Synthetische Senfölbildner, III. Untersuchungen über Dithiocarbamidsäureester als mikrobizid wirksame Substanzen

Rieche, Alfred; Hilgetag, Günter; Martin, Dieter; Kreyzi, I.

doi:10.1002/ardp.19632960508

Cited by 16 publications

(2 citation statements)

References 25 publications

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“…Phenethyldithiocarbamic Acid Phenyl Ester (18d): purified by column chromatography with hexanes/EtOAc (95:5) as eluent and obtained as colorless crystals (60%); mp 70−71 °C (lit . mp 73−74 °C); 1 H NMR δ 2.82 (t, J = 6.6 Hz, 2H), 3.87 (q, J = 6.3 Hz, 2H), 6.55 (s, 1H), 6.94−6.97 (m, 2H), 7.20−7.22 (m, 3H), 7.37−7.39 (m, 4H), 7.42−7.50 (m, 1H); 13 C NMR δ 33.6, 46.9, 126.6, 128.0, 128.4, 128.8, 130.3, 131.0, 135.4, 137.5, 194.8.…”

Section: Methodsmentioning

confidence: 99%

Benzotriazole-Assisted Thioacylation

et al. 2005

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[Chemical reaction: See text] Benzotriazole reagents for thioacylation (RCSBt), thiocarbamoylation (RR'NCSBt), aryl/alkoxythioacylation (ROCSBt), and aryl/alkylthiothioacylation (RSCSBt) are synthesized, and their utility is assessed by syntheses of representative heteroaryl thioureas 3a-g, thioamides 15a-s, thionoesters 16a-h, thiocarbamates 17a-e, dithiocarbamates 18a-d, thiocarbonates 19a-c, and dithiocarbonates 20a-c.

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Section: Methodsmentioning

confidence: 99%

Benzotriazole-Assisted Thioacylation

et al. 2005

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“…Sodium 7-(A -Benzyldithiocarbamoylacetamido)cephalosporanate (14).-To a soln of 11.7 g (0.03 mole) of sodium 7-(2-bromoacetamido)cephalosporanate3 and 2.5 g of NaHCOs in 200 ml of H20 at 10°was added, with vigorous stirring, 6.6 g (0.03 mole) of potassium A'-benzyldithiocarbamate. 6 The soln was stirred in the cold for 1 hr as the pH was kept around 7 with 2 A7 NaHCOs soln. The soln was washed with Et20, layered with 100 ml of EtOAc, and acidified to pH 4 with 429) H3PO4.…”

mentioning

confidence: 99%

.beta.-Lactam antimicrobial agents which possess antifungal activity

Gottstein¹,

Eachus²,

Misco³

et al. 1971

J. Med. Chem.

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Notes hydrazine-HC1, 250 mg of NaOAc, and 1.0 ml of AcOH and refluxed for 40 min. The mixt was poured over a large amount of ice water and the ppt formed w'as collected by filtration. Recrystn from MeOH yielded 900 mg of 6, mp 154-157°.Receptor Binding Studies.^-Uteri from 10 immature rabbits weighing less than 2 kg were removed, minced, and washed several times with buffer to rid the tissue of blood. Uteri were then homogenized in 0.4 vol of buffer (0.01 M Tris-HCl buffer, pH 8.0, contg 0.001 M EDTA and 0.25 M sucrose) at 4°. The homogenates were first centrifuged at 12,000¡? for 30 min, followed by 273,000;? for 1.0 hr. Reaction mixts consisting of (a) 0.2 ml of buffer (0.01 M Tris-HCl, pH 8.0, contg 0.001 M EDTA, 0.25 M sucrose, and 25,000 cpm of progesterone-i/ml), (b) nonradioactive compds reported in this paper at a concn of 100 ng/ml, and (c) 50 µ of uterine cytosol were incubated at 4°for 16 hr. After incubation bound vs. unbound steroids were sepd as earlier reported, and the amt of bound progesterone-f was determined.Acknowledgment.-We wish to thank Dr. I. Scheer and Dr. J. DaVanzo for their encouragement and interest. Thanks are also due to Mrs. E. Kaffitz, Miss C. DeDella, and Mrs. B. Fuller for their technical assistance./3-Lactam Antimicrobial Agents Which Possess Antifungal Activity in the presence of I2 and Nal (method ) 1 2 jV-Benyzlthiocarbamoylmereaptoacetamidocephalosporanic acid (I) ( 14) was prepared from sodium 7-(2-bromoacetamido)cephalosporanate3 4and potassium Ar-benzyldithiocarbamate. Potassium 6-[( -)-a-phenoxypropionamidojthiopenicillanate (II) (15)4 and 6-phenoxyacetamidopenicillanal (III) (16)5 were prepared by published procedures.Antifungal Activity.-Results of the tests are summarized in Table I. As can be seen, the most active compound is sodium (Ar-benzvldithiocarbamoylacetamido)cephalosporanate (I) (Table I, 14). It is noteworthy that this cephalosporin showed two-to fourfold greater antifungal activity than the antifungal acid 176 from which it was derived. It is also of interest that the penicillin aldehyde III (16) which is virtually without activity in vitro aganist bacteria, showed antifungal effects. Compound 14 was tested in an experimental systemic Cryptococcus neoformans infection of mice but was found to case no prolongation of survival time. Thus, the probability exists that, although these compounds are active in vitro, they are not present in an active form in animal tissues at high enough concentrations to give protection against systemic fungal infections.

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Dithiocarbamic Acid and Derivatives

Schubart

2000

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Physical and Chemical Properties 3. Manufacture of Dithiocarbamate Salts 4. Transformation Products 4.1. Thiuram Sulfides 4.1.1. Thiuram Disulfides 4.1.2. Thiuram Monosulfides 4.1.3. Thiuram Trisulfides and Tetrasulfides 4.2. Thiocarbamoylsulfenamides 4.3. Thiocarbamoyl Chlorides 4.4. Dithiocarbamic Acid Esters 4.5. Heterocyclic Compounds 4.6. Other Derivatives 4.6.1. Dithiolanylium Salts 4.6.2. Alkylthioformimidic Chlorides 4.6.3. Isothiocyanates, Isocyanates, and Thioureas 4.7. Photolysis of Dithiocarbamates 5. Uses 5.1. Vulcanization Accelerators 5.2. Pesticides 5.3. Medical Applications 5.4. Radioprotective Agents 5.5. Imaging Technology 5.6. Other Uses 6. Toxicology and Occupational Health

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Synthetische Senfölbildner, III. Untersuchungen über Dithiocarbamidsäureester als mikrobizid wirksame Substanzen

Cited by 16 publications

References 25 publications

Benzotriazole-Assisted Thioacylation

Benzotriazole-Assisted Thioacylation

.beta.-Lactam antimicrobial agents which possess antifungal activity

Dithiocarbamic Acid and Derivatives

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