Indole derivatives

A method for the introduction of a 3-indolyl group in compounds with an active methylene group was developed. The corresponding 3-indolyl diketones were obtained by condensation of 1-acetyl-3-indolinone with dimedone, 4-hydroxycoumarin, 1,2-diphenyl-3,5-pyrazolinedione, and barbituric and thiobarbituric acids and subsequent alkaline hydrolysis of the condensation products. The existence of cyclic six-membered 3-indolyl diketones in the enol form and of cyclic five-membered 3-indoly diketones in the keto form was shown by IR and UV spectroscopy. Depending on the conditions, (1-acetyl-3-indolyl)cyanoacetamide, 1,3-bis(1-acetyl-3-indolyl)-1,3,3-tricyano-2-amino-1-propene, and 1-acetyl-3-indolylmalononitrile are obtained in the condensation of 1-acetyl-3-indolinone with malononitrile. 1-Acetyl-3-indolylmalononitrile exists in equilibrium with the keteneimine form and in protic solvents is converted to 3-cyano-8-acetylpyrrolo[2,3-b]indole by intramolecular cyclization.See [1] for communication CX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 360–368, March, 1977.     

Analysis of erysimoside

Conclusions A method for the chromatophotocolorimetric determination of erysimoside in raw material is given which has been made the basis of the analytical control of its production.Order of the Red Banner of Labor Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 334–336, May–June, 1974.     

Arbuzov rearrangement in the 1,3,2-oxazaphosphinane series

Reactions of 2-alkoxy-1,3,2-oxazaphosphinanes (including 3-alkyl derivatives) with methyl and ethyl bromoacetates give two types of Arbuzov rearrangement products (cyclic and acyclic ones). The ratio between their yields is virtually independent of the nature of the substituent in position 3 of the starting reagent, being mainly determined by the nature of the substituent in the phosphorus bound alkoxy group and varying from 96 : 4 to 2 : 98. Acyclic products can be converted into cyclic ones.Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1915–1918, September, 2004.     

Chromato-spectrophotometric determination of psoberan and psoralen in blood plasma

A procedure has been developed for the quantitative determination of the natural photosensitizers psoberan and psoralen in blood plasma. The furocoumarins are extracted from the plasma with chloroform and are separated from accompanying substances by the TLC method. The quantitative determination is made spectrophotometrically. The sensitivity threshold of the method is 1 µg/ml.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 628–629, September–October, 1985.     

Design of phosphonate analogs of short peptides by “click” chemistry

Methods were developed for the first time for the modification of the natural neuropeptides Ile–Gly–Leu and Leu–Gly–Leu simultaneously with the phosphonate moiety and the triazole ring or solely with the triazole ring by means of click chemistry. All of the peptidomimetics synthesized were isolated as a mixture of diastereomers and were characterized by spectroscopic methods.