Construction and properties of drug molecules modifying octamolybdate hybrid compounds

By introducing antibacterial drug pipemidic acid into octamolybdates, two new compounds, (HPPA)₄[Mo₈O₂₆] 2H₂O (1) and [Ni₂(PPA)₂(H₂O)₄] [Mo₈O₂₆] 3H₂O (2) (PPA?=?8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acid), have been synthesized and characterized by physical methods. Single-crystal X-ray analysis reveal that 1 and 2 crystallize in the triclinic system, space group P-1, in which supramolecular interactions play vital roles in stabilizing the structure of 1 and 2. The results of their antitumor activities in vitro show that the compounds exhibit good anti-SGC7901 and anti-SMMC7721 activities, which indicates that the antitumor activities of Polyoxometalates can be modulated by the surface modification with drugs.     

Solvent Extraction of Sodium with Crown Ethers

Abstract

The solvent extraction separation of sodium was effected with 15-crown-5 (0.01 M) in methylene chloride in presence of 0.01 M picric acid as a counter ion. It was quantitatively extracted at pH 5.0 and was stripped with 3 M hydrochloric acid and determined by flame emission spectroscopy at 589 nm. Sodium was separated from alkali and alkaline earth metals and common anions. The method was extended to the analysis of sodium from real samples.     

Sodium and Onium Persorate Salts as Decontaminants of Neutotoxic Organophosphorus Compounds

Abstract

We compare the Sodium Perborate and various Phosphonium and Ammonium Perborates in their abilities to hydrolyse a series of phosphoric and phosphonic acid esters [OP].     

Ion Chromatographic Determination of Sodium Isethionate

Abstract

Single column anion chromatography with conductivity detection has been used for the determination of sodium isethionate. A mobile phase of aqueous phthalic acid - methanol (pH 2.5) allows for the separation of isethionate from chloride and alkyl isethionate ester surfactants. Commercially available samples of sodium isethionate and alkyl esters were analyzed by the described procedure.     

The Determination of Sodium in Alumina Using a Sodium Selective Ion Electrode

Abstract

A method has been developed for the determination of sodium in alumina using a selective ion electrode. The alumina sample is dissolved in ammonium hydrogen fluoride in platinum crucibles or sintered with boric acid using either platinum, nickel, or zirconium crucibles. Either dissolution technique completely extracts all available sodium. After dissolution, and in the presence of citrate to prevent aluminum hydroxide precipitation, the pH is adjusted to 8.7 with ammonium hydroxide, and the sodium concentration is determined by a sodium selective ion electrode.     

Sodium hypochlorite as volumetric reagent

Summary In presence of 5 N to 6 N hydrochloric acid, ferrous ethylenediamine sulphate was used as a reducing agent to determine indirectly potassium chlorate, potassium bromate, potassium metaperiodate, potassium dichromate, potassium ferricyanide, potassium permanganate, potassium persulphate, hydrogen peroxide, ceric sulphate and chloramine-T. An excess of ferrous ethylenediamine sulphate added to each of the substances in the acid medium was titrated with a standard solution of sodium hypochlorite. Iodine monochloride was used as catalyst and preoxidizer and chloroform was used as an indicator. Chloroform was coloured violet owing to the liberation of iodine during the titration and became very pale yellow at the end-point because of the formation of iodine monochloride.Part I: See Z. analyt. Chem. 160, 429 (1958).     

Two new triterpenoids from Gypsophila oldhamiana

Two new triterpenoids (1–2) were isolated and elucidated from the roots of Gypsophila oldhamiana, together with four known triterpenoids (3–6). Their structures were identified to be 3β-hydroxyolean-13(18)-ene-23, 28-dioic acid (1), 3β, 12α-dihydroxy-23-carboxyolean-28, 13β-olide (2), 3β, 16α-dihydroxy-23-oxoolean-13(18)-en-28-oic acid (3), gypsogenin (4), quillaic acid (5) and gypsogenic acid (6) by spectral methods. All compounds were tested for their cytotoxicities against human tumour cell lines (lung cancer H460 and gastric cancer SGC-7901) and for their antiangiogenic effects using a zebra fish model. All compounds showed interesting antiangiogenic activities and the significant cytotoxicities against H460.     

