121-62-0Relevant academic research and scientific papers
Preparation method of P-acetyl aminobenzene sulfonyl chloride
-
Paragraph 0029-0032, (2021/11/14)
The invention provides a preparation method of p-acetyl aminobenzene sulfonyl chloride. The method uses acetanilide and chlorosulfonic acid as raw materials to prepare p-acetyl aminobenzenesulfonic acid by sulfonation reaction in the presence of a catalyst. The method is simple in process, free of special requirements for equipment, simple and convenient to operate, less in three wastes, good in product quality and suitable for industrial production.
Switching on prodrugs using radiotherapy
Geng, Jin,Zhang, Yichuan,Gao, Quan,Neumann, Kevin,Dong, Hua,Porter, Hamish,Potter, Mark,Ren, Hua,Argyle, David,Bradley, Mark
, p. 805 - 810 (2021/06/14)
Chemotherapy is a powerful tool in the armoury against cancer, but it is fraught with problems due to its global systemic toxicity. Here we report the proof of concept of a chemistry-based strategy, whereby gamma/X-ray irradiation mediates the activation of a cancer prodrug, thereby enabling simultaneous chemo-radiotherapy with radiotherapy locally activating a prodrug. In an initial demonstration, we show the activation of a fluorescent probe using this approach. Expanding on this, we show how sulfonyl azide- and phenyl azide-caged prodrugs of pazopanib and doxorubicin can be liberated using clinically relevant doses of ionizing radiation. This strategy is different to conventional chemo-radiotherapy radiation, where chemo-sensitization of the cancer takes place so that subsequent radiotherapy is more effective. This approach could enable site-directed chemotherapy, rather than systemic chemotherapy, with ‘real time’ drug decaging at the tumour site. As such, it opens up a new era in targeted and directed chemotherapy. [Figure not available: see fulltext.].
Green synthesis method of p-acetamidobenzenesulfonyl chloride
-
Paragraph 0014; 0018-0020; 0025-0026; 0028, (2020/07/24)
The invention discloses a green synthesis method of p-acetamidobenzenesulfonyl chloride. The method comprises the following steps of (a) dissolving acetanilide in liquid sulfur dioxide to obtain a first solution, (b) dropwise adding liquid sulfur trioxide into the first solution for sulfonation reaction to obtain a second solution, (c) dropwise adding liquid thionyl chloride into the second solution for chlorination reaction to obtain a third solution, and collecting hydrogen chloride gas generated in the reaction process by using water, (d) heating the third solution to 20-35 DEG C to obtaina fourth solution, and collecting sulfur dioxide gas, and (e) evaporating the fourth solution to separate excessive thionyl chloride, and drying to obtain p-acetamidobenzenesulfonyl chloride. The method is a green and environment-friendly chemical synthesis process, and generation and discharge of waste acid, wastewater and waste solvents are significantly reduced.
Insights into the electrochemical degradation of sulfamethoxazole and its metabolite by Ti/SnO2-Sb/Er-PbO2 anode
Wang, Yanping,Zhou, Chengzhi,Wu, Jinhua,Niu, Junfeng
supporting information, p. 2673 - 2677 (2020/06/01)
Electrochemical degradation of sulfamethoxazole (SMX) and its metabolite acetyl-sulfamethoxazole (Ac-SMX) by Ti/SnO2-Sb/Er-PbO2 were investigated. Results indicated that the electrochemical degradation of SMX and Ac-SMX followed pseu
An alternative synthetic process of p-acetaminobenzenesulfonyl chloride through combined chlorosulfonation by HClSO3 and PCl5
Tan, Shiyu,Yang, Yang,Luo, Ziping,Zhao, Shuo,Huang, Dafu,Zhang, Jun,Dong, Lichun,Wang, Gang
experimental part, p. 510 - 518 (2012/07/14)
P-Aminobenzene sulfonamide (sulfanilamide, SN) is the simplest and most-used sulfonamide medicine. The key step of SN production via the commonly used chlorosulfonic acid routine is the synthesis of p-acetaminobenzenesulfonyl chloride (P-ASC). A large amount of HSO3Cl has to be used in the traditional process, which results in serious environmental problems. In this study, an alternative chlorosulfonic acid process to synthesize P-ASC was investigated by partially substituting HSO3Cl by PCl5 as the chlorination agent. Compared with the traditional process, the molar ratio of HSO3Cl to acetanilide (the main raw material) can be decreased from 4.96 to 2.1 using CCl4 as the diluent; also, addition of a small amount of NH4Cl was found to significantly increase the P-ASC yield. Operating conditions of the reaction were studied first by single-factor experiments and later by orthogonal experiments to obtain optimum operating conditions under which the P-ASC yield can reach as high as 86.3 %.
