38775-38-1Relevant academic research and scientific papers
New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents
Song, Doona,Yang, Jee Sun,Oh, Changmok,Cui, Shuolin,Kim, Bo-Kyung,Won, Misun,Lee, Jang-Ik,Kim, Hwan Mook,Han, Gyoonhee
, p. 670 - 677 (2013)
RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts that induce apoptosis via up-regulation of RhoB, we synthesized novel aliphatic sulfonamido-quaternary ammonium salts. These new synthetic compounds were evaluated for their biological activities using an in vitro RhoB promoter assay in HeLa cells, and in a growth inhibition assay using human cancer cell lines including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. Compound 5b (ethyl-dimethyl-{3-[methyl-(tetradecane-1-sulfonyl)-amino]-propyl}-ammonium; iodide) was the most promising anticancer agent in the series, based upon the potency of growth inhibition and RhoB promotion. These new aliphatic sulfonamido-quaternary ammonium salts could be a valuable series for development of new anticancer chemotherapeutic agents.
Synthesis and Physicochemical Properties of Alanine-Based Surfactants
Bougueroua,Mousli,Tazerouti
, p. 1121 - 1131 (2016/10/18)
The synthesis of a homologous series of alanine-based surfactants, namely sodium salts of n-alkanesulfonamido-2-propanoic acids in which n-alkane is n-dodecane, n-tetradecane, n–hexadecane, and n-octadecane having the formula RSO2NHCH (CH3)COO?Na+, is described. The starting materials used were a mixture of secondary positional isomers of n-alkanesulfonyl chlorides obtained by photosulfochlorination reaction using sulfuryl chloride and a catalyst. Surface properties of the aqueous solutions of the synthesized surfactants, including the critical micelle concentration and minimal surface tension δmin, were determined using surface tension measurements at 25?°C. The surface excess Γ and minimum area per molecule (Amin) where calculated using the Gibbs equation. The foaming power was also determined by the Bartsh method, and the R5 parameter was calculated to estimate the stability of the foam formed. The results obtained were compared to those of a commercial surfactant, sodium dodecylsulfate, and a series of synthesized glycine-based surfactants. The results obtained clearly show that the alanine-based surfactants possess good surface properties. The investigations highlight the influence on the surface properties of the addition of a methyl group in the hydrophilic part.
Clean and economic synthesis of alkanesulfonyl chlorides from S-alkyl isothiourea salts via bleach oxidative chlorosulfonation
Yang, Zhanhui,Zhou, Bingnan,Xu, Jiaxi
, p. 225 - 229 (2014/03/21)
A simple procedure for clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is disclosed. This procedure is environment- and worker-friendly with the advantages of readily accessible materials and reagents, simple and safe operations, easy purification without chromatography, and affords high yields of up to 99%.
Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents
Song, Doona,Yang, Jee Sun,Kim, Seo Joong,Kim, Bo-Kyung,Park, Song-Kyu,Won, Misun,Kim, Hwan Mook,Choi, Kang-Yell,Lee, Kyeong,Lee, Kiho,Han, Gyoonhee
, p. 788 - 794 (2013/02/23)
RhoB, one of the upstream signaling proteins of the phosphatidylinositol-3- kinase (PI3K)/Akt pathway, is frequently mutated in human cancer. Based on a piperazine alkyl derivative that induced apoptosis via up-regulation of RhoB, we synthesized novel aliphatic amido/sulfonamido-quaternary ammonium salts and evaluated their biological activities using an in vitro growth inhibition assay and RhoB promoter assay in human cancer cells. Compound 3a was the most promising anticancer agent in the series, based upon its potent growth inhibition via RhoB-mediated signaling. These novel aliphatic amido/sulfonamido-quaternary ammonium salts may be useful as a platform for development of anticancer chemotherapeutic agents.
Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation
Yang, Zhanhui,Xu, Jiaxi
, p. 1675 - 1682 (2013/07/27)
A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.
Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation
Yang, Zhanhui,Zheng, Yongpeng,Xu, Jiaxi
supporting information, p. 2165 - 2169 (2013/10/22)
A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.
Surface activities, foam properties, HLB, and krafft point of some n-alkanesulfonates (C14-C18) with different isomeric distributions
Fekarcha, Latifa,Tazerouti, Amel
, p. 419 - 431 (2012/10/29)
A homologue series of sodium secondary n-alkanesulfonates (C14, C16 and C18) were obtained by photosulfochlorination process with two different reaction conditions. Different length chains with different isomeric distributions of n-alkanesulfonates are expected to present variations in physicochemical properties. In this investigation, the relationships between their isomeric distribution and their chain length and micellar behaviors were thoroughly explored. Their CMC at different temperatures were determined using specific conductivity and surface tension measurements. Through surface tension isotherms, the surface activities (γCMC) were obtained. The surface absorption amounts (Cmax) and the molecular areas (Amin) were calculated using Gibb's equation. As expected, these surfactants exhibit good surface properties. It was shown that the CMC values increase with increasing the percentage of secondary isomers, with a surface tension decrease. It was also shown that the CMC values decrease with increasing chain length. The HLB values were calculated for each surfactant and the results obtained suggest that they are O/W emulsifiers. The foam properties of synthesized surfactants were evaluated and compared to those obtained for commercial samples. It was shown that the foamability is influenced both by the length of the hydrophobic moiety and the percentage of secondary isomers. It can be easily concluded that the C14 sulfonates show the best foaming properties independently of their isomeric distribution. The Krafft point values obtained indicate that the micellization and the surfactant solubility mainly depend on the proportion of secondary isomers and the length of hydrophobic moiety. AOCS 2012.
Synthesis and some surface properties of glycine-based surfactants
Mousli, Radia,Tazerouti, Amel
experimental part, p. 65 - 72 (2012/01/13)
A new group of anionic surfactants, namely sodium salts of secondary alkanesulfonamidoacetic acid, were synthesized using n-alkanesulfonyl chlorides as starting materials. These surfactants, having the formula: R-SO 2-NH-CH2-COONa, with R = C12, C14, C16 and C18, were obtained in a simple way with quantitative yields. Different chain lengths and positional isomers of this new type of surfactants are expected to present differences in surface properties and foamability. The surface properties including critical micelle concentrations and minimal surface tensions γmin were determined for each prepared surfactant using surface tension measurements with a Wilhelmy plate. Surface excess and minimum area per molecule at the air-water interface were determined for different concentrations at 25 and 50 °C using the Gibbs equation. The foaming power was also determined by the Bartsch method, and the results obtained were compared to those of a commercial surfactant, the linear alkylbenzenesulfonate. The stability of the foam formed was also evaluated. As expected, these surfactants exhibit good surface properties and show good foaming power.
