Diorganotin(IV) derivatives of substituted benzohydroxamic acids with high antitumor activity

A series of diorganotin(IV) and dichlorotin(IV) derivatives of 4-X-benzohydroxamic acids, [HL(1) (X = Cl) or HL(2) (X = OCH(3))] formulated as [R(2)SnL(2)] (R = Me, Et, nBu, Ph or Cl; L = L(1) or L(2)), along with their corresponding mixed-ligand complexes [R(2)Sn(L(1))(L(2))] have been prepared and characterized by FT-IR, (1)H, (13)C, and (119)Sn NMR spectroscopy, mass spectrometry, elemental analysis, and melting points. In addition, single-crystal X-ray diffraction analyses were carried out for [Me(2)SnL(2)] (L = L(1) or L(2)), which show coordination structures intermediate between distorted octahedra and bicapped tetrahedra. The hydroxamate ligands are asymmetrically coordinated by the oxygen atoms, the carbonyl oxygen atom is further away from the metal center than the other oxygen atom. The complexes are stable monomeric species; most of them are soluble not only in chlorohydrocarbon solvents, but also in alcohols and hydroalcoholic solutions. In polar solvents, the mixed-ligand complexes gradually decompose into the corresponding single-ligand complex couples. The complexes exhibit in vitro antitumor activities (against a series of human tumor cell lines) which, in some cases, are identical to, or even higher than, that of cisplatin. For the dialkyltin complexes, the activity increases with the length of the carbon chain of the alkyl ligand and is higher in the case of the chloro-substituted benzohydroxamato ligand. The [nBu(2)Sn(L(1))(2)] complex displays a high in vivo activity against H22 liver and BGC-823 gastric tumors, and has a relatively low toxicity.     

Synthesis and anti-inflammatory activity of antioxidants, 4-alkylthio-o-anisidine derivatives.

In order to search for anti-inflammatory agents against autoimmune diseases, we synthesized 4-alkylthio-o-anisidine derivatives possessing antioxidant activity, and tested them for anti-inflammatory activity against the Arthus reaction in mice. Experimental inflammations, including the Arthus reaction, concanavalin A, phorbol ester and pyrophosphate-induced edemas in rats were inhibited by 4-propylthio-o-anisidine, which inhibited autoxidation of rat brain homogenate and suppressed the lipopolysaccharide-induced increase in the plasma malondialdehyde level in mice. An antioxidant may be an effective agent in immune complex type inflammation where active oxygen species play an important role.     

Diorganotin(IV) derivatives of arylhydroxamic acids: synthesis, properties and antitumor activity

Series of diorganotin(IV) complexes of 4-X-benzohydroxamic acid [X = NH₂ (HL₁), NO₂ (HL₂) or F (HL₃)] formulated as [R₂SnL₂] and [R₂Sn(L)]₂O (R = Me, Et, nBu or Ph) have been prepared and characterized by FT-IR, ¹H, ¹³C and ¹¹⁹Sn NMR spectroscopies, elemental analyses, FAB⁺-MS and melting point determination. They are stable in air, soluble in alcohols and in hydroalcoholic solution and, in some cases, in water. Their in vitro antitumor activity against a series of human tumor cell lines was tested and, in a few of them, is identical to, or even higher than, that of cisplatin. For the mononuclear dialkyltin compounds, the activity generally increases with the length of the carbon chain of the alkyl ligand, being higher for the complexes with benzohydroxamato ligands bearing an electron-acceptor substituent (X = NO₂ or F). No structure-activity relationship based on the Hammett’s σ_p constant, or related ones, has been recognized.     

Copper(II) complex with 2-(diphenylacetyl)indanedione-1,3: Synthesis and structure

A copper(II) complex with 2-(diphenylacetyl)indanedione-1,3 (HL) was synthesized. CuL₂·0.5C₄H₈O₂ crystals prepared from chloroform + 1,4-dioxane are triclinic, space group P \(\bar 1\), a = 15.0206(9) Å, b = 16.0132(9) Å, c = 16.8323(10) Å, α = 109.6850(10)°, β = 96.4390(10)°, γ = 97.7120(10)°, Z = 4. A unit cell contains two crystallographically independent centrosymmetric dinuclear complexes of the same structure. Each copper(II) atom is coordinated by bidentate cis-oriented deprotonated ligands L at the corners of the square. Bridging 1,4-dioxane molecules make the CN of each metal atom five.     

