenyl acetic acids with appropriate benzaldehydes.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and in vitro and in vivo Evaluations of (Z)‐3,4,5‐Trimethoxystyrylbenzenesulfonamides/sulfonates as Highly Potent Tubulin Polymerization Inhibitors

et al. 2017

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Newer therapeutics can be developed in drug discovery by adopting the strategy of scaffold hopping of the privileged scaffolds from known bioactive compounds. This strategy has been widely employed in drug-discovery processes. Structure-based docking studies illustrate the basic underlying concepts and reveal that interactions of the sulfonamide group and hydrophobic interactions are crucial. On the basis of this strategy, over 60 synthetic analogues were synthesized and evaluated for their cytotoxicity against the NCI panel of 60 human cancer cell lines; the majority of these compounds exhibited promising cytotoxicity with GI values ranging between 18 and 50 nm. Among these compounds, (Z)-N-[2,3-dimethoxy-5-(3,4,5-trimethoxystyryl)phenyl]-4-methoxybenzenesulfonamide (7 a) and (Z)-N-[2-hydroxy-3-methoxy-6-(3,4,5-trimethoxystyryl)phenyl]-4-methoxybenzenesulfonamide (9 a) were found to be potent. Similar results were obtained against three human cancer cell lines with IC values ranging between 0.04 and 3.0 μm. Studies aimed at elucidating the mechanism of action of these new analogues revealed that they inhibited the in vitro polymerization of tubulin and disorganized the assembly of microtubules in HeLa and MCF-7cancer cells. Lead compounds 7 a and 9 a displayed notable in vivo antitumor activity in a HeLa tumor xenograft model. Our studies have resulted in the identification of a scaffold that can target tubulin polymerization, which should have significant potential toward the development of new antitumor drugs.

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Facile Synthesis ofN‐Acylsulfonamide in the Presence of Silica Chloride (SiO₂‐Cl) both under Heterogeneous and Solvent‐Free Conditions

Cited by 11 publications

References 29 publications

ZSM-5-SO3H as a novel, efficient, and reusable catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

ZSM-5-SO3H as a novel, efficient, and reusable catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

Exploring Nitric Oxide (NO)-Releasing Celecoxib Derivatives as Modulators of Radioresponse in Pheochromocytoma Cells

Design, Synthesis, and in vitro and in vivo Evaluations of (Z)‐3,4,5‐Trimethoxystyrylbenzenesulfonamides/sulfonates as Highly Potent Tubulin Polymerization Inhibitors

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Facile Synthesis ofN‐Acylsulfonamide in the Presence of Silica Chloride (SiO2‐Cl) both under Heterogeneous and Solvent‐Free Conditions

Cited by 11 publications

References 29 publications

ZSM-5-SO3H as a novel, efficient, and reusable catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

ZSM-5-SO3H as a novel, efficient, and reusable catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

Exploring Nitric Oxide (NO)-Releasing Celecoxib Derivatives as Modulators of Radioresponse in Pheochromocytoma Cells

Design, Synthesis, and in vitro and in vivo Evaluations of (Z)‐3,4,5‐Trimethoxystyrylbenzenesulfonamides/sulfonates as Highly Potent Tubulin Polymerization Inhibitors

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Facile Synthesis ofN‐Acylsulfonamide in the Presence of Silica Chloride (SiO₂‐Cl) both under Heterogeneous and Solvent‐Free Conditions