Structure-Activity Relationship of Insecticidal Steroids. V. 3β-Benzoyloxystigmastan-6-ones

The toxicity of steroid benzoates 4-10 for Colorado beetle (Leptinotarsa decemlineata Say.) larvae was studied by a contact-intestinal method. The most active growth and development regulator for this insect is 3-benzoyloxy-5-hydroxy-⁷-6-ketosteroid 9a.     

Structure-Activity Relationship of Insecticidal Steroids. IV. 3β-Chlorosubstituted Derivatives of Cholesterol and β-Sitosterol

The toxicity of 3-chlorosteroids 1-8 for colorado beetle (Leptinotarsa decemlineata Say.) larvae was studied by a contact-intestinal method. The most active insect growth and development regulators of the studied compounds are 3-chlorocholest-5-ene (1a), 3-chloro-5,6-diol 6-formate (3b), 3-chloro-7-hydroxy-6-ketone (4a), and 3-chloro-5-bromo-⁴-6-ketone (8).     

Investigations of alkoxysilanes 9.β-floethoxysilanes

Summary -Fluoroethoxysilanes were prepared and described for the first time. Routes to the synthesis of compounds of this type were proposed.Communication 8, see [1].     

Functionalization of the 3β-methyl group of penicillin

A number of penicillins functlonalized at the 3β-methyl position have been syntheslsed. The progenitor of these compounds Is the 3β-hydroxymethyl penicillin 1.     

Effective synthesis of methyl 3β-amino-3-deoxybetulinate

A practical method for preparing methyl 3β-amino-3-dexoybetulinate that is based on column chromatographic separation of 3α- and 3β-t-butoxycarbonates and subsequent removal of the protecting group using formic acid is proposed. The structure of methyl 3β-N-(t-butoxycarbonyl)-3-deoxybetulinate was established by an x-ray structure analysis. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 488–490, September-October, 2008.     

Synthesis of Betulin-3-yl-β-D-Glucopyranoside

Two concise routes toward betulin-3-yl-β-D-glucopyranoside, being different in the protection of primary alcohol of betulin, were developed. The synthesis adopted a stepwise glycosidation method employing glycosyl trichloroacetimidate as donor.     

Reaction of aminoquinolines with unsaturated carboxylic acids. 2. Cyclization of N-quinolyl-β-alanines

The cyclization of N-(3-quinolyl)- and N-(6-quinolyl)--alanines was carried out to give uncondensed hexahydropyrimidine derivatives, while the cyclization of N-(5-quinolyl)- and N-(8-quinolyl)--alanines gave tetrahydrophenanthrolinone derivatives.Communication 1, see ref. [1].Kaunas Technological University, 3028 Kaunas, Lithuania, Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 653–657, May, 2000.     

Synthesis and stereochemistry of chiral azetidin-2-ones and azetidine-2-thiones. 3. Stereodirected construction of theβ-lactam fragment of the thienamycin molecule

It has been shown possible to introduce an -hydroxyethyl group trans-stereospecifically into position 3 of 4-methyl-1-(-methyl-benzl)azetidin-2-one. The stereochemistry of the asymmetric centers C₍₃₎, C₍₃₎, and C₍₄₎ of the diastereoisomers of the 3--hydroxyethyl derivative obtained in larger amount and of the corresponding three adjacent chiral centers C₍₈₎, C₍₆₎, and C₍₅₎ in thienamycin are the same.For part 2 see [1].M. V. Lomonosov Moscow State University, Moscow, 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 254–257, February, 1995. Original article submitted December 14, 1994.     

Total synthesis and properties of prostaglandins. 40. Synthesis ofβ-Oxyaminovinyl bicyclic γ-lactones

Acetylation of oxyiminomethyl bicyclic y-lactones gave the corresponding N-acetyl--oxyaminovinyl derivatives.Latvian Institute of Organic Synthesis, Riga, LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 613-615, May, 1995. Original article submitted March 27, 1995.     

Highly polarized enamines. 2. Synthesis and investigation of the further amination of derivatives of α,α-DIAMINO-β-cyano-β-nitroethylene

Highly polarized enediamines of the a, -diamino--cyano--nitroethylene type have been obtained by the hydrolysis of 4-chloro-5-nitropyrimidines. Several chemical conversions of the enamines obtained have been studied, particularly leading to derivatives of 2-(cyanonitromethylene)imidazoline and -hexahydropyrimidine, and also to derivatives of N, N-bisvinylpiperazine and 7 methylene-1, 4-diazabicyclo(2.2. 1 ]heptane.Center for Drug Chemistry, All-Russian Chemical and Pharmaceutical Research Institute, Moscow 119815. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 811–820, June, 1996. Original article submitted February 6, 1996.For Part 1, see [1].     

