Synthesis of diesters by addition of acids to 5-alkoxycarbonylnorborn-2-ene and related 5-methyl derivatives

The addition of saturated aliphatic acids C₁?CC₅ to 5-alkoxycarbonylnorborn-2-enes and 5-methyl-5-alkoxycarbonylnorborn-2-enes in the presence of catalyst BF₃·O(C₂H₅)₂ was studied and new representatives of the norbornane hydroxyacids diesters were synthesized.     

酰氨基硫脲及其相关杂环衍生物的研究III.1-(5-甲基异唑-3-甲酰基)-4-芳基氨基硫脲及其相关杂环衍生物

Eight 1-(5-methylisoxazol-3-ylcarbonyl)-4-substituted thiosemicarbazides (I), eight 3-(5-methylisoxazol-3-yl)-4-substituted-1,2,4-triazoline-5-thiones (II), seven 2-arylamino-5-(5-methylisoxazol-3-yl)-1,3,4-thiadiazoles, and five 2-arylamino-5-(5-methylisoxazol-3-yl)-1,3,4-oxadiazoles were prepared from isoxazole III and aryl isocyanates. The derivatives I and II showed antitubercular activity and promoted the growth of plumule of wheat in preliminary experiments     

Synthesis and antimicrobial activity of some novel 5-alkyl-6-substituted uracils and related derivatives

6-chloro-5-ethyl-, n-propyl- and isopropyluracils 5a-c were efficiently prepared from the corresponding 5-alkybarbituric acids 3a-c via treatment with phosphorus oxychloride and N,N-dimethylaniline to yield the corresponding 5-alkyl-2,4,6-trichloro-pyrimidines 4a-c, which were selectively hydrolyzed by heating in 10% aqueous sodium hydroxide for 30 minutes. The reaction of compounds 5a-c with 1-substituted piperazines yielded the corresponding 5-alkyl-6-(4-substituted-1-piperazinyl)uracils 6a-j. The target 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-diones 7a-c were prepared via the reaction of 5a-c with sodium azide. Compounds 6a-j and 7a-c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compound 6h displayed potent broad-spectrum antibacterial activity, while compound 6b showed moderate activity against the Gram-positive bacteria. All the tested compounds were practically inactive against Candida albicans.     

Inhibitory activities and inhibition specificities of caffeic acid derivatives and related compounds toward 5-lipoxygenase

Various caffeic acid derivatives were synthesized, and their effects on 5-lipoxygenase (5-LO), 12-lipoxygenase (12-LO) and prostaglandin (PG) synthase activities were investigated. Among them, caffeic acid octyl amide (5) and 1-(3,4-dihydroxyphenyl)-1-octen-3-one (11) showed very potent inhibitory activities toward 5-LO with IC50 values of 4.2 x 10(-8) and 3.5 x 10(-8) M, respectively. They were very selective inhibitors for 5-LO. Compound 11 showed non-competitive inhibition, and the two adjacent hydroxy groups attached to the benzene ring, as well as the hydrophobic alkyl side chain, were required for its strong binding to 5-LO.     

Studies on imidazole derivatives and related compounds. I. Synthesis of novel antineoplastic derivatives of 4-carbamoylimidazolium-5-olate

Acylation of 4-carbamoylimidazolium-5-olate ( 2 ) with a variety of acid chlorides produced 4(5)-carbamoyl-1H-imidazol-5-(4)yl acid carboxylates ( 3a-j ). Treatment of esters 3a,c with sodium hydroxide gave imides, 4a,c . Methylation of 3a and 2 with diazomethane gave the N-3 methyl derivative ( 6 ) and a mixture of the N-3, O-dimethyl derivative ( 9 ), the N-1, N-3-dimethyl derivative ( 10 ) and the O-methyl derivative ( 11 ), respectively. 5-Carbamoyl-1-methylimidazolium-4-olate ( 7 ) and its 4-carbamoyl isomer ( 16 ) were prepared from 2-aminopropanediamides 8 and 15 , respectively. Treatment of the imidazolium compound ( 10 ) with aqueous potassium hydroxide gave the recyclized product, 1-methyl-5-methylcarbamoylimidazolium 4-olate ( 18 ). Methyl derivatives 6, 7 , and 9 except 16 demonstrated the complete lack of antitumor activity against Lewis lung carcinoma or sarcoma 180 in mice.     

5-Trifluoromethylfuran derivatives

Methods for the preparation of 5-trifluoromethylfuran-2-carboxylic acid, 5-tri-fluoromethylfurfural, and 5-trifluoromethyl-2-aminofuran derivatives were developed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1607–1609, December, 1977.     

Synthesis of 7,8-dihydro-6H-pyrazolo[3,4-b]quinolin-5-ones and related derivatives

This paper describes the synthesis of a new series of 4-amino-1-(unsubstituted and chloro or fluoro substituted benzyl)-7,8-dihydro-6H-pyrazolo[3,4-b]quinolin-5-ones 8 and the corresponding 7,8-dihydro-6H,9H-pyrazolo[3,4-b]quinoline-4,5-diones 13 . The derivatives obtained by reaction of these compounds with sodium azide in concentrated sulfuric acid are also reported.     