Organotin(IV) derivatives of mercaptosuccinic and thiodiacetic acids

Di- and tri-organotin(IV) complexes of general formula R₂SnAH, (R₃Sn)₂AH, R₂SnB, (R₃Sn)₂B (A=dianion of mercaptosuccinic acid; B=dianion of thiodiacetic acid; R=Me, Et, nPr, nBu, nOct in R₂Sn and nBu in R₃Sn) have been synthesized and characterized by elemental analysis, IR and ¹H and ¹³C NMR spectroscopy. These data support the preferential binding of sulphur over carboxylate by tin(IV) in R₂SnAH and (R₃Sn)₂AH. R₂SnAH complexes are assigned pentacoordinated bridged polymeric trigonal bipyramidal geometry whereas (R₃Sn)₂AH complexes are monomeric with trigonal bipyramidal geometry at tin arising from a bidentate carboxylate group at one tin atom and from weak bonding via Sn←O?C at the other tin atom. In R₂SnB and (R₃Sn)₂B, tin(IV) binds to two carboxylate groups in a unidentate and a bidentate manner respectively, resulting in tetracoordinated and pentacoordinated structures. Potential uses of these compounds are discussed.     

Synthesis and anti-inflammatory activity of acetylsalicylamino acids and peptides

Several water-soluble acetylsalicylamino acids and peptides containing neutral and acidic amino acids were synthesized and investigated for anti-inflammatory activity. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 169–172, March–April, 2006.     

Synthesis and Crystal Structure of 2-O-(2-hydroxyethyl)-D-glucose

The title compound, 2-O-(2-hydroxyethyl)-D-glucose (C8H16O7 , Mr = 224.21), has been synthesized and its structure was characterized by using NMR spectrum and X-ray single-crystal diffraction. This molecule crystallizes in the monoclinic system, space group P21 , with a = 8.399(17), b = 6.620(14), c = 9.81(2), β = 115.110(17)°, V = 493.7(18)3 , Z = 2, Dc = 1.508 mg/m3 , μ = 0.13 mm-1 , F(000) = 240, the final R = 0.0464 and wR = 0.115 for 1521 observed reflections (Ⅰ > 2σ(Ⅰ)). X-ray crystal structure analysis revealed that the conformation of the pyranosyl ring existed in a slightly distorted 4C1 chair conformation (Cremer-Pople puckering parameters of Q = 0.573(4) , θ = 6.7(3)° and Ф = -5.2(2) °). The molecule exists as a monomer in the solid state, whose conformation is stabilized via multiple inter- and intramolecular hydrogen bonds.     

Oxovanadium(IV) complexes of non-steroidal anti-inflammatory drugs: Synthesis,spectroscopy, and antimicrobial activity

Oxovanadium(IV) complexes with four different non-steroidal anti-inflammatory drugs have been synthesized. These complexes were characterized by different analytical techniques such as CHN, IR, UV-Vis spectroscopy, and mass spectrometry. The IR data show the bidentate nature of the ligands and reveal hexacoordinate geometry in the solid state. The complexes were tested for their biological activity against six different bacterial strains and plant pathogens, and all complexes showed good biological activity with few exceptions The text was submitted by the authors in English.     

8-氨甲基取代木犀草素衍生物的合成和抗炎活性研究

以木犀草素为先导化合物,对其A环8-位碳上进行Mannich反应,合成了10个未见文献报道的8-氨甲基化衍生物,并用1HNMR,IR和MS(HRMS)进行了结构表征。利用二甲苯诱发小鼠耳廓肿胀模型对所合成的七个目标化合物进行了抗炎活性的药理筛选,初步结果表明部分化合物具有良好的抗炎活性。