The inhibitory effect of bis[2-[(E)-2-octenoylamino]ethyl] disulfide on the cyclooxygenase pathway

Bis[2-[(E)-2-octenoylamino]ethyl] disulfide (compd. I-3) inhibited collagen- and arachidonic acid-induced rat platelet aggregation, although not adenosine 5'-diphosphate (ADP)-induced rat platelet aggregation. Based on these results, we then investigated the inhibitory effect of compd. I-3 on thromboxane B2 formation from arachidonic acid in rat platelets, and prostaglandin I2 formation in rat aortae. Compound I-3 inhibited both thromboxane B2 and prostaglandin I2 formation, suggesting that it has an inhibitory effect on cyclooxygenase. The inhibitory effect of compd. I-3 was confirmed in experiments using a crude preparation of sheep seminal vesicle microsomal prostaglandin synthetase. These findings suggested that compd. I-3 has an inhibitory effect on cyclooxygenase activity, like nonsteroidal anti-inflammatory drugs.     

The effect of a cystamine derivative, bis[2-(E-2-hexenoylamino)ethyl] disulfide, on rat platelet aggregation

Bis[2-(E-2-alkenoylamino)ethyl] disulfides (compds. I), synthesized from cystamine and 2-trans fatty acids, inhibited collagen-induced rat and rabbit platelet aggregation. The most potent compound was bis[2-(E-2-hexenoylamino)ethyl] disulfide (compd. I-1), and this compound suppressed thromboxane B2 formation from arachidonic acid in rat platelets. The results suggested that compd. I-1 has an inhibitory effect on cyclooxygenase.     

Further studies on the anti-ulcerogenic effects of compound, 2-(E-2-decenoylamino)ethyl 2-(cyclohexylethyl) sulfide.

Tha anti-ulcerogenic mechanism of 2-(E-2-decenoylamino)ethyl 2-(cyclohexylethyl) sulfide (compd. III-1a) was investigated in various gastric defensive factors. Compound III-1a maintained the high molecular glycoprotein (relative content of Fr. I hexose) and accelerated hexosamine synthesis which were reduced by water immersion stress. But plaunotol did not have these actions. The lipid peroxide level in the gastric mucosa from water immersion stressed rat was lowered by the administration of compd. III-1a. Compound III-1a maintained prostaglandin E2 (PGE2) and PGI2 contents which were reduced in the early phase of the stress and accelerated PGs synthesis in the late phase of the stress. Furthermore, compd. III-1a maintained phospholipase A2 (PLA2) activity which was reduced by the stress. The plaunotol treated group showed the same tendency as the compd. III-1a treated group on the lipid peroxide level, PGE2 and PGI2 contents, and PLA2 activity, but the potency of plaunotol was less than that of compd. III-1a. Compound III-1a accelerated gastric cell proliferation in pyloric glands of hydrocortisone treated rats. Tetragastrin accelerated significantly the cell proliferation in fundic glands. The sucralfate treated group showed the same tendency as the compd. III-1a treated group but the potency of sucralfate was less than that of compd. III-1a. The results in the present study suggest that compd. III-1a has a protective action on gastric mucosa.     

Synthesis of [2-(vinyloxy)ethyl]uracil and [2-(allyloxy)ethyl]uracil

A synthesis is reported for N¹-mono- and N¹,N³-disubstituted uracil derivatives containing a terminal carbon-carbon double bond in the side-chain. Alkylation of vinyl 2-chloroethyl ether by uracil potassium salts leads to a mixture of 1-[2-(vinyloxy)ethyl] and 1,3-di[2-(vinyloxy)ethyl] derivatives while treatment of 2,4-bis(trimethylsilyloxy)pyrimidines by vinyl 2-chloroethyl ether leads exclusively to N¹-monosubstituted products. Alkylation of cytosine by this chloroether gave 1-[2-(vinyloxy)ethyl]cytosine. The synthesis of 1-[2-(allyloxy)ethyl]uracil derivatives was carried out by treatment of uracil potassium salts by 1-(allyloxy)-2-(p-toluenesulfonyloxy)ethane.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 393–397, March, 1993.     

Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols

Structural alteration of the N^b-substituents of psilocin (3-[2-dimethylamino)ethyl]indol-4-ol) ( 12a ) has led to a number of compounds containing known pharmacophoric groups. Further, it is hoped that the subtle changes in the nature of these substituents may lead to a clearer understanding of the structure-activity relationships of the 4-hydroxytryptamine hallucinogens.     

Crystal structure of the benzene solvate of bis[2-(o-diphenylphosphorylphenoxy)ethyl] ether

Using x-ray diffraction analysis, we have determined the molecular structure of the phosphorus-containing podand bis[2-(o-diphenylphosphorylphenoxy) ethyl] ether in the crystal of its benzene solvate. We have established a considerable difference between the conformations of the free podand and its (previously studied) "guest—host" complex with an organic ammonium cation.Institute of Physiologically Active Substances, Russian Academy of Sciences, 142432 Chernogolovka. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 624–629, March, 1992.     

Some transition metal complexes of new terdentate ligands: Bis[2-(diphenylphosphino)ethyl]benzylamine and bis[2-(diphenylarsino)ethyl)benzylamine

Complexes of the terdentate ligands bis[2-diphenylphosphino)ethyl]benzylamine (DPBA) and bis[2-(diphenylarsino)ethyl]benzylamine (DABA) with Co(II), Ni(II), Pd(II), Pt(II), Rh(III), Ir(III), Rh(I) and Ir(I) are reported. The ligand DPBA reacts with Co(II) ion to form two types of complexes: a high-spin, paramagnetic, tetrahedral Co(II) complex of composition [CoCl(DPBA)]Cl and a low-spin, paramagnetic, square-planar complex of composition [CoBr(DPBA)]B(C₆H₅)₄. The reaction of DPBA with Ni(II) ion in methanol yields low-spin, diamagnetic, square-planar complexes of type [NiX(DPBA)]Y [X = Cl, Br or I; Y = Cl or B(C₆H₅)₄]. Four-coordinate, square-planar, cationic complexes of type [MY(L⁺[M = Pd(II), Pt(II), Rh(I) or Ir(I); Y = Cl or P(C₆H₅)₃; L = DPBA or DABA], were obtained on reaction of L with various starting materials containing these metal ions. Reaction of DPBA and DABA with rhodium and iridium trichlorides gave octahedral, neutral complexes of general formula [MCl₃(L)] (M = Rh or Ir, L = DPBA or DABA). All the complexes were characterized on the basis of their elemental analysis, molarconductance data, magnetic susceptibilities, electronic spectra, IR spectral measurements, and¹H and³¹P-{¹H} NMR spectral data.     

Synthesis of S-[2-(4-Aminobenzenesulfonyl)ethyl] and S-[2-(3-Amino-4-methoxybenzenesulfonyl)ethyl] Thiosulfonates

Russian Journal of General Chemistry -     

新树型配体 TBOAA 与钴配合物的研究

研究了新配体N，N’，N”－（三苯甲酰）－三乙氨基胺（TOBAA）与二价钴离子生成配合物的光度特征和电化学特征。在较宽的pH范围内，新试剂和钴离子形成2：1的配合物，并且在一定范围内其吸光度与浓度具有良好的线性关系。     

2'-O-[2-[N,N-(dialkyl)aminooxy]ethyl]-modified antisense oligonucleotides

[structure] Oligonucleotides with two novel modifications, 2'-O-?2-[N, N-(dimethyl)aminooxy]ethyl? (2'-O-DMAOE) and 2'-O-?2-[N, N-(diethyl)aminooxy]ethyl? (2'-O-DEAOE), have been synthesized. These modifications exhibit high binding affinity to target RNA (and not to DNA) and enhance the nuclease stability of oligonucleotides considerably with t(1/2) > 24 h as a phosphodiester.