A New Route for the Synthesis of Alkali Polyphosphate from Economical Starting Materials: Preparation and Characterization of Sodium Cyclotriphosphate

Abstract

Thermal synthesis of sodium cyclotriphosphate (SCTP) – Na₃P₃O₉ was investigated in the temperature range of 150 °C to 750 °C using sodium chloride (NaCl) and 85 wt% orthophosphoric acid (H₃PO₄) as economical starting materials. Reaction temperature had a crucial impact on the chloride elimination rate and the formation of SCTP. The best result was obtained at 600 °C with 96% of elimination of the initial chloride as hydrochloric acid and 84% of selectivity in SCTP. At lower temperatures, residual chloride contents were high. At higher temperatures (650 °C and 750 °C), SCTP was melted and transformed into glassy products.     

Silica Sulfuric Acid Catalysis the Oxidation of Organic Compounds with Sodium Bromate

Abstract

The oxidation of organic compounds by sodium bromate/silica sulfuric acid under solvent‐free conditions and in CH₂Cl₂ have been studied at room temperature.     

The Synthesis of Sodium and Potassium Complexes of Two Calix[4]arene Derivatives

Two compounds (1 and 2) which have calix[4]arene units and their Na⁺ and K⁺-complexes were prepared. All the complexes have a metal-ligand ratio of 1 : 1. The newly prepared compounds were characterized on the basis of their ¹H NMR, IR, UV-visible as well as elemental analysis.     

Spectrophotometric Determination of Palladium with Sodium Ethylene-Bis-Selendglycollate

Abstract

SUMMARY

Palladium was determined spectrophotometrically with sodium ethylene-bis-selenoglycollate in acid medium. The system obeys Beer' law in the range 0.25–0, 3 5 μg.ml^?1 and the molar absorptivity is 2.4 × 10⁴ 1. mol^?1 .cm^?1. Determination of palladium in the presence of many ions is reported.

In spite of the fact that selenium compounds have rarely been used as organic analytical reagents and one finds many palladium determination methods in the literature, this paper fits into the general Purpose reported before ^1,2 :systematic comparison of organic sulphur, sellenium and tellurium compounds as analytical reagents in agreement with propositions made some years agp ^3,4

In previous work⁵ the behaviour of the ethylseleno glycollic (L₁), selenodiglycollic (L₂) and ethylene-bis-selenoglycollic (L₃) anions in acidic solutions of some “soft”, “borderline” and “hard” cations was studied.

The results obtained for Pd(II) afforded evidences that its determination could be run with the three mentioned ligands.

Nevertheless, L₃ was selected because it provides the most sensitive signal and its synthesis is very simple and its overall yield is excellent⁶

From the qualitative study⁵ the foreseen selectivity could present some restrictions, but there is little doubt about the usefulness of the method that will be proposed, in various schemes of determination. Similar comments Beamish have been made about EDTA method for Pd(II) determination⁸     

Platinum(II)-thiosemicarbazone drugs override the cell resistance due to glutathione; assessment of their activity against human adenocarcinoma cells

New platinum(II) compounds of the thiosemicarbazone 1-(1H-Benzimidazol-2-yl)ethan-1-one thiosemicarbazone (BzimetTSCH), [Pt(BzimetTSCH)Cl]·2H₂O (1) and [Pt(BzimetTSCH)(tpp)]Cl·H₂O·MeCN (2) were synthesized. The complexes were characterized by FT-IR spectroscopy and ¹H NMR spectroscopy. The crystal structures of 1 and 2 were determined with single-crystal X-ray diffraction analysis. The coordination around platinum is square planar in both complexes. Compounds 1 and 2 were evaluated for their in vitro cytotoxic activity against human adenocarcinoma breast (MCF-7) and cervix (HeLa) cells. The apoptotic pathway of cell death was confirmed by cell cycle arrest test. Since deactivation of cisplatin caused by glutathione (GSH) seems to be an important determinant of its cytotoxic effects, the reactions of 1 and 2 with GSH were investigated by UV-absorption spectroscopy. The genotoxicities on normal human fetal lung fibroblast cells (MRC-5) caused by 1 and 2 were evaluated by fluorescence microscopy. The absence of micronucleus in MRC-5 cells confirms the in vitro non toxic behavior of the compounds. Moreover, the in vivo genotoxicities of 1 and 2 were evaluated by the Allium cepa test. Due to negligible genototoxic effect and high antitumor activity which is similar to that of cisplatin, 2 could be a candidate for further study as potential drug since the mitotic index is unchanged.     

