Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-diones

A series of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-dione derivatives 6 (a-d) and 7 (a-g) were synthesized with different substituted aromatic sulfonyl chlorides (R-SO(2)-Cl) and alkyl halides (R-X) and were characterized by (1)H NMR, LC/MS, FTIR and elemental analyses. All the compounds synthesised were evaluated for their cell antiproliferation activity by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The antiproliferative effects of the synthesised compounds were tested against viable human skin fibroblast cell line and carcinoma cell lines namely HeLa cells, HT-29 cells, MCF-7 cells, HepG-2 cells by adopting positive and negative control. The importance of the nitro group on thiazolidinone moiety was confirmed and it was concluded that the fourth position of the substituted aryl ring plays a dominant role and was responsible for the antiproliferative activity. Among the synthesized compounds only 6a, 7e and 7g have potent antiproliferative activity on all the carcinoma cell lines tested.     

Synthesis and antimicrobial activity of 1-benzhydryl-sulfonyl-4-(3-(piperidin-4-yl) propyl)piperidine derivatives against pathogens of <Emphasis Type="Italic">Lycopersicon esculentum</Emphasis>: A structure-activity evaluation study

Several 1-benzhydryl-sulfonyl-4-(3-(piperidin-4-yl)propyl)piperidine derivatives 8(a–j) were prepared by the treatment of substituted benzhydryl chlorides with 4-(3-(piperidin-4-yl)propyl)piperidine followed by N-sulfonation with sulfonyl chlorides in the presence of dry methylene dichloride and triethyl amine. The synthesized compounds were characterized by ¹H-NMR, IR, and elemental analysis. All the synthesized compounds were evaluated in vitro for their efficacy as antimicrobial agents by artificial inoculation technique against standard strains of two important bacterial viz., Xanthomonas axonopodis pv. vesicatoria and Ralstonia solanacearum as well as and two fungal pathogens namely Alternaria solani and Fusarium solani of tomato plants. We have briefly investigated the structure-activity relation studies and reveal that the nature of substitutions on benzhydryl ring and sulfonamide ring influences the antibacterial activity. Among the synthesized new compounds 8b, 8d, 8g, 8h, 8i, and 8j were showed significant potent antimicrobial activities compared to the standard drugs Chloramphenicol, Mancozeb.     

Electrochemical oxidation of quercetin in the presence of benzenesulfinic acids

Electrochemical oxidation of quercetin has been studied in the absence and presence of benzenesulfinic acids as nucleophiles in an acetonitrile+water mixture, using cyclic voltammetry and controlled-potential coulometry. The results indicate that the o-quinone derived from quercetin participates in a Michael addition reaction with the benzenesulfinic acids to form the corresponding sulfonyl derivatives. The electrochemical synthesis of these derivatives has been successfully performed at carbon rod electrodes in an undivided cell in good yield and purity.     

Synthesis of N-arylsulfonyl DL-phenylserine derivatives exhibiting anti-inflammatory activity in experimental studies

Synthesis and evaluation of anti-inflammatory activity in rats with adjuvant arthritis of aryl sulfonyl derivatives of nonproteinogenic aromatic amino acids is reported. The studied compounds were synthesized by introducing residues of benzene-, p-toluene-, and p-bromobenzene sulfonic acids into threo-DL-phenylserine and erythro-DL-p-nitrophenylserine structures. From the set of 12 compounds tested in animal screening, N-(p-bromobenzenesulfonyl)-erythro-DL-p-nitrophenylserine ethyl ester 12 demonstrated the most pronounced anti-inflammatory activity. This compound inhibited inflammation process in polyarthritis phase by 53% (P < 0.001) though it was slightly toxic (LD50 > 6,000 mg kg(-1) for mice).     

Synthesis and antimicrobial activity of new substituted anilinobenzimidazoles

A series of benzimidazole derivatives carrying different heterocycles such as 1,2,3-thiadiazole, 1,3,4-thiadiazole, thiazolidine, 2,3-dihydro-thiazole, 1,3,4-oxadiazole, semicarbazone and substituted thiosemi-carbazones were synthesized. Also a series of 1-methylbenzimidazole carrying hydroxy ethyl-amide, substituted sulfonyl hydrazide and benzoyl hydrazide from aminobenzoyl group at position 2 of 1-methylbenzimidazole were synthesized. The antimicrobial evaluation of some of the new compounds was carried out.     

Synthesis and evaluation of 1-benzhydryl-sulfonyl-piperazine derivatives as inhibitors of MDA-MB-231 human breast cancer cell proliferation

A series of novel 1-benzhydryl-sulfonyl-piperazine derivatives 7(a-e) were designed by a nucleophilic substitution reaction of 1-benzhydryl-piperazine with various sulfonyl chlorides and characterized by ¹H nuclear magnetic resonance (NMR), liquid chromatography mass spectrometry (LC/MS), Fourier-transform infrared (FTIR), and elemental analysis. Our research is focused on identifying synthetically occurring chemotherapeutic substances capable of inhibiting, retarding, or reversing the process of multistage carcinogenesis. The title compounds were evaluated for their efficacy in inhibiting MDA-MB-231 breast cancer cell proliferation. Compound 1-benzhydryl-4-(4-tert-butyl-benzenesulfonyl)-piperazine (7d) showed significant inhibitory activity.     

Klinische Erfahrung mit Benzolsulfonsäurechlorid

Zusammenfassung An drei Fällen schildert der Autor den klinischen Verlauf einer perkutanen und über die Schleimhaut erfolgten Aufnahme Von Benzolsulfonsäurechlorid, die zu biologischer Einwirkung auf die Haut und toxischer reversibler Leberschädigung führte.In zwei Fällen entwickelte sich ein schwerster Schock, der nach 1 bis 1,5 Std beherrscht wurde.Es wird eine mögliche allergische Genese des Geschehens von Soforttyp diskutiert.

---

Clinical experience with benzene sulfonyl chloride

The clinical development of a percutaneous benzene sulfonyl chloride absorption, which can also occur on the mucous membrane, has a biological effect on the skin and results in reversible toxic damage to the liver; three such cases are described.Two patients experienced Very severe shock which was brought under control after 1 to 1.5 hrs.A possible allergic genesis reaction of an immediate type is discussed.

     

旱生香茶菜总二萜对人肝癌细胞株增殖、荷人肝癌细胞株裸鼠皮下移植瘤生长的影响

目的:研究旱生香茶菜总二萜(IXD)对人肝癌细胞株(CA)增殖、荷CA裸鼠皮下移植瘤生长的影响。方法:体外试验采用磺酰罗丹明B(SRB)法测试IXD对CA的IC50值,体内试验测定IXD不同剂量对荷CA裸鼠移植瘤增殖的抑制率。结果:IXD对CA的IC50值为6·17μg/ml,其在剂量为100、200(mg·kg)/d应用12d时抑制率分别为33·52%、38·19%,与生理盐水阴性对照组比较具有显著性差异(P<0·05)。结论:IXD对CA有较强的细胞毒活性,对荷CA裸鼠移植瘤生长具有一定的抑制作用。