5-Benzyluracil and its derivatives

5-(Hydroxybenzyl)uracils are obtained by condensation of 5-hydroxymethyluracil (I) with phenols in the presence of CF₃COOH [1]. However, the activity of CF₃COOH is insufficient for aromatic compounds that do not contain electron-donor substituents. Thus, according to PMR data, the reaction between equivalent amounts of I and C₆H₆ in CF₃COOH is complete only after 3 days. However, benzene derivatives containing electron-acceptor substituents are practically unreactive. Anhydrous HP, in which even benzotrifluoride reacts, is a considerably more efficient agent.     

Cyclol derivatives related to ergocornine

Novel cyclol derivatives (Table 1, 15, 16 ) similar in structure to the peptide portion of ergocornine were synthesized. Detailed experimental procedures are given for the preparation of the cis- 13a and the unknown trans- 14a cyclol esters.     

Circular dichroism of A-nor-steroids and related derivatives

The Circular Dichroism (CD.) of several saturated and conjugated keto-A-nor-steroids follows the known rules. Homochiral α,β-epoxy-cyclopentanones and -cyclohexanones give the same sign of the Cotton effect within the R-band, whereas the K-band CD. of the former has opposite sign to that at 300 nm. More examples for the application of the rule for the determination of the CD. of non-coplanar conjugated lactones as well as α,β-epoxy-lactones are presented.     

Synthesis of 4-hydroxyderricin and related derivatives

Naturally occurring chalcones, namely 4-hydroxyderricin (1), xanthoangelol H (2), deoxyxanthoangelol H (3), and deoxydihydroxanthoangelol H (4), were first synthesized and evaluated for antibacterial activities.     

Amphiphilic derivatives of dextran and related nanoparticles

Graft block copolymers of poly(?-caprolactone) containing various amounts of dextran [dextranpoly(?-caprolactone) copolymers] have been prepared and characterized. The methods of obtaining nanoparticles based on the dextran-poly(?-caprolactone) graft block copolymers have been elaborated and optimized. It has been demonstrated that the electrokinetic potential of nanoparticles may be varied relative to the composition of the polymer, the structure of nanoparticles, and the ionic strength of solution. Under physiological conditions, the nanoparticles behave as stable colloids. On the basis of the experimental evidence, conclusions concerning the structure of the nanoparticles have been made.     

Studies on imidazole derivatives and related compounds. 2. Characterization of substituted derivatives of 4-carbamoylimidazolium-5-olate by ultraviolet absorption spectra

The representative mono- and dialkyl-substituted derivatives of 4-carbamoylimidazolium-5-olate (1) were synthesized unequivocally. On the basis of their spectral data for ultraviolet absorption spectra in acidic, basic and neutral solutions, we have found some spectral characteristics which make it facile to clarify the position of substituents.     

Studies on imidazole derivatives and related compounds. 3. Regioselective glycosylation of 4-carbamoylimidazolium-5-olate

In the synthesis of glycosyl derivatives of 4-carbamoylimidazolium-5-olate ( 2 ) by the silyl-Hilbert-Johnson method using trimethylsilyl trifluoromethanesulfonate as catalyst, we obtained N-3 nucleosides 5 as major products and N-1,N-bis-nucleosides 6 as minor ones. The desired N-1 nucleosides 4 were isolated in only low yields. However, the yields of 4 were improved by adding ca. One equivalent of stannic chloride to the silylated 4-carbamoylimidazolium-5-olate ( 3 ). On the basis of nuclear magnetic resonance (¹³C and ²⁹Si) and ultraviolet spectroscopic studies, we verify the formation of σ-complexes between the silylated base 3 and the Lewis acid (stannic chloride or trimethylsilyl trifluoromethanesulfonate), and the propose the structures of these complexes and the reaction mechanism.     

5-Substituted pyrimidine derivatives

The properties and reactivities of 4-hydroxy- and 2,4-dihydroxy-5-(β-hydroxyethyl)pyrimidines and of the products of their transformations have been studied. 4-Chloro- and 2,4-dichloro-5-(β-chloroethyl)pyrimidines have been obtained. A number of 4-alkyl(aryl)amino-5-(β-chloroethyl)pyrimidines have been synthesized, and they have been converted into derivatives of 5,6-dihydropyrrolo[2,3-d]pyrimidine.     

5-Aminoorotic acid derivatives

The 2,4,8-trioxo derivative of pyrimido[5,4-d][1,3]oxazine was synthesized, and esters and amides of 5-acetamidoorotic acid were obtained from it. The acetyl group in 5-acetamido-orotic acid esters is readily hydrolyzed in acidic media to give esters of 5-aminoorotic acid, while the acetyl group in amides of 5-acetamidoorotic acid do not undergo hydrolysis.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 270–272, February, 1973.Deceased.     

酰氨基硫脲及有关的杂环衍生物的研究 I:1-氰乙酰基-4-芳基氨基硫脲及有关的杂环衍生物的合成

合成了九个1-氰乙酰基-4-芳基氨基硫脲类化合物和四个3-氰甲基-4-芳基-1,2,4-三唑啉与硫酮类化合物和四个2-苯基氨基-5-取代-1,3-噻二唑类化合物.并初步研究了这些化合物的抗结核菌活性和植物生长促进作用.