Selenium-Containing Heterocycles: Synthetic Investigation of 3-Amino-2-Ethylselenopyridine Carboxylate Using Sodium Borohydride

3-amino-4,6-dimethyl-2-ethylseleno[2,3-b]pyridine carboxylate (5) was prepared by a reaction of dipyridyl diselenide derivative (3) with sodium borohydride as a reducing agent followed by α-haloester. The reaction of 5 with hydrazine hydrate afforded the corresponding carbohydrazide 8. The benzylidene derivative 9 provided novel heterocycles of pyrimidoseleno pyridine and thiazinoseleno pyridine derivatives (10–12), upon treatment with triethylorthoformate, acetic anhydride, and carbon disulfide, respectively.     

N-[2-(4-Methoxy-phenyl)-ethyl]-2-(quinolin-8-yloxy)acetamide: a receptor for acid binding

Different hydrates of the receptor, N-[2-(4-methoxy-phenyl)-ethyl]-2-(quinolin-8-yloxy)acetamide (I), and its co-crystals with acetic acid and l(+)α-hydroxy-phenylacetic acid are synthesised and their structures are studied. The acids such as acetic acid, l(+)α-hydroxy-phenylacetic acid quench fluorescence of I. The receptor I shows a fluorescence quenching on interaction with perchloric acid in benzene, whereas in methanol the solution of I results in the generation of a new fluorescence emission at higher wavelengths. The crystal structure of the perchlorate salt is determined to explain the protonation behaviour of the receptor I and the perchlorate salt in methanol leads to fluorescence emission at a place different from that of the parent compound.     

Cytotoxic constituents from Helicteres hirsuta collected in Vietnam

Abstract

Phytochemical study on the extract of Vietnamese medicinal plant Helicteres hirsuta Lour. has led to the isolation and structural elucidation of twelve secondary metabolites, 3-O-trans-caffeoylbetulinic acid (1), 3β-benzoylbetulinic acid (2), betulinic acid methyl ester (3), betulinic acid (4), lupeol (5), 4-hydroxybenzoic acid (6), 3,4-dihydroxybenzoic acid methyl ester (7), 4-hydroxy-3,5-dimethoxybenzoic acid (8), 5,8-dihydroxy-7,4′-dimethoxyflavone (9), isoscutellarein 4’-methyl ether 8-O-β-D-glucopyranoside (10), methyl caffeate (11) and stigmasterol (12). Especially, compound 2 was reported as a new natural product. Their structures were elucidated by a combination of 2D NMR and ESI-FT-ICR-MS spectroscopies. Furthermore, eight compounds were tested for their cytotoxicity against five cancer cell lines (Hela, HepG2, SK-LU-1, AGS and SK-MEL-2). The results showed that compounds (1, 3-5, 9) have moderate activities. This is the first study on the chemical constituents and their cytotoxicity of the Vietnamese Helicteres hirsuta L.     

Biotransformation of ursolic acid by Alternaria longipes AS3.2875

Microbial transformation of ursolic acid (1) was carried out by Alternaria longipes AS 3.2875. Six transformed products (2–7) from 1 were isolated and their structures were identified as 3-carbonyl ursolic acid 28-O-β-D-glucopyranosyl ester (2), ursolic acid 3-O-β-D-glucopyranoside (3), ursolic acid 28-O-β-D-glucopyranosyl ester (4), 2α, 3β-dihydroxy ursolic acid 28-O-β-D-glucopyranosyl ester (5), 3β, 21β dihydroxy ursolic acid 28-O-β-D-glucopyranosyl ester (6), and 3-O-(β-D-glucopyranosyl)- ursolic acid 28-O-(β-D-glucopyranosyl) ester (7) based on the analysis of 1D NMR, 2DNMR and MS data. The product 2 was a new compound among them and showed stronger antibacterial activity against S. aureu, MRSA and MRCA than substrate. In this study, we modified structure of ursolic acid through biotransformation to enhance its activities and preliminarily discussed the transformation way of the products.     