Phenylthio-derivatives of α-methylene-γ-lactones as pro-drugs of cytotoxic agents
Fardella, Giuseppe,Barbetti, Paolo,Grandolini, Giuliano,Chiappini, Ione,Ambrogi, Valeria,Scarcia, Vito,Furlani Candiani, Ariella
, p. 515 - 523 (2007/10/03)
A series of substituted phenylthio-derivatives of grosheimin (1), a natural cytotoxic guaianolide, were investigated with the aim of providing insight into their mechanism of action as cytotoxic agents against KB cell lines. Hydrolysis data, kinetics, in the presence and in the absence of H2O2, and the valuation of lipophilicity were correlated with cytotoxicity values and with Hammett-σ-values of substituents (R) at the thiophenol ring. These compounds behave as 'pro-drugs' which release the cytotoxic agent grosheimin by sulphur-oxidation promoted by H2O2 and subsequent retro- elimination which depends on the nature and position of the R substituent.
Substituted benzene derivatives useful as neuraminidase inhibitors
-
, (2008/06/13)
A compound of the Formula (I): STR1 or pharmaceutically-suitable salts or prodrug forms thereof, wherein: n is 0-1; m is 0; p is 0-1; R1 is --CO2 H; R2 is selected from the group consisting of H, --OH, and --NH2 ; R3 is H; R4 is --C(O)NHR8 ; R5 is --NHC(R6)NH2 R6 is selected from the group consisting of =NH, =NOH, =NCN, =O, and =S; and R8 is selected from the group consisting of C1 -C4 linear or branched alkyl substituted with 0-3 halogens on each carbon.
Kinetics of hydrolysis of aromatic mono- and disulfonyl chlorides
Sanecki, Przemyslaw,Rokaszewski, Edward
, p. 2263 - 2267 (2007/10/02)
A continuous polarografic method of recording instantaneous concentrations of - SO2Cl groups in an aqueous acetic acid system containing CH3CO2Na has been elaborated.Ten model monosulfonyl chlorides underwent hydrolysis according to pseudo-first order kinetics (20percent H2O, 80percent v.v.CH3CO2H, 0.5 mol/dm3 CH3CO2Na).Plots of hydrolysis for seven disulfonyl dichlorides with different number of - CH3 groups have been determined.Pseudo-first order rate constants for two consecutive reactions of hydrolysis (k1 and k2) have been computed and the influence of -SO2Cl and -SO3- groups on the reactivity of the second group - SO2Cl has been discussed.The mechanism of nucleophilic substitution has also been discussed.
Process for the preparation of N-acetylaminoarylsulfonic acids in sulfuric acid as solvent
-
, (2008/06/13)
The invention relates to salt-free N-acetylaminoarylsulfonic acids, their preparation by acetylation with acetic anhydride or acetyl chloride, sulfuric acid, which can also contain a small amount of water and/or dimethylformamide and/or N-methylpyrrolidone, serving as the solvent, and the use of the N-acetylaminoarylsulfonic acids for the preparation of their acid chlorides.
STUDIEN ZUM VORGANG DER WASSERSTOFFUEBERTRAGUNG.61. Chemische Reaktivitaet und Halbstufenpotential Vergleichende Versuche am Beispiel einiger Arylsulfonsaeurederivate
Horner, Leopold,Schmitt, Rolf-Erhard
, p. 189 - 212 (2007/10/02)
In arylsulfonyl halides, the half-wave potentials of the corresponding chlorides and fluorides differ by more than 1000 mV, the fluoride being more negative; the influence of para-substituents is small for the chlorides, large for the fluorides.In agreement with the half-wave potentials, arylsulfonyl chlorides are considerably more reactive chemically than the corresponding fluorides.The O-selectivity found for P(O)F compounds is not observed in arylsulfonyl fluorides.Studies of competitive ester formation using primary and secondary alcohols and various arylsulfonyl chlorides yielded no clear analogy to the half-wave potentials.The primary alcohol is always sulfonated in preference to the secondary alcohol, whether the hydroxy functions are present in different molecules or the same molecule.In the latter case, the secondary hydroxyl function is then attacked in a further step by a second, different, arylsulfonyl chloride, giving the compounds 4-8.The further electroreduction of these diesters may be carried out in high yields, giving selective fission of one ester linkage only (that with the more positive potential) provided the difference in the half-wave potentials of the different ester linkages is sufficiently large.In the electroreductive fission the monosulfinic acid and the corresponding alcohol are liberated (see table II).In the competition reaction between phenol and 1:1 mixtures of tosyl chloride (A) and p-carboxyethyl-benzenesulfonyl chloride (B), the chloride with the more positive potential (B), E1/2=72 mV reacts quicker by a factor of 2.5.In competitive Finkelstein reactions, the selectivity was 1:11 at a difference in half-wave potentials of 760 mV (table IV).Arylsulfonates with free secondary alcohol functions may be oxidized smoothly and in high yield to the corresponding ketone using Na2Cr2O7 (3), without effecting the sulfonate linkage.The alkali hydrolysis of n-hexyl para-substituted arylsulfonates follows the Hammett relation but shows a lesser selectivity than was observed in the electroreductive fission of the same esters at the required potentials.Tables VI, VII and VIII concentrate on the preparative importance of the potential-controlled electroreductive fission of aliphatic and aromatic arylsulfonates.The corresponding hydroxy compounds are liberated in yields of up to over 90percent: N-alkyl- and N-aryl arylsulfonamides give analogous results. (table IX)
