127-74-2Relevant academic research and scientific papers
Solid-state reaction between sulfadiazine and acetylsalicylic acid
Liu,Parrott
, p. 564 - 566 (1991)
Kinetic data for the solid-state reaction of sulfadiazine and acetylsalicylic acid are presented. A compaction method was used to observe the influence of applied pressure, particle size, and temperature on the reaction rate.
Synthesis of poly(ethylene glycol) with sulfadiazine and chlorambucil end groups and investigation of its antitumor activity
Jia, Zhongfan,Zhang, Haitao,Huang, Junlian
, p. 2531 - 2534 (2003)
α-Amino-ω-hydroxyl-poly(ethylene glycol) (PEG) with different molecular weight (Mr=2100, 4400, 7200) were synthesized and used as carrier for the combination of sulfadiazine and chlorambucil. In vivo, all these polymer drugs with sulfadiazine and chlorambucil at each end are water soluble and showed the higher antitumor activity against Lewis lung cancer than the same polymers but without the sulfadiazine. The best one is the sample with molecular weight of 2100. In vitro, however, for the samples with same molecular weights, the polymer drugs with and without sulfadiazine showed the similar results against C6 human breast cancer cells. No obvious difference was found.
Evaluation of antimicrobial agents for veterinary use in the ecotoxicity test using microalgae
Eguchi, Kaoru,Nagase, Hiroyasu,Ozawa, Manao,Endoh, Yuuko S.,Goto, Kisako,Hirata, Kazumasa,Miyamoto, Kazuhisa,Yoshimura, Haruo
, p. 1733 - 1738 (2004)
The influence of antimicrobial agents approved as veterinary drugs in Japan on the growth of green algae, Selenastrum capricornutum and Chlorella vulgaris, was studied in accordance with the OECD guidelines for testing chemicals. Among the agents tested, growth inhibitory activity was very varied, i.e. erythromycin showed the strongest activity (EC50, 50% effective concentration, =0.037 mg/l), sulfa drugs had activity to some extent (EC 50s of sulfamethoxazole, sulfadiazine, and sulfadimethoxine were 1.5, 2.2, and 2.3 mg/l, respectively), but ampicillin and cefazolin did not inhibit growth (EC50s > 1000 mg/l). We also investigated synergistic effect of combining sulfa drugs with trimethoprim or pyrimethamine, which are commonly used as a combined drug. By adding trimethoprim, the growth inhibitory activity of sulfamethoxazole and sulfadiazine was significantly enhanced. Growth inhibition by sulfa drugs was reduced by the addition of folic acid, indicating that they inhibit folate synthesis in green algae.
Inhibition of carbonic anhydrase II by sulfonamide derivatives
Xuan,Zhan,Zhang,Li,Zheng
, p. 412 - 415 (2021/11/22)
A series of sulfonamide derivatives were synthesized, and the enzyme inhibitory activity of the synthesized compounds on carbonic anhydrase II was evaluated. Through molecular docking studies, it was found that compounds 1b, 1e, 2a, 2b, 3a have a strong binding affinity to carbonic anhydrase II. The IC50 values of the four compounds 1e, 2b, 3a, and 3b were lower than that of the positive control drug acetazolamide. What’s more, the compounds had a high inhibitory activity for A549 lung cancer cell growth, among them, 1e and 3a could inhibit both carbonic anhydrase II and lung cancer cell proliferation.
Structure-activity relationships of agonists for the orphan G protein-coupled receptor GPR27
Blavier, Jeremy,Charles, Ma?lle,Hanson, Julien,Kronenberger, Thales,Laschet, Céline,Müller, Christa E.,Pillaiyar, Thanigaimalai,Rosato, Francesca,Wozniak, Monika
, (2021/08/27)
GPR27 belongs, with GPR85 and GPR173, to a small subfamily of three receptors called “Super-Conserved Receptors Expressed in the Brain” (SREB). It has been postulated to participate in key physiological processes such as neuronal plasticity, energy metabolism, and pancreatic β-cell insulin secretion and regulation. Recently, we reported the first selective GPR27 agonist, 2,4-dichloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (I, pEC50 6.34, Emax 100%). Here, we describe the synthesis and structure-activity relationships of a series of new derivatives and analogs of I. All products were evaluated for their ability to activate GPR27 in an arrestin recruitment assay. As a result, agonists were identified with a broad range of efficacies including partial and full agonists, showing higher efficacies than the lead compound I. The most potent agonist was 4-chloro-2,5-difluoro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7y, pEC50 6.85, Emax 37%), and the agonists with higher efficacies were 4-chloro-2-methyl-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7p, pEC50 6.04, Emax 123%), and 2-bromo-4-chloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7r, pEC50 5.99, Emax 123%). Docking studies predicted the putative binding site and interactions of agonist 7p with GPR27. Selected potent agonists were found to be soluble and devoid of cellular toxicity within the range of their pharmacological activity. Therefore, they represent important new tools to further characterize the (patho)physiological roles of GPR27.