Synthesis and Biological Activity of 2-Hydroxy-N(5-methylene-4-oxo-2-aryl-thiazolidin-3-yl)-benzamide

2-Hydroxy benzoic acid hydrazide (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding 2-hydroxy benzoic acid arylidene hydrazides (2a–h) in good yields. Cyclocondensation of compounds 2a–h with thioglycolic acid yields 2-hydroxy-N(4-oxo-2-aryl-thiazolidin-3-yl)-benzamides (3a–h). These 3a–h compounds are for the reacted with benzaldehyde in the presence of sodium ethanolate affords, giving 2-hydroxy-N(5-methylene-4-oxo-2-aryl-thiazolidin-3-yl)-benzamides (4a–h). The structures of these compounds were established on the basis of analytical and spectral data. All the newly synthesized compounds were evaluated for their antibacterial and antifungal activities.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Cytotoxic triterpenes from Salvia buchananii roots

A pentacyclic triterpene, named salvibuchanic acid (1), together with five known compounds, were isolated from the roots of Salvia buchananii Hedge (Lamiaceae). The structural characterisation of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR and HRESIMS experiments. The lupane triterpene (1) and hyptadienic acid (2) were investigated for their potential cytotoxic activity on Jurkat, HeLa and MCF7 cell lines. Both compounds showed an interesting antiproliferative activity with similar potency in all cell lines. By means of flow cytometric studies, hyptadienic acid (2) induced in HeLa cells a S cell cycle block, while 1 elicited both cytostatic and cytotoxic responses.     

A new dihydrobenzofuran lignan and potential α-glucosidase inhibitory activity of isolated compounds from Mitrephora teysmannii

A new dihydrobenzofuran lignan, (2R,3S)-2-(3′,4′-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydrobenzofuran-3-methyl acetate, named as mitredrusin (1), was isolated from the leaves of Mitrephora teysmannii (Annonaceae) together with 12 known compounds including a related dihydrobenzofuran lignan: (?)-3′,4-di-O-methylcedrusin (2), four polyacetylenic acids: 13(E)-octadecene-9,11-diynoic acid (3), 13(E),17-octadecadiene-9,11-diynoic acid (4), octadeca-9,11,13-triynoic acid (5) and octadeca-17-en-9,11,13-triynoic acid (6), five lignans: (?)-eudesmin (7), (?)-epieudesmin (8), (?)-phillygenin (9), magnone A (10) and forsythialan B (11) and two megastigmans: (3S,5R,6S,7E,9R)-7-megastigmene-3,6,9-triol (12) and annoionol A (13). The chemical structures of these compounds were established on the basis of their 1-D and 2-D NMR spectroscopic data. All compounds were evaluated for their α-glucosidase inhibitory activity. Among these isolates, polyacetylenic acids 3 and 4 showed more than 20-fold much higher activity compared with that of the antidiabetic drug acarbose.     

Betulinic acid derivatives: a new class of α-glucosidase inhibitors and LPS-stimulated nitric oxide production inhibition on mouse macrophage RAW 264.7 cells

Chemical manipulation studies were conducted on betulinic acid (1), twenty-one new rationally designed analogues of 1 with modifications at C-28 were synthesized for their evaluation of inhibitory effects on α-glucosidase and LPS-stimulated nitric oxide production in mouse macrophage RAW 264.7 cells. Compound 2 (IC₅₀ = 5.4 μM) exhibited an almost 1.4-fold increase in α-glucosidase inhibitory activity on yeast α-glucosidase while analogues 5 (IC₅₀ 16.4 μM) and 11 (IC₅₀ 16.6 μM) exhibited a 2-fold enhanced inhibitory activity on NO-production than betulinic acid.