4-hydroxy-2-quinolenes. 24. Improved synthesis and biological properties of hydrochlorides ofβ-dialkylaminoalkylamides of 1-alkyl-2-oxo-4-hydroxyquinoline-3-carboxylic acids

High-purity hydrochlorides of-dialkylaminoalkylamides of 1-R-2-oxo-4-hydroxyquinoline-3-carboxylic acids have been obtained from N-alkyl-2-carbalkoxyanilides of malonic acid. The synthesized compounds have been tested for certain forms of pharmacological activity.For Communication 23, see [1].Ukrainian Pharmaceutical Academy, Khar'kov 310002. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1400–1405, October, 1994. Original article submitted November 8, 1994.     

Practical Preparation of Resveratrol 3-O-β-D-Glucuronide

Abstract

A practical synthesis of resveratrol 3-O-β-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large-scale preparation of resveratrol is also reported.     

Synthesis of 6-chloronicotinates of steroidal 3β,5α,6β-triols and 3β,5-dihydroxy-6-ketones

New esters of 3β,5α,6β-trihydroxysteroids and 3β,5-dihydroxy-6-ketosteroids containing 6-chloropyridine groups characteristic of the alkaloid epibatidine were synthesized by acylation with 6-chloronicotinoylchloride. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 175-179, March-April, 2009.     

Hypochlorous Acid. A Synthesis of α-Chloro-β-Lactones

Herein we report that the reaction of hypochlorous acid with certain α,β-unsaturated acids in a two phase system^1,2 affords α-chloro-β-lactones^3,4 in poor to fair yield. Thus, β-lactones 4, 5, and 6 are obtained from acids 1, 2 and 3, respectively, where the β-carbon of the acid is disubstituted.     

Synthesis and properties of azoles and their derivatives. 45. Regio-and stereoselectivity of the [2+3]-cycloaddition ofE-β-nitrostyrene toZ-C-phenyl-N-arylnitrones

It is shown using spectroscopic methods that the [2+3]-cycloaddition of Z-C-phenyl-N-arylnitrones to E--nitrostyrene is regiospecific and leads to a mixture of the corresponding (3SR,4SR,5SR)- and (3SR,4SR,5SR)-2-aryl-4-nitro-3,5-diphenylisoxazolidines. The regioselectivity of the reaction is explained in terms of hard and soft acid and base theory.For communication 44, see [1]Institute of Organic Chemistry and Technology, T. Kosciuszko Krakow Polytechnic, 31–155 Krakow. Poland: e-mail: pebarans(ausk.pk.edu.pl. Translated from Khimiya Geterotsiklicheskikh Soedinenii No. 6. pp. 840–846, June, 2000.     

NMR spectra of cyclic nitrones. 6. Tautomeric equilibrium of Β-oxo-nitrones — 3-Imidazoline 3-oxide derivatives

It is demonstrated by ¹³C NMR spectroscopy that -oxo nitrones (3-imidazoline-3-oxide derivatives) exist in the form of an equilibrium mixture of three tautomeric forms with preponderance of the enolo nitrone and enehydroxylamino ketone forms.For communication 5, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 192–195, February, 1991.     

Synthesis of Amides of 3-O-Acetyl-18-βH-glycyrrhetic Acid

Methods of preparing amides of 3-O-acetyl-18-H-glycyrrhetic acid from certain amines are described. The structures of the prepared amides have been confirmed by chemical and spectral analyses     

Emodin-8-O-β-D-glucoside from Polygonum amplexicaule D. Don var. sinense Forb. promotes proliferation and differentiation of osteoblastic MC3T3-E1 cells

Polygonum amplexicaule D. Don var. sinense Forb. (Polygonaceae) (PAF) is a famous traditional herb used to treat fractures, rheumatoid arthritis, muscle injury and pain. The present study was designed to investigate a PAF derived-chemical compound emodin-8-O-β-D-glucoside (EG) on the proliferation and differentiation of osteoblastic MC3T3-E1 cell in vitro. A compound was isolated from PAF extract by HPLC and identified as emodin-8-O-β-D-glucoside (EG) by spectroscopic methods. EG significantly promoted cell proliferation at 0.1-100 ng/mL, and increased the cell proportion in S-phase from 16.34% to 32.16%. Moreover, EG increased alkaline phosphatase (ALP) expression in MC3T3-E1 cells at the concentration from 0.1 to 100 ng/mL and inhibited PGE(2 )production induced by TNF-α in osteoblasts at the concentrations ranging from 10-100 ng/mL, suggesting that cell differentiation was induced in MC3T3-E1 osteoblasts. Taken together, these results indicated compound EG directly stimulated cell proliferation and differentiation of osteoblasts, therefore this study preliminarily explored the pharmacological mechanism of PAF to promote the healing of bone rheumatism and various fractures.