3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF
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Paragraph 00243, (2017/10/06)
The present invention provides compounds, compositions thereof, and methods of using the same.
A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-Narylacetamides catalyzed by SOCl2
Wang, Gong-Bao,Wang, Lin-Fa,Li, Chao-Zhang,Sun, Jing,Zhou, Guang-Ming,Yang, Da-Cheng
experimental part, p. 77 - 89 (2012/05/20)
Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides. Springer Science+Business Media B.V. 2011.
2-[N1-2-Pyrimidyl-aminobenzenesulfonamido] ethyl 4-bis(2-chloroethyl) aminophenyl butyrate: A potent antitumor agent
Huang, Zhaohua,Yang, Genjin,Lin, Zhaoliang,Huang, Junlian
, p. 1099 - 1103 (2007/10/03)
2-[N1-2-Pyrimidyl-aminobenzenesulfonamido] ethyl 4-bis(2-chloroethyl) aminophenyl butyrate has been prepared by reaction of chlorambucil with sulfadiazine derivative. Schiff's base has been used as the protective group of the aromatic amine in the synthesis. It can be completely removed by the irradiation of 365 nm UV light at room temperature. The title compound exhibits a high antitumor activity with a therapeutic index (TI) of 47.55 which is twice that of chlorambucil's (TI: 22.84).
A novel kind of antitumour drugs using sulfonamide as parent compound
Huang, Zhaohua,Lin, Zhaoliang,Huang, Junlian
, p. 863 - 872 (2007/10/03)
To obtain potent antitumour agents with low toxicity, sulfonamide derivatives containing 5-flurouracil and nitrogen mustard, respectively are designed and synthesised. 1-(3-(4-Acetylaminobenzenesulfonamido)-3-oxopropyl)-5-fluoropyrimidine-2, 4-dione (4) was obtained by the coupling of p-acetamidobenzenesulfonamide with 3-(5-fluorouracil-1-yl) propionic acid. The hydrolysis of 4 led to 1-(3-(4-aminobenzenesulfonamido)-3-oxopropyl)-5-fluoropyrimidine-2,4-dione (5). Treatment of p-acetamidobenzenesulfonyl chloride with bis(2-chloroethyl) amine led to 4-acetylamino-N,N-bis(2-chloroethyl)benzenesulfonamide (6). Subsequent hydrolysis of 6 in hydrochloric acid led to 4-amino-N,N-bis(2-chloroethyl)benzenesulfonamide hydrochloride (7). Two different synthetic route were investigated in the synthesis of 2-[N1-2-pyrimidyl-aminobenzenesulfonamido] ethyl 4-bis(2-chloroethyl) aminophenyl butyrate (12b). Carbobenzyloxy was proved to be unsuitable for the protection of the aromatic amino group of sulfadiazine since the pyrimidine ring was also hydrogenated at the last step of the first route under the deprotection condition. In another route, acetyl was firstly used as the protective group, then it was replaced by the Schiff's base. The reaction of chlorambucil with 2-[N1-2-pyrimidinyl-(p-acetyl)aminobenzenesulfonamido] ethanol (10b) afforded 2-[N1-2-pyrimidinyl-(p-benzylidene)aminobenzenesulfonamido] ethyl 4-bis(2-chloroethyl) aminophenyl butyrate (11b). Compound 12b was obtained by the hydrolysis of 11b. The acute toxicity and antitumour activity of 5, 7 and 12b have been investigated in mice. Compound 12b exhibited high antitumour activity and low toxicity with a therapeutic index (TI) of 47.55.
